flavor composition and edible composition

专利摘要:
IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS. Flavor composition comprising a compound according to formula (I) or its edible salts, (I) wherein RI is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, RI together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, where R3 is H or together with R2 and the N atom to which they are attached, a ring of 5-membered, is an amino acid residue, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.
公开号:BR112014023016B1
申请号:R112014023016-1
申请日:2013-03-28
公开日:2020-10-27
发明作者:Feng Shi；Harry Renes；Esther Van Ommeren；Santi VORSTER；Yili Wang；Adri De klerk；Xiaogen Yang
申请人:Givaudan Sa；
IPC主号:

专利说明:

[0001] The present invention relates to certain carboxylic acid - amino acid conjugates, flavor compositions containing said conjugates, and their use in edible compositions.
[0002] WO 2009/141294 describes particularly acylamino acid compounds in which the acyl group is unsaturated and contains a cis double bond. These compounds are used in sufficient quantity to exert a tingling sensation but with a concomitant reduced burning sensation. Such compounds are useful in food products as a replacement for conventional flavorings such as chilli to take into account the needs of consumers who like spicy food, which would be delicately hot, but do not cause an excessive burning sensation in the oral cavity.
[0003] The availability of such flavor ingredients in the food scientists' toolbox, which exert their very pronounced flavor characteristics to a food product, is of niche value for particular types of food categories. However, there are a lot of food applications where a spicy, tingling or hot taste would be considered inappropriate or unpleasant.
[0004] There is a need to provide flavor ingredients that to complement the flavors of edible compositions in which they are incorporated in order to accentuate the flavors and oral sensation of said compositions, instead of exercising their own characteristics of particular taste; and thus serve a very wide spectrum of use across a wide range of food and drink categories.
[0005] The present invention provides in one of its aspects the use of a compound according to formula (I) or its edible salts,
where Ri is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, Ri together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR2R3, where R3 is H or together with R2 and the N atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma acid -aminobutyric or beta alanine, or a 1-amino cycloalkyl carboxylic acid.
[0006] Edible salts include those typically used in the food and beverage industry and include chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates and lactates.
[0007] Proteinogenic amino acids are alanine (Ala), cysteine (Cys), aspartic acid (Asp), phenylalanine (Phe), glutamic acid (Glu), histidine (His), isoleucine (lie), lysine (Lys), leucine (Leu), methionine (Met), asparagines (Asn), glutamine (Gin), arginine (Arg), serine (Ser), threonine (Thr), valine (Vai), tryptophan (Trp), tyrosine (Tyr), proline (Pro) or glycine (Gly).
[0008] The three code letters in parentheses are common abbreviations used in relation to amino acids and will be used from now on.
[0009] Carboxylic acids can likewise be represented by abbreviations. From now on, carboxylic acid residues can be mentioned by the abbreviation Cn, where "n" represents the number of carbon atoms in the residue. For example, the residue of a carbon acid 18 can be abbreviated to C18. Furthermore, if carbon acid 18 is saturated, for example, stearic acid. It can be abbreviated as C18: 0 (because it contains zero double bonds), while a carbon acid 18 having a double bond - for example, oleic acid - can be abbreviated as C18: 1. Furthermore, if C18 acid has a single double bond in the cis configuration, then it can be abbreviated as C18: 1c. Similarly, if the double bond was in the trans configuration, then the abbreviation becomes C18: 11.
[00010] The compounds of formula (I) can also be represented in terms of these abbreviations. For example, the compound of formula (I) which consists of a residue of a C18 carboxylic acid and a residue of the amino acid Proline can be represented by the abbreviation C18-Pro. For simplicity the compounds of formula (I) from now on can be represented in this short form.
[00011] As is evident from the above formula (I), an amino nitrogen atom on the amino acid residue is attached to a carbonyl carbon atom of the carboxylic acid residue to form an amide bond. Some amino acids (ornithine and lysine) have more than one amino group, and the amide bond can be formed from any of these amino groups.
[00012] In a particular embodiment of the present invention the carboxylic acid residue is a fatty acid residue.
[00013] The fatty acid residue can be the residue of a fatty acid from C8 to C22. The fatty acid can be mammalian or non-mammalian. A mammalian fatty acid is a natural or synthetic fatty acid that is identical in structure to one naturally produced in a mammal, including, but not limited to myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, arachidonic acid, eicosapentenoic acid, and docosatetraenoic acid. A non-mammalian fatty acid is a natural or synthetic fatty acid not normally produced by a mammal, including, but not limited to, pentadecanoic acid; heptadecanoic acid; nonadecanoic acid; heneicosanoic acid; 9-trans-tetradecenoic acid; 10-trans-pentadecenoic acid; 9-transhexadecenoic acid; 10-trans-heptadecenoic acid; 10-trans-heptadecenoic acid; 7-trans-nonadecenoic acid; 10,13-nonadecadienic acid; 11-trans-eicosenoic acid; and 12-transenicosenoic acid.
[00014] Fatty acid residues can be saturated or unsaturated. If they are unsaturated, it is preferred that they have 1, 2 or 3 double bonds, which can have a cis or trans configuration.
[00015] More particularly, the preferred fatty acid residues are C16 to C18, and can be saturated or unsaturated.
[00016] The knowledgeable person will appreciate, however, that natural sources of these fatty acids, for example, almond oil, avocado oil, castor oil, coconut oil, corn oil, cotton wool oil, olive oil , peanut oil, rice bran oil, safflower oil, sesame oil, soy oil, sunflower oil, palm oil and canola oil, each consist of a complex mixture of fatty acids. For example, saffron oil is predominantly a source of C18: 2 linoleic acid, however it can contain other fatty acids, such as linolenic acid (C18: 3) and palmitic acid (C16: 0), among others. Correspondingly, reference here to a compound containing a particular fatty acid residue, for example, a C18 fatty acid residue, can be a reference to a pure or substantially pure C18 fatty acid residue, or it can refer to a mixture of fatty acid residues with the predominant residue being a C18 residue. Preferred fatty acid residues are C16 to C18.
[00017] Compounds of formula (I) can contain chiral atoms, and as such they can exist in racemic form, as a mixture of stereoisomers or as decomposed as simple isomers. The use of the term "a compound of the formula (I)" can refer to both mixtures of isomers or single decomposed isomers.
[00018] In particular, the compounds of formula (I) may contain D- or L-amino acid residues.
[00019] The compounds of formula (I) can be formed by known methods using commercially available starting materials, reagents and solvents, and a detailed discussion is not justified here. In one embodiment of the present invention, conjugates can be formed by reacting an amino acid with a carboxylic acid halide, for example, a chloride under basic conditions in aqueous conditions such as a THF / water solvent system. Yield and retention times can be improved by applying heat to the reaction mixture. In an alternative embodiment, a carboxylic acid can be reacted with an amino acid in dioxane in the presence of DCC (dicyclohexylcarbodiimide) and 1-hydroxypyrrolidine-2,5-dione.
[00020] In yet another embodiment, an amino acid alkyl ester can be reacted with a carboxylic acid chloride under basic conditions in an aqueous based solvent, such as a THF / water solvent system. After that, the ester can be hydrolyzed carefully without affecting the amide bond in aqueous basic methanol solution
[00021] In yet another embodiment, a carboxylic acid and an amino acid alkyl ester can be reacted in dioxane in the presence of DCC (dicyclohexylcarbodiimide) and 1-hydroxypyrrolidine-2,5-dione. The ester can be hydrolyzed carefully without affecting the amide bond in dilute aqueous basic methanol solution
[00022] In yet another embodiment, an anhydride (mixed) of a carboxylic acid is reacted with an amino acid in dioxane.
[00023] In yet another embodiment, an alkyl ester of carboxylic acid can be reacted with an amino acid in dioxane
[00024] In yet another embodiment, an alkyl ester of amino acid is reacted with a triglyceride, optionally in the presence of a cosolvent. The amino acid ester thus formed is then hydrolyzed according to a method described above.
[00025] In yet another embodiment, an amino acid is reacted with a triglyceride, optionally in the presence of a cosolvent.
[00026] In yet another embodiment, an amino acid is reacted with a triglyceride in the presence of a lipase, esterase, protease, peptidase, amidase or acylase, optionally in the presence of a cosolvent and / or water.
[00027] In yet another embodiment an alkyl ester of carboxylic acid is reacted with an amino acid in the presence of a lipase, esterase, protease, peptidase, amidase or acylase, optionally in the presence of a co-solvent and / or water.
[00028] In an embodiment of the present invention, compounds of the formula (I) represented by the formula are provided
edible salts, and their use in edible compositions
[00029] where Ri, is defined here above, and n is 1,2, 3 or 4.
[00030] Preferred compounds are those where "n" is 1.
[00031] The amino acid residue revealed in the above formula can be abbreviated as "ACCA".
[00032] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA.
[00033] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA, wherein the carboxylic acid residue is saturated.
[00034] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00035] The compounds include those specified above in which the cycloalkane ring in the amino acid residue is cyclopropane (n = 1).
[00036] Particularly preferred compounds are N-palmitoyl 1-amino-cyclopropyl carboxylic acid (C16: 0-ACCA), N-stearoyl 1-amino-cyclopropyl carboxylic acid (C18: 0-ACCA), N-linoleoyl 1-amino acid - cyclopropyl carboxylic (C18: 2-ACCA), N-linolenoyl 1-amino-cyclopropyl carboxylic acid (C18: 2-ACCA), N-oleoyl 1-amino-cyclopropyl carboxylic acid (C18: 1-ACCA), N- (9-palmitenoyl) 1-amino-cyclopropyl carboxylic acid (C 16: 1-ACCA), N-decanoyl 1-amino-cyclopropyl carboxylic acid (C10: 0-ACCA) and N-geranoyl 1-amino-cyclopropyl carboxylic acid (C10 : 2-ACCA).
[00037] The present invention provides in another embodiment the compounds of formula (I) represented by the formula
and its edible salts, and their use in edible compositions in which Ri, here is more defined above, in is 0 or 1.
[00038] It will be evident to the person skilled in the art that when m is 1, the amino acid residue is a gamma amino butyric acid (GABA) residue, while when m is 0, the amino acid residue is a residue of beta-alanine (Beta Ala). Both the compounds of formula (I) where m is 1 and the amino acid residue is a GABA residue, and the compounds of formula (I) where m is 0 and the amino acid residue is a beta-alanine residue, their edible salts, as well as their use in edible compositions, are all embodiments of the present invention.
[00039] These compounds are particularly useful to incorporate into an edible product to provide a remarkable oral, body and increased perception of fat; or an enhanced umami flavor or salt flavor; or a cooling and wealth. They are particularly useful in low fat, salt and umami applications. They are also useful in fat-free formulations such as drinks and oral care applications. They are also used in dairy applications and in vanilla, cocoa and chocolate.
[00040] The compounds include C8-GABA, C9-GABA, C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, C20-GABA and C22-GABA.
[00041] The compounds include C8-GABA, C9-GABA, C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, C20-GABA and C22-GABA, wherein the carboxylic acid residue is saturated.
[00042] The compounds include C8-GABA, C9-GABA, C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, C20-GABA and C22-GABA, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00043] Particularly preferred compounds include C10-GABA, C12-GABA, more particularly C12: 1-GABA, C14-GABA, C16-GABA, more particularly C16: 1-GABA, C18-GABA, more particularly C18: 1-GABA , even more particularly C18: 1c-GABA and C18: 1t-GABA. Most preferred is a C18: 2-GABA compound.
[00044] The compounds include C8-Beta Ala, C9-Beta Ala, C10-Beta Ala, C12-Beta Ala, C14-Beta Ala, C16-Beta Ala, C18-Beta Ala, C20-Beta Ala and C22-Beta Ala .
[00045] The compounds include C8-Beta Ala, C9-Beta Ala, C10-Beta Ala, C12-Beta Ala, C14-Beta Ala, C16-Beta Ala, C18-Beta Ala, C20-Beta Ala and C22-Beta Ala , in which the carboxylic acid residue is saturated.
[00046] The compounds include C8-Beta Ala, C9-Beta Ala, C10-Beta Ala, C12-Beta Ala, C14-Beta Ala, C16-Beta Ala, C18-Beta Ala, C20-Beta Ala and C22-Beta Ala , where the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00047] A preferred compound is C18: 2-Beta Ala.
[00048] The present invention provides in another embodiment the compounds of formula (I) represented by the formula
and its edible salts, and their use in edible compositions in which Ri, is defined here above, R3 is hydrogen or methyl, and R4 is methyl, ethyl or isopropyl.
[00049] Particular compounds are those in which R3 θ hydrogen and R4 is isopropyl; R3 is methyl and R4 is methyl; and R3 is methyl and R4 is ethyl. The skilled person will appreciate that the amino acid residue where R3 is hydrogen and R4 is isopropyl is the Leucine (Leu) residue, while the amino acid residue where R3 is methyl and R4θ methyl is the Valine residue (Val); and The amino acid residue where R3 is methyl and R4 is ethyl is the iso-Leucine (He) residue.
[00050] The compounds in which R3 is hydrogen and R4 is isopropyl; R3 is methyl and R4 is methyl; and R3 is methyl and R4 is ethyl, as well as its use in edible compositions, are all embodiments of the present invention.
[00051] These compounds are particularly useful for increasing the profiles of authentic fruit. They can also find use in flavored bedding, yogurt and ice cream with fruit.
[00052] The compounds include C8-Leu, C9-Leu, C10-Leu, C12-Leu, C14-Leu, C16-Leu, C18-Leu, C20-Leu and C22-Leu.
[00053] The compounds include C8-Leu, C9-Leu, C10-Leu, C12-Leu, C14-Leu, C16-Leu, C18-Leu, C20-Leu and C22-Leu, where the carboxylic acid residue is saturated.
[00054] The compounds include C8-Leu, C9-Leu, C10-Leu, C12-Leu, C14-Leu, C16-Leu, C18-Leu, C20-Leu and C22-Leu, where the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00055] Particular compounds bearing the Leu residue include N-palmitenoyl-L-leucine, N-palmitoyl-L-leucine, N-linolenoyl-L-leucine, N-linoleoyl-L-leucine and N-oleoyl-L- leucine.
[00056] The compounds include C8-lle, C9-lie, C10-He, C12-He, C14-He, C16-He, C18-He, C20-He and C22-He.
[00057] The compounds include C8-lle, C9-He, C10-He, C12-He, C14-He, C16-He, C18-He, C20-He and C22-He, wherein the carboxylic acid residue is saturated.
[00058] The compounds include C8-lle, C9-He, C10-He, C12-He, C14-He, C16-He, C18-He, C20-He and C22-He, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00059] A particularly preferred compound carrying the He residue is N-oleoyl-lle.
[00060] The compounds include C8-Val, C9-Val, C10-Val, C12-Val, C14-Val, C16-Val, C18-Val, C20-Val and C22-Val.
[00061] The compounds include C8-Val, C9-Val, C10-Val, C12-Val, C14-Val, C16-Val, C18-Val, C20-Val and C22-Val, where the carboxylic acid residue is saturated.
[00062] The compounds include C8-Val, C9-Val, C10-Val, C12-Val, C14-Val, C16-Val, C18-Val, C20-Val and C22-Val, where the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00063] Particularly preferred compounds that carry the residue from Vai include N-palmitenoyl-L-valine, N-palmitoyl-L-valine, N-linolenoyl-L-valine, N-linoleoyl-L-valine and N-oleoyl-L -valine.
[00064] In another embodiment of the invention, compounds of formula (I) are provided which correspond to the formula
its edible salts, and its use in edible compositions in which Ri, is defined here above.
[00065] The skilled person will appreciate that the amino acid residue in the compounds defined above is the proline (Pro) residue.
[00066] These compounds are particularly effective in increasing typical citrus authenticity and juiciness. They find use particularly in powdered drinks and soft drinks, and also in dairy applications, such as milk, yogurt and fruit flavored ice cream.
[00067] The compounds include C8-Pro, C9-Pro, C10-Pro, C12-Pro, C14-Pro, C16-Pro, C18-Pro, C20-Pro and C22-Pro.
[00068] The compounds include C8-Pro, C9-Pro, C10-Pro, C12-Pro, C14-Pro, C16-Pro, C18-Pro, C20-Pro and C22-Pro, wherein the carboxylic acid residue is saturated.
[00069] The compounds include C8-Pro, C9-Pro, C10-Pro, C12-Pro, C14-Pro, C16-Pro, C18-Pro, C20-Pro and C22-Pro, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00070] Particularly preferred compounds which carry the Pro residue of N-geranoil-Pro, N-palmitoil-Pro, N-palmiteneoil-Pro, N-stearoyl-Pro, N-linoleoil-Pro and N-linolenoyl-Pro.
[00071] In another embodiment of the invention, compounds of formula (I) are provided which correspond to the formula
its edible salts, and its use in edible compositions in which Ri, here is more defined above, Xé OH or NH2e
[00072] The skilled person will appreciate that when p is 0 and X is OH, the amino acid residue indicated in the above formula is an aspartic acid residue, while when p is 1, and X is OH the residue is that of glutamic acid , while when p is 0 and X is NH2, the residue is that of asparagine (Asn), and when p is 1 and X is NH2, the residue is that of glutamine (Gin).
[00073] Compounds that carry an aspartic acid residue, compounds that carry a glutamic acid residue, compounds that carry an asparagine residue, and compounds that carry a glutamine residue, as well as their edible salts, and their use in edible compositions, each represents particular embodiments of the present invention.
[00074] These compounds are particularly useful for increasing spicy character, oral sensation and overall taste, juiciness and salivation performance. They can find use in low salt, low umami and low fat content as well as fruit flavored drinks as well as dairy applications.
[00075] The compounds include C8-Glu, C9-Glu, C10-Glu, C12-Glu, C14-Glu, C16-Glu, C18-Glu, C20-Glu and C22-Glu.
[00076] The compounds include C8-Glu, C9-Glu, C10-Glu, C12-Glu, C14-Glu, C16-Glu, C18-Glu, C20-Glu and C22-Glu, wherein the carboxylic acid residue is saturated.
[00077] The compounds include C8-Glu, C9-Glu, C10-Glu, C12-Glu, C14-Glu, C16-Glu, C18-Glu, C20-Glu and C22-Glu, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00078] Particularly preferred compounds that carry the Glu residue include N-geranoyl-Glu, N-palmitoyl-Glu, N-palmitenoyl-Glu, N-stearoyl-Glu, N-linoleoyl-Glu and N-linolenoyl-Glu.
[00079] The compounds include C8-Asp, C9-Asp, C10-Asp, C12-Asp, C14-Asp, C16-Asp, C18-Asp, C20-Asp and C22-Asp.
[00080] The compounds include C8-Asp, C9-Asp, C10-Asp, C12-Asp, C14-Asp, C16-Asp, C18-Asp, C20-Asp and C22-Asp, where the carboxylic acid residue is saturated.
[00081] The compounds include C8-Asp, C9-Asp, C10-Asp, C12-Asp, C14-Asp, C16-Asp, C18-Asp, C20-Asp and C22-Asp, where the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00082] Particularly preferred compounds that carry the Asp residue include N-geranoyl-Asp, N-palmitoyl-Asp, N-palmitenoyl-Asp, N-stearoyl-Asp, N-linoleoyl-Asp and N-linolenoyl-Asp.
[00083] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gln, C14-Gin, C16-Gin, C18-Gin, C20-Gin and C22-Gin.
[00084] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gln, C14-Gin, C16-Gin, C18-Gin, C20-Gin and C22-Gin, wherein the carboxylic acid residue is saturated.
[00085] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gln, C14-Gin, C16-Gin, C18-Gin, C20-Gin and C22-Gin, wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00086] Particularly preferred compounds which carry the Gin residue include N-geranoyl-GIn, N-palmitoyl-GIn, N-palmitenoyl-Gln, N-stearoyl-GIn, N-linoleoyl-GIn and N-linolenoyl-GIn.
[00087] The compounds include C8-Asn, C9-Asn, C10-Asn, C12-Asn, C14-Asn, C16-Asn, C18-Asn, C20-Asn and C22-Asn.
[00088] The compounds include C8-Asn, C9-Asn, C10-Asn, C12-Asn, C14-Asn, C16-Asn, C18-Asn, C20-Asn and C22-Asn, wherein the carboxylic acid residue is saturated.
[00089] C8-Asn, C9-Asn, C10-Asn, C12-Asn, C14-Asn, C16-Asn, C18-Asn, C20-Asn and C22-Asn, in which the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00090] Particularly preferred compounds that carry the Asn residue include N-geranoyl-Asn, N-palmitoyl-Asn, N-palmitenoyl-Asn, N-stearoyl-Asn, N-linoleoyl-Asn and N-linolenoyl-Asn.
[00091] In another embodiment of the invention, compounds of formula (I) are provided which correspond to the formula
its edible salts, and its use in edible compositions in which Ri, is defined here above.
[00092] The skilled person will appreciate that in the above formula the amino acid residue is the methionine residue (Met).
[00093] These compounds are particularly effective in increasing juiciness and salivation, as well as the authenticity of fruits. They are also useful in refrigerant applications for their masking properties.
[00094] The compounds include C8-Met, C9-Met, C10-Met, C12-Met, C14-Met, C16-Met, C18-Met, C20-Met and C22-Met.
[00095] The compounds include C8-Met, C9-Met, C10-Met, C12-Met, C14-Met, C16-Met, C18-Met, C20-Met and C22-Met, where the carboxylic acid residue is saturated.
[00096] The compounds include C8-Met, C9-Met, C10-Met, C12-Met, C14-Met, C16-Met, C18-Met, C20-Met and C22-Met in which the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[00097] Particularly preferred compounds that carry the Met residue include N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met.
[00098] In another embodiment of the invention, compounds of formula (I) are provided which correspond to the formula
its edible salts, and its use in edible compositions in which Ri, is defined here above.
[00099] The skilled person will appreciate that in the formula above the amino acid residue is the serine residue (Ser).
[000100] These compounds find particular use in flavored drinks and / or dairy applications with low salt, umami and fat fruit.
[000101] The compounds include C8-Ser, C9-Ser, C10-Ser, C12-Ser, C14-Ser, C16-Ser, C18-Ser, C20-Ser and C22-Ser.
[000102] The compounds include C8-Ser, C9-Ser, C10-Ser, C12-Ser, C14-Ser, C16-Ser, C18-Ser, C20-Ser and C22-Ser, wherein the carboxylic acid residue is saturated.
[000103] The compounds include C8-Ser, C9-Ser, C10-Ser, C12-Ser, C14-Ser, C16-Ser, C18-Ser, C20-Ser and C22-Ser in which the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in the cis configuration, in the trans configuration or a mixture of cis and trans configuration.
[000104] Particularly preferred compounds that carry the Ser residue include N-palmitoyl-Ser, N-palmitenoyl-Ser, N-stearoyl-Ser, N-linoleoyl-Ser and N-linolenoyl-Ser.
