EDIBLE OR DRINK COMPOSITION INCLUDING N-ACYL DERIVATIVES RANGE AMINO-BUTYRIC ACID AND STANDARD SOLUT

专利摘要:
n-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavoring compounds, stock solution, use and compositions containing the same the present invention relates to a flavor composition comprising a compound according to the formula ( i) edible salts thereof, wherein r1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms having 1 to 6 double bonds, r1 together with the carbonyl group to to which it is attached is a residue of a carboxylic acid, and m is 0 or 1.
公开号:BR112014023448B1
申请号:R112014023448-5
申请日:2013-03-28
公开日:2021-06-22
发明作者:Feng Shi；Santi VORSTER；Harry Renes；Esther Van Ommeren；Yili Wang；Adri De klerk；Chris Winkel
申请人:Givaudan Sa；
IPC主号:

专利说明:

[001] The invention is related to certain carboxylic acid-amino acid conjugates, flavor compositions containing said conjugates, and their use in edible compositions.
[002] Many food flavor ingredients are known in the art to show their own very pronounced flavor characteristics to a food product. Such ingredients can be of great value in niche areas for particular types of food categories, but they can be incongruous, or even offensive, when used in other food categories.
[003] There is a need to provide broad-spectrum flavor ingredients that act to complement or enhance the taste and taste characteristics of the edible compositions in which they are incorporated.
[004] Applicant has now found a group of compounds that can be employed in flavoring ingredients that complement or enhance the taste and taste characteristics of edible compositions in which they are incorporated in a broad category of flavor applications.
[005] The present invention provides in a first aspect, compounds of formula (I) represented by the formula
edible salts thereof, and their use in edible compositions wherein 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 m is 0 or 1.
[006] It will be evident to the person skilled in the art that when m is 1, the amino acid residue connected to the carbon carbonyl atom is a gamma amino butyric acid (GABA) residue, whereas when m is 0, the residue of amino acid is a residue of beta-alanine (Beta Ala). Both compounds of formula (I) wherein m is 1 and the amino acid residue is a GABA residue, and compounds of formula (I) wherein m is 0 and the amino acid residue is a beta-alanine residue, their edible salts, as well as their use in edible compositions, are all embodiments of the present invention.
[007] Edible salts include those typically employed in the food and beverage industry and include chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates and lactates.
[008] Carboxylic acids can likewise be represented by abbreviations. Hereinafter, 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. Also, if carbon 18 acid is saturated, for example stearic acid. It can be abbreviated as C18:0 (because it contains zero double bond), whereas a carbon 18 acid having a double bond - for example oleic acid - can be abbreviated as C18:1. Also, if the 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 C18:1t.
The compounds of formula (I) may likewise be represented in terms of these abbreviations. For example, the compound of formula (I) consisting of a residue of a C18 carboxylic acid and an amino acid residue of Beta Alanine can be represented by the abbreviation C18-Beta Ala. For simplicity, the compounds of formula (I) hereinafter can be represented in this abbreviated form.
[010] As is evident from formula (I) above, the amino nitrogen atom in the amino acid residue is bonded to a carbonyl carbon atom of the carboxylic acid residue to form an amide bond. Thus, the abbreviated form C18-Beta Ala represents the compound of formula (I) in which the Beta Alanine residue is connected via its nitrogen atom to the carbonyl carbon atom of a C18 carboxylic acid.
[011] In a particular embodiment of the present invention, the carboxylic acid residue is a fatty acid residue.
[012] The fatty acid residue can be the residue of a fatty acid from C8 to C22. The fatty acid can be mammalian or non-mammal. A mammalian fatty acid is a natural or synthetic fatty acid that is identical in structure to one naturally produced in a mammal, including, but not limited to, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, acid eicosatrienoic acid, arachidonic acid, eicosapentenoic acid, and docosatetraenoic acid. A non-mammalian fatty acid is a natural or synthetic fatty acid not normally produced by a mammal, including, but not limited to, pentadecanoic acid; heptadecanoic acid; nonadecanoic acid; heneicosanoic acid; 9-trans-tetradecenoic acid; 10-trans-pentadecenoic acid; 9-trans-hexadecenoic acid; 10-trans-heptadecenoic acid; 10-trans-heptadecenoic acid; 7-trans-nonadecenoic acid; 10,13-nonadecadienoic acid; 11-trans-eicosenoic acid; and 12-transhenicosenoic acid.
[013] Fatty acid residues can be saturated or unsaturated. If they are unsaturated, it is preferred that they have 1, 2 or 3 double bonds which can be in the cis or trans configuration. More particularly, preferred fatty acid residues are C16 to C18, and can be saturated or unsaturated.
[014] However, the knowledgeable person will appreciate that the natural sources of these fatty acids, eg 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 of which consists of a complex mixture of fatty acids. For example, safflower oil is predominantly a source of C18:2 linoleic acid, yet it may contain other fatty acids such as linolenic acid (C18:3) and palmitic acid (C16:0), among others. Accordingly, reference herein to a compound containing a particular fatty acid residue, for example, a C18 fatty acid residue, may be a reference to a pure, or substantially pure, C18 fatty acid residue, or may refer to a mixture of fatty acid residues with the predominant residue being a C18 residue. Preferred fatty acid residues are C16 to C18.
Compounds include C8-GABA, C9-GABA, C10-GABA, C12-GABA, C14-GABA, C16-GABA, C18-GABA, C20-GABA and C22-GABA.
[016] 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.
[017] 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. Double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
Particularly preferred compounds include C10-GABA, C12-GABA, more particularly C12:1-GABA, C14-GABA, C16-GABA, more particularly C16:1-GABA, C18-GABA, more particularly C18:1-GABA , even more particularly C18:1c-GABA and C18:1t-GABA. Most preferred is a C18:2-GABA compound.
[019] 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 .
[020] 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 , wherein the carboxylic acid residue is saturated.
[021] 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 , wherein the carboxylic acid residue is unsaturated and contains 1, 2 or 3 double bonds. Double bonds can be in cis configuration, trans configuration or a mixture of cis and trans configuration.
[022] Preferred compounds include C18:2-Beta Ala and C18:2-gaba.
[023] Compounds of formula (I) can be formed by known methods using commercially available starting materials, reagents and solvents, and a detailed discussion is not warranted here. In one embodiment of the present invention, conjugates can be formed by reacting an amino acid with a fatty acid halide, for example, a chloride under basic conditions in aqueous conditions such as a water/THF solvent system. Yield and reaction times can be improved by applying heat to the reaction mixture. In an alternative embodiment, a fatty acid can be reacted with an amino acid in dioxane in the presence of DCC (dicyclohexylcarbodiimide) and 1-hydroxypyrrolidine-2,5-dione.
