FLAVORIZING COMPOSITION IN POWDER, AS WELL AS EDIBLE COMPOSITIONS OF SNACK AND POWDER REFRESHMENT UN

专利摘要:
invention patent summary: "powder flavoring composition". the present invention relates to a powdered flavoring composition comprising a compound according to formula (i) (1) or edible salts thereof, and at least one flavoring co-ingredient in which r1 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, r1 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-aminobutyric acid or beta alanine, or a 1- amino cycloalkyl carboxylic.
公开号:BR112014023941B1
申请号:R112014023941-0
申请日:2013-03-28
公开日:2020-07-14
发明作者:Harry Renes；Santi VORSTER；Adri De klerk；Feng Shi；Esther Van Ommeren；Yili Wang
申请人:Givaudan S.A.；
IPC主号:

专利说明:

[001] The present invention relates to flavoring compositions in the form of powders, edible compositions containing said flavoring compositions and methods of forming them. The invention also relates to methods of maintaining the organoleptic quality of flavoring oils, even if these are converted into powder form.
[002] In the field of food technology, it is conventional to convert flavoring oils into powder form, and there are many procedures currently available. Spray drying is a commonly used industrial method, along with freeze drying, continuous vacuum bed drying, and low temperature and reduced pressure drying methods that employ vacuum dryers.
[003] Spray drying involves presenting a flavoring oil in a liquid form, as in the form of a pure liquid, a solution, an emulsion or a dispersed particulate slurry. The flavoring oil is then introduced into a carrier gas stream, which then feeds it into a dispersive unit, such as a pressure nozzle, rotating disc or the like, which divides the liquid into small droplets and discharges them into a drying chamber. where the small droplets are dried within a very short time scale (on the order of 5 to 30 seconds) to form a powder.
[004] Spray drying is a very convenient method for mass production of powders. However, when flavoring oils are processed in this way, high conventional processing temperatures can result in loss of essential flavoring oil components through evaporation, or degradation of essential oil components, which will ultimately have a negative impact on quality. of the flavoring powder.
[005] Retention of flavor quality can be particularly problematic for flavorants that are relatively volatile, or that are prone to degradation at high temperatures. A particular problem arises in this regard with citrus oils. US2005 / 0031769 (Ajinomoto) and US 2013/0022728 (IFF) address this problem and both propose the use of low temperature spray drying procedures. While both of the described processes claim increased flavoring quality, however, low temperature procedures are less efficient and add processing time and costs.
[006] There is still a need to provide flavoring powders that maintain a good quality of flavoring oil and thus give intense, fresh and authentic flavors that are desired by consumers, regardless of the methods used to form them.
[007] The applicant met the problems of the prior art and found a simple and elegant solution to the problem that can maintain the quality of flavoring oils used in the formation of powders, regardless of the process used to form the powders, the solution lies in incorporating particular amino acid-fatty acid conjugates in powder compositions.
[008] Consequently, the invention provides in a first aspect a powdered flavoring composition comprising a compound according to formula (I) or edible salts thereof, and at least one flavoring co-ingredient
[009] where
[0010] 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-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.
[0011] Edible salts include those typically used in the food and beverage industry and include chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates and lactates.
[0012] As will be evident to the element skilled in the art, the proteinogenic amino acids are alanine (Ala), cysteine (Cys), aspartic acid (Asp), phenylalanine (Phe), glutamic acid (Glu), histidine (His), isoleucine (He), lysine (Lys), leucine (Leu), methionine (Met), asparagines (Asn), glutamine (Gin), arginine (Arg), serine (Ser), teronine (Thr), valine (Vai), tryptophan (Trp), tyrosine (Tyr), proline (Pro) or glycine (Gly).
[0013] The three letter codes in parentheses are common abbreviations used in relation to amino acids and these must be used from now on.
[0014] Carboxylic acids can also be represented by abbreviations. Henceforth, carboxylic acid residues can be referred to by the abbreviation Cn, where "n" represents the number of carbon atoms in the residue. For example, the residue of an 18-carbon acid can be abbreviated as C18. In addition, if the 18-carbon acid is saturated, for example, stearic acid. This can be abbreviated as C18: 0 (since it contains zero double bonds), while an 18-carbon acid that has a double bond - for example, oleic acid - can be abbreviated as C18: 1. In addition, 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 is in the trans configuration, then the abbreviation becomes C18: 11.
[0015] 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) can now be represented in that abbreviated form.
[0016] As is evident from the above formula (I), an amino nitrogen atom in the amino acid residue is attached to a carbonyl carbon atom of the carboxylic acid residue to form an amide bond. Some amino acids have more than one amino group, and the amide bond can be formed at any of these amino groups. However, for any of the compounds specifically described below, if the amino acid residue contains more than one amino group, the link is made to the alpha amino group.
[0017] In a particular embodiment of the present invention, the carboxylic acid residue is a fatty acid residue.
[0018] The fatty acid residue can be the residue of a C8 to C22 fatty acid. 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 that 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; henicosanoic 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-nonadecadienoic acid; 11-trans-eicosenoic acid; and 12-transenicosenoic acid.
[0019] Fatty acid residues can be saturated or unsaturated. If these are unsaturated, it is preferred that they have 1, 2 or 3 double bonds, which can be in cis- or trans- configuration. More particularly, the preferred fatty acid residues are C16 to C18, and can be saturated or unsaturated.
[0020] Elements skilled in the art will assess, however, that the natural sources of these fatty acids, for example, almond oil, avocado oil, castor oil, coconut oil, corn oil, cottonseed oil, olive oil, peanut oil, rice bran oil, safflower oil, sesame oil, soybean 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 may contain other fatty acids, such as linolenic acid (C18: 3) and palmitic acid (C16: 0), among others. Consequently, a 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.
[0021] The compounds of the formula (I) can contain chiral atoms, and just as these can be presented in racemic form, as a mixture of stereoisomers or as resolved as simple isomers. The use of the term "a compound of the formula (I)" can refer to both mixtures of resolved isomers or simple isomers.
[0022] In particular, the compounds of formula (I) may contain the residue of D- or L-amino acids.
[0023] 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 carried out 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 water-based solvent / THF system. Yield and reaction times can be increased 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.
[0024] In yet another embodiment, an alkyl ester amino acid can be reacted with a carboxylic acid chloride under basic conditions in an aqueous-based solvent, such as a water-based solvent / THF system. Then, the ester can be carefully hydrolyzed without affecting the amide bond in aqueous basic methanol solution.
[0025] 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 carefully hydrolyzed without affecting the amide bond in dilute aqueous basic methanol solution.
[0026] In yet another modality, an anhydride (mixed) of a carboxylic acid is reacted with an amino acid in dioxane.
[0027] In yet another embodiment, an alkyl ester carboxylic acid can be reacted with an amino acid in dioxane. In yet another embodiment, an alkyl ester amino acid is reacted with a triglyceride, optionally in the presence of a cosolvent. The ester amino acid formed in this way is then hydrolyzed according to a method described above.
[0028] In yet another modality, an amino acid is reacted with a triglyceride, optionally in the presence of a cosolvent.
[0029] In yet another modality, an amino acid is reacted with a triglyceride in the presence of a lipase, esterase, peptidase, amidase or acylase, optionally in the presence of a cosolvent and / or water.
[0030] In yet another embodiment, an alkyl ester carboxylic acid is reacted with an amino acid in the presence of a lipase or acylase, optionally in the presence of a co-solvent and / or water.
[0031] In an embodiment of the present invention, the compounds of formula (I) represented by formula
[0032] its edible salts, and their use in edible compositions
[0033] where
[0034] Ri is defined above, and
[0035] n is 1,2, 3 or 4.
[0036] Preferred compounds are those where "n" is 1.
[0037] The amino acid residue described in the formula above can be abbreviated as "ACCA".
[0038] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and
[0039] Compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA.
[0040] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA, where the carboxylic acid residue is saturated.
[0041] The compounds include C8-ACCA, C9-ACCA, C10-ACCA, C12-ACCA, C14-ACCA, C16-ACCA, C18-ACCA, C20-ACCA and C22-ACCA, where the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. The double bonds can be in cis-, trans- configuration or a mixture of cis- and trans- configuration.
[0042] The compounds include those specified above in which the cycloalkane ring in the amino acid residue is cyclopropane (n = 1).
[0043] 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 - cyclopropyl carboxylic acid (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 (C16: 1-ACCA), N-decanoyl 1-amino-cyclopropyl carboxylic acid (C10: 0-ACCA) and N-geranoyl 1-amino-cyclopropyl carboxylic acid (C10: 2-ACCA).
[0044] The present invention provides in another embodiment the compounds of formula (I) represented by the formula
[0045] and its edible salts, and their use in edible compositions
[0046] where Ri, is defined above, and
[0047] m is 0 or 1.
[0048] It will be evident to the skilled person 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 beta-alanine residue. (Beta Wing). Both compounds of formula (I) where m is 1 and the amino acid residue is a GABA residue, and 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 embodiments of the present invention.
[0049] Those compounds are particularly useful for incorporation into an edible product to impart a remarkable mouth feeling, body and high fat perception; or a strong umami or salt flavor; or refreshing and rich. These are particularly useful in low-fat, salt and umami applications. These are also useful in fat-free formulations such as drinks and mouth care applications. These also find use in applications in dairy products and in vanilla, cocoa and chocolate.
The compounds include C8-GABA, C9-GABA, C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, C20-GABA and C22-GABA.
[0051] 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.
[0052] 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 cis-, trans- configuration or a mixture of cis- and trans- configuration.
[0053] 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. A C18: 2-GABA compound is more preferred.
[0054] 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 .
[0055] 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.
[0056] 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 cis configuration, trans configuration or a mixture of cis and trans configuration.
[0057] A preferred compound is C18: 2-Beta Ala.
[0058] The present invention provides in another embodiment the compounds of formula (I) represented by the formula
[0059] and its edible salts, and their use in compositions edible compositions
[0060] where
[0061] Ri, it's defined above,
[0062] R3 is hydrogen or methyl, and
[0063] R4 is methyl, ethyl or isopropyl.
[0064] Particular compounds are those in which R3 is hydrogen and FU is isopropyl; R3 is methyl and FU is methyl; and R3 is methyl and FU is ethyl. The person skilled in the art will assess 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 FU is methyl, is the Valine (Vai) residue; and the amino acid residue, where R3 is methyl and FU is ethyl, is the iso-Leucine (He) residue.
[0065] The compounds in which R3 is hydrogen and R4 is isopropyl, R3 is methyl and FU is methyl; and R3 is methyl and R4 is ethyl, as well as its use in edible compositions, are embodiments of the present invention.
[0066] These compounds are particularly useful for enhancing authentic fruity profiles. These can also find use in milk, yogurt and fruit flavored ice cream.
The compounds include C8-Leu, C9-Leu, C10-Leu, C12-Leu, C14-Leu, C16-Leu, C18-Leu, C20-Leu and C22-Leu.
[0068] 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.
[0069] 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 is contains 1, 2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[0070] Particular compounds containing 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.
The compounds include C8-lle, C9-He, C10-He, C12-He, C14-He, C16-He, C18-He, C20-lie and C22-He.
[0072] 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.
[0073] The compounds include C8-lle, C9-He, C10-He, C12-He, C14-He, C16-He, C18-He, C20-He and C22-lie, wherein the carboxylic acid residue is unsaturated is contains 1,2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[0074] A particularly preferred compound having the He residue is N-oleoyl-lle.
[0075] The compounds include C8-Val, C9-Val, C10-Val, C12-Val, C14-Val, C16-Val, C18-Val, C20-Val and C22-Val.
[0076] 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.
[0077] 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 is contains 1, 2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[0078] Particularly preferred compounds having the Vai residue include N-palmitenoyl-L-valine, N-palmitoyl-L-valine, N-linolenoyl-L-valine, N-linoleoyl-L-valine and N-oleoyl-L -valine.
[0079] In another embodiment of the invention, compounds of formula (I) corresponding to formula
[0080] its edible said, and its use in edible compositions
[0081] where
[0082] Ri, it is defined above.
[0083] The person skilled in the art will assess that the amino acid residue in the compounds defined above is the proline residue (Pro).
[0084] These compounds are particularly effective in increasing the typical citrus juiciness and authenticity. These find use particularly in powdered drinks and soft drinks, and also in applications in dairy products, such as milk, yogurt and fruit flavored ice cream.
[0085] The compounds include C8-Pro, C9-Pro, C10-Pro, C12-Pro, C14-Pro, C16-Pro, C18-Pro, C20-Pro and C22-Pro.
[0086] 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.