[000105] Other compounds useful in the present invention include: N-octanoyl-L-phenylalanine, N-eicosanoyl-L-phenylalanine, N-palmitoleoyl-L-phenylalanine, N-palmitoyl-L-phenylalanine, N-linolenoyl-L -phenylaniline, N-linoleoyl-L-phenylalanine, N-oleoyl-L-phenylalanine, N-SDA-L-phenylalanine, N-DPA-L-phenylalanine, and N-tetracosa-hexaenoyl-L-phenylala- nine; N-palmitoyl-L-alanine, N-linolenoyl-L-alanine, N-linoleoyl-L-alanine; N-palmitoyl-L-tyrosine, N-linoleoyl-L-tyrosine, N-oleoyl-L-tyrosine, N-linolenoyl-L-tyrosine; N-palmitoyl-L-tryptophan, N-linolenoyl-L-tryptophan, N-linoleoyl-L-tryptophan; and N-linoleoyl-glycine.
[000106] Preferably, compounds of formula (I) of not include compounds C12: 1-Ala; C12: 1-Gly; C12: 2-Ala; C18: 3-Ala; and C16: 1-Ala, particularly when a double bond is in the cis configuration; C18: 3-Ala; C20: 5-Ala; C16: 0-Ala; C22: 0-Gly, in particular C22: 6-Gly; C18: 2-Leu; C23: 1-Leu; C18: 1-lle; C8: 0-Glu; C12: 0-Asp; C18: 1-Ser; and C20: 4-Ser.
[000107] The compounds of formula (I) provide remarkable organoleptic properties to edible compositions to which they are added. In particular, they provide a highly intense, authentic and harmonious flavor, and a circularity and fullness to the edible compositions containing them.
[000108] This finding was totally the most surprising considering that when the applicant tasted the compounds in the diluted aqueous solution, they exhibited a disappointingly weak greasy taste profile. As such, they appeared to be totally unsuitable for use in flavor applications. Only their combination with flavor co-ingredients and the careful selection of their levels of use was it possible to discover the remarkable organoleptic properties of these compounds. Their effect on edible compositions is quite unusual in that they really complement, elevate or accentuate the essential or authentic flavor and characteristics of the mouthfeel of the food or drink in which they are incorporated. Correspondingly, the compounds of the present invention find use in a wide spectrum of applications in the food and beverage industry, as well as in health and well-being.
[000109] Correspondingly, the invention provides in another aspect, a method of conferring taste and / or oral sensation to, or improvement of taste and / or oral sensation of an edible composition, a method which comprises addition to said composition of a compound of formula (I) defined here.
[000110] The remarkable organoleptic effects are observed when the compounds of formula (I) are incorporated into an edible composition containing one or more of flavor co-ingredients.
[000111] The flavor co-ingredients can be sugars, fats, salt (eg sodium chloride), MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.
[000112] In a particular embodiment, sugars are present in amounts from 0.001% to 90%, more particularly from 0.001% to 50%, even more particularly from 0.001% to 20% based on the total weight of an edible composition.
[000113] In a particular embodiment, fats are present in amounts from 0.001% to 100%, more particularly from 0.001% to 80%, more particularly from 0.001% to 30%, even more particularly from 0.001% to 5% based on total weight of an edible composition.
[000114] In a particular embodiment, salt (e.g., sodium chloride) is present in amounts from 0.001% to 20%, more particularly from 0.001% to 5% based on the total weight of an edible composition.
[000115] In a particular embodiment, MSG is present in amounts from 0.001% to 2% based on the total weight of an edible composition.
[000116] In a particular embodiment, calcium is present in amounts from 0.001% to 50% more particularly from 0.001% to 20%, even more particularly from 0.001% to 1% based on the total weight of an edible composition.
[000117] In a particular embodiment, organic acids are present in amounts from 0.001% to 10%, more particularly from 0.001% to 7% based on the total weight of an edible composition.
[000118] Types of organic acids include citric, malic, tartaric, furmatic, lactic, acetic and succinic. Types of edible compositions containing organic acids include drinks, such as carbonated soda drinks, still drinks, juices, powdered soft drinks, liquid concentrates, alcoholic beverages and functional drinks.
[000119] In a particular embodiment, phosphorus is present in an amount of up to 0.5% by weight of an edible composition. Typically phosphorus will be present as a phosphate or as a phosphoric acid.
[000120] In a particular embodiment, purines are present in an amount of up to 0.5% by weight of an edible composition. The term "purines" includes ribonucleotides such as IMP and GMP.
[000121] Despite its interesting organoleptic properties, however, the applicant found that formulation of the compounds of formula (I) was not a trivial issue. The discovered potency of the compounds suggested that they could be employed at very low levels in flavor applications, and thus for ease of handling, mixing and processing with other ingredients, although it is possible to use the compounds in pure form, it is desirable to extend or add volume to physical form of the compounds by incorporating them in a suitable vehicle, for example, a diluent, such as solvent. However, the compounds are solid or viscous oils at room temperature, and have very limited solubility in water. The applicant has found that at least about 0.01% of standard solution, more particularly about 0.01 - 1% of standard solution of a compound of formula (I) has achieved a balance with respect to acceptable solvent levels for ease of handling and mixing, and the desire to limit the amount of solvent that would have to be removed from the standard solution when further processing the compounds in flavor and edible products for reasons of palatability, effectiveness, cost and the like. The applicant has found that solvents suitable for the standard solution include ethanol, triacetin, glycerol and migliol.
[000122] In order to assist in the solubilization process and produce a standard solution and minimize the amount of solvent, it is preferred to use compounds of formula (I) formed from a mixture of carboxylic acids, instead of a pure carboxylic acid.
[000123] Correspondingly, the invention provides in another aspect at least about 0.01% of standard solution, more particularly about 0.01 - 1% of standard solution of a compound of formula (I).
[000124] The standard solution may contain other materials such as adjuvants and / or vehicle materials more fully described below. In a particular embodiment, the standard solution contains an antioxidant selected from the group consisting of vitamin C, vitamin E, rosemary extract, anthrancine, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Antioxidants are preferably employed to prevent, or significantly reduce, generation of volatile debris as a result of degradation of the compounds of formula (I). Antioxidants are particularly preferred when the compounds of formula (I) carry an unsaturated fatty acid residue. Antioxidants are particularly preferred if the fatty acid residue contains more than 1 double bond. Determination of an effective amount of antioxidant is within the field of action of the skilled person, however amounts in the range of about 10 ppm to 1000 ppm based on the weight of the standard solution may be present.
[000125] In preparing the flavor compositions of the present invention, the compounds of formula (I) can be used in any physical form. They can be used in pure form, in the form of a standard solution described above; can be used in the form of an emulsion; or they can be used in a powder form. If the compounds of formula (I) were presented in the form of a powder, the powder form can be produced by a dispersed evaporation process, such as a spray drying process as is more fully described below. The powder form can be prepared by subjecting a liquid formulation containing a compound of formula (I) to a dispersed evaporation process. The liquid formulation can comprise a solution, suspension or emulsion comprising the compound of formula (I). In particular, the liquid formulation can take the form of the standard solution described here above. The liquid formulation can contain other ingredients such as carrier material and / or an adjuvant as described more fully below.
[000126] A powder comprising a compound of formula (I) forms another aspect of the present invention.
[000127] The compounds of formula (I) can be incorporated into an edible composition alone, or in the form of a flavor composition comprising one or more flavor co-ingredients.
[000128] A flavor composition comprising a compound according to formula (I) forms another aspect of the present invention.
[000129] In one embodiment of the present invention, the flavor formulation comprises a compound of formula (I) and at least one flavor co-ingredient.
[000130] In a particular embodiment of the present invention the flavor composition comprises: a compound according to formula (I); at least one flavor co-ingredient; optionally a vehicle material; and optionally at least one adjuvant.
[000131] By the term "flavor co-ingredient" is an ingredient that is able to contribute or provide or modify in a positive or pleasant way the taste of an edible composition.
[000132] All types of flavor co-ingredients can be employed in a composition according to the present invention, including, but not limited to, natural flavors, artificial flavors, spices, seasonings, and the like. Flavor co-ingredients include synthetic-flavored oils and aromatics and / or oils, oily resins, essences, distillates, and extracts derived from plants, leaves, flowers, fruits, and so on, and combinations comprising at least one of the above.
[000133] Flavor oils include green mint oil, cinnamon oil, gualteria oil (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise oil, eucalyptus oil , thyme oil, cedar leaf oil, nutmeg oil, allspice oil, sage oil, apple, bitter almond oil, and cassia oil; Useful flavoring agents include artificial, natural and synthetic fruit flavors such as vanilla, and citrus oils including lemon, orange, lime, grapefruit, yazu, sudachi, and fruit essences including apple, pear, peach, grape, blueberry, strawberry, raspberry , cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and the like.
[000134] Additional exemplary flavors provided by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as green tea flavor, oolong tea flavor, tea flavor, cocoa flavor, chocolate flavor, and coffee flavor; mint flavors, such as a peppermint flavor, a green mint flavor, and a Japanese mint flavor; spicy flavors, such as asafetida flavor, ajowan flavor, anise flavor, angelica flavor, fennel flavor, aica jelly pepper flavor, cinnamon flavor, chamomile flavor, flavor mustard, a cardamom flavor, a cumin flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a spicy flavor, a Zanthoxili Fructus flavor, a flavor perilla, a juniper berry flavor, a ginger flavor, a star anise flavor, a spicy horseradish flavor, a thyme flavor, a tarragon flavor, a dill flavor, a pepper flavor, a flavor of nutmeg, a taste of basil, a taste of marjoram, a taste of rosemary, a taste of baileaf, and a taste of wasabi (Japanese horseradish); a nutty flavor such as almond flavor, a hazelnut flavor, a macadamia flavor, a peanut flavor, a pecan flavor, a pistachio flavor, and a nutty flavor; alcoholic flavors, such as wine flavor, whiskey flavor, cognac flavor, rum flavor, gin flavor, and liquor flavor; floral flavors; and vegetable flavors, such as onion flavor, garlic flavor, cabbage flavor, carrot flavor, celery flavor, mushroom flavor, and a tomato flavor.
[000135] In some embodiments, said flavor co-ingredients include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl format 49, p-methylamisol, and so on. Other examples of aldehyde flavorings include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, that is, alpha-citral (lemon, lime), neral, ie is, beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanilla (vanilla, cream), heliotrope, that is, piperonal (vanilla, cream), vanilla (vanilla, cream), alpha-amyl cinnamaldehyde ( spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies, many types), decanal (citrus fruits), C-8 aldehyde (citrus fruits), C-9 aldehyde (citrus fruits) , C-12 aldehyde (citrus fruits), 2-ethyl butyraldehyde (berries), hexenal, ie trans-2 (berries), tolyl aldehyde (cherry, almond), veratraldehyde (vanilla), 2,6 -dimethyl-5-heptenal, that is, melonal (melon), 2,6-dimethyloctanal (green fruit), and 2-dodecenal (citrus, mandarin), and the like.
[000136] Further examples of other flavor co-ingredients can be found in "Chemicals Used in Food Processing", publication 1274, pgs. 63-258, by the National Academy of Sciences.
[000137] Flavor co-ingredients can also include salt flavors, umami flavors, and spicy flavor compounds. Non-limiting examples include: NaCI, KCI, MSG, guanosine monophosphate (GMP), inosine monophosphate (IMP), ribonucleotides such as disodium inosinate, disodium guanylate, N- (2-hydroxyethyl) - lactamide, N-lactoyl-GMP, N -lactoyl tyramine, gamma amino butyric acid, allyl cysteine, 1- (2-hydroxy-4-methoxyphenyl) -3- (pyridine-2-yl) propan-1-one, arginine, potassium chloride, ammonium chloride, acid succinic, N- (2-methoxy-4-methyl benzyl) -N '- (2- (pyridin-2-yl) ethyl) oxalamide, N- (heptan-4-yl) benzo (D) (1,3) dioxole-5-carboxamide, N- (2,4-dimethoxybenzyl) -N '- (2- (pyridin-2-yl) ethyl) oxalamide, N- (2-methoxy-4-methyl benzyl) -N'-2 (2- (5-methyl pyridin-2-yl) ethyl) oxalamide, cyclopropyl-E, Z-2,6-nonadienamide.
[000138] In particular embodiments of the present invention, the flavor co-ingredient is selected from the compounds and compositions disclosed in WO 2005102701, WO 2006009425, WO 2005096843, WO 2006046853 and WO 2005096844, all of which are incorporated herein by reference in its entirety.
[000139] Flavor co-ingredients can include salt flavors, umami flavors, and known spicy flavor compounds. Non-limiting examples include: NaCI, KCI, MSG, guanosine monophosphate (GMP), inosine monophosphate (IMP), ribonucleotides such as disodium inosinate, disodium guanylate, N- (2-hydroxyethyl) - lactamide, N-lactoyl-GMP, N-lactoyl tyramine, gamma amino butyric acid, allyl cysteine, 1- (2-hydroxy-4-methoxyphenyl) -3- (pyridine-2-yl) propan-1-one, arginine, potassium chloride, ammonium chloride, succinic acid, N- (2-methoxy-4-methyl benzyl) -N '- (2- (pyridin-2-yl) ethyl) oxalamide, N- (heptan-4-yl) benzo (D) (1,3 ) dioxole-5-carboxamide, N- (2,4-dimethoxybenzyl) -N '- (2- (pyridin-2-yl) ethyl) oxalamide, N- (2-methoxy-4-methyl benzyl) -N'- 2 (2- (5-methyl pyridin-2-yl) ethyl) oxalamide, cyclopropyl-E, Z-2,6-nonadienamide.
[000140] The vehicle material can be used in the compositions according to the invention to encapsulate or to trap the other components of the composition in a matrix. The role of the vehicle material may be merely that of a processing aid or a swelling agent, or it may be employed to guard or protect the other components from the effects of moisture or oxygen or any other aggressive medium. The vehicle material can also act as a means of controlling taste release from edible compositions.
[000141] Vehicle materials may include mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins. Examples of particular carrier materials include sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentatol, arabinose, pentose, xylose, galactose, maltodextrin, dextrin, starch chemically modified, hydrogenated starch hydrolyzate, succinylated or hydrolyzed starch, agar, carrageenan, gum arabic, acacia gum, tragacanth, alginates, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose, derivatives and mixtures thereof. Naturally, the skilled person will appreciate that the materials cited are given here by way of example and should not be construed as limiting the invention.
[000142] By "flavor adjuvant" is meant an ingredient capable of providing additional added benefit to the compositions of the present invention such as color, high strength, chemical stability and the like. Suitable adjuvants include solvents (including water, alcohol, ethanol, triacetin, oils, fats, vegetable oil and migliol), binders, diluents, disintegrating agents, lubricants, coloring agents, preservatives, antioxidants, emulsifiers, stabilizers, anti-forming agent pie, and the like. In a particular embodiment, the flavor composition comprises an antioxidant. Said antioxidants may include vitamin C, vitamin E, rosemary extract, anthrancine, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).
[000143] Examples of such carriers or adjuvants for flavor compositions can be found in, for example, "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, N.J., 1960; in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in "Saborings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), 1st ed., The Cosmetic, Tóleoetry and Fragrance Association , Inc., Washington, 1988.
[000144] Other suitable and desired ingredients of flavor compositions are described in standard texts, such as "Handbook of Industrial Chemical Additives", ed. M. and I. Ash, 2nd Ed., (Synapse 2000).
[000145] Flavor compositions according to the present invention can be provided in any suitable physical form. For example, they can be in the form of oils, emulsions or dispersions in a hydrous liquid or organic liquid for use in edible compositions, or in a solid form, such as powders.
[000146] If flavor compositions are provided in the form of a powder composition, they can be prepared by dispersive evaporation technologies generally known in the art, such as spray drying.
[000147] Correspondingly, in another aspect of the present invention there is provided a method of forming a powder composition, comprising the steps of providing a liquid composition comprising a compound of formula (I) and one or more optional ingredients selected from at least minus a flavor co-ingredient, a carrier material and an adjuvant, and dispersible evaporation to said liquid composition to form a powder composition.
[000148] Thus, a compound of the formula (I) or a flavor composition comprising said compound can be presented in a powder form.
[000149] The liquid composition used in the preparation of a powder can be in the form of a solution, emulsion, dispersion or paste. The liquid may contain water, and / or an organic liquid, such as ethanol, glycerol, triacetin, migliol (MCT) which is acceptable for use in edible compositions.
[000150] Powder compositions according to the present invention can be prepared according to methods and apparatus known in the art for the production of powders on an industrial scale. A particularly suitable method is spray drying. Spray drying apparatus and techniques are well known in the art and require no detailed discussion here. The spray drying apparatus, methods and techniques described in US 2005/0031769 and US 2013/0022728, as well as those techniques, apparatus and methods described in those documents are suitable for the production of powder compositions of the present invention and are incorporated herein. by reference in its entirety.
[000151] The manner in which the compounds of formula (I) are incorporated into the powdered flavor compositions of the invention is not critical. For example, the compounds can be added to the liquid composition described above and undergo a dispersed evaporation process along with all other components of the flavor composition. Alternatively, compounds can be added to the flavor composition after it has been formed as a powder.
[000152] Many of the flavor co-ingredients described here are volatile and / or may be sensitive to oxidative degradation, particularly when subjected to elevated temperature, and under wet conditions. Correspondingly, particular problems can arise when subjecting the flavor co-ingredients described above to dispersive evaporation processes such as spray drying. A non-exhaustive list of ingredients that may be particularly susceptible include, those ingredients containing artificial, natural or synthetic flavors such as vanilla, chocolate, coffee, cocoa and citrus oil, including lemon, orange, grape, lime and grapefruit, and fruit essences including apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple, apricot and the like. The volatile components of these flavor co-ingredients can include, but are not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate. Flavor co-ingredients containing volatile esters or aldehydes include, for example, cinnamyl acetate, cinnamaldehyde, citral, diethyl acetate, dihydrocarvyl acetate, eugenyl formate, and p-methylanisole. Other examples of volatile compounds that can be presented as co-ingredients include acetaldehyde (apple); benzaldehyde (cherry, almond); cinnamic aldehyde (cinnamon); citral, that is, alpha citral (lemon, lime); neral, that is, beta citral (lemon, lime); decanal (orange, lemon); vanilla ethyl (vanilla, cream); heliotropin, that is, piperonal (vanilla, cream); vanilla (vanilla, cream); alpha-amyl cinnamaldehyde (spicy fruity flavors); butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); citronellal (modifies, many types); decanal (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethyl butyraldehyde (berries); hexenal, that is, trans-2 (berries); tolyl aldehyde (cherry, almond); veratraldehyde (vanilla); 2,6-dimethyl-5-heptenal, that is, melon (melon); 2-6-dimethyloctanal (green fruit); and 2-dodecenal (citrus, mandarin); cherry; or grape and its mixtures.
[000153] The applicant surprisingly found that the inclusion of a compound of the formula (I) in a powdered flavor composition, it was possible to obtain flavor quality reminiscent of flavor oils.
[000154] Correspondingly, in another aspect, the invention provides a method of maintaining the taste quality of a powdered taste composition comprising the step of including in the distant powdery taste composition a compound of the formula (I)
[000155] As stated herein above, compounds of formula (I) or flavor compositions containing such compounds can be incorporated into edible compositions, and an edible composition containing such a compound or flavor composition forms another aspect of the present invention.
[000156] The term "edible composition" refers to products for consumption by an individual, typically via the oral cavity (although consumption can occur via non-oral means such as inhalation), for at least one of the purposes of satisfaction, nutrition, or health and wellness benefits. Edible compositions can be presented in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, strips, powders, gels, gums, pastes, pastes, syrups, aerosols and sprays. The term also refers to, for example, nutritional and dietary supplements. Edible compositions include compositions that are placed inside the oral cavity for a period of time before being discarded but not swallowed. They can be put in the mouth before being consumed, or they can be kept in the mouth for a period of time before being discarded. An edible composition as defined herein above includes compositions whose flavor is modified in the manner described herein by the addition of compounds of formula (I) or whose flavor is thus modified by processing so that it is enriched in a compound of formula (I).
[000157] Broadly, the edible composition includes, but is not limited to foodstuffs of all kinds, confectionery, bakery products, sweet products, tasty products, fermented products, dairy products, drinks and oral care products.
[000158] In a particular embodiment the term "edible compositions" refers to products for consumption by an individual, typically via the oral cavity (although consumption can occur via non-oral means such as inhalation), for one of the purposes of satisfaction or nutrition.