[024] In yet another embodiment, an amino acid alkyl ester can be reacted with a fatty acid chloride under basic conditions in an aqueous-based solvent, such as a water/THF solvent system. Thereafter, the ester can be carefully hydrolyzed without affecting the amide bond in the basic methanol water solution.
[025] In yet another embodiment, a fatty 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 the dilute basic methanol water solution.
[026] In yet another embodiment, a (mixed) anhydride of a fatty acid is reacted with an amino acid in dioxane.
[027] In yet another embodiment, a fatty acid alkyl ester can be reacted with an amino acid in dioxane.
[028] In yet another embodiment, an amino acid alkyl ester is reacted with a triglyceride, optionally in the presence of a co-solvent. The amino acid ester thus formed is then hydrolyzed according to a method described above.
[029] In yet another embodiment, an amino acid is reacted with a triglyceride, optionally in the presence of a co-solvent.
[030] In yet another embodiment, 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 co-solvent and/or water.
[031] In yet another embodiment, a fatty acid alkyl ester is reacted with an amino acid in the presence of a lipase or an acylase, optionally in the presence of a co-solvent and/or water.
[032] The compounds of formula (I) impart remarkable organoleptic properties to edible compositions to which they are added. In particular, they impart highly intense, authentic and harmonious flavor, and vigor and volume to edible compositions that contain them.
[033] More particularly, the compounds can be incorporated into an edible product to impart an extraordinary taste, enhanced fat perception and body; or an enhanced umami or salty taste; or a cool and sumptuousness. They are particularly useful in low-fat, salt and umami applications. They are also useful in non-fat formulations such as beverage and oral care applications. They also find use in applications in the dairy industries and in vanilla, cocoa and chocolate.
[034] This finding was even more surprising considering that when the applicant tasted the compounds in dilute aqueous solution, they were either tasteless or they exhibited a slightly greasy, disappointing taste profile. As such, they appeared to be quite unsuitable for use in flavor applications. Only their combination with flavor co-ingredients and the careful selection of their levels of use made it possible to discover the remarkable organoleptic properties of these compounds. Their effect on edible compositions is quite unusual in that, rather than exerting a characteristic flavor profile for a foodstuff or beverage, they actually complement, elevate or accentuate the essential or authentic flavor and taste characteristics of the food. or drinks in which they are incorporated. Consequently, the compounds of the present invention find utility in a wide spectrum of applications in the food and beverage industry, as well as in health and wellness.
[035] Consequently, the invention provides in another of its aspects, a method of imparting taste and/or taste to, or improving taste and/or taste of an edible composition, which method comprises adding to said composition a compound of formula (I ) defined here.
[036] Extraordinary organoleptic effects are observed when the compounds of formula (I) are incorporated into an edible composition containing one or more flavor co-ingredients.
[037] Flavor co-ingredients can be sugars, fats, salt (eg sodium chloride), MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.
[038] 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.
[039] In a particular modality, 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.
[040] In a particular embodiment, salt (eg, 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.
[041] In a particular modality, MSG is present in amounts from 0.001% to 2% based on the total weight of an edible composition.
[042] In a particular embodiment, calcium is more particularly present in amounts of 0.001% to 50%, 0.001% to 20%, even more particularly 0.001% to 1% based on the total weight of an edible composition.
[043] 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.
[044] Types of organic acids include citric, malic, tartaric, fumaric, lactic, acetic, succinic. Types of edible compositions containing organic acids include beverages such as carbonated soft drinks, soft drinks, juices, powdered soft drinks, liquid concentrates, alcoholic beverages and functional beverages.
[045] In a particular embodiment, phosphorus is present in an amount up to 0.5% by weight of an edible composition. Typically, phosphorus is present as a phosphate or phosphoric acid.
[046] 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.
[047] Despite its interesting organoleptic properties, however, the applicant found that the formulation of the compounds of formula (I) was not a trivial matter. The discovered potency of the compounds suggested that they could be employed at very low levels in flavor applications, and thus for ease of handling, mixing and processing with other ingredients, although it is possible to use the compounds in pure form, it is desirable to extend or add volume to the physical form of the compounds by incorporating them into a suitable vehicle, for example, a diluent such as a solvent. However, the compounds are solid or viscous oils at ambient temperatures, and have very limited solubility in water. Applicants have found that at least about 0.01% standard solution, more particularly about 0.01 - 1% standard solution of a compound of formula (I) has been balanced with respect to acceptable solvent levels for ease of handling and mixing, and the desire to limit the amount of solvent that would have to be removed from the standard solution when further processing the compounds into flavor compositions and edible products for reasons of palatability, efficiency, cost and the like. Applicant has found that suitable solvents for the standard solution include ethanol, triacetin, glycerol and migliol.
[048] To aid in the solubilization process and produce a standard solution and minimize the amount of solvent, it is preferred to use the compounds of formula (I) formed from a mixture of carboxylic acids rather than a pure carboxylic acid.
[049] Accordingly, the invention in other aspects of the invention provides at least about 0.01% standard solution, more particularly about 0.01 - 1% standard solution of a compound of formula (I).
[050] The standard solution may contain other materials such as carrier materials and/or adjuvants more fully described below. In a particular modality, the standard solution contains an antioxidant, selected from the group consisting of vitamin C, vitamin E, rosemary extract, anthracin, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Antioxidants are preferably employed to prevent, or significantly reduce, the generation of volatile notes as a result of degradation of the compounds of formula (I). Antioxidants are particularly preferred when the compounds of formula (I) carry a residue of an unsaturated fatty acid. Antioxidants are particularly preferred if the fatty acid residue contains more than 1 double bond. Determining an effective amount of antioxidant is within the competence of the skilled person, however amounts in the range of about 10 ppm to 1000 ppm based on the weight of the standard solution may be present.
[051] In preparing the flavor compositions of the present invention, the compounds of formula (I) can be employed in any physical form. They can be used in pure form, in the form of a standard solution described above; they can be used in the form of an emulsion; or they can be used in a powdered form. If the compounds of formula (I) are presented in powder form, the powder form can be produced by a dispersive evaporation process, such as a spray drying process as is more fully described below. The powder form can be prepared by subjecting a liquid formulation containing a compound of formula (I) to a dispersive evaporation process. The liquid formulation may comprise a solution, suspension or emulsion comprising the compound of formula (I). In particular, the liquid formulation may take the form of the standard solution described above. The liquid formulation may contain other ingredients such as a carrier material and/or an adjuvant as more fully described below.
[052] A powder comprising a compound of formula (I) forms another aspect of the present invention.
[053] The compounds of formula (I) may be incorporated into an edible composition alone, or in the form of a flavor composition comprising one or more flavor co-ingredients.
[054] A flavor composition comprising a compound according to formula (I) forms another aspect of the present invention.