[0087] The compounds include C8-Pro, C9-Pro, C10-Pro, C12-Pro, C14-Pro, C16-Pro, C18-Pro, C20-Pro and C22-Pro, where the carboxylic acid residue is unsaturated is contains 1,2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[0088] Particularly preferred compounds have the residue Pro N-geranoil-Pro, N-palmitoyl-Pro, N-palmiteneoil-Pro, N-stearoil-Pro, N-linoleoil-Pro and N-linolenoyl-Pro.
[0089] In another embodiment of the invention, compounds of formula (I) corresponding to formula
[0090] its edible said, and its use in edible compositions
[0091] where
[0092] Ri, it's defined above,
[0093] XéOHouNH2e
[0094] P is 0 or 1.
[0095] The technician will evaluate that when p is 0 and X is OH, the amino acid residue presented 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).
[0096] Compounds that have an aspartic acid residue, compounds that have a glutamic acid residue, compounds that have an asparagine residue, and compounds that have a glutamine residue, as well as their edible salts, and their use in edible compositions, each represents particular embodiments of the present invention.
[0097] These compounds are particularly useful for enhancing the salty character, taste and performance of full flavor, juiciness and salivation. These can find use in low salt, low umami and low fat applications as well as fruit flavored drinks as well as dairy products.
The compounds include C8-Glu, C9-Glu, C10-Glu, C12-Glu, C14-Glu, C16-Glu, C18-Glu, C20-Glu and C22-Glu.
[0099] 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.
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 is contains 1,2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[00101] Particularly preferred compounds that have the Glu residue include N-geranoyl-Glu, N-palmitoyl-Glu, N-palmitenoyl-Glu, N-stearoyl-Glu, N-linoleoyl-Glu and N-linolenoyl-Glu.
[00102] The compounds include C8-Asp, C9-Asp, C10-Asp, C12-Asp, C14-Asp, C16-Asp, C18-Asp, C20-Asp and C22-Asp.
[00103] 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.
[00104] 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 is contains 1, 2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[00105] Particularly preferred compounds which have the Asp residue include N-geranoyl-Asp, N-palmitoyl-Asp, N-palmitenoyl-Asp, N-stearoyl-Asp, N-linoleoyl-Asp and N-linolenoyl-Asp.
[00106] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gin, C14-Gin, C16-Gin, C18-Gin, C20-Gin and C22-Gin.
[00107] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gin, C14- Gin, C16- Gin, C18- Gin, C20- Gin and C22- Gin, wherein the carboxylic acid residue is saturated.
[00108] The compounds include C8-Gln, C9-Gin, C10-Gin, C12-Gin, C14- Gin, C16- Gin, C18- Gin, C20- Gin and C22- Gin, wherein the carboxylic acid residue is unsaturated is contains 1,2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[00109] Particularly preferred compounds which have the Gin residue include N-geranoyl-GIn, N-palmitoyl-GIn, N-palmitenoyl-GIn, N-stearoyl-GIn, N-linoleoyl-GIn and N-linolenoyl-GIn.
[00110] The compounds include C8-Asn, C9-Asn, C10-Asn, C12-Asn, C14-Asn, C16-Asn, C18-Asn, C20-Asn and C22-Asn.
[00111] 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.
[00112] 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 é contains 1, 2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[00113] Particularly preferred compounds which have the Asn residue include N-geranoyl-Asn, N-palmitoyl-Asn, N-palmitenoyl-Asn, N-stearoyl-Asn, N-linoleoyl-Asn and N-linolenoyl-Asn.
[00114] In another embodiment of the invention, compounds of formula (I) corresponding to formula
[00115] its edible salts, and their use in edible compositions
[00116] where
[00117] Ri is defined above.
[00118] The element skilled in the art will evaluate that in the above formula the amino acid residue is the methionine residue [Met).
[00119] These compounds are particularly effective in increasing juiciness and salivation, as well as the authenticity of fruits. These are also useful in soft drink applications for their masking properties.
[00120] The compounds include C8-Met, C9-Met, C10-Met, C12-Met, C14-Met, C16-Met, C18-Met, C20-Met and C22-Met
[00121] 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.
[00122] 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 é contains 1, 2 or 3 double bonds. The double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[00123] Particularly preferred compounds that have the Met residue include N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met.
[00124] In another embodiment of the invention, compounds of formula (I) corresponding to formula
[00125] its edible salts, and their use in edible compositions
[00126] where
[00127] Ri is defined above.
[00128] The element skilled in the art will evaluate that in the formula above the amino acid residue is the serine residue (Ser).
[00129] These compounds find particular use in low salt, umami and fat applications, fruit flavored drinks and / or dairy products.
[00130] The compounds include C8-Ser, C9-Ser, C10-Ser, C12-Ser, C14-Ser, C16-Ser, C18-Ser, C20-Ser and C22-Ser.
[00131] 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.
[00132] 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 cis configuration, trans configuration or a mixture of cis and trans configuration.
[00133] Particularly preferred compounds having the Ser residue include N-palmitoyl-Ser, N-palmitenoyl-Ser, N-stearoyl-Ser, N-linoleoyl-Ser and N-linolenoyl-Ser.
[00134] Other compounds useful in the present invention include:
[00135] N-octanoyl-L-phenylalanine, N-eicosanoil-L-phenylalanine, N-palmitoleoyl-L-phenylalanine, N-palmitoyl-L-phenylalanine, N-linolenoyl-L-phenylalanine, N-linoleoyl-L-phenylalanine , N-oleoyl-L-phenylalanine, N-SDA-L-phenylalanine, N-DPA-L-phenylalanine, and N-tetracosaexaenoyl-L-phenylalanine;
[00136] N-palmitoyl-L-alanine, N-linolenoyl-L-alanine, N-linoleoyl-L-alanine;
[00137] N-palmitoyl-L-tyrosine, N-linoleoyl-L-tyrosine, N-oleoyl-L-tyrosine, N-linolenoyl-L-tyrosine;
[00138] N-palmitoyl-L-tryptophan, N-linolenoyl-L-tryptophan, N-linoleoyl-L-tryptophan; and N-linoleoyl-glycine.
[00139] Preferably, the compounds of formula (I) do 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.
[00140] The compounds of formula (I) impart remarkable organoleptic properties to edible compositions to which they are added. In particular, they give a highly intense, authentic and harmonious flavor, and a harmony and vigor to edible compositions that contain them.
[00141] This discovery was the most surprising considering that when the applicant tasted the compounds in dilute aqueous solution, they exhibited a disappointing, slightly greasy taste profile. As a result, these appeared to be totally unsuitable for use in flavor applications. Only its combination with flavoring co-ingredients and the careful selection of their levels of use was it possible to discover the remarkable organoleptic properties of these compounds. If effect on edible compositions is quite unusual, because instead of presenting a flavor profile characteristic of a foodstuff or a drink, they really complement, elevate or accentuate the essential or authentic flavor and mouthfeel characteristics of food or drinks in which these are incorporated. Consequently, 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.
[00142] Consequently, the invention provides in another aspect, a method of imparting taste and / or mouthfeel, or improving the taste and / or mouthfeel of an edible composition, that method comprises adding to said composition a compound of the formula [I ] defined here.
[00143] The remarkable organoleptic effects are observed when the compounds of formula (I) are incorporated into an edible composition containing one or more flavoring co-ingredients.
[00144] The flavoring co-ingredients can be sugars, fats, salt (for example, sodium chloride), MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.
[00145] In a particular embodiment, sugars are present in amounts of 0.001% to 90%, more particularly 0.001% to 50%, even more particularly 0.001% to 20% based on the total weight of an edible composition.
[00146] In a particular embodiment, fats are present in amounts from 0.001% to 100%, more particularly 0.001% to 80%, more particularly 0.001% to 30%, even more particularly 0.001% to 5% based on the total weight of an edible composition.
[00147] In a particular embodiment, salt (for example, sodium chloride) is present in amounts of 0.001% to 20%, more particularly 0.001% to 5% based on the total weight of an edible composition.
[00148] In a particular embodiment, MSG is present in amounts from 0.001% to 2% based on the total weight of an edible composition.
[00149] In a particular embodiment, calcium is present in amounts of 0.001% to 50% more particularly 0.001% to 20%, even more particularly 0.001% to 1% based on the total weight of an edible composition.
[00150] In a particular embodiment, organic acids are present in amounts of 0.001% to 10%, more particularly 0.001% to 7% based on the total weight of an edible composition.
[00151] Types of organic acids include citric, malic, tartaric, fumaric, lactic, acetic and succinic acid. Types of edible compositions containing organic acids include drinks, such as carbonated drinks, non-carbonated drinks, juices, powdered soft drinks, liquid concentrates, alcoholic beverages and functional drinks.
[00152] 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 phosphoric acid.
[00153] In a particular embodiment, purines are present in an amount up to 0.5% by weight of an edible composition. The term "purines" includes ribonucleotides such as IMP and GMP.
[00154] Despite its interesting organoleptic properties, however, the applicant has found that the formulation of the compounds of formula (I) is not a trivial issue. The discovered potency of the compounds suggested that they could be used at very low levels in flavor applications, and so for ease of handling, mixing and processing with other ingredients, although it is possible to use the compounds in pure form, it is desired to extend or add volume to the physical form of the compounds by incorporating them in a suitable vehicle, for example, a diluent, such as a solvent. However, the compounds are solid or viscous oils at room temperatures, and have very limited water solubility. The applicant found that at least about 0.01% of stock solution, more particularly about 0.01 -1% of stock solution of a compound of formula (I) obtained a balance regarding acceptable solvent levels for ease of handling and mixing, and the desire to limit the amount of solvent that could be removed from the stock solution when further processing of the compounds into flavoring compositions and edible products for reasons of palatability, efficiency, cost and the like. The Applicant has found that suitable solvents for the stock solution include ethanol, triacetin, glycerol and migliol.
[00155] To assist the solubilization process and produce a stock solution and minimize the amount of solvent, it is preferred to use the compounds of formula (I) formed from a mixture of carboxylic acids, instead of a pure carboxylic acid.
[00156] Consequently, the invention provides in another aspect at least about 0.01% stock solution, more particularly about 0.01 -1% stock solution of a compound of formula (I).
[00157] The stock solution may contain other materials such as carrier materials and / or adjuvants more fully described below. In a particular embodiment, the stock solution contains an antioxidant selected from the group consisting of vitamin C, vitamin E, rosemary extract, anthrancine, butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT). Antioxidants are preferably employed to prevent or significantly reduce the generation of unwanted volatile notes as a result of degradation of the compounds of formula (I). Antioxidants are particularly preferred when the compounds of formula (I) have an unsaturated fatty acid residue. Antioxidants are particularly preferred if the fatty acid residue contains more than 1 double bond. The determination of an effective amount of antioxidant is within the purview of the element skilled in the art, however, amounts in the range of about 10 ppm to 1000 ppm based on the weight of the stock solution may be present.
[00158] When preparing the flavoring compositions of the present invention, the compounds of formula (I) can be used in any physical form. These can be used in pure form, in the form of a stock solution described above; these can be used in the form of an emulsion; or these can be used in a powder form. If the compounds of formula (I) are in the form of a powder, the powder form can be produced by a dispersive evaporation process, such as a spray drying process as more fully described below. The powder form can be prepared by subjecting a liquid formulation containing a compound of formula (I) to a dispersive evaporation process. The liquid formulation can comprise a solution, suspension or emulsion that comprises the compound of formula (I). In particular, the liquid formulation can take the form of the stock solution described above. The liquid formulation can contain other ingredients such as a carrier material and / or an adjuvant as more fully described below.
[00159] A powder composition comprising a compound of formula (I) forms another aspect of the present invention.
[00160] The compounds of formula (I) can be incorporated into an edible composition individually, or in the form of a powdered flavoring composition comprising one or more flavoring co-ingredients.
[00161] A powdered flavoring composition comprising a compound according to formula (1) and at least one flavoring co-ingredient forms another aspect of the present invention.
[00162] In a particular embodiment of the present invention, the powdered flavor composition comprises:
[00163] i) a compound according to formula (I);
[00164] ii) at least one flavoring co-ingredient;
[00165] iii) optionally a vehicle material; and
[00166] iv) optionally at least one adjuvant.
[00167] The term "flavoring co-ingredient" is understood to mean an ingredient that is capable of contributing or conferring or modifying in a positive or pleasant way the flavor of an edible composition.
[00168] Any form of flavoring co-ingredients can be used in a composition according to the present invention, including, but not limited to, natural flavors, artificial flavors, spices, seasonings, and the like. Flavoring co-ingredients include synthetic and aromatic oils and / or flavoring oils, oleoresins, essences, distillates, and extracts derived from plants, leaves, flowers, fruits, and so on, and combinations that comprise at least one of the above.
[00169] Flavoring oils include 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, nutmeg flower, bitter almond oil, and cinnamon 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, raisins, cola, guarana, neroli, pineapple, banana, melon, apricot, japanese plum, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya and the like.