[000159] In a more particular embodiment the term "edible compositions" refers to products for consumption by an individual, typically via the oral cavity (although consumption can occur via non-oral means such as inhalation), for the purpose of satisfaction, even more particularly, the term refers to foodstuffs and beverages.
[000160] In a particular embodiment, the term "edible composition" does not refer to pharmaceutical compositions.
[000161] In a particular embodiment, the term "edible composition" does not refer to nutritional supplements.
[000162] Exemplary foodstuffs include, but are not limited to, chilled snacks, tasty and sweet snacks, fruit snacks, chips / crisps, extruded snacks, tortilla / corn snacks, popcorn, pretzels, nuts, other tasty snacks and sweets, snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacement products, slimming products, convalescence drinks, ready meals, canned ready meals, meals frozen ready meals, dehydrated ready meals, chilled ready meals, dinner mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, over chilled, uht soup, frozen soup, paste, canned paste, dry paste, chilled / fresh pasta, pasta pasta, simple pasta pasta, instant pasta pasta, instant cup / bowl pasta pasta, instant pasta pasta s purse, chilled pasta pasta, snack pasta pasta, dry food, dessert mixes, sauces, seasonings and condiments, herbs and spices, spreads, jams and preserved fruits, honey, chocolate spread, spread based walnut, yeast-based spreads.
[000163] Exemplary confectionery products include, but are not limited to, chewing gum (which includes sugared gum, sugar-free gum, functional gum and gum and functional gum), centerfill confections, chocolate and other chocolate products, medical sweets, lozenges, tablets, lozenges, mints, standard mints, powdered mints, chewy candies, hard candies, baked candies, strips or films for oral breath care and others, candy canes, lollipops, gummy candy , jellies, chocolate candy, caramel, soft or hard pot products, toffee, butter caramel, licorice, jelly candies, gum lozenges, jelly beans, nougats, fondants, combinations of one or more of the above, and compositions of edible flavors that incorporate one or more of the above.
[000164] Exemplary bakery products include, but are not limited to alfajores, bread, packaged / industrial bread, unpackaged / artisan bread, pastries, pies, packaged / industrial pies, unpacked / artisanal pies, cookies, coated cookies with chocolate, sandwich cookies, stuffed cookies, tasty cookies and crackers, bread substitutes,
[000165] Exemplary sweet products include, but are not limited to, breakfast cereals, ready-to-use cereals ("rte"), family breakfast cereals, flakes, muesli, other ready-to-eat cereals, coffee cereals for children, hot cereals,
[000166] Exemplary tasty products include, but are not limited to, tasty snacks (potato snacks, crisps, nuts, toasted tortilla, pretzels, cheese snacks, corn snacks, potato snacks, ready to use popcorn, popcorn microwave, crackling, nuts, crackers, biscuit snacks, breakfast cereals, meat, meat jelly, cured meats (ham, bacon), meats / breakfast meats (hotdogs, cold cuts, sausage), tomato, margarine, peanut butter, soup (clear, canned, creamy, instant, UHT), canned vegetables, pasta sauces.
[000167] Exemplary dairy products include, but are not limited to, cheese, cheese sauces, cheese products, ice cream, impulse ice cream, single serving dairy ice cream, single serving ice cream, multiple dairy ice cream packaging, multi-pack aqueous ice cream, take-home ice cream, take-home dairy ice cream, ice cream desserts, bulk ice cream, take-home water ice cream, frozen yogurt, artisanal ice cream, dairy products, milk, milk fresh / pasteurized, fresh whole / pasteurized milk, semi-skimmed / pasteurized fresh milk, UHT / long-life milk, long-life / UHT milk, long-life semi-skimmed milk / UHT milk, long-life skimmed / UHT milk, milk goat, condensed / evaporated milk, simple / evaporated condensed milk, flavored, functional and other condensed milk, flavored milk drinks, dairy flavored milk drinks, aromatic milk drinks served with fruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffee whiteners, powdered milk, flavored powdered milk drinks, cream, yogurt, plain / natural yogurt, flavored yogurt, fruity yogurt, probiotic yogurt, drinking yogurt, regular drinking yogurt, probiotic drinking yogurt, chilled and semi-stable desserts, dairy-based desserts, soy-based desserts.
[000168] Exemplary drinks include, but are not limited to, flavored water, soft drinks, fruit drinks, coffee-based drinks, tea-based drinks, juice-based drinks (includes fruit and vegetable), drinks based on milk, gel drinks, carbonated or non-carbonated drinks, powdered drinks, alcoholic or non-alcoholic drinks.
[000169] Exemplary fermented foods include, but are not limited to, cheese and cheese products, meat and meat products, soy and soy products, fish and fish products, grain and grain products, fruit and fruit products.
[000170] In a particular embodiment the consumable product is selected from the group consisting of soy sauce, cheese, soup, hot and cold sauces, fruits, vegetables, ketchups, tea, coffee, snacks such as potato snacks or extruded snacks.
[000171] The compounds of the formula (I), when added to a flavor composition and / or an edible composition, act in a composition to complement their taste and / or oral sensation to make them more delicious and authentic. The effects can be temporal or related to intensity, for example, compounds can act by improving, strengthening, softening, penetrating a flavor, or producing more salivation. The compounds of formula (I) can also affect the time profile of a flavor, that is, they can affect the initial impact of a flavor, the body of a flavor, or its prolonged effect.
[000172] The compounds of formula (I) can modify any aspect of the temporal flavor or taste profile of an edible composition. In particular, the compounds improve oral sensation and provide more fatty and creamy sensations. Compounds of formula (I) or flavor compositions containing them can be added to edible compositions in widely transported amounts. The amount will depend on the nature of the edible composition to be flavored, and on the desired effect, as well as on the nature of the ingredients present in said flavor composition. In order to obtain the remarkable beneficial effects attributed to the presence of the compounds of the formula (I), the flavor composition would be used in quantities so that the compounds of the formula (I) are present in quantities of 1 part per billion to 10 parts per million based on the total weight of the edible composition. While higher amounts than this can be used, the beneficial effects are considerably less and undesirable and apparent disadvantages can become increasingly evident.
[000173] Interesting organoleptic effects, for example, salt, alcohol or soda reinforcing effects, in edible compositions containing salt or alcohol or soda compounds can be achieved when compounds of formula (I) are employed at levels of 1 to 100 ppb .
[000174] Interesting organoleptic effects, for example, umami boosting effects, in edible compositions containing umami flavorings can be achieved when compounds of formula (I) are employed at levels of 100 to 250 ppb.
[000175] Interesting organoleptic effects, in particular oral sensation enhancing effects, in edible compositions can be achieved when compounds of formula (I) are employed at levels of 250 to 500 ppb.
[000176] Interesting organoleptic effects, for example, fat reinforcing effects, in edible compositions containing fats can be achieved when compounds of formula (I) are employed at levels of 500 to 1000 ppb.
[000177] It is particularly advantageous to incorporate compounds of the formula (I) into edible compositions that are formed under high temperature conditions, such as cooking, frying or that are processed by heat treatments such as pasteurization or under UHT conditions. Under high temperatures of preparation or processing, volatile flavor ingredients can be lost or degraded with the result that flavor intensity can be reduced and authentic and essential flavor characteristics can be decreased. Such edible products include dairy products, snack foods, bakery products, powdered soft drinks and similar dry mixes, and the like, fats and seasonings, mayonnaise, desserts, soups and broths, and drinks.
[000178] A particularly preferred class of edible composition according to the present invention is powdered soft drink and similar dry mix applications. Dry mix applications are known in the art and products included in powder form that are intended to be reconstituted prior to consumption. They include powdered soups, powdered pie mix, powdered chocolate drinks, instant coffees, spices and fonds, and the like.
[000179] Dry powders formed by dispersive evaporation processes, such as spray drying, represent a very convenient vehicle for providing flavor oil quality flavorings to edible compositions.
[000180] Unfortunately, flavor oils, and in particular citrus flavor oils, can be particularly sensitive to dispersive evaporation processes, especially processes carried out at high temperature. Flavored oils tend to evaporate to form products with unfavorable disadvantages. Powdered flavor compositions, particularly those containing citrus oils, may be of poor quality and exhibit relatively short half-lives as a result.
[000181] Surprisingly, the incorporation of compounds of formula (I) or flavor compositions containing them in powder compositions, results in powder compositions that exhibit the impact and authenticity of the flavor oils used in their preparation, essentially maintaining quality of flavor oil in powder flavor formulations.
[000182] Correspondingly, the invention provides in another aspect a powdered taste composition comprising a compound according to formula (I) and at least one additional flavoring ingredient.
[000183] In another aspect of the invention there is provided a powdered soft drink composition or other dry mix composition comprising a compound according to formula (I).
[000184] In yet another aspect of the present invention there is provided a powdered soft drink composition or other dry mix composition comprising a powdered taste composition comprising a compound of formula (I).
[000185] In yet another aspect of the present invention there is provided a method of forming a powdered taste composition comprising the step of incorporating into said composition a compound according to formula (I).
[000186] In a particular embodiment of the compound of formula (I), the powdered flavor composition formed may be added, or the flavor composition may be added before the powder forms.
[000187] Another particularly preferred class of edible composition according to the present invention is snack foods. Snack foods are a product category well known to the person well versed in the food industry. These products are described above and include, without limitation, pretzels, corn snacks, potato snacks, puff products, extruded products, tortilla snacks and the like. Even more particularly, the invention deals with low fat snack food compositions. Low fat snack food compositions contain less than 30% by weight of fat, more particularly between 5 to 25% by weight of fat.
[000188] A problem with reducing fat in a snack food composition is the loss in flavor and texture. Fats play a role in the way that dough behaves during processing and greatly affects the quality, flavor and texture of ready-to-use products. When the fat content in snack products is reduced or replaced with other ingredients (for example, nondigestible fat, protein, fiber, gums), adverse organoleptic effects (for example, mouthwash, drying, lack crunchiness and lack flavor) are increased. Adverse organoleptic effects result in products having reduced palatability.
[000189] Considerable efforts were spent in planning flavor compositions to overcome the problems associated with low-fat snack food products. Flavors can be applied to a snack food as topical coatings in the form of dry powders and / or as liquids (for example, oil-based, water-based). Another approach was to add flavor to the dough.
[000190] Despite these various approaches that have been taken to improve consumer attraction and palatability of snack foods, and particularly low-fat snack foods, there is still a need for improved low-fat snack foods having coatings applied to them with the visual attraction, flavor, and texture of total fat snack foods.
[000191] Compounds according to formula (I) or flavor compositions containing them can be incorporated into snack foods to provide a striking flavor and oral sensation with remarkable circularity and fullness. Furthermore, the effects of taste and oral sensation can be achieved even in low-fat snack foods.
[000192] Correspondingly, the invention provides in another aspect of it a snack food comprising a flavor composition as described above. In a particular embodiment of the invention the snack food has a fat content of about 40% or less by weight based on the total weight of the snack food, more particularly about 30% or less, even more particularly 25% or less , more particularly still about 10% or less, even more particularly about 5% or less, even more particularly about 3% or less.
[000193] Examples of snack foods are described above and include products processed by oven cooking, extrusion or frying, and which are made from potatoes and / or corn and / or various grains such as rice or wheat.
[000194] Another particularly preferred class of the edible composition according to the present invention is alcoholic beverages.
[000195] The applicant surprisingly found that compounds according to formula (I) incorporated in an alcoholic drink had the effect of increasing the alcohol impact of the drink.
[000196] Correspondingly, the invention provides in another aspect of an alcoholic beverage comprising a compound according to formula (I).
[000197] In yet another aspect of the invention there is provided a method of producing an increased alcoholic impression in an alcoholic beverage by incorporating a compound according to formula (I) in said drink.
[000198] Compounds of formula (I) can be incorporated into said alcoholic beverage in quantities of 1 ppb to 1 ppm.
[000199] Another class of edible compositions are products taken orally in the form of tablets, capsules, powders, multiparticles and the like. Such compounds can include pharmaceutical dosage form or nutraceutical dosage form.
[000200] Certain groups of people have problems swallowing tablets or capsules, powders, multiparticles and the like. This problem can be particularly pronounced in certain consumer groups, such as children and the elderly or the sick. The applicant has surprisingly found that compounds according to formula (I) when taken into the oral cavity produce a pronounced salivation effect. Incorporation of the compounds in these forms, particularly as part of a coating around said dosage form, can facilitate the swallowing process for consumers, in particular children and the elderly or infirm.
[000201] Correspondingly, in another aspect the invention provides an oral administrable dosage form, in particular in the form of capsule, powder or multiparticulate tablets comprising a compound according to formula (I).
[000202] Another preferred class of the edible composition is bakery products. Compounds of formula (I) can be incorporated topically or in dough. Incorporated at levels of 1 ppb to 1 ppm, the compounds of formula (I) make bakery products less dry and more juicy.
[000203] Another preferred class of edible compositions are caloric or non-calorie drinks containing carbohydrate sweeteners, such as sucrose, high fructose corn syrup, fructose and glucose, or non-nutritious, high intensity sweeteners such as aspartame, acesulfame K , sucralose, cyclamate, sodium saccharin, neotame, rebaudioid A, and / or other stevia-based sweeteners; as well as other optional ingredients such as juices, organic acids such as citric acid, alcohol and functional ingredients.
[000204] Incorporated at levels of 1 ppb to 10 ppm, compounds of formula (I) provide said drinks containing sweeteners at levels of less than 1% and up to about 20%, an advanced sweetener and oral sensation that is reminiscent of sugar.
[000205] Other preferred edible compositions are flavorful compositions, in particular those that are soy-based or fish-based.
[000206] Incorporated at levels of 1 ppb to 10 ppm, in a soy-based composition (such as soy sauce) or a fish-based composition (such as fish sauce) containing from 5 to 40% salt, the compositions have been shown to exhibit strong umami flavors that are long lasting and rich.
[000207] Another preferred edible composition is a cloudy-looking beverage composition.
[000208] Certain drinks such as juices have relatively higher turbidity and thus have an opaque appearance. It is often desired that the drink has a relatively high turbidity. This could be desirable to provide a more natural appearance to drinks with a low juice content, or it could be for reasons related to sedimentation masking or "ringing" (where oils of flavor or color rise to the surface of a container during storage). Cloudy drinks are usually formed by using a clouding agent. Turbidity agents are usually supplied in the form of emulsions, or the turbid agent may be part of a powdered beverage which upon reconstitution will form an emulsion providing a permanent turbidity to the beverage.
[000209] Compounds of formula (I), in addition to their remarkable organoleptic properties, can provide stability to turbid agents and drink compositions containing them.
[000210] Correspondingly, the invention provides in another aspect of it a composition comprising a beverage cloudy composition and a compound of the formula (I).
[000211] In a particular embodiment of the invention, a flavor composition as defined herein can be provided in the form of an emulsion. Such an emulsion composition can be particularly useful in cloudy beverage applications, in particular, where it is intended to employ a cloudy agent.
[000212] In yet another aspect of the invention there is provided a cloudy beverage composition comprising a cloudy agent and a compound of the formula (I).
[000213] Other preferred edible compositions are those compositions that are formed by an improvement process.
[000214] In food processing, it often happens that a food needs to remain for a prolonged period of time and under well-defined conditions to obtain the food with the necessary and recognized quality. A commonly used term for this process is enhancement. Enhancement is well known in processing certain types of cheese, meat, soy sauce and wine, as well as beer sausage, sauerkraut, tempeh and tofu. There are also specific steps that are carried out for specific reasons (such as removing water, or removing clogging) that have beneficial effects on food products. Examples of this are the formation of chocolate shell and the drying of pasta, vegetables and fruits. The transformations that improve the quality of the food are induced by chemical conversions, enzymatically catalyzed conversions or fermentative transformations. All of these conversions are slow and therefore expensive; they are also not fully predictable or controllable.
[000215] The compounds of formula (I), having regard to their remarkable property of addition to the authentic flavor characteristics of the edible compositions in which they are incorporated, can be added to an edible product during its improvement process in order to reduce time of storage without adversely affecting the taste quality of the improved product.
[000216] Correspondingly, in another aspect of the invention there is provided a method for improving a product selected from the group consisting of cheese, meat, soy sauce and wine, beer, sausage, sauerkraut, tempeh and tofu, comprising the step of product improvement in the presence of a compound according to formula (I).
[000217] In another aspect of the invention, a method of forming a chocolate shell is provided, said method comprising the step of adding to chocolate a compound according to formula (I), or a flavor composition containing the same.
[000218] Below is a series of non-limiting examples that serve to illustrate the invention. Synthesis examples Route A: (DCC method)
[000219] In a 250 ml round-bottom flask fatty acid (3.93 mmol) was mixed with 1-hydroxypyrrolidine-2,5-dione (0.498 g, 4.32 mmol) in dioxane (50 mL) to give a colorless solution. The solution was cooled to 10 ° C and DCC (0.892 g, 4.32 mmol) was added while stirring. Stirring was continued for three hours at room temperature. The formed solids were filtered (dicyclohexylurea) and the filtrate was added to a solution of amino acid (6.48 mmoles) in a 2% solution of sodium bicarbonate (0.363 g, 4.32 mmoles) in water. The reaction mixture was stirred for 4 hours at 50 ° C. Dioxane was evaporated and the aqueous residue was further diluted with water, acidified with a diluted hydrochloric acid solution and extracted with ethyl acetate. Organic layers were combined, washed with brine, dried and evaporated to provide 1.3 g of a white solid. Product was purified by flash column chromatography, eluent DCM / methanol.
[000220] 1 g of 85-90% pure product could be obtained. Route B (DCC method with protection group) Step 1:
[000221] To a solution of an O-methylated amino acid (16.51 mmol) in DCM (100 ml) was added triethylamine (1.519 g, 15.01 mmol) at minus 15 ° C. A fatty acid (.01 mmol) was added while stirring, a solution of DCC (15.01 mmoles) in 10 ml of DCM was added dropwise at 0 ° C. The reaction mixture was stirred at 0 ° C for 1 hour and stirring was continued at room temperature for 3 hours. The dicyclohexylurea was removed by filtration from the reaction mixture. The filtrate was washed with a saturated sodium bicarbonate solution, diluted hydrochloric acid solution and water. Organic layer was separated, dried and evaporated to provide 3 g of an oil. This oil was purified by flash column chromatography, eluent DCM / methanol. The intermediate ester compound could be isolated in 95% purity. Step 2:
[000222] The O-methylated N-acyl-amino acid (4.91 mmol) was dissolved in a mixture of Ethanol (8.00 ml) and water (8 ml). To this mixture was added a solution of 32% sodium hydroxide (2.453 g, 19.63 mmoles) and the mixture was stirred at room temperature for three hours. The mixture rests for a period of 14 hours.
[000223] After 14 hours the mixture was acidified with a concentrated hydrochloric acid solution (1.612 ml, 19.63 mmoles), diluted with water and extracted with mtbe. Organic layer was separated, dried and evaporated. 1.3 g of a semi-solid yellow residue were obtained. NMR confirmed the structure of the title compound, 95% purity Route C (acid chloride)
[000224] An amino acid (20 mmoles) was dissolved in a solution of sodium hydroxide (54.5 mmoles) in water (40 ml).
[000225] Tetrahydrofuran (60 ml) was added. Fatty acid chloride (18.18 mmoles) was added dropwise at room temperature. Stirring was continued for 2 hours. The mixture was diluted with water, acidified with a 37% hydrochloric acid solution (2.99 ml, 36.4 mmoles) and extracted with ethyl acetate.
[000226] Organic layers were combined, dried and evaporated.
[000227] The residue contains about 20% free fatty acid according to NMR. The solids were stirred with heptane for 30 minutes, filtered and dried. This resulted in 2.4 g of the title compound as a cream colored solid, (95% purity) Table of synthesized compounds Table 1: List of synthesized compounds