[055] In an embodiment of the present invention, the flavor formulation comprises a compound of formula (I) and at least one flavor co-ingredient.
[056] In a particular embodiment of the present invention, the flavor composition comprises: a compound according to formula (I); at least one flavor co-ingredient; optionally a vehicle material; and optionally at least one adjuvant.
[057] By the term "flavor co-ingredient" is an ingredient that can contribute or impart or modify in a positive or pleasing way the taste of an edible composition.
[058] All manner of flavor co-ingredients may be employed in a composition in accordance with the present invention, including, but not limited to, natural flavors, artificial flavors, seasonings, seasonings, and the like. Flavor co-ingredients include synthetic flavor and aromatic oils and/or flavor oils, oleoresins, essences, spirits, and extracts derived from plants, leaves, flowers, fruits, and so on, and combinations comprising at least one of the foregoing.
[059] Flavor oils include spearmint oil, cinnamon oil, oil of wintergreen (methyl salicylate), peppermint oil, Japanese spearmint oil, clove oil, laurel oil, anise oil, eucalyptus oil , thyme oil, cedar leaf oil, nutmeg oil, allspice, sage oil, apple, bitter almond oil, and cassia oil; useful flavoring agents include artificial, natural and synthetic fruit flavors, such as vanilla, and citrus oils, including lemon, orange, lemon, grapefruit, yazu, sudachi, and fruit essences, including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, prunes, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruits, mango, mangosteen, pomegranate, papaya and similar.
[060] Additional exemplary flavors imparted by a flavoring agent include a milk flavor, a butter flavor, a cheese flavor, a cream flavor, and a yogurt flavor; a vanilla flavor; tea or coffee flavors, such as a green tea flavor, an oolong tea flavor, a tea flavor, a cocoa flavor, a chocolate flavor, and a coffee flavor; mint flavors, such as a peppermint flavor, a mint flavor, and a Japanese mint flavor; spicy flavors, such as an asafoetida flavor, an ajowan flavor, an anise flavor, an angelica flavor, an fennel flavor, an allspice flavor, a cinnamon flavor, a chamomile flavor, a flavor mustard, a cardamom flavor, a caraway flavor, a cumin flavor, a clove flavor, a pepper flavor, a coriander flavor, a sassafras flavor, a salty flavor, a flavor Zanthoxyli Fructus , a perilla flavor, a juniper berry flavor, a ginger flavor, a star anise flavor, a horseradish flavor, a thyme flavor, a tarragon flavor, a dill flavor, a capsicum flavor, a flavor of nutmeg, a basil flavor, a marjoram flavor, a rosemary flavor, a bay leaf flavor, and a wasabi (Japanese horseradish) flavor; a nut flavor such as an almond flavor, a hazelnut flavor, a macadamia nut flavor, a peanut flavor, a nut flavor, a pistachio flavor, and a walnut 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, such as an onion flavor, a garlic flavor, a cabbage flavor, a carrot flavor, a celery flavor, a mushroom flavor, and a tomato flavor.
[061] In some embodiments, said flavor co-ingredients include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarvil acetate, eugenyl formate 49, p-methylamisol, and so on may be used . Other examples of aldehyde flavorings include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e. alpha-citral (lemon, lime), neral, or ie, beta-citral (lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope, ie, piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amyl cinnamaldehyde ( spicy fruity flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronellal (modifies several types), decanal (citrus fruits), C-8 aldehyde (citrus fruits), C-9 aldehyde (citrus fruits), aldehyde C-12 (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 fruit), and 2-dodecenal (citrus, mandarin), and the like.
[062] Other examples of other flavor coingredients can be found in "Chemicals Used in Food Processing", publication 1274, pages 63-258, by the National Academy of Sciences.
[063] Flavor coingredients may also include salt flavors, umami flavors, and salty flavor compounds. Non-limiting examples include: NaCl, KCl, 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-methoxylphenyl)-3-(pyridin-2-yl)propan-1-one, arginine, potassium chloride, chloride ammonium, succinic acid, N-(2-methoxy-4-methylbenzyl)-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-methylbenzyl)-N '-2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide, cyclopropyl-E,Z-2,6-nonadienamide.
[064] In particular embodiments of the present invention, the flavor co-ingredient is selected from the compounds and compositions described in WO2005102701, WO2006009425, WO2005096843, WO2006046853 and WO2005096844, all of which references are hereby incorporated by reference in their entirety.
[065] Flavor coingredients can include known salt flavors, umami flavors, and salty flavor compounds. Non-limiting examples include: NaCl, KCl, 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-methoxylphenyl)-3-(pyridin-2-yl)propan-1-one, arginine, potassium chloride, chloride ammonium, 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-methylpyridin-2-yl)ethyl)oxalamide, cyclopropyl-E,Z-2,6-nonadienamide.
[066] carrier material can be used in compositions according to the invention to encapsulate or to imprison in a matrix the other components of the composition. The role of the carrier material may merely be that of a processing aid or bulking agent, or it may be employed to shield or protect the other components from the effects of moisture or oxygen or any other aggressive medium. The carrier material can also act as a method of controlling flavor release from edible compositions.
[067] 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, starch chemical modified, hydrogenated starch hydrolyzate, succinylated or hydrolyzed starch, agar, carrageenan, gum acacia, gum acacia, tragacanth, alginates, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose, derivatives and mixtures thereof. Indeed, the knowledgeable recipient would appreciate that the materials cited were hereby provided by way of example and not to be construed as limiting the invention.
[068] By "flavor adjuvant" is meant an ingredient capable of providing additional added benefit to the compositions of the present invention such as a color, lightfastness, 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-caking agents, and the like. In a particular embodiment, the flavor composition comprises an antioxidant. Said antioxidants may include vitamin C, vitamin E, rosemary extract, anthracin, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).
[069] Examples of such vehicles or adjuvants for flavor 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 "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), first edition, The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.
[070] Other suitable and desirable ingredients of flavor compositions are described in standard texts such as "Handbook of Industrial Chemical Additives", ed. M. and I. Ash, Second Edition, (Synapse 2000).
[071] Flavor compositions according to the present invention may be provided in any suitable physical form. For example, they may be in the form of oils, emulsions or dispersions in a hydrous liquid or organic liquid suitable for use in edible compositions, or solid form such as powders.
[072] If flavor compositions are provided in the form of a powdered composition, they can be prepared by dispersive evaporation techniques generally known in the art, such as spray drying.
[073] Accordingly, in another aspect of the present invention there is provided a method of forming a powdered composition, comprising the steps of providing a liquid composition comprising a compound of formula (I) and one or more optional ingredients selected from at least a flavor co-ingredient, a carrier material and an adjuvant, and dispersively evaporating said liquid composition to form a powder composition.