[00170] Additional exemplary flavorings conferred by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; flavors of tea or coffee, such as green tea flavor, oolong tea flavor, tea flavor, cocoa flavor, chocolate flavor, and coffee flavor; mint flavors, like a peppermint flavor, a mint flavor, and a Japanese mint flavor; spicy flavors, such as asafetida flavor, ajowan flavor, anise flavor, angelica flavor, fennel flavor, allspice flavor, cinnamon flavor, chamomile flavor, flavor mustard flavor, cardamom flavor, caraway flavor, cumin flavor, clove flavor, pepper flavor, coriander flavor, sassafras flavor, salty flavor, Zanthoxyli Fructus flavor, flavor perilla, juniper berry flavor, ginger flavor, star anise flavor, horseradish flavor, thyme flavor, tarragon flavor, dill flavor, capsule flavor, nutty flavor - nutmeg, a basil flavor, a marjoram flavor, a rosemary flavor, a bay leaf flavor, and a wasabi flavor (Japanese horseradish); a nutty flavor like an 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 a wine flavor, a whiskey flavor, a cognac flavor, a rum flavor, a gin flavor, and a liquor flavor; floral flavors; and vegetable flavors, like an onion flavor, a garlic flavor, a cabbage flavor, a carrot flavor, a celery flavor, a mushroom flavor, and a tomato flavor.
[00171] In some embodiments, said flavoring co-ingredients include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal, dihydrocarvyl acetate, eugenyl 49 format, p-methylamisole, and so on. Additional examples of aldehyde flavorings include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (liquor, analysis), cinnamic aldehyde (cinnamon), citral, that is, alpha-citral (lemon, lime), neral, ie is, beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope, that is, piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde ( spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies, many types), decanal (citrus), aldehyde C-8 (citrus), aldehyde C-9 (citrus) , C-12 aldehyde (citrus fruits), 2-ethyl butyraldehyde (wild fruits), hexenal, ie, trans-2 (wild fruits), tolyl aldehyde (cherry, almond), veratraldehyde (vanilla), 2,6-dimethyl -5-heptenal, that is, melonal (melon), 2,6-dimethyloctanal (green fruits), and 2-dodecenal (citrus, mandarin), and the like.
[00172] Additional examples of flavoring co-ingredients can be found in "Chemicals Used in Food Processing", publication 1274, pages 63-258, by the National Academy of Sciences.
[00173] Flavoring co-ingredients can also include salt flavors, umami flavors, and savory flavor compounds. Non-limiting examples include: NaCI, KC1, 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) dioxol-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.
[00174] In particular embodiments of the present invention, the flavoring co-ingredient is selected from the compounds and compositions described in W02005102701, W02006009425, W02005096843, W02006046853 and W02005096844, whose references are hereby incorporated by reference in their entirety.
[00175] Flavoring co-ingredients may include salt flavors, umami flavors, and known savory flavoring compounds. Non-limiting examples include: NaCI, KCI, MSG, guanosine monophosphate (GMP), inosine monophosphate (IMP), ribonucleotides such as disodium inosinate, disodium guanylate, N- (2-hydroxy ethyl) -lactamide, N-lactoyl-GMP, N-lactoyl tyramine, gamma amino butyric acid, allyl cysteine, 1- (2-hydroxy-4-methoxyphenyl) -3- (pyridin-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 ] dioxol-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.
[00176] The carrier material can be used in compositions according to the invention to encapsulate or trap the other components of the composition in a matrix. The function of the carrier material can be simply that of a processing aid or a bulking agent, or it can be used to protect the other components from the effects of moisture or oxygen or any other aggressive medium. The carrier material can also act as a means of controlling the release of flavor from edible compositions.
[00177] The carrier materials may include mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, 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, chemically starch modified, hydrogenated starch hydrolyzate, succinylated or hydrolyzed starch, agar, carrageenan, gum arabic, acacia gum, tragacanth, alginates, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, derivatives and mixtures thereof. Naturally, those skilled in the art will appreciate that the materials cited are provided here by way of example and should not be construed as limiting the invention.
[00178] By "flavoring adjuvant" is meant an ingredient capable of conferring additional benefits to the compositions of the present invention such as color, resistance to light, 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-exhaust agents, 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).
[00179] Examples of such vehicles or adjuvants for flavoring compositions can be found, for example, in "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 Flavors, E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), 1sted., The Cosmetic, Toiletrye Fragrance Association, Inc ., Washington, 1988.
[00180] Other suitable and desired ingredients of flavoring compositions are described in standard texts, such as "Handbook of Industrial Chemical Additives", ed. M. and I. Ash, 2nd Ed., (Synapse 2000).
[00181] Powder flavoring compositions are prepared by any dispersive evaporation techniques generally known in the art. An example of this technique is spray drying.
[00182] The manner in which the compounds of formula (I) are incorporated into the powdered flavoring compositions of the invention is not important. For example, flavoring co-ingredients, and any additional optional ingredients, can be formed into a powder, before the compound of formula (I) is mixed with the powder. Alternatively, the compounds of formula (I), flavoring co-ingredients and any optional ingredients can be mixed to form a liquid composition, the total is then subjected to a dispersive evaporation process.
[00183] The liquid composition used in the preparation of the powder may be in the form of a solution, emulsion, dispersion or slurry. 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.
[00184] Consequently, in one embodiment of the invention, a method of producing a powdered flavoring composition is provided which comprises:
[00185] I) providing a liquid composition comprising at least one flavoring co-ingredient, and any optional ingredients including a carrier material or an adjuvant in the form of droplets dispersed in a gaseous atmosphere; and
[00186] II) drying said droplets to form a powder.
[00187] In a particular embodiment, a compound of formula (I) forms part of said liquid composition.
[00188] In another particular embodiment, a compound of formula (I) is added to the powder formed during step II).
[00189] Powder flavoring compositions according to the present invention can be prepared according to methods and apparatus known in the art to produce powders on an industrial scale. A particularly suitable method is spray drying. Spray drying devices and techniques are well known and do not need detailed discussion here. The spray drying techniques, apparatus and methods described in US2005 / 0031769 and US2013 / 0022728, as well as those techniques, apparatus and methods described in those documents are suitable for producing powder compositions of the present invention and are incorporated herein by reference in its entirety.
[00190] Many of the flavoring co-ingredients described here are volatile and / or may be sensitive to oxidative degradation, particularly when subjected to high temperature, and under humid conditions. Consequently, particular problems can arise when the flavoring co-ingredients described above are subjected to dispersive evaporation processes such as spray drying. A non-exhaustive list of ingredients that may be particularly susceptible includes, those ingredients that contain artificial, natural or synthetic fruit flavors such as vanilla, chocolate, coffee, cocoa and citrus oil, which include lemon, orange, grape, lime and grapefruit, and fruit essences that include apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple, apricot and the like. The volatile components of these flavoring co-ingredients can include, but are not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate. Flavoring co-ingredients containing volatile aldehydes or esters include, for example, cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl formate, and p-methylanisole. Additional examples of volatile compounds that may be present 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); ethyl vanillin (vanilla, cream); heliotropin, that is, piperonal (vanilla, cream); vanillin (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 (wild fruits); hexenal, that is, trans-2 (wild fruits); 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); cherry; or grape and mixtures of these.
[00191] By incorporating a compound of formula (I) into a powdered flavoring composition, it is possible to obtain flavor quality reminiscent of flavoring oils used in the formation of powders.
[00192] Consequently, the invention provides in another aspect a method of maintaining the flavor quality of a powdered flavoring composition comprising the step of including in said powdery flavoring composition a compound of formula (I).
[00193] The powdered flavoring compositions of the present invention can be incorporated into edible compositions. An edible composition containing a powdered flavoring composition forms another aspect of the present invention.
[00194] Powder flavoring compositions can be added in powder form to an edible composition. Alternatively, the powdered flavoring composition can be reconstituted in a suitable liquid and added to an edible composition in the form of a solution, dispersion, emulsion, paste, or the like. Flavoring compositions according to the present invention can be provided in any suitable physical form. For example, these can be in the form of oils, emulsions or dispersions in a fluid or organic liquid suitable for use in edible compositions, or solid form, such as powders.
[00195] The term "edible composition" refers to products for consumption by an individual, typically through the oral cavity (although consumption may occur through non-oral means such as inhalation), for at least one of the purposes of satisfaction benefits, nutrition or health and well-being. Edible compositions can be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, tapes, powders, gels, gums, pastes, pastes, syrups, aerosols and sprays. The term also refers, for example, to dietary and nutritional supplements. Edible compositions include compositions that are placed inside the oral cavity for a period of time before being discarded, but not swallowed. These can be put in the mouth before they are consumed, or they can be kept in the mouth for a period of time before being discarded. An edible composition as defined above includes compositions whose flavor is modified in the manner described herein by adding compounds of formula (I) or whose flavor is then modified by processing so that it is enriched in a compound of formula (I).
[00196] In general, the edible composition includes, but is not limited to, foodstuffs of all kinds, confectionery products, bakery products, sweet products, salty products, fermented products, dairy products, drinks and oral hygiene products .
[00197] In a particular embodiment, the term "edible compositions" refers to products for consumption by an individual, typically through the oral cavity (although consumption may occur through non-oral means such as inhalation), for one of the purposes of satisfaction or nutrition.
[00198] In a more particular embodiment, the term "edible compositions" refers to products for consumption by an individual, typically through the oral cavity (although consumption may occur through non-oral means such as inhalation), for the purpose of satisfaction . Even more particularly, the term refers to food and drink.
[00199] In a particular embodiment, the term "edible composition" does not refer to pharmaceutical compositions.
[00200] In a particular modality, the term "edible composition" does not refer to nutritional supplements.
[00201] Exemplary foodstuffs include, but are not limited to, chilled, sweet and savory snacks, fruit snacks, chips / crisps, extruded snacks, corn tortilla / snacks, popcorn, pretzels, nuts, other sweet and savory snacks, bars snack bars, granola bars, morning bars, energy bars, fruit bars, other snack bars, meal replacement products, weight loss products, replenishing drinks, ready meals, canned ready meals, frozen ready meals, dry ready meals, meals ready-made chilled, dinner mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, chilled soup, uht soup, frozen soup, pasta, canned pasta, dry pasta, chilled / fresh pasta, macaroni, simple noodles, instant noodles, instant noodles in a glass / bowl, instant noodles in bags, refrigerated instant noodles, dry foods, mixtures for dessert, sauces, seasonings and condiments, herbs and spices, pastes, jellies and preserves, honey, chocolate pastes, walnut-based pastes, and yeast-based pastes.
[00202] Exemplary confectionery products include, but are not limited to, chewing gum (which includes sugared gum, sugar-free gum, functional gum and gum), confectionery with central filling, chocolate and other chocolate products, medicinal confectionery, tablets , lozenges, candies, candies, energy candies, chewy candies, hard candies, baked candies, breath films and other oral hygiene films or tapes, candy canes, lollipops, gums, gelatins, fudge, caramel, sugary products hard and soft, toffee, butterscotch, licorice, jelly candies, jelly beans, jelly beans, nougats, fondants, combinations of one or more of these, and edible flavoring compositions that incorporate one or more of these.
[00203] Exemplary bakery products include, but are not limited to, alfajores, bread, packaged / processed bread, unpacked / artisan bread, pastries, cakes, packaged / industrialized cakes, unpacked / artisan cakes, cookies, biscuits chocolate, biscuit sandwich, stuffed cookies, crackers and crackers, bread substitutes. Exemplary sweet products include, but are not limited to, breakfast cereals (breakfast cereals, ready for consumption "rte"), family cereals, flakes, muesli, other ready-to-eat cereals, children's breakfast cereals, hot cereals.
[00204] Exemplary savory products include, but are not limited to, snacks (potato chips, nuts, toasted tortilla, pretzels, cheese snacks, corn snacks, potato snacks, ready-to-eat popcorn, micro-popcorn waves, crackling, nuts, crackers, crunchy snacks, breakfast cereals, meats, aspic, cured meats (ham, bacon), cold cuts / cold cuts (hot dogs, sausages), tomato products, margarine, peanut butter, soup (thin, canned, cream, instant, UHT), canned vegetables, pasta sauces.