NMR data (examples) Structure 5 ACC-C18: 1

[000228] 1H NMR (600 MHz, CHLOROFORM-c /) δ ppm 0.88 (t, J = 7.05 Hz, 3 H, HC (18)) 1.09 - 1.21 (m, 2 H HC (22,23)) 1,21- 1,1,39 (m, 20 H, HC (4, 5, 6, 7, 12, 13, 14, 15, 16, 17)) 1.54 - 1, 68 (m, 4 H, H- C (3, 22, 23)) 1.91 - 2.07 (m, 4 H, HC (8, 11)) 2.18 (t, J = 7.73 Hz , 2 H, HC (2)) 5.26 - 5.44 (m, 2 H, HC (9, 10)) 6.28 (s, 1 H, HN (19))
[000229] 13C NMR (150 MHz, CHLOROFORM-d) δ ppm 14,13 (C (18) 18,01 (C (22, 23)) 22,69 (C (17)), 25,45 (C ( 3)), 27.19 (C (11) 27.23 (C11)) 29.16 (04)) 29.18 (06)) 29.26 (0 (5)) 29.33 (0 (13, 15)) 29.45 (0 (14)) 29.72 (0 (7)) 29.78 (0 (12)) 31.91 (0 (16, 21)) 33.47 (0 (2)) 129.76 (0 (10)) 129.99 (0 (9)) 175.15 (C (1)) 177.39 (0 (20)) Structure 7 GABA-C10: 0

[000230] 1H NMR (600 MHz, DMSO-C / Θ) δ ppm 0.83 - 0.87 (m, 3 H, H-C (10)) 1.18 - 1.29 (m, 12 H, HC ( 4, 5, 6, 7, 8, 9) 1.46 (quin, J = 7.22 Hz, 2 H, HC (14)) 1.59 (quin, J = 7.22 Hz, 2 H, HC (3)) 2.02 (t, J = 7.39 Hz, 2 H, HC (2)) 2.19 (t, J = 7.39 Hz, 2 H, HC (13)) 3.00 - 3.05 (m, 2 H, H-C (15)) 7.77 (t, J = 5.50 Hz, 1 H, HN (15)
[000231] 13C NMR (150 MHz, DMSO-cfe) δ ppm 13.95 (C (10)) 22.09 (C (9)) 24.64 (C (14)) 25.29 (C (3) ) 28.64 (C (5)) 28.66 (C (7)) 28.78 (C (6)) 28.90 (C (4)) 31.07 (C (13)) 31.27 ( C (8)) 35.38 (C (2)) 35.77 (C (15)) 172.03 (C (1)) 174.21 (C (12)) Structure 8 GABA-C12: 0