[074] In this manner, a compound of formula (I) or a flavor composition comprising said compound may be presented in a powder form.
[075] The liquid composition used in the preparation of a powder can be in the form of a solution, emulsion, dispersion or suspension. 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.
[076] Powder compositions according to the present invention can be prepared according to methods and mechanisms known in the art to produce powders on an industrial scale. A particularly suitable method is spray drying. Spray drying techniques and apparatus are well known in the art and not necessary in the detailed description herein. 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 their entirety. .
[077] The manner in which the compounds of formula (I) are incorporated into the inventive flavor powder compositions is not critical. For example, the compounds can be added to the liquid composition described above and subjected to a dispersive evaporation process along with all the other components of the flavor composition. Alternatively, compounds can be added to the flavor composition after it has been formed into a powder.
[078] Many of the flavor co-ingredients described here above are volatile and/or may be sensitive to degradation by oxidation, particularly when subjected to elevated temperature, and under humid conditions. Consequently, particular problems can arise when subjecting the flavor co-ingredients described above to dispersive evaporation processes such as spray drying. A non-exhaustive list of ingredients that may be particularly susceptible includes those ingredients containing artificial, natural or synthetic fruit flavors such as vanilla, chocolate, coffee, cocoa and citrus oil, including lemon, orange, grape, lime and grapefruit, and essences of fruit, including apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple, apricot and the like. Volatile components of these flavor co-ingredients can include, but are not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate. Flavor co-ingredients containing volatile aldehydes or esters include, for example, cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvil acetate, eugenyl formate, and p-methylanisole. Other 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); decan (orange, lemon); ethyl vanillin (vanilla, cream); heliotropin, i.e. 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); C-8 aldehyde (citrus fruits); aldehyde C-9 (citrus fruits); C-12 aldehyde (citrus fruits); 2-ethyl butyraldehyde (wild berries); hexenal, that is, trans-2 (wild fruits); tolyl aldehyde (cherry, almond); veratraldehyde (vanilla); 2,6-dimethyl-5-heptenal, i.e. melonal (melon); 2-6-dimethyloctanal (green fruit); and 2-dodecenal (citrus, mandarin); Cherry; or grape and mixtures thereof.
[079] Applicant surprisingly found that the inclusion of a compound of formula (I) in a powdered flavor composition made it possible to maintain the flavor quality of the flavor composition converted to powder form by a dispersive evaporation process.
[080] Accordingly, the invention provides in other of its aspects a method of maintaining the flavor quality of a powdered flavor composition comprising the step of including in said powdered flavor composition a compound of formula (I).
[081] As stated above, compounds of formula (I) or flavor compositions containing such compounds may be incorporated into edible compositions, and an edible composition containing such a compound or flavor composition forms another aspect of the present invention.
[082] The term "edible composition" refers to products for consumption by an individual, typically via the oral cavity (although consumption may occur through non-oral methods such as inhalation), for at least one of the purposes of pleasure, nutrition or health and wellness benefits. Edible compositions may be present in any form including, but not limited to, liquids, solids, semi-solids, tablets, capsules, lozenges, bands, powders, gels, gums, pastes, suspensions, syrups, aerosols and sprays. The term also refers to, for example, dietary and nutritional supplements. Edible compositions include compositions that are placed into the oral cavity for a period of time before being discarded, but not swallowed. It can be placed in the mouth before consumption, or it can be kept in the mouth for a period of time before being discarded. An edible composition as defined hereinabove includes compositions whose taste is modified in a manner described herein by the addition of compounds of formula (I) or whose taste is thereby modified by processing so that it is enriched in a compound of formula (I) .
[083] In a particular modality, the term "edible compositions" refers to products for consumption by an individual, typically via the oral cavity (although consumption may occur through non-oral methods, such as inhalation), to one of the purposes of pleasure or nourishment.
[084] In a more particular modality the term "edible compositions" refers to products for consumption by an individual, typically through the oral cavity (although consumption may occur through non-oral methods such as inhalation), to the purpose of pleasure. Even more particularly, the term refers to foodstuffs and beverages.
[085] In a particular embodiment, the term "edible composition" does not refer to pharmaceutical compositions.
[086] In another embodiment, the term "edible composition" does not refer to nutritional supplements.
[087] Generally speaking, edible composition includes, but is not limited to, foods of all types, confectionery, bakery products, sweet products, savory products, fermented products, dairy products, beverages and oral care products.
[088] Exemplary food products include, but are not limited to, refrigerated snacks, sweet and savory, fruit snacks, potato chips/crunchies, extruded snacks, corn tortilla/crunchies, popcorn, pretzels, nuts, other sweet and savory snacks , snack bars, granola bars, breakfast bars, energy bars, fruit bars, other snack bars, meal replacement products, slimming products, convalescence drinks, ready meals, canned ready meals, dishes frozen ready-to-eat ready meals, frozen ready meals, dinner mixes, frozen pizza, pizza, soup, canned soups, dehydrated soups, instant soups, iced soup, UHT soup, frozen soup, noodles, canned pasta, dry pasta, refrigerated pasta /fresh noodles, simple noodles, instant noodles, cups/bowl of instant noodles, instant noodles, refrigerated bag noodles, snack noodles, food dry s, dessert mixes, sauces, sauces and condiments, herbs and condiments, pastes, jams and preserves, honey, chocolate pastes, nut-based pastes, and yeast-based pastes.
[089] Exemplary confectionery products include, but are not limited to, chewing gum (which includes sugared gum, sugarless gum, functional gum and bubble gum), Centerfill confections, chocolate and other chocolate products, medicated confectionery , lozenges, pills, lozenges, candies, regular candies, energy candies, chewy candies, hard candies, baked candies, breath and other oral care films or strips, candy sticks, lollipops, gummy candies, jellies , fudge, caramel, hard and soft fried products, caramel, caramel, licorice, jelly candies, gum drops, jelly beans, nougats, fondants, combinations of one or more of the above, and edible flavor compositions incorporating one or more of the above .
[090] Exemplary baked goods include, but are not limited to, alfajores, bread, packaged/industrial bread, unwrapped/crafted bread, sweets, cakes, packaged/packaged cakes, unpackaged/craft cakes, biscuits, biscuits with chocolate icing, sandwich cookies, sandwich cookies, savory cookies and crackers, bread substitutes,
[091] Exemplary sweet products include, but are not limited to, breakfast cereals, ready-to-eat ("rte") cereals, family breakfast cereals, flakes, muesli, other ready-to-eat cereals, breakfast cereals. kids for breakfast, hot cereal,
[092] Examples of savory products include, but are not limited to, snack foods (chips, crisps, nuts, tortillatostada, pretzels, cheese snacks, corn snacks, potato snacks, ready-to-eat popcorn, microwave popcorn , cracklings, nuts, crackers, cracker snacks, breakfast cereals, meats, jellies, cured meats (ham, bacon), lunch/cold meats (hot dogs, cold meats, sausage), tomato products, margarine, butter peanuts, soup (white, canned, cream, instant, UHT), canned vegetables, paste sauces.