[00205] Exemplary dairy products include, but are not limited to, cheese, cheese sauces, cheese-based products, ice cream, ice cream for immediate consumption, milk-based ice cream for single portion, water-based ice cream for single portion , multipacked milk-based ice cream, multipackaged water-based ice cream, take-home ice cream, milk-based ice cream to take home, ice cream desserts, bulk ice cream, water-based ice cream to take for home, frozen yogurt, artisanal ice cream, dairy products, milk, fresh / pasteurized milk, fresh / pasteurized whole milk, fresh / pasteurized semi-skimmed milk, long-life milk / uht, long-life milk / uht whole, long-life milk / uht semi-skimmed milk, long-life milk / uht nonfat, goat milk, condensed / evaporated milk, simple condensed / evaporated milk, flavored, functional and other condensed milk, flavored dairy drinks, flavored dairy drinks with milk, dairy drinks flavored with fruit juice, soy milk, sour milk drinks, fermented milk drinks, coffee cream, powdered milk, flavored powdered milk drinks, cream, yogurt, plain yogurt / natural, flavored yogurt, fruit yogurt, probiotic yogurt, drinking yogurt, normal drinking yogurt, probiotic drinking yogurt, chilled desserts and non-perishable desserts, milk-based desserts, soy-based desserts.
[00206] Exemplary drinks include, but are not limited to, flavored water, soft drinks, fruit drinks, coffee-based drinks, tea-based drinks, juice-based drinks (including fruits and vegetables), drinks based on milk, gel drinks, carbonated or non-carbonated drinks, powdered drinks, alcoholic or non-alcoholic drinks.
[00207] 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 fish products based on grain, fruit and fruit-based products.
[00208] In a particular modality, 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 chips or snacks extruded.
[00209] The compounds of formula (I), when added to a flavoring composition and / or an edible composition, act on a composition to complement its taste and / or mouthfeel to make it more tasty and authentic. The effects can be temporal or related to the intensity, for example, the compounds can act to increase, accentuate, soften, sharpen a flavor, or produce 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 lasting effect.
[00210] The compounds of formula (I) can modify any aspect of the time profile of taste or taste of an edible composition. In particular, the compounds improve mouthfeel and give you more creamy and greasy sensations.
[00211] The compounds of the formula (I) or flavoring compositions containing them can be added to the edible compositions in widely countable quantities. The amount will depend on the nature of the edible composition to be flavored, and the desired effect, as well as the nature of the ingredients present in said flavoring composition. To obtain the notable beneficial effects attributed to the presence of the compounds of the formula (I), the flavoring composition must 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 with based on the total weight of the edible composition. Although larger amounts than this can be used, the beneficial effects are considerably less evident and unwanted notes can become more and more evident.
[00212] Interesting organoleptic effects, for example, salt, alcohol or soda enhancing effects, in edible compositions containing salt or alcohol or soda compounds can be obtained when the compounds of formula (I) are used at levels from 1 to 100 ppb .
[00213] Interesting organoleptic effects, for example, umami stimulating effects, in edible compositions containing umami flavorings can be obtained when the compounds of formula (I) are employed at levels of 100 to 250 ppb.
[00214] Interesting organoleptic effects, in particular stimulating effects of mouthfeel, in edible compositions can be obtained when the compounds of formula (I) are used at levels of 250 to 500 ppb.
[00215] Interesting organoleptic effects, for example, fat-stimulating effects, in edible compositions containing fats can be obtained when the compounds of formula (I) are employed at levels of 500 to 1000 ppb.
[00216] It is particularly advantageous to incorporate the compounds of the formula (I) in 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 flavoring ingredients can be lost or degraded with the result that flavor intensity can be reduced and essential and authentic flavor characteristics can be reduced. These edible products include dairy products, snacks, bakery products, powdered soft drinks and similar dry mixes, and the like, fats and seasonings, mayonnaise, spices, soups and broths, and drinks.
[00217] A particularly preferred class of edible composition according to the present invention is that of powdered soft drinks and similar dry mix applications. Dry mix applications are known in the art and include products in powder form that are intended to be reconstituted prior to consumption. These include powdered soups, powdered cake mixes, powdered chocolate drinks, instant coffees, spices, and the like.
[00218] Dry powders formed by dispersive evaporation processes, such as spray drying, represent a very convenient vehicle for imparting oil quality flavors to edible compositions.
[00219] Unfortunately, flavoring oils, and in particular citrus flavoring oils, can be particularly sensitive to dispersive evaporation processes, especially processes carried out at high temperature. Flavoring oils tend to evaporate or degrade to form products that have unfavorable undesirable notes. Powdered flavoring compositions, particularly those containing citrus oils, may be of low quality and exhibit relatively short shelf life as a result.
[00220] Surprisingly, the incorporation of compounds of the formula (I) or flavoring compositions containing them in powder compositions, results in powder compositions that exhibit the impact and authenticity of the flavoring oils used in their preparation, maintaining essentially the oil quality flavoring in a powder flavoring formulation.
[00221] Consequently, the invention provides in another aspect a powdered flavoring composition comprising a compound according to formula (I) and at least one additional flavoring co-ingredient.
[00222] In another aspect of the invention, a powdered soft drink composition or other dry blend composition is provided which comprises a compound according to formula (I).
[00223] In yet another aspect of the present invention, a powdered soft drink composition or other dry blend composition is provided which comprises a powdered flavoring composition comprising a compound of formula (I).
[00224] In yet another aspect of the present invention, there is provided a method of forming a powdered flavoring composition comprising the step of incorporating a compound according to formula (I) into said composition.
[00225] In a particular embodiment, the compound of formula (I) can be added to the formed powder flavor composition, or it can be added to the flavor composition before forming the powder.
[00226] Another particularly preferred class of edible composition according to the present invention is snacks. Snacks are a product category well known for its element in the food industry. These products are described above and include, without limitation, pretzels, corn chips, potato chips, tufted products, extruded products, tortilla chips and the like. Even more particularly, the invention relates to low-fat snack compositions. Low-fat snack compositions contain less than 30% by weight of fat, more particularly between 5 to 25% by weight of fat.
[00227] A problem with reducing fat in a snack composition is the loss of flavor and texture. Fats play an important role in the way the dough behaves during processing and greatly affect the quality, flavor and texture of products ready for consumption. As the fat content in snack products is reduced or replaced by other ingredients (for example, nondigestible fat, protein, fiber, gums), the adverse organoleptic effects (for example, feeling of mouth covering, dryness, lack of crispness and lack of flavor) increase. The adverse organoleptic effects result in products that have reduced palatability.
[00228] Considerable efforts have been made to develop flavoring compositions to overcome the problems associated with low-fat snack products. The flavors can be applied to a snack as topical coatings in the form of dry powders and / or as liquids (for example, oil-based, water-based). Another approach is to add flavor to the dough.
[00229] Despite these various approaches that have been taken to increase the appeal and palatability of the snack consumer, and particularly low-fat snacks, there is still a need for improved low-fat snacks that have toppings applied to those with the visual appeal, flavor, and texture of whole snacks.
[00230] The compounds according to formula (I) or flavoring compositions containing them can be incorporated into snacks to impart a striking flavor and mouthfeel with remarkable harmony and vigor. In addition, the taste and mouthfeel effects can be obtained even in low-fat snacks.
[00231] Consequently, the invention provides in another aspect a snack comprising a flavoring composition as described above. In a particular embodiment of the invention, the snack has a fat content of about 40% or less by weight based on the total weight of the snack, 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.
[00232] Examples of snacks 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.
[00233] Another particularly preferred class of edible composition according to the present invention is alcoholic beverages.
[00234] The applicant has surprisingly discovered that the compounds according to formula (I) incorporated in an alcoholic drink have the effect of increasing the alcoholic impact of the drink.
[00235] Consequently, the invention provides in another aspect an alcoholic beverage comprising a compound according to formula (I).
[00236] In yet another aspect of the invention, there is provided a method of producing an intensified alcoholic impression in an alcoholic beverage by incorporating a compound according to formula (I) in said drink.
[00237] The compounds of formula (I) can be incorporated into said alcoholic beverage in quantities of 1 ppb to 1 ppm.
[00238] Another class of edible compositions consists of products administered orally in the form of tablets, capsules, powders, multiparticulates and the like. Such compounds can include pharmaceutical dosage forms or nutraceutical dosage forms.
[00239] Some groups of people have problems swallowing tablets or capsules, powders, multiparticulates and the like. This problem can be particularly pronounced in some consumer groups, such as children and the elderly or the sick. The applicant has surprisingly found that the compounds according to formula (I) when administered into the oral cavity produce a pronounced salivation effect. The incorporation of the compounds in these forms, particularly as part of a coating around said dosage forms, can facilitate the swallowing process of consumers, in particular children and the elderly or infirm.
[00240] Consequently, the invention provides in another aspect an orally administrable dosage form, in particular in the form of tablets, capsules, powders or multiparticulates comprising a compound according to formula (I).
[00241] Another preferred class of edible composition consists of bakery products. The compounds of formula (I) can be incorporated typically or by mass. Incorporated in levels of 1 ppb to 1 ppm, the compounds of formula (I) make bakery products less dry and more juicy.
[00242] Another preferred class of edible compositions consists of caloric or non-calorie drinks containing carbohydrate-based sweeteners, such as sucrose, high-fructose corn syrup, fructose and glucose, or high-intensity, non-nutritive sweeteners such as aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside 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.
[00243] Incorporated in levels of 1 ppb to 10 ppm, the compounds of formula (I) give said drinks containing sweeteners in levels less than 1% and up to about 20%, an initial sweetener and mouthfeel that is reminiscent of sugar.
[00244] Other preferred edible compositions are salty compositions, in particular those that are soy-based or fish-based.
[00245] Incorporated in levels of 1 ppb to 10 ppm, in a soy-based composition (like soy sauce) or a fish-based composition (like fish sauce) containing 5 to 40% salt, the compositions are considered to exhibit strong umami flavors that are long lasting and rich.
[00246] Another preferred edible composition is a cloudy drink composition.
[00247] Some drinks like juices have relatively higher turbidity and thus have an opaque appearance. Generally, it is desired that the drink has a relatively high turbidity. This may be desired to provide a more natural appearance to drinks with a low juice content, or it may be for reasons related to masking sedimentation or "ringing" (where the flavor or colored oils rise to the surface of a container during storage) . Cloudy drinks are generally formed by using a turbid agent. The clouding agents are generally supplied in the form of emulsions, or the clouding agent may be part of a powdered drink which upon reconstitution will form an emulsion which provides a permanent clouding to the drink.
[00248] The compounds of formula (I), in addition to their remarkable organoleptic properties, can provide stability to turbid agents and drink compositions containing them.
[00249] Consequently, the invention provides in another aspect a composition that comprises a beverage turbid composition and a compound of the formula (I).
[00250] In a particular embodiment of the invention, a flavoring 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 a turbidity agent is to be employed.
[00251] In yet another aspect of the invention there is provided a cloudy beverage composition comprising a turbid agent and a compound of the formula (I).
[00252] Other preferred edible compositions are those compositions that are formed by a maturation process.
[00253] In food processing, it often happens that a food needs to remain for a long period of time and under well-defined conditions to obtain the food with the necessary and recognized quality. A term commonly used for this process is maturation. Maturation is well known in the processing of some types of cheese, meat, soy sauce and wine, as well as beer, sausage, sauerkraut, tempeh and tofu. There are also specific steps that are performed for specific reasons (such as removing water, or unwanted notes) that have beneficial effects on food products. Examples of this are chocolate scoop and the drying of pasta, vegetables and fruits. Transformations that increase food quality are induced by chemical conversions, enzymatically catalyzed conversions or fermentative transformations. All of these conversions are slow and therefore expensive; these are also not fully predictable or controllable.
[00254] The compounds of formula (I), taking into account 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 maturation process to reduce the time of storage without adversely influencing the quality of the flavor of the cured product.
Consequently, in another aspect of the invention there is provided a method of maturing a product selected from the group consisting of cheese, meat, soy sauce and wine, beer, sausage, sauerkraut, tempeh and tofu, which comprises the maturation stage the product in the presence of a compound according to formula (I).
[00256] In another aspect of the invention, a method of chocolate scooping is provided, said method comprising the step of adding to the chocolate a compound according to formula (I), or a flavoring composition containing the same.