[000232] 1H NMR (600 MHz, DMSO-cfe) δ ppm 0.85 (t, J = 6.87 Hz, 3 H, HC (12)) 1.15 - 1.33 (m, 16 H, HC (4 , 5, 6, 7, 8, 9, 10, 11) 1.41 - 1.51 (m, 2 H, HC (3)) 1.59 (quin, J = 7.22 Hz, 2 H, HC (16)) 2.02 (t, J = 7.56 Hz, 2 H, HC (2)) 2.19 (t, J = 7.56 Hz, 2 H, HC (15)) 3.02 ( q, J = 6.53 Hz, 2 H, (HC (17)) 7.77 (t, J = 5.33 Hz, 1 H, HN (13))
[000233] 13C NMR (150 MHz, DMSO-cfe) δ ppm 13.95 (0 (12)) 22.09 (C (11)) 24.64 (C (16 ((25.29 (C (3)) ) 28.64 (C (9)) 28.71 (C (15)) 28.77 (C (6)) 28.95 (C (8)) 29.00 (C (5)) 29.02 ( C (4)) 31.06 (C (7)) 31.29 (C (10)) 35.77 (C (17)) 172.02 (C (1)) 174.20 (C14)) Structure 17 GABA-C18: 2

[000234] 1H NMR (600 MHz, CHLOROFORM-c /) δ ppm 0.89 (t, J = 6.87 Hz, 3 H, HC (18)) 1.26 - 1.39 (m, 14 H, HC (4, 5, 6, 7, 15, 16, 17) 1.57 - 1.65 (m, 2 H, HC (3)) 1.84 (quin, J = 6.96 Hz, 2 H, HC (22)) 2.05 (q, J = 7.22 Hz, 4 H, HC (8), HC (14)) 2.19 (t, J = 7.73 Hz, 2 H, H- C (2)) 2.40 (t, J = 7.05 Hz, 2 H, HC (21)) 2.77 (t, J = 6.87 Hz, 2 H, H-C (11)) 3, 33 (q, J = 6.53 Hz, 2 H, HC (23)) 5.30 - 5.41 (m, 4 H, HC (9, 10, 12.13) 5.96 (br, s „ 1 H, HN (19))
[000235] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14.08 (C (18) 22.58 C (17)) 24.74 (C3)) 25.63 (C (22)) 25.75 (C (11)) 27.20 (C 8, 14)) 29.15 (C (6)) 29.26 (C (5, 21)) 29.35 (C (15)) 29.62 (C (4)) 31.49 C (7)) 31.52 C (16)) 36.73 C (2)) 38.84 (C23)) 127.90 (C12)) 128.06 (C (10) ) 130.03 (C (9) 130.25 (C (13)), 174.17 (C (1) 177.43 (C (20)) Structure 22 beta-Alanine-C18: 2

[000236] 1H NMR (600 MHz, DMSO-cfe) δ ppm 0.85 (t, J = 7.05 Hz, 3 H, HC (18)) 1.11-1.37 (m, 14 H, HC (4, 5, 6, 7, 15, 16, 17) 1.37-1.53 (m, 2 H, HC (3)) 1.94 - 2.08 (m, 6 H, HC (2, 8, 14) 2.34 (t, J = 6.87 Hz, 2 H, HC (21)) 2.73 (t, J = Q, 70 Hz, 2 H, HC (11)) 3.13 - 3.27 (m, 2 H, H- C (22)) 5.24 - 5.40 (m, 4 H, HC (12, 13)) 7.84 (t, J = 5.67 Hz, 1 H, H- N (19))
[000237] 13C NMR (150 MHz, DMSO-cfe) δ ppm 13.91 (C (18)) 21.97 (C (17)) 25.21 (C (3)) 25.24 (C (11) ) 26.60 (C (8)) 26.63 (0 (14)) 28.58 (C (6)) 28.63 (0 (5)) 28.68 (C (15)) 28.73 ( C (4)) 29.04 (C (7)) 30.89 (0 (16)) 33.98 (0 (21)) 34.70 (C (22)) 35.27 (C (2)) 127.73 (C (10, 12)) 129.71 (0 (9, 13)) (C (1)) 172.91 (C (20)) Structure 28 Asp-C18: 2

[000238] 1H NMR (600 MHz, DMSO-cfe) δ ppm 0.86 (t, J = 6.87 Hz, 3 H, HC (18)) 1.17 - 1.38 (m, 14 H, HC (4, 5, 6, 7, 15, 16, 17) 1.42 - 1.50 (m, 2 H, HC (3) 2.01 (q, J = 7.10 Hz, 4 H, HC ( 8, 14) 2.06 - 2.10 (m, 2 H, HC (2)) 2.48 - 2.55 (m, 1 H, HC (22)) 2.62 - 2.68 (m, 1 H, HC (22)) 2.73 (t, J = 6.87 Hz, 2 H, HC (11)) 4.49 (d, J = 6.53 Hz, 1 H, HC (21)) 5.18 - 5.42 (m, 4 H, HC (9, 10, 12, 13) 8.09 (d, J = 7.90 Hz, 1 H, H- N (19))
[000239] 13C NMR (150 MHz, DMSO-cfe) δ ppm 13.93 (C (18) 21.97 (C (17)) 25.21 (0 (3), 26.60 (C (11)) 26.65 (C (8)) 28.55 (C (14)) 28.59 (C (6)) 28.70 (0 (4)) 28.73 (C (5)) 29.05 (C (15)) 30.69 (C (7)) 30.89 (C (16)) 35.06 (0 (2)) 36.25 (C (22) 48.49 (C (21)) 127, 75 (C (10, 12)) 129.74 (C (9, 13) 171.73 (C (20)) 172.02 (C (1)) 172.61 (C23)) Structure 33 Glu-C18: 1

[000240] 1H NMR (600 MHz, CHLOROPHORMUM-d) δ ppm 0.88 (t, J = 7.05 Hz, 3 H, HC (18) 1.19 - 1.39 (m, 20 H, HC ( 4, 5, 6, 7, 12, 13, 14, 15, 16, 17) 1.56 - 1.68 (m, 2 H, HC (3)) 1.94 - 2.04 (m, 4 HC (8, 12)) 2.08 (dt, J = 13.83, 6.66 Hz, 1 H, HC (22)) 2.20 - 2.25 (m, 3 H, H-C (22) ) 2.43 - 2.55 (m, 2 H, HC (23)) 4.64 (q, J = 6.87 Hz, 1 H, HC (21)) 5.30 - 5.38 (m, 2 H, HC (9.10)) 6.70 (d, J = 7.22 Hz, 1 H, HN (19))
[000241] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14,13 (C (18) 22,69 (C (17)) 25,57 (C (3) 26,81 (C (22) 27, 20 (C (11) 27.24 (C (8) 29.18 (C (6)) 29.22 (C (4)) 29.26 (C (5) 29.33 (0 (13, 15)) 29.55 (C (14)) 29.75 (C (7)) 29.78 (C (12)) 29.88 (C (23) 31.91 (C (16)) 36.36 (C ( 2)) 51.60 (C (21)) 129.71 (C (10)) 130.02 (C (9)) 174.62 (C (1)) 175.66 (C (20) 177.95 (C (24)) Structure 37Gln-C10: 2

[000242] 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 1.56 - 1.61 (s, 3 H, HC (10) 1.67 (s, 3 H, HC (8)) 2.05 - 2.14 (m, 6 H, HC (4, 14, 15) 2.15 - 2.20 (m, 3 H, HC (9)) 2.39 (dd, J = 15.46, 7.22 Hz, 2 H, H- C (5)) 4.51 (d, J = 6.19 Hz, 1 H, HC (13)) 5.01 - 5.13 (m, 1 H, HC (6) 5.60 - 5.72 (s, 1 H, HC (2)) 6.63 (br, s „1 H, HN (11)) 7.14 (br, s„ 2 H, H2-N))
[000243] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 17.69 (C (10) 18.52 (C (9) 25.67 (C (8)) 26.17 (C (5)) 30 , 95 (C (14)) 31.68 (C (15) 40.97 (C (4)) 51.92 (C (13)) 117.22 (C (2)) 123.14 (C (6) )) 132.39 (C (7)) 156.33 (C (3)) 167.95 (C (1) 174.69 (C (16)) 177.12 (0 (12)) Structure 44 Met- C12: 1

[000244] 1H NMR (300 MHz, CD3OD) δ ppm 0.92 (t, J = 6.9 Hz, 3H, H-C (12)), 1.32-1.38 (m, 8H, HC ( 8, 9, 10, 11), 1.63-1.73 (q, J = 7.5 Hz, 2H, HC (3)), 1.98-2.16 (m, 9H, HC (4, 7, 16, 18), 2.28 (t, J = 7.2 Hz, 2H, H-C (2)), 2.48-2.65 (m, 2H, HC (17)), 4.56 (d, d, J = 5.1, 9.9 Hz, 1H, H-C (15)), 5.33-5.46 (m, 2H, HC (5, 6)),
[000245] 13C NMR (300 MHz, CD3OD) δ ppm 14.43 (C (12) 15.21 (C (18)) 23.71 (C (11)) 27.01 (C (4)) 27, 70 (C (3)) 28.22 (C (7)) 30.08 (C (9)) 30.83 (C (17)) 31.31 (C (8)) 32.19 (C (16 )) 32.95 (C (10)) 36.37 (C (2)) 52.59 (C (15)) 129.81 (C (5)) 131.80 (C (6)) 175.17 (C (14)) 176.28 (C (1)) Structure 46 Met-C18: 1

[000246] 1H NMR (300 MHz, CD3OD) δ ppm 0.90 (t, J = 6.6 Hz, 3H, H-C (18)), 1.27-1.34 (m, 20H, HC ( 4,5, 6, 7, 12, 13, 14, 15, 16, 17), 1.60-1.65 (m, 2H, HC (3)), 1.90-2.19 (m, 9H , HC (8, 11, 22, 24), 2.25 (t, J = 6.3 Hz, 2H, HC (CH (2)), 2.49-2.62 (m, 2H, HC (23 )), 4.55 (d, d, J = 4.8, 9.9 Hz, 1H, HC (21)), 5.30-5.40 (m, 2H, HC (9, 10),
[000247] 13C NMR (300 MHz, CD3OD) δ ppm 14.44 (C (18)), 15.24 (C (24)), 23.76, (C (17)) 26.96 (C (3 )), 28.16 (C (11)), 30.26 (C (8)), 30.28 (C (6)), 30.37 (C (4)), 30.47 (C (5 )), 30.62 (C (15), 30.85 ((C13, 14)), 30.87 (C (23)), 31.33 (C (7.12)), 32.18 (C (22)), 33.12 (C (16)), 36.84 (C (2)), 52.60 (C (21)), 131.22 (C (9, 10)), 175.20 (C (1)), 176.61 (C (20)) Structure 51 Proline-C18: 2

[000248] 1H NMR (600 MHz, CHLOROPHORUM-c /) δ ppm 0.78 - 0.85 (m, 3 H, HC (18)) 1.18 - 1.33 (m, 14 H, HC (4 , 5, 6, 7, 15, 16, 17) 1.54 - 1.65 (m, 2 H, HC (3)) 1.84 - 1.92 (m, 1 H, H_C (22)) 1 , 92 - 2.03 (m, 6 H, H_C (8, 14, 23)) 2.26 - 2.32 (m, 2 H, HC (2)) 2.44 (ddd, J = 12.29 , 6.10, 2.92 Hz, 1 H, HC (22)) 2.70 (t, J = 6.70 Hz, 2 H, HC (11)) 3.39 (td,> 9.62, 6.87 Hz, 1 H, HC (24)) 3.47 - 3.53 (m, 1 H, HC (24)) 4.53 (dd,> 8.08, 1.89 Hz, 1 H, HC (21)) 5.16-5.36 (m, 4 H, HC (9, 10, 12, 13)
[000249] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14.07 (C (18)) 22.57 (C (17)) 24.48 (C (3)) 24.79 C (23)) 25.62 (C11)) 27.05 (C (22)) 27.17 (C (8)) 27.19 (C (14)) 29.10 C (6)) 29.27 (C (4, 15)) 29.34 (C (5)) 29.60 C (7)) 31.51 C ((16)) 34.45 C (2)) 47.98 C (24)) 60.25 (C (21)) 128.07 (C (12)) 128.07 (C (10)) 130.00 (C (9)) 130.24 C (13)) 171.87 (C (1)) 175, 87 (C20)) Structure 55 Serine-18: 2

[000250] 1H NMR (600 MHz, DMSO-cfe) δ ppm 0.85 (t, J = 6.87 Hz, 3 H, HC (18) 1.18 - 1.35 (m, 16 H, HC ( 3, 4, 5, 6, 7, 15, 16, 17) 1.43 - 1.51 (m, 2 H, HC (2)) 2.01 (q, J = 6.87 Hz, 4 H, HC (8, 14)) 2.12 (t, J = 7.39 Hz, 2 H, HC (2) 2.73 (t, J = 6.70 Hz, 2 H, HC (11)) 3, 58 (dd, J = 10.83, 4.30 Hz, 1 H, HC (22)) 3.65 (dd, J = 10.83, 4.30 Hz, 1 H, H-C (22) 4 , 21 - 4.27 (m, 1 H, HC (21)) 5.26 - 5.38 (m, 4 H, HC (9, 10, 12, 13)) 7.90 (d, J = 7 , 90 Hz, 1 H, HN (19) _
[000251] 13C NMR (150 MHz, DMSO-cfe) δ ppm 13.91 (C (18)) 22.01 (C (17)) 25.22 (C (3)) 25.24 (C (11) ) 26.63 (C (8)) 26.68 (C (14)) 28.65 (C (6)) 28.69 (C (4)) 28.77 (C (5, 15)) 20, 09 (C (7)) 30.93 (C16)) 35.07 (C (2)) 54.55 (C (21)) 61.49 (C (22)) 127.74 (C (10, 12) )) 129.72 (C (9, 13)) 172.19 (C (1)) 172.27 (C (20)) Structure 59 Leucine 16: 1

[000252] 1H NMR (600 MHz, CHLOROPHORUM-c /) δ ppm 0.85 - 0.90 (m, 3 H, HC (16)) 0.91 - 0.98 (m, 6 H, HC (22 , 23)) 1.19 - 1.40 (m, 14 H, HC (4, 5, 6, 7, 12, 13, 14)) 1.49 - 1.75 (m, 7 H, HC (3 , 15, 20, 21)) 2.01 (q, J = Q, 07 Hz, 4 H, HC (8, 11)) 2.24 (t, J = 7.73 Hz, 2 H, HC (2 )) 4.54 - 4.59 (m, 1 H, HC (19)) 5.24 - 5.43 (m, 2 H, HC (9, 10)) 6.14 (d,> 8.25 Hz, 1 H, HN (19))
[000253] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14,11 (016)) 21,9 (C (15) 22,66 (C (22) 22,86 (C (23) 24,91 ( C21)) 25.63 (C (3)) 27.18 (0 (11)) 27.23 (0 (8)) 28.99 (C (6)) 29.16 (0 (4)) 29, 20 (C (5)) 29.25 (0 (13)) 29.71 (C (7)) 29.73 (C (12)) 31.79 (C (14)) 36.51 (C (2 )) 41.32 (0 (20)) 50.87 (0 (19)) 129.73 (C (9)) 130.00 (C (10)) 173.95 (0 (1)) 176.38 (C (18)) Structure 61 Leu-C18: 1

[000254] 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 0.77 - 0.84 (m, 3 H, HC (18)) 0.85 - 0.93 (m, 6 H, HC (24, 25)) 1.14 - 1.29 (m, 20 H, HC (4, 5, 6, 7, 12, 13, 14, 15, 16, 17) 1.48 - 1.59 (m, 3 H , HC (3, 22) 1.60 - 1.69 (m, 2 H, CH (22, 23) 1.90 - 1.99 (m, 4 H, HC (8, 11)) 2.17 ( t,> 7.39 Hz, 2 H, HC (2)) 4.55 (td,> 8.51, 4.64 Hz, 1 H, HC (21)) 5.15 - 5.35 (m, 2 H, HC (9.10) 5.95 (d,> 7.56 Hz, 1 H, HN (19))
[000255] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 13.68 (C (18)) 21.43 (C (17)) 22.24 (C (25) 22.40 (C (24) 24 , 45 (C (23)) 25.14 (C (3)) 26.74 (0 (11) 26.78 (C (8)) 28.71 (C (6)) 28.73 (C (4 )) 28.78 (C (5)) 28.88 (C (13, 15)) 29.09 (C (14)) 29.26 (C (7)) 31.46 (C16)) 36.04 (C (2)) 40.70 (C (22)) 50.41 (C (21)) 129.28 (C (9, 10) 173.64 (C (1) 176.11 (C (20) ) Structure 65 Val-C16: 0