[093] Examples of dairy products include, but are not limited to, cheese, cheese sauces, cheese-based products, ice cream, impulse ice cream, single-serve dairy ice cream, single-serve water ice cream, packaged dairy ice cream multiple, multi-pack water ice cream, take-home ice cream, take-home dairy ice cream, ice cream desserts, bulk ice cream, water take home ice cream, frozen yogurt, artisan ice cream, dairy products, milk , fresh/pasteurized milk, fresh/pasteurized whole milk, fresh/pasteurized semi-skimmed milk, uht/long-life milk, uht/long-life whole milk, uht/long-life semi-skimmed milk, uht/long-life milk without fat, goat milk, condensed/evaporated milk, simple condensed/evaporated milk, flavored condensed milk, functional and other, flavored milk drinks, milk-only flavored milk drinks, flavored milk drinks with juice fruit, soy milk, sour milk beverages, fermented milk beverages, coffee whiteners, powdered milk, flavored powdered milk beverages, cream, yogurt, plain/natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, yogurt drinking, regular drinking yogurt, probiotic drinking yogurt, shelf-stable and chilled desserts, dairy-based desserts, soy-based desserts.
[094] Examples of beverages include, but are not limited to, flavored water, soft drinks, fruit drinks, coffee-based beverages, tea-based beverages, juice-based beverages (includes fruit and vegetable), beverages with based on milk, gel drinks, carbonated or non-carbonated beverages, powdered beverages, alcoholic or non-alcoholic beverages.
[095] Examples of fermented foods include, but are not limited to, cheese and cheese products, meat and meat products, soy and soy products, fish and fish products, cereal and cereal products, fruit and meat products. fruit.
[096] 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 extruded snacks.
[097] The compounds of formula (I), when added to a flavor composition and/or an edible composition act on the composition to complement its taste and/or mouthfeel to make it more delicious and authentic. Effects can be temporal or intensity-related, for example, the compounds can act to enhance, intensify, smooth, shape a taste, or make more salivating. The compounds of formula (I) can also affect the temporal profile of a taste, that is, they can affect the initial impact of a taste, the body of a taste, or its lingering effect.
[098] The compounds of formula (I) can modify any aspect of the temporal flavor or flavor profile of an edible composition. In particular, the compounds improve mouthfeel and give creamier and more greasy sensations.
[099] Compounds of formula (I) or flavor compositions containing them can be added to edible compositions in broad transport 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 flavor composition. In order to obtain the extraordinary beneficial effects attributed to the presence of the compounds of formula (I), the flavor composition must be employed in amounts such that the compounds of formula (I) are present in amounts from 1 part per billion to 10 parts per million based on the total weight of the edible composition. Although larger amounts than this can be employed, the beneficial effects are considerably less evident and unwanted unpleasant notes may become increasingly evident.
[0100] Interesting organoleptic effects, for example, salt, alcohol or cooling enhancing effects, in edible compositions containing salt or alcohol or refrigerant compounds can be obtained when compounds of formula (I) are employed at levels from 1 to 100 ppb.
[0101] Interesting organoleptic effects, eg umami enhancement effects, in edible compositions containing umami flavors can be obtained when compounds of formula (I) are employed at levels from 100 to 250 ppb.
[0102] Interesting organoleptic effects, in particular mouthfeel enhancing effects, in edible compositions can be obtained when compounds of formula (I) are employed at levels from 250 to 500 ppb.
[0103] Interesting organoleptic effects, for example, fat-enhancing effects, in edible compositions containing fats can be obtained when compounds of formula (I) are employed at levels from 500 to 1000 ppb.
[0104] It is particularly advantageous to incorporate compounds of formula (I) into edible compositions which are formed under high temperature conditions such as cooking, frying or which are processed by heat treatments such as pasteurization or under UHT conditions. Under elevated preparation or processing temperatures, volatile flavor ingredients can be lost or degraded with the result that flavor intensity can be reduced and essential and authentic flavor characteristics can be diminished. Such edible products include dairy products, snack foods, baked goods, powdered soft drinks and similar dry mixes, and the like, fats and flavorings, mayonnaise, sauces, soups and broths, and beverages.
[0105] A particularly preferred class of edible composition in accordance with the present invention are powdered soft drinks and similar dry mix applications. Dry mix applications are known in the art and include products in powder form which are intended to be reconstituted before consumption. They include powdered soups, powdered cake mixes, powdered chocolate drinks, instant coffees, spices and fonds, and the like.
[0106] Dry powders formed by dispersive evaporation processes, such as spray drying, represent a very inconvenient vehicle for releasing flavor oil quality flavors to edible compositions.
[0107] Unfortunately, flavoring oils, and in particular citrus flavor oils can be particularly sensitive to dispersive evaporation processes, especially processes carried out at elevated temperature. Flavored oils tend to evaporate or degrade to form products having unpleasant unfavorable notes. Powdered flavor compositions, particularly those containing citrus oils, can be of low quality and exhibit relatively short shelf life as a result.
[0108] Surprisingly, the incorporation of compounds of formula (I) or flavor compositions containing them in powder compositions, results in powder compositions that exhibit the impact and authenticity of the flavor oils used in their preparation, essentially maintaining quality of flavor oil in powdered flavor formulations.
[0109] Accordingly, the invention provides in another aspect a powdered flavor composition comprising a compound according to formula (I) and at least one additional flavor co-ingredient.
[0110] In another aspect of the invention there is provided a powdered soft drink composition or other dry mix composition comprising a compound according to formula (I).
[0111] In yet another aspect of the present invention there is provided a powdered soft drink composition or other dry mix composition comprising a powdered flavor composition comprising a compound of formula (I).
[0112] In yet another aspect of the present invention there is provided a method of forming a powdered flavor composition comprising the step of incorporating in said composition a compound according to formula (I).
[0113] In a particular embodiment the compound of formula (I) may be added to the powdered flavor composition formed, or may be added to the flavor composition prior to forming the powder.
[0114] Another particularly preferred class of edible composition according to the present invention are snack foods. Snack foods are a product category well known to the person versed in the food industry. These products are described above and include, without limitation, pretzels, corn crunches, potato chips, puff pastry products, extruded products, tortilla chips and the like. Even more particularly, the invention relates to low-fat snack food compositions. Low-fat snack food compositions contain less than 30% by weight of fat, more particularly between 5 to 25% by weight of fat.