[00257] Now follows a series of examples that serve to illustrate the invention. Synthesis Examples Route A: (DCC method)
[00258] 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 obtain 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 solids formed were filtered (dicyclohexylurea) and the filtrate was added to a solution of amino acid (6.48 mmol) in 2% of a solution of sodium bicarbonate (0.363 g, 4.32 mmol) in water. The reaction mixture was stirred for 4 hours at 50 ° C. The dioxane was evaporated and the aqueous residue was further diluted with water, acidified with a diluted hydrochloric acid solution and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried and evaporated to produce 1.3 g of a white solid. The product was purified by flash column chromatography, eluent DCM / methanol.
[00259] 1 g of 85-90% pure product could be obtained.Step 1: Route B (DCC method with protection group)
[00260] 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 15 ° C. A fatty acid (.01 mmol) was added during stirring. A solution of DCC (15.01 mmol) in 10 ml of DCM was added by dropping at 0 ° C. The reaction mixture was stirred at 0 ° C for 1 hour and stirring continued at room temperature for 3 hours. The dicyclohexylurea was removed by filtration of the reaction mixture. The filtrate was washed with a saturated sodium bicarbonate solution, diluted hydrochloric acid solution and water. The organic layer was separated, dried and evaporated to produce 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:
[00261] 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 32% sodium hydroxide solution (2.453 g, 19.63 mmol) and the mixture was stirred at room temperature for three hours.
[00262] The mixture rested for 14 hours.
[00263] After 14 hours, the mixture was acidified with a concentrated hydrochloric acid solution (1.612 ml, 19.63 mmol), diluted with water and extracted with mtbe. The organic layer was separated, dried and evaporated. 1.3 g of a semi-solid yellow residue was obtained. NMR confirmed the structure of the title compound, 95% purity. Route C (acid chloride)
[00264] An amino acid (20 mmol) was dissolved in a solution of sodium hydroxide (54.5 mmol) in water (40 ml).
[00265] Tetrahydrofuran (60 ml) was added. Fatty acid chloride (18.18 mmol) was added by dropping at room temperature. Stirring was continued for 2 hours. The mixture was diluted with water, acidified with 37% hydrochloric acid solution (2.99 ml, 36.4 mmol) and extracted with ethyl acetate.
[00266] The organic layers were combined, dried and evaporated.
[00267] 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 creamy colored solid, (95% purity) 1.4 All synthesized compounds Table 1: List of synthesized compounds
[00268] 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 0.88 (t, 7 = 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, / = 7.73 Hz, 2 H, H-C (2)) 5.26 - 5.44 (m, 2 H, HC (9, 10)) 6.28 (s, 1 H, HN (19))
[00269] 13C NMR (150 MHz, CHLOROPHORM) d 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 (C4)) 29.18 (C6)) 29.26 (C (5)) 29.33 (C (13, 15)) 29.45 (C (14)) 29.72 (C (7)) 29.78 (C (12)) 31.91 (C (16, 21)) 33.47 (C (2)) 129.76 (C (10)) 129.99 (C (9)) 175.15 (C (1)) 177.39 (C (20)) 2.2 Structure 7 GABA-C10: 0
[00270] 1H NMR (600 MHz, DMSO-cfe) ppm 0.83 - 0.87 (m, 3 H, H-C (IO)) 1.18-1.29 (m, 12 H, H-C (4, 5, 6, 7, 8, 9) 1.46 (quin, J = 7.22 Hz, 2 H, HC (14)) 1.59 (quin, 7 = 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, HC (15)) 7.77 (t, J = 5.50 Hz, 1 H, HN (15)
[00271] 13C NMR (150 MHz, DMSO-c 6) 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 (0 (4)) 31.07 (C (13)) 31.27 (C (8)) 35.38 (C (2)) 35.77 (C (15)) 172.03 (C (l)) 174.21 (C (12)) 2.3 Structure 8 GABA-C12.0
[00272] NMR (600 MHz, DMSO-d 6) 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, (H- C (17)) 7.77 (t, J = 5.33 Hz, 1 H, HN (13))
[00273] 13C NMR (150 MHz, DMSO-c 6) δ ppm 13.95 (C (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 (l)) 174.20 (C14)) 2.4 Structure 17 GABA-C18: 2
[00274] 1H NMR (600 MHz, CHLOROFORM-cQ 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, H- C (22)) 2.05 (q, J = 7.22 Hz, 4 H, HC (8), HC (14)) 2.19 (t, J = 7.73 Hz, 2 H, HC (2 )) 2.40 (t, = 7.05 Hz, 2 H, HC (21)) 2.77 (t, J = 6.87 Hz, 2 H, HC (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))
[00275] 13C NMR (150 MHz, CHLOROPHORM) d ppm 14.08 (C (18) 22.58 C (17)) 24.74 (C3)) 25.63 (C (22)) 25.75 (C (ll)) 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 (l) 177.43 (C (20)) 2.5 Structure 22 beta-Alanine-C18: 2
[00276] 1H NMR (600 MHz, DMSO-d 6) 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 = Q, 87 Hz, 2 H, HC (21)) 2.73 (t, J = 6.70 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, HN (19))
[00277] 13C NMR (150 MHz, DMSO-d 6) δ ppm 13.91 (C (18)) 21.97 (C (17)) 25.21 (C (3)) 25.24 (C (11 )) 26.60 (C (8)) 26.63 (C (14)) 28.58 (C (6)) 28.63 (C (5)) 28.68 (C (15)) 28.73 (C (4)) 29.04 (C (7)) 30.89 (C (16)) 33.98 (C (21)) 34.70 (C (22)) 35.27 (C (2) ) 127.73 (C (10, 12)) 129.71 (C (9, 13)) (C (l)) 172.91 (C (20)) 2.6 Structure 28 Asp-C18: 2
[00278] 1H NMR (600 MHz, DMSO-d 6) 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, = 6.87 Hz, 2 H, HC (ll)) 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, HN (19))
[00279] 13C NMR (150 MHz, DMSO-d 6) δ ppm 13.93 (C (18) 21.97 (C (17)) 25.21 (C (3), 26.60 (C (11) ) 26.65 (C (8)) 28.55 (C (14)) 28.59 (C (6)) 28.70 (C (4)) 28.73 (C (5)) 29.05 ( C (15)) 30.69 (C (7)) 30.89 (C (16)) 35.06 (C (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 (l)) 172.61 (C23)) 2.7 Structure 33 Glu- C18: 1
[00280] 1H NMR (600 MHz, CHLOROFORM-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 H - C (8, 12)) 2.08 (dt, J = 13.83, 6.66 Hz, 1 H, HC (22)) 2.20 - 2.25 (m, 3 H, HC (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, = 7.22 Hz, 1 H, HN (19)) <13> C NMR (150 MHz, CHLOROPHORM-d) 13 ppm 14,13 (0 (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 (0 (5) 29.33 (0 (13, 15) 29.55 (C (14)) 29.75 (0 (7)) 29, 78 (C (12)) 29.88 (0 (23) 31.91 (C (16)) 36.36 (0 (2)) 51.60 (C (21)) 129.71 (C (10) ) 130.02 (0 (9)) 174.62 (C (1)) 175.66 (C (20) 177.95 (C (24)) 2.8 Structure 37 Gln-C10: 2
[00281] 1H NMR (600 MHz, CHLOROFORM-d) Õ 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, HC (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, H- C (2)) 6.63 (br, s „1 H, HN (11)) 7.14 (br. S„ 2 H, H 2-N) )
[00282] 13C NMR (150 MHz, CHLOROPHORM) d 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)) 2.9 Structure 44 Met -C12: 1
[00283] 1H NMR (300 MHz, CD 3OD) δ ppm 0.92 (t, / = 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, = 7.2Hz, 2H, H-C (2)), 2.48-2.65 (m, 2H, HC (17)), 4.56 (d, dj = 5.1, 9.9 Hz, 1H, HC (15)], 5.33-5.46 (m, 2H, HC (5, 6)).
[00284] 13C NMR (300 MHz, CD3OD) 5 ppm 14.43 (C (12) 15.21 (C (18)) 23.71 (C (11)) 27.01 (C (4)) 27, 70 (0 (3)) 28.22 (C (7)) 30.08 (0 (9)) 30.83 (C (17)) 31.31 (C (8)) 32.19 (C (16 )) 32.95 (0 (10)) 36.37 (0 (2)) 52.59 (0 (15)] 129.81 (C (5)) 131.80 (C (6)) 175.17 (0 (14)) 176.28 (C (l)) 2.10 Structure 46 Met-C18: 1
[00285] 1H NMR (300 MHz, CD 3OD) Õ 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, / = 4.8, 9.9 Hz, 1H, HC (21)), 5.30-5.40 (m, 2H, HC (9, 10).
[00286] 13C NMR (300 MHz, CD3OD) δ ppm 14.44 (C (18)), 15.24 (C (24)), 23.76, (0 (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)). 2.11 Structure 51 Proline-C18: 2
[00287] 1H NMR (600 MHz, CHLOROPHORM) d ppm 0.78 - 0.85 (m, 3H, 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, J = 9.62, 6 , 87 Hz, 1 H, HC (24)) 3.47 - 3.53 (m, 1 H, HC (24)) 4.53 (dd, J = 8.08, 1.89 Hz, 1 H, HC (21)) 5.16 - 5.36 (m, 4 H, HC (9, 10, 12, 13)
[00288] 13C NMR (150 MHz, CHLOROFORM-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)) 2.12 Structure 55 Serine-18: 2
[00289] 1H NMR (600 MHz, DMS0-d6) δ ppm 0.85 (t, J = 6.87 Hz, 3 H, HC (18) 1.18 - 1.35 (m, 16 H, H- C (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, H- 0 (22)) 3.65 (dd, J = 10.83, 4.30 Hz, 1 H, HC (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)
[00290] 13C NMR (150 MHz, DMSO-c) 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 (I)) 172.27 (C (20)) 2.12 Structure 59 Leucine 16: 1
[00291] 1H NMR (600 MHz, CHLOROFORM-d) 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 = 6.07 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))
[00292] 13C NMR (150 MHz, CHLOROFORM-d) δ ppm 14,11 (C16)) 21,9 (C (15) 22,66 (C (22) 22,86 (C (23) 24,91 ( C21)) 25.63 (C (3)) 27.18 (C (11)) 27.23 (C (8)) 28.99 (C (6)) 29.16 (C (4)) 29, 20 (C (5)) 29.25 (C (13)) 29.71 (C (7)) 29.73 (C (12)) 31.79 (C (14)) 36.51 (C (2 )) 41.32 (C (20)) 50.87 (C (19)) 129.73 (C (9)) 130.00 (C (10)) 173.95 (C (l)) 176.38 (C (18)) 2.13 Structure 61 Leu-C18: 1
[00293] 1H NMR (600 MHz, CHLOROPHORM) d 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 ( tj = 7.39 Hz, 2 H, HC (2)) 4.55 (tdj = 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))
[00294] 13C NMR (150 MHz, CHLOROFORM-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 (C (11) 26.78 (C (8)) 28.71 (C (6)) 28.73 (C (4 )) 28.78 (CC5)) 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 (l) 176.11 (C (20)) Structure 65 Val-C16: 0
[00295] 1H NMR (600 MHz, CHLOROFORM-d) ppm 0.88 (t, / = 7.05Hz, 3 H, HC (16)) 0.95 (d, J = 6.87 Hz, 3 H, HC (21)) 0.98 (d, J = 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, HC (3) ) 4.59 (dd, J = 8.59, 4.81 Hz, 1 H, HC (18)) 6.19 (d, J = 8.59 Hz, 1 H, HN (17))
[00296] 13C NMR (150 MHz, CHLOROPHORMUM-d) 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 Snack Product
[00297] A snack product consisting of a crisp base, containing 35% fat and flavored with cheese seasoning containing salt, MSG, dairy products, organic acids, sugars, and a flavoring formulation. The following compounds were added to the snack product at the indicated levels and the tasting results were reported:
[00298] C18: 2 gaba 1 ppm: Greasy, high cheese, cheese crust, long lasting,
[00299] C18: 2 gaba 0.5ppm: increased dairy content, high cheese content.
[00300] C18: 1-ACCA 1ppm: intensified Umami flavor, salty.
[00301] C18: 1-ACCA 0,5ppm: increased salt content
[00302] C18: 1 met 0,5ppm: increased cheese content, creamy, salty and juicy
[00303] C18: 1 met 0.25ppm: Salted, cured, juicy cheese Air expanded base
[00304] An air-expanded base (rice, wheat, tapioca, potato, salt, sugar, modified starch), containing 3% fat and flavored with cheese seasoning containing salt, MSG, dairy products, organic acids, sugars and flavor. The following compounds were added to the base at the indicated levels and tasting results were reported:
[00305] C18: 2 gaba 2ppm: Cover base with high fat content, high cheese content, cheese crust, long lasting.
[00306] C18: 2 gaba 0.5ppm: increased dairy content, cheese.
[00307] C18: 1-ACCA 1ppm: intensified Umami flavor, salty.
[00308] C18: 1-ACCA 0,5ppm: Enhanced salty flavor Test in 3 in 1 coffee
[00309] In a Nestle 3-in-1 coffee drink (market product) sweetened with 13.2% sucrose and containing cream (2.1% fat), C18: 2-gaba was added.
[00310] The samples were evaluated by expert tasters. The tasters were required to describe the samples with a focus on authentic taste, mouthfeel, vigor, salivation, sweetness, juiciness, long-lasting and fat content.
[00311] The base is a 3-in-1 coffee drink (market product) sweetened with sucrose and containing cream with fat
[00312] Base: coffee, sweet, light dairy
[00313] Base plus C18: 2-gaba at 1 ppm: very pleasant mouthfeel effect, creamy as if coffee cream was added, sweeter. Test in Tanq
[00314] In an orange powdered Tang soft drink (market product) sweetened with sucrose plus high intensity sweetener and containing citric acid, C18: 2-gaba and C18: 2-pro were tested.
[00315] All samples were evaluated by expert tasters. The tasters were required to describe the samples focusing on authentic taste, mouth & body sensation, juiciness, long-lasting, salivation, sweetness, masking unwanted notes of high intensity sweetener.
[00316] Base is Tang flavor orange
[00317] Base: sweet, orange, licorice, and unwanted high intensity sweetener notes, bitter, thin base plus C18: 2-gaba at 0.5 ppm: increases the juicy juicy orange notes, improved mouthfeel. In addition, the unwanted notes of the high intensity sweetener have been suppressed.
[00318] Base plus C18: 2-Pro at 1 ppm: very fresh, intensifies the notes of sweet juicy orange, characteristic of authentic fresh orange. In addition, the unwanted notes of the high intensity sweetener have been suppressed. Non-carbonated mango flavor containing different levels of juice.
[00319] In a non-carbonated mango flavored drink, sweetened with 8% sucrose and containing 0.1% citric acid and 1%, 4% and 6% clear mango juice flavored with a Mango flavor @ 0.05 %, C18: 2-gaba and C18: 2-Pro were added, as such (separate) and in combination. All samples were evaluated by expert tasters. The tasters were required to describe the samples focusing on authentic flavor, mouthfeel, juiciness, long-lasting, salivation, sweetness.
[00320] In a non-carbonated mango flavored drink, sweetened with 8% sucrose & containing 0.1% citric acid and 1% clear mango juice flavored with Mango flavor @ 0.05%, C18: 2- gaba and C18: 2- Pro were added, as such (separate) and in combination.
[00321] Base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice (% very low juice), flavored with mango flavor, dosed in 0.05%
[00322] Base: sweet, fruity, mango, fine
[00323] Base plus C18: 2-Pro at 0.5 ppm: sweeter, similar to sugar, very juicy and long lasting sweet, salivation
[00324] Base plus C18: 2-gaba at 1 ppm: greasy, very juicy, authentic mango, much more mouthfeel, lasting mango flavor, mouthfeel is similar to the whole juice product
[00325] 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, mouth feeling very close to a whole juice product.
[00326] In a non-carbonated mango flavored drink, 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 (separate) and in combination.
[00327] Base is water, 8% sucrose, 0.1% citric acid, 4% clear mango juice (30% reduced juice), flavored with mango flavor, dosed in 0.05%
[00328] Base: sweet, fruity, mango, low mouth feeling
[00329] Base plus C18: 2-Pro in a 0.5 ppm range: sweeter, like sugar, very juicy and long lasting sweet, salivation
[00330] Base plus C18: 2-gaba at 1 ppm: greasy, very juicy, authentic mango, long-lasting mango flavor, more mouthfeel than whole juice product
[00331] Base plus C18: 2-Pro at 0.5 ppm and C18: 2-gaba at 1 ppm: very juicy and sweet, authentic thick mango, long-lasting sweet and long-lasting mango flavor, more mouth feel than a whole juice product
[00332] In a non-carbonated mango flavored drink, 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 (separate) and in combination.
[00333] Base is water, 8% sucrose, 0.1% citric acid, 6% clear mango juice (whole juice), flavored with mango flavor, dosed in 0.05%.
[00334] Base: Sweet, mango, full mouth feeling
[00335] Base plus C18: 2-Pro in 0.5 ppm sweeter, like sugar, very juicy and long lasting sweet, salivation, syrupy.
[00336] Base plus C18: 2-gaba at 1 ppm: greasy, very thick, authentic mango, long lasting, rich mango flavor.
[00337] 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, very rich mango flavor.