[000256] 1H NMR (600 MHz, CHLOROPHORUM-O) δ ppm 0.88 (t, J = 7.05 Hz, 3 H, HC (16)) 0.95 (d, J = 6.87 Hz, 3 H, HC (21)) 0.98 (d,> 6.87 Hz, 3 H, HC (20)) 1.19 - 1.37 (m, 24 H, HC (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14) 1.59 - 1.71 (m, 2 H, HC (3)) 2.20 - 2.32 (m, 3 H, H- C (3)) 4.59 (dd,> 8.59, 4.81 Hz, 1 H, HC (18)) 6.19 (d,> 8.59 Hz, 1 H, HN (17))
[000257] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14,13 C (16)) 17.70 C (20)) 19,02 C (21)) 22,71 C (15)) 25,78 C (3)) 29.25 C (6)) 29.35 C (9)) 29.38 (C (13) 29.52 C (5)) 29.64 C (4)) 29.68 (C (7, 10)) 29.72 C (8, 11, 12)) 31.00 (C (19)) 31.94 (C (14)) 36.69 (C (2)) 57.08 C ( 18)) 174.23 (C (1)) 175.49 C (22) Application examples Condiments and fats
[000258] The following formulations were prepared and were flavored by prepared panel members. Sodium-based product Pure salt level product between 5-40%
[000259] Salt level in the application of 0.3-1.0%
[000260] C18: 2 gaba - (0.5 ppm) was added to a 1% kikoman soy sauce with reduced diluted salt content (9% salt). The resulting composition was considered to be stronger, more umami, long lasting, richer
[000261] C18: 2 gaba - (0.5 ppm) was added to kikoman soy sauce with pure reduced salt content (9% salt). The resulting composition was considered to be strong in oral and body sensation, and more salty. C18: 1-ACCA - (0.5 ppm) was added to kikoman soy sauce with reduced pure salt content (9% salt). The resulting composition was considered to have strong prolonged advanced salinity, very strong salinity. two . Based on fish
[000262] Pure salt level product between 5-40%
[000263] Salt level in the application of 0.3-1.0%
[000264] C18: 2 gaba - (0.5 ppm) was added to a sauce of 1% diluted fish sauce (0.27% salt). The resulting composition was considered to be stronger in umami, longer lasting and richer.
[000265] C18: 2 gaba - (0.5 ppm) was added to pure fish sauce (27% salt). The resulting composition was considered to be strong in oral and body sensation, more salty, richer and with more rounded fish marks.
[000266] C18: 1-ACCA - (0.5ppm) was added to pure fish sauce. The composition was considered to exhibit strong prolonged salinity and with a strong oral and body sensation. 3. Colloid Emulsions 3.1 - Water in oil
[000267] Butter
[000268] Fat levels of 20-90%
[000269] Salts level of 0.1-1.7%
[000270] Blue ribbon of 82% fat 1.5% salt
[000271] C18: 2 gaba added at 1 ppm. The composition was considered to exhibit a more authentic butter flavor, with more oral sensation Pilaf
[000272] Standard cooked rice with 10% of the butter flavored with 18: 2 gaba mentioned above was considered to have more oral sensation, with an extended creamy authentic butter flavor. 3.2 - Oil in water Mayonnaise
[000273] Fat levels of between 10-80%
[000274] In low-fat mayonnaise (27% fat, 9% carbohydrates (whose 5% sugar), 1.4% salt)
[000275] C18: 1-ACCA (0.5 ppm) added to mayonnaise was considered to produce well-balanced compositions with a total oral feel and a greater egg flavor.
[000276] C18: 2 gaba (0.5 ppm) added to mayonnaise was considered to produce a thick, creamy oral sensation with an impression of total fat. 3.3 - Sauces
[000277] Oil levels 0.5-50%
[000278] Acidity of PH 3-6
[000279] low fat salad dressing (13.6% fat, 8% carbohydrates (whose 5.3% sugar))
[000280] C18: 1-ACCA (0.5 PPM) was added to the sauce and produced a composition with a more oral feeling with body and less acid
[000281] C18: 2 gaba (0.5PPM) was added to the sauce and produced a better oral sensation that was impressively creamy. 4 - Soups and Broths
[000282] Fat levels of 0.1 -10%
[000283] Salts level of 0.3-1.4%
[000284] Standard chicken stock base, 0.7% salt, 0.5% fat
[000285] C10: 0 ACCA @ 0,5 PPM - better chicken profile, prolonged Umami, good strong salty
[000286] C10: 0 ACCA @ 0.2 PPM - extended body plus umami
[000287] C18: 1-ACCA @ 0.5 PPM - more body and fatty flavors, salivation and good aftertaste
[000288] C18: 1-ACCA @ 0.2 PPM - saltier, stronger and more umami
[000289] C18: 2 ACCA @ 0,2 PPM - fatter chicken, full body, creamy
[000290] Geranoil ACCA @ 0.2 PPM - extended Umami oral sensation plus saltiness
[000291] Meat broth base of 1.0% salt, 0.5% fat
[000292] C18: 1 met @ 1,0 PPM - Full body, long lasting, plus oral sensation
[000293] C18: 1 met @ 0.5 PPM - very salty and rich
[000294] C18: 2 gaba @ 0.5 PPM - strong, salty, Umami, oral sensation
[000295] C16: 1 read @ 0.5PPM - strong and rich salty
[000296] C18: 2 goes @ 0.5PPM - more body and oral sensation, more umami 5 - Juice and Broth
[000297] Meat broth
[000298] C18: 1-ACCA @ 40PPB - total, greasy, salty profile is increased 6 - Cheese
[000299] Fat level of 1 - 40%
[000300] Salt of 0.3 - 2%
[000301] ERU spreadable cheese
[000302] C18: 2 gaba @ 0,5PPM - Cheese bite, full, salty, more ripe
[000303] C18: 1-ACCA @ 0,5PPM - Cheese bite, prolonged, umami, strong
[000304] Cheese sauce: 5% fat 1.6% salt
[000305] C18: 2 gaba @ 0,5PPM - Cheese bite, full, salty, expansion
[000306] C18: 1-ACCA @ 0,5PPM - Bite of cheese, umami, strong, expansion 7 - Meat and Poultry
[000307] High temperature differentiator 100-250 degrees Celsius in a frying in the oil process
[000308] C18: 2 gaba @ 2.0 PPM in 135 grams of frying oil (blue ribbon, 82% fat) 450 grams of chicken fillet for 2 minutes over high heat and 5 minutes over medium heat.
[000309] The chicken's flavor is more juicy, juicy, drawn out more white meat
[000310] The oil also has notes of golden brown, more tasty. 8 - Bakery and Pizza Products
[000311] High temperature differentiator at 100-250 degrees Celsius in a hot air cooking process
[000312] C18: 2 gaba @ 0.5PPM in the crust and @ 0.5 PPM in the tomato sauce
[000313] The pizza was completed with cheese and was baked in a hot air oven @ 200 degrees Celsius.
[000314] The crust was less dry, more juicy and the tomato was richer, sweeter and the total lingering aftertaste was very rich and pleasant 9 - Snack product
[000315] A snack product consisting of a crisp base, containing 35% fat and flavored with cheese seasoning containing salt, MSG, dairy, organic acids, sugars, and a flavor formulation. The following compounds were added to the snack product at the indicated levels and the taste results are reported:
[000316] C18: 2 gaba 1 ppm: Cheese crust, long-lasting, greasy, full, cheesy
[000317] C18: 2 gaba 0.5 ppm: increased dairy, cheesy.
[000318] C18: 1-ACCA 1 ppm: Umami increased, salted.
[000319] C18: 1-ACCA 0.5 ppm: increased salty
[000320] C18: 1 met 0,5 ppm: enlarged, creamy, salty and juicy cheese
[000321] C18: 1 met 0.25 ppm: salted, aged, juicy cheese 10 - Base enlarged with air
[000322] An expanded base with air (rice, wheat, tapioca, potato, salt, sugar, modified starch), containing 3% fat and flavored with cheese seasoning containing salt, MSG, dairy, organic acids, sugars and flavor. The following compounds were added to the base, at the indicated levels and the taste results are reported:
[000323] C18: 2 gaba 1 ppm: Cheese crust, full, greasy, cheesy, long lasting, covering base
[000324] C18: 2 gaba 0.5 ppm: increased dairy, cheese.
[000325] C18: 1-ACCA 1 ppm: Umami increased, salted.
[000326] C18: 1-ACCA 0.5 ppm: increased salty 11 - Testing on Dairy Products
[000327] The following tests were performed on dairy products processed by fermentation, pasteurization or UHT. The products contain fat, protein and calcium.
[000328] UHT cream flavored, unsweetened and different levels of fat
[000329] In a UHT milk containing 0%, 1.5% and 3% fat, flavored with a proprietary cream flavor dosed at 0.03% C18: 2 gaba was added at 2 ppm.
[000330] Samples were evaluated by expert tastemakers.
[000331] Savorers were asked to describe samples that focus on authentic flavor, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat. The results are shown below:
[000332] 0% fat UHT milk, cream flavor (0.03%): Milky, aqueous, residual cardboard taste
[000333] UHT milk 0% fat, cream flavor (0.03%) but with C18: 2 gaba added at 2 ppm: Very creamy, milky, long lasting.
[000334] 1.5% fat UHT milk, cream flavor (0.03%): Milky, slightly creamy
[000335] 1.5% fat UHT milk, cream flavor (0.03%) with C18: 2 gaba added at 2 ppm: very creamy, milky, long-lasting, salivation.
[000336] 3.0% fat UHT milk, cream flavor (0.03%): Milky, slightly creamy
[000337] UHT milk of 3.00% fat, cream flavor (0.03%) with C18: 2 gaba added at 2 ppm: very creamy, milky, long lasting, flavor like whipped cream.
[000338] UHT-sweetened banana flavored milk, with different levels of fat from
[000339] In a UHT Milk with 0% and 3% fat sweetened with 4% by weight of sucrose, flavored with proprietary banana flavor administered dosed at 0.04%. C18: 2 gaba was added at 0.25 ppm, 0.5 ppm and 1 ppm.
[000340] Samples were evaluated by expert tastemakers. Tasteers were asked to describe the samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000341] 0% fat UHT milk, banana flavor (0.04%): strong, sterile banana, eugenol type, unbalanced.
[000342] 0% fat UHT milk, banana flavor (0.04%) C18: 2 - gaba (0.25 ppm): fuller, more authentic, sweeter banana.
[000343] 0% fat UHT milk, Banana flavor (0.04%), C18: 2- gaba (0.5 ppm): fuller, authentic, creamy and sweet banana, more oral sensation
[000344] 0% fat UHT milk, banana flavor (0.04%), C18: 2 -gaba (1 ppm): creamy, creamy banana, sweet aftertaste, more oral and very long lasting sensation
[000345] 3% fat UHT milk, banana flavor (0.04%): strong sterile banana, eugenol type, spicy
[000346] 3% fat UHT milk, banana flavor (0.04%), C18: 2 -gaba (0.25 ppm): more authentic, less banana and more round
[000347] 3% fat UHT milk, Banana flavor (0.04%), C18: 2- gaba (0.5 ppm): creamy banana
[000348] 3% fat UHT milk, banana flavor (0.04%), C18: 2- gaba (1 ppm): long-lasting and more authentic creamy and more impact.
[000349] Flavored yogurt cream, unsweetened and different levels of fat
[000350] In a Yogurt containing 0%, 1.5% and 3% fat, flavored with proprietary cream flavor administered dosage at 0.03%, C18: 2-gaba was added at 2 ppm. Samples were evaluated by expert tastemakers.
[000351] Tasteers were asked to describe samples that focus on authentic flavor, acidity, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000352] 0% fat yogurt, cream flavor (0.03%): very acidic, metallic
[000353] 0% fat yogurt, cream flavor (0.03%), C18: 2- gaba at 2 ppm: less acid, slightly creamy aftertaste
[000354] 1.5% fat yogurt, cream flavor (0.03%): moderately creamy yogurt
[000355] 1.5% fat yogurt, cream flavor (0.03%), C18: 2-gaba 2 ppm: very creamy, thick, beautiful, long lasting, note of whipped cream.
[000356] 3% fat yogurt, cream flavor (0.03%): acidic, creamy aftertaste
[000357] 3% fat yoghurt, cream flavor (0.03%), C18: 2- gaba 2 ppm: less acid, much more creamy, long-lasting creamy aftertaste.
[000358] Yogurt sweetening with strawberry flavored sugar
[000359] In a 1.5% fat yogurt base, sweetened with 8% sucrose by weight, flavored with a proprietary strawberry flavor @ 0.015% of several different N-acyl amino acids were added.
[000360] Base: strawberry, fruity
[000361] Base plus C18: 2-gaba at 2 ppm: very creamy and fresh strawberry
[000362] Base plus C18: 0-read at 5 ppm: very juicy full, 3D, more pleasant strawberry stronger, long-lasting salivation.
[000363] Base plus C18: 0 read at 2 ppm: full juicy, 3D, more pleasant strawberry, long lasting creamy good taste.
[000364] Base plus C18: 0-gaba at 2 ppm: full juicy, pasty
[000365] Base plus C18: 0-gln at 2 ppm: full juicy, beautiful, slightly sulphurous sweet
[000366] Base plus C18: 1-gin at 2ppm: juicy, beautiful, greasy aftertaste.
[000367] Base plus C18: 2-asn to 2ppm: fresh green, beautiful, greasy beautiful fuller
[000368] Active strawberry yogurt
[000369] In an active strawberry flavor yogurt, whole containing 13.5% sugar, 3.2% fat C18: 2-gaba and C18: 0-read at 2 ppm
[000370] Active: pasty strawberry, green and creamy
[000371] Activates more C18: 2-gaba at 2 ppm: very creamy, full and fresh strawberry
[000372] Activates more C18: 0-read at 2 ppm: very juicy full strawberry, 3D, stronger strawberry, long lasting and creamy.
[000373] 3.0% fat vanilla flavored milk
[000374] In a 3% fat milk drink, sweetened with 4% sucrose by weight, flavored with Vanilla @ 10 ppm and vanilla extract @ 0.03% C18: 2-gaba, C18: 1- ACCA and C18: 1-glu were added at 0.5 or 2 ppm.
[000375] Samples were evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000376] Base: 3% fat milk, 4% sugar, 10 ppm vanilla, 0.03% vanilla extract
[000377] Base: vanillic sweet, very slightly grainy
[000378] Base: C18: 2-gaba 2 ppm: granular, greasy, authentic, sweet
[000379] Base: C18-ACCA (propyl cylinder) 0.5 ppm: sweet, sugar-like, vanillic
[000380] Base: C18: 1-glu 2 ppm: full, greasy, improved vanilla bean, like whipped cream
[000381] Chocolate milk with different fat content
[000382] In a chocolate milk of 1.8% and 2.7% C18: 2-gaba fat was added at 0.5 and 1 ppm.
[000383] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000384] Chocolate milk 1.8% fat: cocoa powder flavor, sweet, slightly creamy
[000385] Chocolate milk 1.8% fat C18: 2-gaba at 0.5 ppm: stronger cocoa brand, more chocolate vs cocoa
[000386] Chocolate milk 1.8% C18 fat: 2-gaba at 1 ppm: chocolate, very creamy and long-lasting chocolate flavor.
[000387] Chocolate milk 3% fat: cocoa powder, sweet, creamy flavor
[000388] Chocolate milk 3% fat C18: 2-gaba at 0.5 ppm: very creamy, cocoa brand increased.
[000389] Chocolate milk 3% fat C18: 2-gaba at 1 ppm: very creamy, long lasting, sweet, almost chocolate ice cream flavor. Soy milk
[000390] In a soy milk (1.8% fat) sweetened with 5% sucrose by weight, flavored with a proprietary milk flavor in a dosage of 0.1%, C18: 2-gaba was added at 2 ppm
[000391] Samples were evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000392] Soy milk, 5% sucrose, milk flavor @ 0.1%: sweet, dry, green, soy flavor
[000393] Soy milk, 5% sucrose, milk flavor @ 0.1%, C18: 2-gaba at 2 ppm: pure, creamy, good masking of the soy flavor, creamy and milky. 12 - Caloric & non-caloric drinks
[000394] Testing on beverage products containing carbohydrate sweeteners such as sucrose, high fructose corn syrup, fructose and glucose; or non-nutritive, high intensity sweeteners such as Aspartame Acesulfame K, Sucralose, Cyclamate, Na + Saccharin, Neotame, Rebaudioside A and / or other sweeteners based on stevia.
[000395] Sweetener in beverage applications varies from 0-20%. Examples:
[000396] Carbonated soft drink: <1% to 15% of sweetener
[000397] Still drinks (non-alcoholic): <1% to 15% of sweetener
[000398] Juice drinks; <1% to 15% sweetener
[000399] Powdered refreshment: <1% to 20% of sweetener
[000400] Concentrated liquids: <1% to 20% of sweetener
[000401] Alcoholic beverages: <1% to 40% of sweetener
[000402] Functional drinks: <1% to 20% of sweetener
[000403] Coffee-based drinks: <1% to 15% sweetener
[000404] Tea-based beverages: <1% to 15% sweetener Test in 3 in 1 coffee
[000405] In a Nestlé 3-in-1 coffee drink (commercialized product) sweetened with 13.2% sucrose and containing (2.1% fat) C18: 2-gaba more creamy was added.
[000406] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat.
[000407] Base is a 3-in-1 coffee drink (marketed product) sweetened with sucrose and containing creamer with fat Base: coffee, sweet, smooth dairy
[000408] Base plus C18: 2-gaba at 1 ppm: very good oral sensation, creamy as if coffee cream agent was added, sweeter. Test at Tanq
[000409] In a powdered drink flavored with Tang orange (commercialized product) sweetened with sucrose plus high intensity sweetener containing citric acid, C18: 2-gaba and C18: 2-pro were tested.
[000410] All samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic flavor, oral & body sensation, improvement, richness, juiciness, long-lasting, salivation, sweetening power, masking bad taste of high intensity sweetener Base is Tanq flavored orange
[000411] Base: sweet, orange, licorice, and bad taste of long-lasting, bitter, fine high-intensity sweetener.
[000412] Base plus C18: 2-gaba at 0.5 ppm: improves sweet juicy orange marks, increased oral sensation. In addition, the disadvantages of the high intensity sweetener have been eliminated.
[000413] Base plus C18: 2-Pro at 1 ppm: very fresh, increases sweet juicy orange marks, characteristic of authentic fresh orange fruit. In addition, the disadvantages of the high intensity sweetener have been eliminated.
[000414] Drink still flavored with mango containing different levels of juice.
[000415] In a drink still flavored with mango, sweetened with 8% sucrose and containing 0.1% citric acid and 1%, 4% and 6% clear mango juice flavored with the proprietary mango flavor @ 0, 05%, C18: 2-gaba and C18: 2-Pro were added, as such (separate) and in combination.
[000416] All samples were evaluated by expert tastemakers. Tasteers were asked to describe the samples that focus on authentic flavor, juicy oral sensation, improvement, richness, juiciness, long-lasting, salivation, sweetener.
[000417] In a drink still flavored with mango, sweetened with 8% sucrose & containing 0.1% citric acid and 1% clear mango juice flavored with proprietary mango flavor @ 0.05%, C18: 2- gaba and C18: 2-Pro were added, as such (separate) and in combination.
[000418] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice (% very low juice), flavored with mango flavor, dosed 0.05%
[000419] Base: sweet, fruity, mango, fine
[000420] Base plus C18: 2-Pro at 0.5 ppm: sweeter, sugar-like, very juicy and long-lasting sweet, salivation
[000421] Base plus C18: 2-gaba at 1 ppm: like greasy, very juicy skin, authentic mango, much more oral sensation, long-lasting mango flavor, oral sensation is close to the full juice product
[000422] Base plus C18: 2-Pro at 0.5 ppm and C18: 2-gaba at 1 ppm: very juicy and sweet, authentic mango, long-lasting sweet and long-lasting mango flavor, very close in oral sensation to a full juice product
[000423] In a drink still flavored with mango, sweetened with 8% sucrose & containing 0.1% citric acid and 4% clear mango juice flavored with mango flavor @ 0.05%, C18: 2- gaba and C18: 2-Pro were added, as such (separated) and in combination.
[000424] Base is water, 8% sucrose, 0.1% citric acid, 4% clear mango juice (30% reduced juice), flavored with mango flavor, dosed 0.05%
[000425] Base: sweet, fruity, mango, some low oral sensation
[000426] Base plus C18: 2-Pro at a range of 0.5 ppm: sweeter, sugar-like, very juicy and long-lasting sweet, salivation
[000427] Base plus C18: 2-gaba at 1 ppm: as a greasy, very juicy skin, authentic mango, long-lasting mango flavor, more oral sensation than full juice product
[000428] Base plus C18: 2-Pro at 0.5 ppm and C18: 2-gaba at 1 ppm: very juicy and sweet, thick, authentic mango, long-lasting sweet and long-lasting mango flavor, plus oral sensation than a full juice product
[000429] In a drink still flavored with mango, sweetened with 8% sucrose & containing 0.1% citric acid and 6% clear mango juice flavored with mango flavor @ 0.05%, C18: 2- gaba and C18: 2-Pro were added, as such (separated) and in combination.
[000430] Base is water, 8% sucrose, 0.1% citric acid, 6% clear mango juice (full juice), flavored with mango flavor, dosed at 0.05%. Base: Sweet, fruity mango, full oral sensation
[000431] Base plus C18: 2-Pro at 0.5 ppm sweeter, sugar-like, very juicy and long-lasting sweet, salivation, syrupy.
[000432] Base plus C18: 2-gaba at 1 ppm: as a very thick, greasy, juicy skin, authentic mango, long-lasting, rich mango flavor.
[000433] Base plus C18: 2-Pro at 0.5 ppm and C18: 2-gaba at 1 ppm: juicy and sweet, authentic thick mango, long-lasting sweet and long-lasting mango flavor, very rich. 13 - Testing alcoholic beverage products
[000434] Test on Baileys cream liqueur:
[000435] In Baileys cream liqueur (marketed product) containing 17% alcohol, 25% carbohydrates and 13% C18: 2- gaba fat were added at 1 ppm.
[000436] Samples were evaluated by expert tastemakers. Tasteers were asked to describe the samples that focus on authentic taste, alcohol impact, oral sensation, fullness, salivation, sweetener, bitterness, richness, long-lasting and fat.
[000437] Base is Baileys cream liqueur
[000438] Base: alcoholic, cream, cocoa
[000439] Base plus C18: 2-gaba at 1 ppm: alcohol effect strongly increased, more cocoa, very creamy and long lasting aftertaste. Test on Heineken beer:
[000440] In Heineken beer (marketed product) containing 4% C18: 2-gaba alcohol was added at 0.5 ppm.
[000441] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic flavor, alcohol impact, malt flavor, hop flavor, oral sensation, fullness, salivation, sweetener, bitterness, richness, long-lasting and fat.
[000442] Base is Heineken beer
[000443] Base: Bitter, hop type, fruity, malted, alcoholic
[000444] Base plus C18: 2-gaba at 0.5 ppm: more hops, more bitter, more malt and stronger alcohol impact. Breezer orange test:
[000445] Breezer orange (commercial product) containing 4% C18: 2-gaba alcohol was added at 1 ppm.
[000446] Samples were evaluated by expert tastemakers. Tasteers were asked to describe the samples that focus on authentic taste, alcohol impact, juiciness, oral sensation, fullness, salivation, sweetener, bitterness, richness, long-lasting and fat.
[000447] Base is orange Breezer
[000448] Base: Bitter, orange, soapy (burning), burning, alcoholic