[0115] One problem with reducing fat in a snack composition is the loss in flavor and texture. Fats play an important role in the way dough behaves during processing and significantly affect the quality, taste and texture of ready-to-eat products. When the fat content in snack products is reduced or replaced with other ingredients (eg non-digestible fat, protein, fiber, gums), adverse organoleptic effects (eg mouth coating, drying, lack of sharpness and lack of flavor) are increased. Adverse organoleptic effects result in products having reduced palatability.
[0116] Considerable efforts have been expended in crafting flavor compositions to overcome the problems associated with low-fat snack food products. Flavors can be applied to a snack as topical coatings in the form of dry powders and/or as liquids (eg oil-based, water-based). Another method was to add flavor to the dough.
[0117] Despite these various methods that have been employed to improve consumer appeal and palatability of snack foods, and particularly low-fat snack foods, there is still a need for improved low-fat snack foods having coatings applied over them with the visual appeal, flavor, and texture of high-fat snack foods.
[0118] Compounds according to formula (I) or flavor compositions containing the same can be incorporated into snack foods to impart a high impact flavor and mouthfeel with remarkable roundness and fullness. Furthermore, the taste and mouthfeel effects can be obtained even in low-fat snack foods.
[0119] Consequently, the invention provides in another of its aspects a snack comprising a flavor composition as previously described. In a particular embodiment of the invention the snack food has a fat content of about 40% or less by weight based on the total weight of the snack food, more particularly about 30% or less, even more particularly 25% or less , more particularly about 10% or less, even more particularly about 5% or less, even more particularly about 3% or less.
[0120] Examples of snack foods are described above and include products processed by baking, extruding or frying and which are made from potatoes and/or corn and/or various cereals such as rice or wheat.
[0121] Another particularly preferred class of edible composition according to the present invention are alcoholic beverages.
[0122] Applicant surprisingly found that compounds according to formula (I) incorporated into an alcoholic beverage had the effect of increasing the alcohol impact of the beverage.
[0123] Consequently, the invention provides in another of its aspects an alcoholic beverage comprising a compound according to formula (I).
[0124] In yet another aspect of the invention there is provided a method of producing an increased alcoholic impression in an alcoholic beverage by incorporating in said beverage a compound according to formula (I).
[0125] Compounds of formula (I) can be incorporated in said alcoholic beverage in amounts from 1 ppb to 1 ppm.
[0126] Another preferred class of edible compositions are ingested products in the form of tablets, capsules, powders, multi-particulates and the like, which may include pharmaceuticals and nutraceuticals.
[0127] Certain groups of people have had trouble swallowing pills or capsules, powders, multiparticulates and the like. This problem can be particularly pronounced in certain consumer groups, such as children and the very old or infirm. The Applicant has surprisingly found that the compounds according to formula (I) when placed inside the oral cavity produce a pronounced salivation effect. Incorporating the compounds into these dosage forms, particularly as part of a coating around said dosage forms, can facilitate the swallowing process for consumers, in particular children and the elderly or infirm.
[0128] Accordingly, the invention provides in another of its aspects an orally administrable dosage form, in particular in the form of tablets, capsules, powders or multiparticulates comprising a compound according to formula (I).
[0129] Another preferred class of edible composition is baked goods. Compounds of formula (I) can be incorporated topically or in bulk. Incorporated at levels from 1 ppb to 1 ppm, the compounds of formula (I) make baked products less dry and more succulent.
[0130] Another preferred class of edible compositions are caloric or non-caloric beverages containing carbohydrate sweeteners such as sucrose, high fructose, fructose and glucose corn syrup, or non-nutritive, high intensity 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.
[0131] Incorporated at levels from 1 ppb to 10 ppm, the compounds of formula (I) impart to said beverages containing sweeteners at levels less than 1% and up to about 20%, an initial sweetness and mouthfeel that is reminiscent of sugar.
[0132] Other preferred edible compositions are savory compositions, in particular those that are based on soy or based on fish.
[0133] Incorporated at levels of 1 ppb to 10 ppm, in a soy-based composition (such as soy sauce) or a fish-based composition (such as fish sauce) containing 5 to 40% salt, as compositions are found to exhibit strong umami flavors that are long-lasting and rich.
[0134] Another preferred edible composition is a cloudy beverage composition.
[0135] Certain beverages such as juices have relatively greater turbidity and thus have an opaque appearance. Often, it is desired for the beverage to have a relatively high turbidity. This may be desirable to provide a more natural appearance to low juice beverages, or it may be for reasons related to masking sedimentation or "buzz" (where flavor or color oils rise to the surface of a container during storage ). Cloudy beverages are usually formed using a clouding agent. Clouding agents are generally provided in the form of emulsions, or the clouding agent may be part of a beverage powder which on reconstitution will form an emulsion providing permanent cloudiness to the beverage.
[0136] Compounds of formula (I), in addition to their remarkable organoleptic properties, can provide stability to clouding agents and beverage compositions containing them.
[0137] Consequently, the invention provides in another of its aspects a composition comprising a beverage haze composition and a compound of formula (I).
[0138] In a particular embodiment of the invention, a flavor composition as defined herein may be provided in the form of an emulsion. This emulsion composition may be particularly useful in cloudy beverage applications, in particular where a clouding agent is to be employed.
[0139] In yet another aspect of the invention there is provided a cloudy beverage composition comprising a clouding agent and a compound of formula (I).
[0140] Other preferred edible compositions are those compositions which are formed by a ripening process.
[0141] In food processing, it often occurs that a food needs to remain for an extended period of time and under well-defined conditions to obtain the food with the required and recognized quality. A commonly used term for this process is ripening. Ripening is well known for processing certain types of cheese, meat, soy sauce and wine, as well as beer, sausage, sauerkraut, tempeh and tofu. There are also specific steps that are performed for specific reasons (such as water removal, or unpleasant note removal) that have beneficial effects on food products. Examples of this are chocolate shelling and drying of pasta, vegetables and fruits. Transformations that improve food quality are induced by chemical conversions, enzymatically catalyzed conversions or fermentative transformations. All these conversions are slow and therefore expensive; they are also not fully predictable or controllable.
[0142] The compounds of formula (I), taking into account their remarkable addition property to the authentic flavor characteristics of the edible compositions in which they are incorporated, can be added to an edible product during its ripening process in order to reduce storage time without adversely influencing the quality of the matured product's flavor.
[0143] Consequently, in another aspect of the invention, a method of maturing a product is provided, selected from the group consisting of cheese, meat, soy sauce and wine, beer, sausage, sauerkraut, tempeh and tofu, comprising the step of maturing the product in the presence of a compound according to formula (I).
[0144] In another aspect of the invention there is provided a method of conching chocolate, said method comprising the step of adding to chocolate a compound according to formula (I), or a flavor composition containing the same.