权利要求:
Claims (7)
[0001]
e sais comestíveis do mesmo, em que n é 1, Ri é um resíduo de alquila contendo 10 a 18 átomos de carbono, ou um resíduo de alceno contendo de 10 a 18 átomos de carbono com 1 a 3 ligações duplas; b) e sais comestíveis do mesmo, em que m é 0 ou 1, Ri é um resíduo de alquila contendo 10 a 18 átomos de carbono, ou um resíduo de alceno contendo de 10 a 18 átomos de carbono com 1 a 3 ligações duplas; c) e sais comestíveis do mesmo, em que Ri é um resíduo de alquila contendo 10 a 18 átomos de carbono, ou um resíduo de alceno contendo de 10 a 18 átomos de carbono com 1 a 3 ligações duplas, Ra é hidrogênio ou metila, e R4 é metila, etila ou iso-propila; d) selecionado dentre N-geranoil-Pro, N-palmitoil-Pro , N- palmitenoil-Pro, N-estearoil-Pro, N-oleoil-Pro, N-linoleoil-Pro, e N- linolenoil-Pro, e sais comestíveis do mesmo; em que X é OH ou NH2 e p é 0 ou 1, Ri é um resíduo de alquila contendo 10 a 18 átomos de carbono, ou um resíduo de alceno contendo de 10 a 18 átomos de carbono com 1 a 3 ligações duplas, com a condição de que, quando X é OH e p é 1, o composto é selecionado dentre N-geranoil-Glu, N-palmitoil-Glu, N-palmitenoil-Glu, N-estearoil-Glu, N-oleoil-Glu, N-linoleoil-Glu, e N-linolenoil-Glu; e sais comestíveis do mesmo, selecionado dentre N-geranoil-Met, N-palmitoil-Met, N- palmitenoil-Met, N-estearoil-Met, N-oleoil-Met, N-linoleoil-Met e N- linolenoil-Met e sais comestíveis do mesmo; g) Ri selecionado dentre N-palmitoil-Ser, N-palmitenoil-Ser, N- estearoil-Ser, N-linoleoil-Ser e N-linolenoil-Ser, e sais comestíveis do mesmo; e pelo menos um coingrediente flavorizante, em que o coingrediente flavorizante é selecionado do grupo que consiste em açúcares, gorduras, sal, MSG, íons de cálcio, íons de fosfato, ácidos orgânicos, proteínas, purinas e misturas desses, e opcionalmente um material veículo.1. Powder flavoring composition, characterized by the fact that it comprises a compound according to a formula or edible salt of the same in quantities of 1ppb to 10ppm based on the total weight of the composition, in which the compound according to the formula is selected of the group consisting of: and edible salts thereof, where n is 1, R1 is an alkyl residue containing 10 to 18 carbon atoms, or an alkene residue containing 10 to 18 carbon atoms with 1 to 3 double bonds; B) and edible salts thereof, where m is 0 or 1, Ri is an alkyl residue containing 10 to 18 carbon atoms, or an alkene residue containing 10 to 18 carbon atoms with 1 to 3 double bonds; ç) and edible salts thereof, where Ri is an alkyl residue containing 10 to 18 carbon atoms, or an alkene residue containing 10 to 18 carbon atoms with 1 to 3 double bonds, Ra is hydrogen or methyl, and R4 it is methyl, ethyl or iso-propyl; d) selected from N-geranoil-Pro, N-palmitoil-Pro, N-palmitenoil-Pro, N-stearoil-Pro, N-oleoil-Pro, N-linoleoil-Pro, and N-linolenoil-Pro, and edible salts of the same ; where X is OH or NH2 and p is 0 or 1, Ri is an alkyl residue containing 10 to 18 carbon atoms, or an alkene residue containing 10 to 18 carbon atoms with 1 to 3 double bonds, with the proviso that when X is OH and p is 1, the compound is selected from N-geranoyl-Glu, N-palmitoyl-Glu, N-palmitenoyl-Glu, N-stearoyl-Glu, N-oleoyl-Glu, N-linoleoyl- Glu, and N-linolenoyl-Glu; and edible salts thereof, selected from N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-oleoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met and edible salts thereof; g) Ri selected from N-palmitoyl-Ser, N-palmitenoil-Ser, N-stearoyl-Ser, N-linoleoyl-Ser and N-linolenoyl-Ser, and edible salts thereof; and at least one flavoring co-ingredient, in which the flavoring co-ingredient is selected from the group consisting of sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof, and optionally a carrier material .
[0002]
2. Powder flavoring 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-stearoyl 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); C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, N-palmitenoyl-L-leucine, N-palmitoyl-L-leucine, N-linolenoyl-L-leucine, N-linoleoil-L- leucine and N-oleoyl-L-leucine; N-oleoyl-lle; N-palmitenoyl-L-valine, N-palmitoyl-L-valine, N-linolenoyl-L-valine, N-linoleoyl-L-valine and N-oleoyl-L-valine; N-geranoyl-Pro, N-palmitenoyl-Pro, N-stearoyl-Pro, N-linoleoyl-Pro and N-linolenoyl-Pro; N-geranoyl-Glu, N-palmitoyl-Glu, N-palmitenoyl-Glu, N-stearoyl-Glu, N-linoleoyl-Glu and N-linolenoyl-Glu; N-geranoyl-Asp, N-palmitoyl-Asp, N-palmitenoyl-Asp, N-stearoyl-Asp, N-linoleoyl-Asp and N-linolenoyl-Asp; N-geranoyl-GIn, N-palmitoyl-GIn, N-palmitenoyl-GIn, N-stearoyl-GIn, N-linoleoyl-GIn and N-linolenoyl-GIn; N-geranoyl-Asn, N-palmitoyl-Asn, N-palmitenoyl-Asn, N-stearoyl-Asn, N-linoleoyl-Asn and N-linolenoyl-Asn; N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met, N-oleoyl-Met, N-linoleoyl-Met and N-linolenoyl-Met; N-palmitoyl-Ser, N-palmitenoyl-Ser, N-stearoyl-Ser, N-linoleoyl-Ser and N-linolenoyl-Ser; N-palmitoleoyl-L-phenylalanine, N-palmitoyl-L-phenylalanine, N-linolenoyl-L-phenylalanine, N-linoleoyl-L-phenylalanine, and N-oleoyl-L-phenylalanine; 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; in quantities of 1ppb to 10ppm based on the total weight of the composition.
[0003]
3. Powder flavoring composition according to claim 1 or 2, characterized by the fact that it comprises a flavoring co-ingredient containing vanilla, chocolate, coffee, cocoa, citrus oil, selected from lemon, orange, grape, lime and grapefruit; fruit essences selected from apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple and apricot; ingredients containing the components acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate; ingredients containing volatile esters or aldehydes selected from cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl format, and p-methylanisole; or acetaldehyde; benzaldehyde; cinnamic aldehyde; alpha citral; beta citral; decanal; ethyl vanillin; piperonal; vanillin; alpha-amyl cinnamaldehyde; butyraldehyde; valeraldehyde; citronellal; decanal; aldehyde C-8; aldehyde C-9; aldehyde C-12; 2-ethyl butyraldehyde; hexenal trans-2, tolyl aldehyde; veratraldehyde; 2,6-dimethyl-5-heptenal; 2-6-dimethyloctanal; and 2-dodecenal; cherry; or grape and mixtures of these.
[0004]
Powder flavoring composition according to any one of claims 1 to 3, characterized in that it comprises at least one flavoring co-ingredient selected from the group consisting of sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof, and optionally a carrier material.
[0005]
5. Snack, characterized by the fact that it comprises a powdered flavoring composition as defined in any one of claims 1 to 4.
[0006]
6. Powdered refreshment, characterized in that it comprises a powdered flavoring composition as defined in any one of claims 1 to 4.
[0007]
7. Powdered refreshment according to claim 6, characterized by the fact that it is in the form of a caloric or non-caloric drink containing carbohydrate-based 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.