[000449] Base plus C18: 2-gaba at 0.5 ppm: more alcoholic, sweeter, more juicy orange, less soapy 14 - Test with drinks containing 0.01% to 7% organic acids Test 18: 2 boasts of organic acids in a drink.
[000450] In a solution containing water, 7% sucrose by weight, and different organic acids, 18: 2 gaba were added at 1ppm. We observed the effects on acid perception in the addition of 18: 2 gaba.
[000451] 7% sucrose plus 0.121% by weight tartaric acid
[000452] Base is water, 7% sucrose by weight, tartaric acid at 0.121% by weight
[000453] Base: sharp acid, astringent aftertaste
[000454] Base plus C18: 2-gaba at 1 ppm accentuated perception of acid decreased, oral sensation of full body, with higher, more immediate mouth water (advanced success), and an impression of the fruit fruit (grape) , apple, banana, like pear)
[000455] 7% sucrose plus 0.1081% malic acid by weight
[000456] Base is water, 7% sucrose by weight, malic acid 0.1081% by weight
[000457] Base: acidic, green, slightly astringent
[000458] Base plus C18: 2-gaba at 1 ppm accentuated perception of acid decreased, gave fuller body, oral sensation, with higher mouth water, and an impression of the skin marks and saves fruit (apple) fruit
[000459] 7% sucrose plus 0.1% citric acid by weight
[000460] Base is water, 7% sucrose by weight, citric acid at 0.1% by weight
[000461] Base: acid, sharp fresh
[000462] Base plus C18: 2-gaba at 1 ppm accentuated perception of acid decreased, oral sensation of full body, with higher mouth water, and an impression of the juicy marks of citrus fruit (orange, lemon)
[000463] 7% sucrose plus 0.0936 wt% furmonic acid
[000464] Base is water, 7% sucrose by weight, 0.0936% by weight ferric acid
[000465] Base: sour, acid, astringent
[000466] Base plus C18: 2-gaba at 1 ppm: accentuated acid perception, oral sensation of full body effects, higher sweet effects, and an impression of full marks characteristic of red & vanillic flavor types (vanilla, chocolate, raspberry, cherry, especially benzaldehyde) 15 - Testing of Gaba derivatives and beta Ala
[000467] Samples were prepared and evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-lasting and fat. Tests on low salt Kikkoman soy sauce
[000468] Base is Kikkoman soy sauce
[000469] Base: salty, dark roasted taste, umami
[000470] Base plus C18: 2-gaba at 0.5 ppm: much more salty, sweet and long lasting. Test on spreadable cheese "Eru prestige"
[000471] Base is Eru prestige (commercialized product)
[000472] Base: Frothy, bite of cheese, slightly bitter
[000473] Base plus C18: 2-gaba at 0.5 ppm full salt, much more cheese bite, umami, prolonged, long lasting. Menthol fondant test (1%)
[000474] Base is 65% fondant, 34% sugar syrup and 1% proprietary menthol flavor
[000475] Base: Cooling, menthol, sweet.
[000476] Base plus C18: 2-gaba at 2 ppm: increased menthol impact, stronger cooling, sweeter, long-lasting, fresh. Low-fat salad dressing Calve (13.6% fat):
[000477] Base is salad dressing Calve (commercialized product)
[000478] Base: acidic, rancid, watery
[000479] Base plus C18: 2-gaba at 0.5 ppm much more full, creamy, rich, less acid. Calve 60% reduced fat content mayonnaise
[000480] Base is 60% reduced fat content mayonnaise (marketed product)
[000481] Base: rancid, acidic, empty
[000482] Base plus C18: 2-gaba at 0.5 ppm full, rich, creamy, more flavor of egg yolk. Comparison on a mango juice drink
[000483] Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, and a 0.05% proprietary mango flavor.
[000484] Base: fruity mango
[000485] Base plus C16: 1 gaba at 2 ppm: juicy, rich, full authentic
[000486] Base plus C18: 1 gaba at 2 ppm: juicy, long-lasting, rich
[000487] Base plus C18: 2 gaba at 2 ppm: as a greasy, juicy, authentic skin
[000488] Base: fruity mango
[000489] Base plus C16: 0-beta wing at 2 ppm more juicy
[000490] Base plus C 18: 1-beta wing at 2 ppm more succulent, lasting
[000491] Base plus C18: 2-beta wing at 2 ppm nice long-lasting juicy, almost an almost a little salty Comparison in broth
[000492] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000493] Base: salted, umami, powder
[000494] Base plus C16: 0-beta wing at 2 ppm umami salivation plus salt
[000495] Base plus C18: 1-beta wing at 2 ppm umami salivation plus salt
[000496] Base plus C18: 2-beta wing at 2 ppm salty, tasty, full
[000497] Comparison on a strawberry drink
[000498] Base is 7% sucrose, 0.1% citric acid, and proprietary strawberry flavor @ 0.015%
[000499] Base: sweet, fruity, rich strawberry
[000500] Base plus C16: 1-gaba at 2 ppm juicy, fruity, greasy, long lasting, good oral sensation
[000501] Base plus C18: 1-gaba at 2 ppm greasy and long-lasting strawberry
[000502] Base plus C18: 2-gaba at 2 ppm creamy strawberry with a greasy, fruity and juicy oral sensation
[000503] Base plus C18: 0-gaba at 0.5 ppm moderate creamy, fruity, juicy and long lasting Test on a strawberry yogurt
[000504] Base: Yogurt 1.5% fat yogurt, 8% sucrose, proprietary strawberry flavor @ 0.015%
[000505] Base: fruity, strawberry
[000506] Base plus C18: 2-gaba at 2 ppm, creamy, authentic fruity strawberry, stronger strawberry, ripened, long-lasting, juicy Test on vanilla milk:
[000507] Base: 0.15% fat milk, sweetened with 4% sucrose by weight, flavored with proprietary vanillin flavor @ 10 ppm + ext. Vanilla @ 0.03%
[000508] Base: sweet vanillic, slightly grainy flavor
[000509] Base plus C18: 2-gaba at 2 ppm: authentic greasy vanilla, long-lasting, vanilla bean flavor is increased Test on flavored chocolate drink:
[000510] Base: Water, 4% sucrose, 0.03% proprietary chocolate flavor
[000511] Base: vanillic sweet, cocoa
[000512] Base plus C18: 2-gaba at 2 ppm: full, sweeter, more vanillic, chocolate milk is increased, very long lasting Test on pear flavored drink:
[000513] Base: water, 7% sugar, 0.1% citric acid, 0.025% proprietary pear flavor
[000514] Base: pleasant pear, fruity, green
[000515] Base plus C18: 2-gaba at 1 ppm: long-lasting, juicy and like very authentic greasy skin, like eating fruit instead of drinking a drink Test on peach flavored drink:
[000516] Base is water, 8% sugar, 0.1% citric acid, and 0.05% proprietary peach flavor
[000517] Base: fruity peach
[000518] Base plus C18: 2-gaba at 1 ppm fruity peach, long-lasting, juicy and like very authentic greasy skin Test on pineapple flavored drink:
[000519] Base is water, 8% sugar, 0.1% citric acid and 0.03% proprietary pineapple flavor
[000520] Base: sweet pineapple, pasty
[000521] Base plus C18: 2-gaba at 1 ppm very matured, pasty, long-lasting and sweet 16 - Testing of C18 amino cyclopropanic acid derivative (ACCA)
[000522] Samples were prepared and were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, salinity, umami, sweetener, juiciness, richness, long-lasting and fat. Test on low salt Kikkoman soy sauce
[000523] Pure salt level product between 5-40% Application salt level of 0.3-1.0%
[000524] C18: 1-ACCA: 0.5 ppm strong prolonged advanced salinity, very strong salinity Test in fish sauce
[000525] Pure salt level product between 5-40%
[000526] Salt level in the application of 0.3-1.0%
[000527] C18: 1-ACCA 0.5 ppm, strong prolonged salinity, strong oral sensation of body Mayonnaise Test Fat levels of between 10-80%
[000528] Low-fat Mayonnaise (27% fat)
[000529] C18: 1-ACCA 0.5ppm- Well balanced, full oral sensation, increased egg character Sauce testing
[000530] Oil levels 0.5 - 50% PH 3-6 acidity Low fat salad dressing (13.6% fat)
[000531] C18: 1-ACCA 0,5 ppm - Body with increased oral sensation, less acid Test in Soups and Broths
[000532] Fat levels of 0.1-10%
[000533] Salt levels of 0.3 - 1.4%
[000534] Standard chicken stock base
[000535] 0.7% salt, 0.5% fat
[000536] C18: 1-ACCA 0,5ppm - more body and greasy notes, salivation and residual good taste
[000537] C18: 1-ACCA 0,2ppm - Saltier, stronger and more umami Test on Juices and Broths Broth
[000538] C18: 1-ACCA 40 ppb - more salty, greasy, total profile is increased Cheese Test
[000539] Fat level: from 1 - 40%
[000540] Salt: from 0.3 - 2% ERU spreadable cheese
[000541] C18: 1-ACCA 0.5 ppm - strong umami, prolonged cheese bite Gueijo sauce: 5% fat 1.6% salt
[000542] C18: 1-ACCA O.δppm - strong umami, cheese bite, expanding
[000543] 17 - Testing of derivatives of glutamic acid and aspartic acid
[000544] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-term and fat. Comparison on a mango juice drink
[000545] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000546] Base: fruity mango
[000547] Base plus C18: 1-glu at 1 ppm heavy, pasty, increased mango, more sulfurous, l umami
[000548] Base plus C16: 1-glu at 1 ppm full, heavy, pasty, long lasting
[000549] Base plus C18: 0-glu at 1 ppm greasy, full, sweet juicy
[000550] Base plus C16: 0-glu at 1 ppm slightly more succulent impact Comparison on a mango juice drink
[000551] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000552] Base: fruity mango
[000553] Base plus C16: 0-asp at 1 ppm apple skin, soft, greasy
[000554] Base plus C18: 1-asp at 1 ppm as juicy fruit
[000555] Base plus C18: 0-asp at 1 ppm fatty, fruity, long-lasting
[000556] Base plus C18: 2-asp at 1 ppm greasy, authentic fruit type, light raspberry and pear flavor Comparison on a strawberry drink
[000557] Base is water, 7% sucrose, 0.1% citric acid, proprietary strawberry flavor @ 0.015%
[000558] Base: sweet, fruity, rich, strawberry
[000559] Base plus C18: 1-glu at 0.5 ppm: good oral sensation, more natural strawberry, full juicy
[000560] Base plus C16: 1 -glu at 0,5 ppm: full, greasy, creamy
[000561] Base plus C18: 0-glu at 0.5 ppm: fruity, juicy, long-lasting Comparison on a vanilla milk drink
[000562] Base: 0.15% fat milk, sweetened with 4% sucrose by weight, flavored with proprietary Vanillin @ 10 ppm + vanilla extract @ 0.03%
[000563] Base: sweet vanillic, slightly grainy flavor
[000564] Base plus C18: 0-glu at 1 ppm full, greasy, like whipped cream
[000565] Base plus C 16: 1-glu at 1 ppm full, greasy, creamy, sweet vanilla
[000566] Base plus C16: 0-glu at 1 ppm as ice cream, sweet, very full
[000567] Base plus C18: 1-glu at 1 ppm full, grainy, sweeter
[000568] Base: sweet vanillic, slightly grainy flavor
[000569] Base plus C18: 2-asp at 2 ppm: very natural vanilla full sweet Test on flavored chocolate flavored drink
[000570] Base: water, 4% sucrose, proprietary chocolate flavor @ 0.03%
[000571] Base: sweet vanilli, cocoa
[000572] Base plus C18: 2-asp at 2 ppm: cardboard, dry jam
[000573] Base: sweet vanilla, cocoa
[000574] Base plus C18: 1 -glu at 0.5 ppm full cocoa, good, sweet
[000575] Base plus C16: 0-glu at 0.5 ppm sweet, fatty cocoa, sulfur is increased, flaked cocoa flavor increased Comparison in a broth
[000576] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000577] Base: salted, umami, powder
[000578] Base plus C16: 0-asp at 1 ppm salted, peppered
[000579] Base plus C18: 1-asp at 1 ppm non-special
[000580] Base plus C18: 0-asp at 1 ppm a lot of fullness and body, less salty Comparison on a pear drink
[000581] Base: water, 7% sugar, 0.1% citric acid, 0.025% proprietary pear flavor
[000582] Base: good pear, fruity, sterile, green
[000583] Base plus C18: 1-glu at 0.5 ppm greasy good, juicy, long lasting
[000584] Base plus C16: 0-glu at 0.5 ppm greasy of long duration
[000585] Base: good pear, fruity, sterile, green
[000586] Base plus C18: 2-asp at 1 ppm very juicy, authentic, 3D pear-like texture Comparison on a peach drink
[000587] Base is water, 8% sugar, 0.1% citric acid, 0.05% proprietary peach flavor
[000588] Base: fruity peach
[000589] Base plus C18: 1-glu at 1 ppm ripe, much more juicy, long lasting, more greasy and sweet
[000590] Base plus C16: 0-glu at 1 ppm fruity, good, juicy, sweet, soft peach skin
[000591] Base: fruity peach
[000592] Base plus C18: 2-asp at 1 ppm as greasy skin, light apple flavor Baileys cream liqueur test:
[000593] Base: Baileys cream liqueur (containing 17% alcohol, 25% carbohydrates and 13% fat)
[000594] Base: alcoholic, cream, cocoa
[000595] Base plus C18: 2 gaba 1 ppm: strongly increased alcohol effect, more cocoa, very creamy and long lasting aftertaste. Test on Heineken beer:
[000596] Base: Heineken beer (containing 4% alcohol)
[000597] Base: Bitter, like hops, fruity, malty, alcoholic
[000598] Base plus C18: 2 gaba 0.5 ppm: more hops, more bitter, more malt and stronger alcohol impact. Mouthwash test:
[000599] Base: Paradontax alcohol-free mouthwash.
[000600] Base: spicy, eugenol, mint, cool, burning, bitter
[000601] Base plus C18: 2 gaba 1 ppm: much less bitter, very sweet, soft, less fiery, full spicy, with more mint and more cooling. 18 - Testing of Leucine, IsoLeucine and Valine derivatives
[000602] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, salinity, umami, sweetener, juiciness, richness, long-lasting and fat. Comparison on a mango juice drink
[000603] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000604] Base: fruity mango
[000605] Base plus C16: 0-read at 2 ppm very fruity, ripe mango flavor, strawberry flavor
[000606] Base plus C18: 1-read at 2 ppm very long-lasting, ripe, fruity, juicy
[000607] Base plus C18: 0-read at 2 ppm as long-lasting, ripe, fruity strawberry
[000608] Base: fruity mango
[000609] Base plus C18: 2-val at 1 ppm ripe, very juicy good, full body, long lasting Test on a strawberry drink
[000610] Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavor @ 0.015%
[000611] Base: sweet, fruity, sterile, strawberry
[000612] Base plus C18: 0-read at 0.5 ppm authentic fruity strawberry, stronger strawberry, ripe, long-lasting, juicy Test on a strawberry yogurt
[000613] Base: Yogurt 1.5% fat yogurt, 8% sucrose, proprietary strawberry flavor @ 0.015%
[000614] Base: strawberry, fruity
[000615] Base plus C18: 0-read at 2 ppm authentic fruity strawberry, stronger, ripe, long-lasting, juicy, creamy yogurt. Test on peach flavored drink:
[000616] Base is water, 8% sugar, 0.1% citric acid, 0.05% proprietary peach flavor
[000617] Base: fruity peach
[000618] Base plus C18: 1-val at 1 ppm tropical, greasy, "skin", juicy
[000619] Base plus C16: 0-val at 1ppm very juicy Cam broth test:
[000620] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000621] Base: salted, umami, powder
[000622] Base plus C18: 2- val at 1 ppm plus umami, salivation, salty 19 - Test of proline derivatives
[000623] Samples were evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-lasting and fat. Comparison on a mango juice drink
[000624] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000625] Base: Fruity mango
[000626] Base plus C16: 0-pro at 1 ppm ultra-mature, long lasting orange flavor
[000627] Base plus C18: 1 -pro at 1 ppm sweet, albedo orange
[000628] Test on orange drink
[000629] Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavor @ 0.06%.
[000630] Base: orange, slightly sweet, fruity
[000631] Base plus C18: 2-pro at 1 ppm: authentic orange, very juicy Test on lemon drink
[000632] Base: water, 7% sucrose, 0.15% citric acid, proprietary lemon flavor
[000633] Base: floral, citral, lemon
[000634] Base plus C18: 2-pro at 1 ppm: very juicy, more citral type, very authentic Broth test
[000635] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000636] Base: salted, umami, powder
[000637] Base plus C16: 0-pro at 1 ppm: saltier, fuller, darker, more meat-like
[000638] Base plus C18: 1-pro at 1 ppm: full, plus umami, long lasting 20 - Test with methionine derivatives
[000639] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-lasting and fat
[000640] Comparison on a mango juice drink
[000641] Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000642] Base: fruity mango
[000643] Base plus C18: 2-met at 1 ppm: fresh, good, juicy
[000644] Base plus C18: 1-met at 1 ppm: more sweet, juicy, salivation.
[000645] Base plus C16: 0-met at 1 ppm: greasy, full body, juicy, metallic
[000646] Base plus C12: 1-met at 1 ppm: full ripe, more juicy, slightly metallic
[000647] Base plus 8: 0-met at 1 ppm: fresh green, no additional body Comparison in broth
[000648] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000649] Base: salted, umami, powder
[000650] Base plus C18: 2-met at 1 ppm: salivation, umami
[000651] Base plus C 18: 1-met at 1 ppm: very strong salty impact and residual taste
[000652] Base plus C16: 0-met at 1 ppm: salty, full, good salivation, prolonged
[000653] Base plus C12: 1 -met at 1 ppm: saltier
[000654] Base plus C8: 0-met at 1 ppm: saltier, no additional fullness
[000655] Base: salted, umami, powder
[000656] Base plus C18: 1-met at 1 ppm: very salty impact and residual taste, more greasy, oral sensation, prolonged full body
[000657] Base plus C18: 1-met at 50 ppb: saltier, more broth flavor
[000658] Base plus C18: 1-met at 25 ppb: more peppery, more salty Test on orange drink
[000659] Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavor @ 0.06%
[000660] Base: orange, slightly sweet, fruity
[000661] Base plus C16: 0-met at 1 ppm: slightly metallic, fresh
[000662] Base plus C18: 1-met at 1 ppm: very juicy, authentic, juicy fresh
[000663] Base plus C12: 1-met at 1 ppm: good orange, fresh Test on lemon drink
[000664] Water-based, 7% sucrose, 0.15% citric acid, proprietary lemon flavor
[000665] Base: floral, citrus, lemon
[000666] Base plus C 18: 1-met at 1 ppm: fresh, less floral, very juicy, very authentic
[000667] Base plus C12: 1-met at 1 ppm: fresh, slightly more citral 21 - Testing of serine derivatives
[000668] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, salinity, umami, sweetener, juiciness, richness, long-lasting and fat Comparison on a mango juice drink
[000669] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%.
[000670] Base: fruity mango
[000671] Base plus C18: 0-be at 1 ppm: good sweet, pineapple, long lasting
[000672] Base plus C18: 2-be at 1 ppm: apple note, less acidic, juicy
[000673] Comparison in meat sauce
[000674] Base is 1 tablet of Maggi broth in 500 ml of hot water
[000675] Base: salted, umami, powder
[000676] Base plus C18: 0-be at 1 ppm: saltier, richer, more umami
[000677] Base plus C18: 2-be at 1 ppm: more umami, slightly more salty, sweet Test on orange drink
[000678] Base is water, 7% sugar, 0.1% citric acid, proprietary orange flavor @ 0.06%.
[000679] Base: orange, slightly sweet, fruity
[000680] Base plus C18: 2-be at 1 ppm: very fresh, authentic, slightly less sweet, more juicy 22 - Testing of glycine derivatives
[000681] Samples were evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salivation, sweetener, juiciness, richness, long-lasting and fat
[000682] Comparison on an orange drink
[000683] Base: water, 8% sucrose, 0.1% citric acid, proprietary orange flavor @ 0.06%.
[000684] Base: orange, slightly sweet, fruity
[000685] Base plus C16: 0-gly at 1 ppm sweet after juicy taste
[000686] Base plus C18: 3-gly at 1 ppm advanced sweet, juicy, authentic, long lasting and residual sweet taste
[000687] Base plus C18: 2-gly at 1 ppm very juicy, salivation, authentic, long lasting and residual sweet taste. 23 - Testing of asparagine and qlutamate derivatives
[000688] Samples were evaluated by expert savorers, savorers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-lasting and fat. Test in pineapple flavored drink:
[000689] Base is water, 8% sugar, 0.1% citric acid and 0.03% proprietary pineapple flavor
[000690] Base: sweet pineapple, pasty
[000691] Base plus C18: 2-asn at 1 ppm very matured, pasty, long-lasting, authentic Test on pear flavored drink:
[000692] Base is water, 8% sugar, 0.1% citric acid, 0.025% proprietary pear flavor
[000693] Base: good pear, fruity, sterile, green
[000694] Base plus C18: 2-asn at 1 ppm very ripe, authentic pear, very juicy, long-lasting Base plus C18: 1-glu at 1 ppm ripe, authentic pear, juicy, like greasy skin Test on a strawberry drink
[000695] Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavor @ 0.015%
[000696] Base: sweet, fruity, rich, strawberry
[000697] Base plus C18: 2-asn at 0.5 ppm fuller, sweeter, pasty residual taste, long lasting
[000698] Base plus C18: 1 -gin to 0.5 ppm more juicy, creamy, long-lasting fruity
[000699] Comparison on a vanilla milk drink
[000700] Base: 0.15% fat milk, sweetened with 4% sucrose by weight, flavored with proprietary Vanillin @ 10 ppm + Vanilla extract @ 0.03%
[000701] Base: sweet vanillic, slightly grainy flavor
[000702] Base plus C18: 2-asn at 1 ppm sweeter plus greasy full Base plus C18: 1-glu at 1 ppm vanillic sweet
[000703] Base plus C18: 2-glu at 1 ppm vanillic, creamy, granular sweet 24 - Test alanine derivatives
[000704] Samples were evaluated by expert tastemakers. Tasteers were asked to describe samples that focus on authentic taste, oral sensation, fullness, salinity, salivation, umami, sweetener, juiciness, richness, long-lasting and fat. Test in the mango juice drink
[000705] Base is 8% sucrose, 0.1% citric acid, 1% clear mango juice, proprietary mango flavor @ 0.05%
[000706] Base: fruity mango
[000707] Base plus C18: 2-wing at 1 ppm: greasy, juicy, apple skin flavor Test on a strawberry drink
[000708] Base is 7% sucrose, 0.1% citric acid, proprietary strawberry flavor @ 0.015%
[000709] Base: sweet, fruity, strawberry, stero
[000710] Base plus C18: 2-wing at 0.5 ppm: creamy, fruity, juicy, green, long-lasting, strawberry Test on peach flavored drink:
[000711] Base is water, 8% sugar, 0.1% citric acid, 0.05% proprietary peach flavor
[000712] Base: fruity peach
[000713] Base plus C18: 2-wing at 1 ppm: improved sulfur note, powdered, soft peach skin type, authentic peach, light raspberry flavor