[0145] In this context now follows a series of non-limiting examples that serve to illustrate the invention. Examples of General Structure Synthesis
where: R1 is a straight-chain hydrocarbon group having 9 to 21 carbon atoms and containing zero to three double bonds or R1 is a [(1E)-2,6-dimethylhepta-1,5-dien-1-yl] group] en = 1 or 2. Synthesis 2.1 Routine A: (DCC method)
[0146] In a 250 ml round base flask was mixed fatty acid (3.93 mmol) with 1-hydroxypyrrolidine-2,5-dione (0.498 g, 4.32 mmol) in dioxane (50 ml) to provide 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 the amino acid (6.48 mmol) in a 2% solution of sodium bicarbonate (0.363 g, 4.32 mmol) in water. The reaction mixture was stirred for 4 hours at 50 °C. Dioxane was evaporated and the aqueous residue was also diluted with water, acidified with a dilute hydrochloric acid solution and extracted with ethylacetate. Organic layers were combined, washed with brine, dried and evaporated to yield 1.3 g of a white solid. Product was purified by flash column chromatography, DCM/methanol eluent.
[0147] 1 g of 85 to 90% pure product can be obtained. 2.2. Routine B (DCC method with protection group) Step 1:
[0148] To a solution of an O-methylated amino acid (16.51 mmol) in DCM (100 ml) was added triethylamine (1.519 g, 15.01 mmol) at minus 15 °C. A fatty acid (.01 mmol) was added while stirring. A solution of DCC (15.01 mmol) in 10 mL of DCM was added dropwise at 0 °C. The reaction mixture was stirred at 0°C for 1 hour and stirring was continued at room temperature for 3 hours. Dicyclohexylurea was removed by filtration from the reaction mixture. The filtrate was washed with a saturated sodium bicarbonate solution, dilute hydrochloric acid solution and water. The organic layer was separated, dried and evaporated to yield 3 g of an oil. This oil was purified by flash column chromatography, eluent DCM/methanol. The intermediate ester compound can be isolated in 95% purity. Step 2:
[0149] 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 a 32% solution of sodium hydroxide (2.453 g, 19.63 mmol) was added and the mixture was stirred at room temperature for three hours. The mixture rests for 14 hours.
[0150] 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 yellow semi-solid residue was obtained. NMR confirmed the structure of the title compound, purity 95% 2.3 Routine C (acid chloride)
[0151] An amino acid (20 mmol) was dissolved in a solution of sodium hydroxide (54.5 mmol) in water (40 ml).
[0152] Tetrahydrofuran (60 ml) was added. Fatty acid chloride (18.18 mmol) was added dropwise at room temperature. Stirring was continued for 2 hours. The mixture was diluted with water, acidified with a 37% hydrochloric acid solution (2.99 ml, 36.4 mmol) and extracted with ethyl acetate.
[0153] The organic layers were combined, dried and evaporated.
[0154] The residue contains about 20% free fatty acid according to NMR. The solids were stirred with heptane for 30 minutes, filtered and dried. This resulted in 2.4 g of the title compound as a cream colored solid. (purity 95%). 2.4 All synthesized compounds Table 1: List of synthesized compounds


NMR Data (Examples) 3.1 Structure 1 GABA-C10:0

[0155] 1H NMR (600 MHz, DMSO-d6) δ ppm 0.83 - 0.87 (m, 3H, H-C(10)) 1.18 - 1.29 (m, 12H, HC( 4, 5, 6, 7, 8, 9) 1.46 (quin, J=7.22 Hz, 2 H, HC(14)) 1.59 (quin, J=7.22 Hz, 2 H, HC (3)) 2.02 (t, J=7.39 Hz, 2H, HC(2)) 2.19 (t, J=7.39 Hz, 2H, HC(13)) 3.00 - 3.05 (m, 2H, HC(15)) 7.77 (t, J=5.50Hz, 1H, HN(15)
[0156] 13C NMR (150 MHz, DMSO-d6) δ ppm 13.95 (C(10)) 22.09 (C(9)) 24.64 (C(14)) 25.29 (C(3) ) 28.64 (C(5)) 28.66 (C(7)) 28.78 (C(6)) 28.90 (C(4)) 31.07 (C(13)) 31.27 ( C(8)) 35.38 (C(2)) 35.77 (C(15)) 172.03 (C(1)) 174.21 (C(12)) 3.2 Structure 2 GABA-C12:0

[0157] 1H NMR (600 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.87 Hz, 3H, HC(12)) 1.15 - 1.33 (m, 16H, 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, 2H, HC(2)) 2.19 (t, J=7.56 Hz, 2H, HC(15)) 3, 02 (q, J=6.53 Hz, 2 H, (HC(17)) 7.77 (t, J=5.33 Hz, 1 H, HN(13))
[0158] 13C NMR (150 MHz, DMSO-d6) 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(1)) 174.20 (C14)) 3.3 Structure 11 GABA-C18:2

[0159] 1H NMR (600 MHz, CHLOROFORM-d) δ ppm 0.89 (t, J=6.87 Hz, 3H, HC(18)) 1.26 - 1.39 (m, 14H, HC (4, 5, 6, 7, 15, 16, 17) 1.57 - 1.65 (m, 2 H, HC(3)) 1.84 (quin, J=6.96 Hz, 2 H, HC (22)) 2.05 (q, J=7.22 Hz, 4H, HC(8), HC(14)) 2.19 (t, J=7.73 Hz, 2H, HC(2)) ) 2.40 (t, J=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, 2H, HC(23)) 5.30 - 5.41 (m, 4H, HC(9, 10, 12.13) 5.96 (br.s., 1H, HN (19))
[0160] 13C NMR (150 MHz, CHLOROFORM-d) δ ppm 14.08 (C(18) 22.58 C(17)) 24.74 (C3)) 25.63 (C(22)) 25.75 (C(11)) 27.20 (C 8, 14)) 29.15 (C(6)) 29.26 (C(5, 21)) 29.35 (C(15)) 29.62 (C (4)) 31.49 C(7)) 31.52 C(16)) 36.73 C(2)) 38.84 (C23)) 127.90 (C12)) 128.06 (C(10) ) 130.03 (C(9) 130.25 (C(13)), 174.17 (C(1) 177.43 (C(20)) 3.4 Structure 16 beta-alanine-C18: 2
[0161] 1H NMR (600 MHz, DMSO-d6) δ ppm 0.85 (t, J=7.05Hz, 3H, HC(18)) 1.11 - 1.37 (m, 14H, HC (4, 5, 6, 7, 15, 16, 17) 1.37 - 1.53 (m, 2H, HC(3)) 1.94 - 2.08 (m, 6H, HC(2 , 8.14) 2.34 (t, J=6.87 Hz, 2H, HC(21)) 2.73 (t, J=6.70Hz, 2H, HC(11)) 3.13 - 3.27 (m, 2H, HC(22)) 5.24 - 5.40 (m, 4H, HC(12,13)) 7.84 (t, J=5.67Hz, 1H , HN(19))
[0162] 13C NMR (150 MHz, DMSO-d6) 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(1)) 172.91 (C(20)) Application Examples Condiments and fats
[0163] The following formulations were prepared and tasted by trained guests. Soy based product
[0164] Pure product with a salt level between 5-40%
[0165] Salt level in application 0.3-1.0%
[0166] C18:2-gaba - (0.5 ppm) was added to a low salt Kikoman soy sauce diluted to 1% (9% salt). The resulting composition was considered to be stronger, more umami, longer lasting, richer.