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引用文献:

---

公开号 | 申请日 | 公开日 | 申请人 | 专利标题

---

---

US2835590A|1954-09-21|1958-05-20|Gen Foods Corp|Process of producing an artificial chocolate flavor and the resulting product|

---

US3024272A|1958-04-22|1962-03-06|Du Pont|Organic acid salts of basic amino acids and their use|

---

DE1262216B|1966-04-15|1968-03-07|Roehm & Haas Gmbh|Surface-active compounds as detergents and cleaning agents and as wetting, dispersing, emulsifying and leveling agents|

---

JPS4614357Y1|1967-06-06|1971-05-20|

---

FR1603799A|1968-12-20|1971-05-24|Acyl methionic acids composns|

---

NL7013043A|1969-09-06|1971-03-09|

---

US3624114A|1969-12-18|1971-11-30|Jean V Morelle|Fatty acid amido-methionine products|

---

US3947589A|1971-01-23|1976-03-30|Rikagaku Kenkyusho|Fungicidal methods employing amino acid derivatives|

---

DE2111361C3|1971-03-10|1973-09-20|Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt|

---

US3878305A|1972-05-25|1975-04-15|Procter & Gamble|Fortification of foodstuffs with n-acyl derivatives of sulphur-containing l-amino acids|

---

DE2234399A1|1972-07-17|1974-01-31|Thomae Gmbh Dr K|SKIN PROTECTION PRODUCTS|

---

US4016287A|1972-07-17|1977-04-05|Boehringer Ingelheim Gmbh|Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof|

---

US4093740A|1973-02-16|1978-06-06|Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessier|Fodder for ruminants|

---

US3940500A|1973-08-10|1976-02-24|Sortwell Iii Daniel Richard|Flavoring seafood with S-methyl methionine salt|

---

JPS5247022B2|1973-09-14|1977-11-29|

---

GB1471894A|1973-12-12|1977-04-27|Wilkinson Sword Ltd|Compositions for application to or consumption by the body and containing a compound having a physiological cooling effect|

---

CA1078664A|1975-12-10|1980-06-03|The Procter And Gamble Company|Fortification of foodstuffs with amino acids and derivatives|

---

US4066799A|1975-12-22|1978-01-03|Miles Laboratories, Inc.|Sodium chloride flavor substitute composition and use thereof|

---

JPS53118516A|1977-03-24|1978-10-17|Ajinomoto Co Inc|Inactivation disinfectant of hepatitis-b virus|

---

US4448785A|1978-01-09|1984-05-15|Sandoz, Inc.|N-Unsaturated fatty acid amides of tryptophan ester homologues and anti-cholesteric use thereof|

---

DE3070478D1|1979-12-06|1985-05-15|Procter & Gamble|A method for making a stabilized sulfur-containing amino acid fortified foodstuff|

---

JPS5690046A|1979-12-21|1981-07-21|Ajinomoto Co Inc|Lysine derivative|

---

JPS6234011B2|1980-03-05|1987-07-24|Lion Corp|

---

US4442090A|1980-11-09|1984-04-10|Kyoto Yakuhin Kogyo Kabushiki Kaisha|Absorption-promoting compounds, compositions thereof with pharmaceuticals and/or bases for rectal administration and method of use|

---

US4479974A|1982-10-19|1984-10-30|General Foods Corporation|Amino acids as dry beverage mix ingredients|

---

US4757066A|1984-10-15|1988-07-12|Sankyo Company Limited|Composition containing a penem or carbapenem antibiotic and the use of the same|

---

WO1986003944A1|1985-01-03|1986-07-17|Joyce Patrick J|Heat stabilized peptide table salt substitutes|

---

CA1249842A|1985-04-15|1989-02-07|Miles Laboratories, Inc.|Method for preparing s-2-hydroxy-2-methyl-hexanoic acid|

---

US4649147A|1985-07-08|1987-03-10|G. D. Searle & Co.|Treating elastin degradation with 1-azacycloalkyl carboxylic acids and derivatives|

---

US4837026A|1985-10-03|1989-06-06|Rajakhyaksha Vithal J|Transdermal and systemic preparation and method|

---

DE3643007A1|1986-12-17|1988-06-30|Basf Ag|CURABLE POLYESTER MOLDING MATERIALS|

---

FR2609998B1|1987-01-26|1994-04-15|Morelle Jean|NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS|

---

US5000877A|1988-08-12|1991-03-19|Mitsubishi Petrochemical Co., Ltd.|Aqueous liquid detergent containing an N-acylaspartate and a betaine or imidazoline surfactant|

---

JP2845245B2|1988-10-20|1999-01-13|味の素株式会社|Toothpaste composition|

---

JPH03236315A|1989-12-05|1991-10-22|Nippon Oil & Fats Co Ltd|Antipsychotic agent|

---

FR2657259B1|1990-01-25|1994-08-19|Adir|

---

MY107820A|1990-06-05|1996-06-29|Ajinomoto Kk|Detergent composition.|

---

JP2824158B2|1990-06-05|1998-11-11|花王株式会社|Detergent composition|

---

DE69225631T2|1991-02-19|1998-12-17|Nat Food Research Inst Ministr|Acylamino acid compounds and process for their preparation|

---

AU675778B2|1991-11-27|1997-02-20|Bioresearch Inc.|Specific eatable taste modifiers|

---

US5176934A|1991-12-12|1993-01-05|Kraft General Foods, Inc.|Seasoned food product with a salt enhancer|

---

US5286480A|1992-06-29|1994-02-15|The Procter & Gamble Company|Use of N-acetylated amino acid complexes in oral care compositions|

---

JP3025725B2|1992-11-24|2000-03-27|花王株式会社|Method for separating and purifying N-long-chain acylamino acids|

---

US5312831A|1993-05-12|1994-05-17|American Cyanamid Company|Urethanes and ureas that induce cytokine production|

---

JPH08103242A|1994-10-06|1996-04-23|T Hasegawa Co Ltd|Sustainable flavor/scent imparting agent/modifier|

---

JP2977750B2|1994-10-26|1999-11-15|鐘紡株式会社|Anti-aging skin cosmetics|

---

CA2200209A1|1995-07-26|1997-02-13|Firmenich S.A.|Flavoured products and process for their preparation|

---

EP0904072A4|1996-04-12|2003-07-30|Peptide Technology Pty Ltd|Methods of treating immunopathologies using polyunsaturated fattyacids|

---

JP3654710B2|1996-05-28|2005-06-02|太陽化学株式会社|Flavor improving composition|

---

FR2765109B1|1997-06-25|2001-02-09|Seppic Sa|COMPOSITION COMPRISING A LIPOAMINOACID AND THE CONSTITUENTS OF A TANNIN-RICH PLANT EXTRACT AND USE IN COSMETICS|

---

KR19990013817A|1997-07-14|1999-02-25|후쿠다 다케지|N-acylamino acid and cosmetic material using the same|

---

US6251931B1|1998-11-24|2001-06-26|The Scripps Research Institute|Inhibitors of gap junction communication|

---

DE19842416A1|1998-09-16|2000-04-13|Max Planck Gesellschaft|Secondary amines for the prevention and therapy of diseases caused or intensified by oxidation processes|

---

WO2000057726A1|1999-03-29|2000-10-05|The Nutrasweet Company|NUTRACEUTICALS HAVING N-[N--L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER|