权利要求:
Claims (4)
[0001]
1. Flavor composition, characterized by the fact that it comprises a compound selected from the group consisting of: N-palmitoyl 1-amino-cyclopropyl carboxylic acid (C16: 0-ACCA), N-styroyl-1-amino-cyclopropyl carboxylic acid ( C18: 0-ACCA), N-linoleoyl 1-amino-cyclopropyl carboxylic acid (C18: 2-ACCA), N-linolenoyl 1-amino-cyclopropyl carboxylic acid (C18: 2-ACCA), N-oleoyl 1-amino acid -cyclopropyl carboxylic (C18: 1-ACCA), N- (9-palmitenoyl) 1-amino-cyclopropyl carboxylic acid (C16: 1-ACCA), N-decanoyl 1-amino-cyclopropyl carboxylic acid (C10: 0-ACCA) and N-geranoyl 1-amino-cyclopropyl carboxylic acid (C10: 2-ACCA) together with at least one flavoring co-ingredient selected from the group consisting of sugars, fats, salts, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof, optionally a carrier material and optionally an adjuvant.
[0002]
2. Edible composition, characterized by the fact that it comprises the flavor composition as defined in claim 1.
[0003]
3. Caloric or non-caloric drink according to claim 2, characterized by the fact that it contains carbohydrate sweeteners, selected from sucrose, high fructose corn syrup, fructose and glucose, or high intensity non-nutritive sweeteners selected from aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and / or other stevia-based sweeteners.
[0004]
4. Edible soy-based composition, characterized by the fact that it is as defined in claim 2.

类似技术:

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公开号 | 公开日

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US20200290952A1|2020-09-17|

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EP2830440A2|2015-02-04|

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EP2830440B1|2019-03-20|

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WO2013148965A3|2013-12-05|

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US20200290951A1|2020-09-17|

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WO2013148965A2|2013-10-03|

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US20150072060A1|2015-03-12|

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US20200299229A1|2020-09-24|

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SG11201405104PA|2014-10-30|

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JP6250029B2|2017-12-20|

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JP2015519298A|2015-07-09|

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KR20140146146A|2014-12-24|

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法律状态:
2018-05-02| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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2019-06-18| B06T| Formal requirements before examination [chapter 6.20 patent gazette]|

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2020-01-07| B07A| Technical examination (opinion): publication of technical examination (opinion) [chapter 7.1 patent gazette]|

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2020-05-05| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-10-27| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 28/03/2013, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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US201261617796P| true| 2012-03-30|2012-03-30|

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US61/617,796|2012-03-30|

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