---

EP1263286B1|1999-10-28|2006-02-22|University of North Texas|Methods for extending the freshness of cut flowers|

---

EP1259470A4|2000-02-07|2005-06-15|Zhenhua Yang|A group of anti-cancer compounds with specific structure and their production method|

---

US7320807B2|2001-04-12|2008-01-22|Sorrento Lactalis, Inc.|Co-extruded cheese snacks|

---

GB0112324D0|2001-05-21|2001-07-11|Croda Int Plc|Compounds|

---

US20030099722A1|2001-10-09|2003-05-29|Baxter Jeffrey H.|Methods and compositions for providing glutamine|

---

ES2389069T3|2001-10-25|2012-10-23|Laboratorios Miret, S.A.|Use of cationic preservative in food products|

---

CA2706833C|2002-01-11|2013-01-15|Ohgen Research Laboratories Ltd.|Geranyl compounds|

---

AU2003207241A1|2002-02-18|2003-09-04|Ajinomoto Co., Inc.|Dry powder holding flavor and aroma components and process for producing the same|

---

EP1356744B1|2002-04-22|2008-02-20|Société des Produits Nestlé S.A.|Flavouring compositions containing N-acetylglycine|

---

DE10227462A1|2002-06-20|2004-01-08|Symrise Gmbh & Co. Kg|Production of cis-pellitor and use as a flavoring|

---

AU2003290387A1|2002-11-18|2004-06-15|Natural Asa|Dietry supplements and foods product comprising oleylethanolamide|

---

WO2004075663A1|2003-02-26|2004-09-10|Firmenich Sa|Aminoacid derivatives of dicarboxylic acids as flavor ingredients|

---

JP4476219B2|2003-06-10|2010-06-09|キリン協和フーズ株式会社|seasoning|

---

US7018560B2|2003-08-05|2006-03-28|Rohm And Haas Electronic Materials Cmp Holdings, Inc.|Composition for polishing semiconductor layers|

---

US7329767B2|2003-10-03|2008-02-12|International Flavors & Fragrances Inc.|Conjugated dienamides, methods of production thereof, compositions containing same and uses thereof|

---

KR101299364B1|2004-04-06|2013-08-22|지보당 네덜란드 서비시즈 비.브이.|Taste improving substances|

---

EP1806977B1|2004-10-29|2016-04-13|Givaudan S.A.|Flavour modulating substances|

---

BRPI0509713B1|2004-04-06|2013-12-31|PROCESS TO MAKE FLAVOR MAILLARD PREPARATION, FLAVOR MAILLARD PREPARATION, AND, PRODUCT|

---

EP1758468B1|2004-04-20|2011-03-02|Givaudan Nederland Services B.V.|Taste improving substances|

---

EP1588854A1|2004-04-22|2005-10-26|Kba-Giori S.A.|Ink supply device for printing machine|

---

JP5164258B2|2004-07-20|2013-03-21|ジボダンネーダーランドサービシーズビー．ブイ．|Flavor improving substance|

---

ITMI20041567A1|2004-07-30|2004-10-30|Maycos Italiana Di Comini Miro|"N-ACYLATED DERIVATIVES OF BICARBOXYLIC ACIDS WITH AMINO ACIDS AND WITH HYDROLYZED VEGETABLE PROTEINS AND THEIR APPLICATION IN COSMETIC, DERMO-PHARMACEUTICAL AND PHARMACEUTICAL PRODUCTS"|

---

FR2878439B1|2004-11-26|2007-07-20|Seppic Sa|NOVEL N-ACYL DERIVATIVES OF AMINOACIDS AND THEIR USE IN COSMETICS AND PHARMACY|

---

JP4679132B2|2004-12-20|2011-04-27|小川香料株式会社|Carbonated beverage additive|

---

JP2008105945A|2005-02-07|2008-05-08|Ajinomoto Co Inc|Acylamide compound having action of promoting or inducing secretion of adiponectin|

---

JP4530906B2|2005-04-25|2010-08-25|小川香料株式会社|Flavor enhancer for food and drink|

---

CN101597239B|2005-12-15|2012-08-08|天津药业研究院有限公司|Method for synthesizing theanine|

---

US20100063156A1|2006-10-05|2010-03-11|Hugo Streekstra|Anandamide|

---

EP2119373B1|2006-12-27|2019-02-20|Japan Tobacco Inc.|Sweet-type seasoning compositions containing high proportion of amino acid and yeast for obtaining the same|

---

RU2335926C1|2007-01-18|2008-10-20|Василий Михайлович Григорьев|Food vitamin-mineral supplement|

---

WO2009021558A1|2007-08-16|2009-02-19|Symrise Gmbh & Co. Kg|Mixtures comprising pellitorin and uses thereof|

---

DE102007041217B3|2007-08-31|2009-04-30|Clariant International Limited|Use of compositions as corrosion inhibitors containing amphoteric surfactants and the compositions|

---

EP2058297B1|2007-11-08|2015-05-20|Symrise AG|Use of alkamides for masking an unpleasant flavor|

---

MY156453A|2008-05-20|2016-02-26|Nestec Sa|Acylamino acid compounds and food preparations containing same|

---

EP2140770A1|2008-07-04|2010-01-06|Nestec S.A.|Acylamino acid compounds and food preparations containing same|

---

GB2463013A|2008-08-27|2010-03-03|Barry Callebaut Ag|Extruded inclusion product|

---

EP2184051A1|2008-11-11|2010-05-12|KPSS-Kao Professional Salon Services GmbH|Cleansing composition|

---

JP5223664B2|2008-12-25|2013-06-26|味の素株式会社|Production method of flavor raw materials|

---

US20110081473A1|2009-10-01|2011-04-07|Uha Mikakuto Co., Ltd.|Food ingredient having milk taste-enhancing action, production method thereof, method of enhancing milk taste of food or seasoning and milk taste-enhanced milk-based hard candy|

---

WO2011105985A1|2010-02-27|2011-09-01|Colorado Synthetics, Inc.|Controlled release biocidal salts|

---

FR2959936B1|2010-05-14|2012-08-03|Physica Pharma|NASAL COMPOSITION WITH A SYSTEMIC VIEW BASED ON COCOYL PROLINE OR AT LEAST ONE OF ITS COMPONENTS|

---

JP2012029616A|2010-07-30|2012-02-16|Ogawa & Co Ltd|Flavor enhancer|

---

US20120292022A1|2010-11-22|2012-11-22|E. I. Du Pont De Nemours And Company|Composition for improving oil recovery including n-lauroyl amino acid-based compounds and microbes|

---

US20130022728A1|2011-03-04|2013-01-24|International Flavor & Fragrances Inc.|Spray-Dried Compositions Capable of Retaining Volatile Compounds and Methods of Producing the Same|

---

EP2731453A1|2011-07-15|2014-05-21|Givaudan SA|Flavour modifying compounds|

---

EP2597082A1|2011-11-24|2013-05-29|Symrise AG|Compounds for masking an unpleasant taste|

---

WO2013149012A1|2012-03-30|2013-10-03|Givaudan S.A.|N-acyl amino acid derivatives as food flavouring compounds|

---

WO2013149025A1|2012-03-30|2013-10-03|Givaudan, S., A.|N-acyl serine derivatives as food flavouring compounds|

---

WO2013149008A2|2012-03-30|2013-10-03|Givaudan, S.A.|Improvements in or relating to organic compounds|

---

EP2830438B1|2012-03-30|2019-09-04|Givaudan SA|N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds, powder compositions containing them|

---

EP2830440B1|2012-03-30|2019-03-20|Givaudan SA|N-acyl-aminocyclopropyl carboxylic acidsas food flavouring compounds|

---

EP2830441B1|2012-03-30|2019-11-13|Givaudan SA|N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds|

---

EP2830437B1|2012-03-30|2018-12-26|Givaudan SA|N-acylated 1-aminocycloalkyl carboxylic acidsas food flavouring compounds|

---

US10913922B2|2012-03-30|2021-02-09|Givaudan S.A.|N-acylated methionine derivatives as food flavoring compounds|

---

WO2013149035A2|2012-03-30|2013-10-03|Givaudan S.A.|Improvements in or relating to organic compounds|

---

EP2833739B1|2012-03-30|2020-12-02|Givaudan SA|N-acyl proline derivatives as food flavouring compounds|

---

US9560846B2|2012-08-10|2017-02-07|Paragonix Technologies, Inc.|System for hypothermic transport of biological samples|EP2830437B1|2012-03-30|2018-12-26|Givaudan SA|N-acylated 1-aminocycloalkyl carboxylic acidsas food flavouring compounds|

---

EP2830438B1|2012-03-30|2019-09-04|Givaudan SA|N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds, powder compositions containing them|

---

EP2833739B1|2012-03-30|2020-12-02|Givaudan SA|N-acyl proline derivatives as food flavouring compounds|

---

US10913922B2|2012-03-30|2021-02-09|Givaudan S.A.|N-acylated methionine derivatives as food flavoring compounds|

---

EP2830441B1|2012-03-30|2019-11-13|Givaudan SA|N-acyl derivatives of gamma amino-butyric acid as food flavouring compounds|

---

EP2830440B1|2012-03-30|2019-03-20|Givaudan SA|N-acyl-aminocyclopropyl carboxylic acidsas food flavouring compounds|

---

WO2013149035A2|2012-03-30|2013-10-03|Givaudan S.A.|Improvements in or relating to organic compounds|

---

US10674755B2|2013-10-02|2020-06-09|Givaudan S.A.|Organic Compounds|

---

GB201317424D0|2013-10-02|2013-11-13|Givaudan Sa|Improvements in or relating to organic compounds|

---

EP3052472B1|2013-10-02|2019-02-27|Givaudan S.A.|N-acylated 2-aminoisobutyric acid compounds and flavour compositions containing them|

---

CN105658089B|2013-10-02|2019-07-09|奇华顿股份有限公司|Organic compound|

---

WO2015048990A1|2013-10-02|2015-04-09|Givaudan Sa|Organic compounds having taste-modifying properties|

---

WO2015050535A1|2013-10-02|2015-04-09|Givaudan S.A.|Organic compounds|

---

US10834950B2|2013-10-02|2020-11-17|Givaudan S.A.|Organic compounds|

---

JP6275460B2|2013-11-26|2018-02-07|株式会社ファンケル|Cocoa drink|

---

CN105001119B|2015-07-06|2017-05-31|湖北中烟工业有限责任公司|A kind of preparation method of aldehyde perfume derivative and the application in cigarette blending|

---

CN105077270A|2015-07-16|2015-11-25|上海冬泽特医食品有限公司|Nutrient supplemented composite powder as well as preparation method and use thereof|

---

US10385015B2|2015-09-30|2019-08-20|Givaudan S.A.|N-acylated methionine sulfoxides as food flavouring compounds|

---

US20180070614A1|2016-09-15|2018-03-15|Givaudan, S.A.|Flavored beverages|

---

CN108244689A|2017-12-12|2018-07-06|河南中烟工业有限责任公司|A kind of fragrance module formula for improving burnt fragrant and sweet leaf group odor characteristic and its application in cigarette|

---

EP3575283A1|2018-05-28|2019-12-04|Université de Bourgogne|Linoleic acid derivatives, pharmaceutical composition or food composition comprising said linoleic acid derivatives, and their uses|

---

CN110577480B|2019-07-16|2021-07-23|成都医学院|Preparation method and application of compound with anti-beta amyloid activity|

---

WO2021070941A1|2019-10-10|2021-04-15|味の素株式会社|Surfactant and composition|

法律状态:
2018-05-02| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|

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2019-06-04| B06T| Formal requirements before examination|

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2020-01-28| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

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2020-05-19| B09A| Decision: intention to grant|

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2020-07-14| 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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PCT/US2013/034395|WO2013149031A2|2012-03-30|2013-03-28|Powder flavour composition|

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