[0167] C18:2-gaba - (0.5 ppm) was added to a pure low salt Kikoman soy sauce (9% salt). The resulting composition was considered to be stronger in body and taste and more salty. based on fish
[0168] Pure product with a salt level between 5-40%
[0169] Salt level in application 0.3-1.0%
[0170] C18:2-gaba - (0.5 ppm) was added to a fish sauce diluted to 1% (0.27% salt). The resulting composition was judged to be stronger in umami, longer lasting and richer.
[0171] C18:2-gaba - (0.5 ppm) was added to pure fish sauce (27% salt). The resulting composition was considered to be strong in body and palate, saltier, richer with more rounded fish notes. Emulsions-Colloidal Water in Oil Butter
[0172] Fat levels 20-90%
[0173] Salt Levels 0.1-1%
[0174] Blueband "halvarine" 39% fat, 0.35% salt
[0175] C18:2-gaba added at 1ppm. The composition was considered to exhibit a more authentic butter flavor with more taste. Pilaf
[0176] Standard cooked rice with 10% of the aforementioned C18:2-gaba flavored butter was judged to have more flavor, with a lasting creamy authentic butter flavor. oil in water mayonnaise
[0177] Fat levels between 10-80%
[0178] Low-fat mayonnaise (27% Fat)
[0179] C18:2-gaba (0.5 ppm) added to the mayonnaise was found to produce a creamy taste, consistent with a high-fat impression. Sauces (Dressings)
[0180] Oil Levels 0.5-50%
[0181] Acidity PH 3-6
[0182] Low Fat Salad Dressing (13.6% Hard Fat)
[0183] C18:2-gaba (0.5PPM) was added to the sauce and produced a better taste that was impressively creamy. Soups and Broths
[0184] Fat levels 0.1-10%
[0185] Salt Levels 0.3-1.4%
[0186] Standard chicken broth base, 0.7% salt, 0.5% hard fat,
[0187] C18:2-gaba @ 0.5PPM. Strong, Salty, Umami, 6-Cheese Taste
[0188] Fat level 1-40%
[0189] Salt 0.3-2%
[0190] ERU spreadable cheese
[0191] C18:2-gaba @ 0.5PPM Whole, Salty, cheese bite, riper,
[0192] Cheese sauce: 5% fat 1.6% salt
[0193] C18:2-gaba @ 0.5PPM Whole, Salty, cheese bite expan ding Beef and Poultry
[0194] Differentiator, high temperature 100-250 degrees Celsius one in-process frying with oil
[0195] C18:2-gaba @ 2.0 PPM in 135 grams of frying oil (Blue band 82% Fat) 450 grams of chicken fillet 2 minutes over high heat and 5 minutes over medium heat.
[0196] Chicken flavor becomes juicy, juicy, meat slightly whiter
[0197] Likewise the oil has tastier golden brown notes. Baked goods and Pizza
[0198] Differentiator, high temperature 100-250 degrees Celsius in hot air cooking process
[0199] C18:2-gaba @ 0.5PPM in the crust and @ 0.5PPM in the tomato sauce
[0200] The pizza was covered with cheese and baked in a hot air oven at @ 200 degrees Celsius
[0201] The crust became less dry, more succulent, and the tomato became richer, sweeter and the total lingering aftertaste was very rich and pleasant Snack
[0202] A snack consisting of a potato chip base, containing 35% fat and flavored with a cheese flavoring containing salt, MSG, dairy, organic acids, sugars, and a flavor formulation. The following compounds have been added to the snack product at the indicated levels, and tasting results are reported:
[0203] C18:2-gaba 1 ppm: Fat, cheese, cheese crust, hard,
[0204] C18:2-gaba 0.5 ppm: fortified dairy, from cheese. Expanded air base
[0205] An air-expanded base (Rice, Wheat, Tapioca, Potato, Salt, Sugar, Modified Starch) containing 3% fat and flavored with cheese flavoring containing salt, MSG, dairy, organic acids, sugars and flavor. The following compounds have been added to the base at the indicated levels, and tasting results are reported:
[0206] C18:2-gaba 1 ppm: Fat, cheese, cheese rind, hard, base coat
[0207] C18:2-gaba 0.5 ppm: Reinforced dairy, cheese. Testing on Dairy Products
[0208] The following tests were performed on dairy products processed by fermentation, pasteurization or UHT. Products contain fat, protein and calcium. Flavored UHT cream, unsweetened and with different fat levels
[0209] In a UHT milk containing 0% 1.5% and 3% fat, flavored with a patented cream flavor dosed at 0.03%
[0210] C18:2 - gaba was added at 2ppm.
[0211] The samples were evaluated by expert tasters.
[0212] The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat. The results are presented below: -
[0213] UHT milk 0% fat, cream flavor (0.03%): Milky, slightly creamy, cardboard aftertaste
[0214] UHT milk 0% fat, cream flavor (0.03%) but with C18:2 added at 2 ppm: Very creamy, Milky, long lasting.
[0215] UHT milk 1.5% fat, cream flavor (0.03%): Milky, slightly creamy
[0216] UHT milk 1.5% fat, cream flavor (0.03%) with C18:2 gaba added at 2 ppm: very creamy, Milky, long lasting, salivation.
[0217] UHT milk 3.0% fat, cream flavor (0.03%): Milky, slightly creamy
[0218] UHT milk 3.0% fat, cream flavor (0.03%) with C18:2 gaba added at 2 ppm: very creamy, Milky, long-lasting, whipped cream-like taste. UHT sweetened banana flavored milk with different fat levels
[0219] In a UHT milk with 0% and 3% fat sweetened with 4% sucrose by weight, flavored with patented banana flavor dosed at 0.04%. C18:2 gaba was added at 0.25 ppm, 0.5 ppm and 1 ppm.
[0220] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0221] UHT milk 0% fat, Banana flavor (0.04%): Strong banana, estery, eugenol type, unbalanced.
[0222] UHT milk 0% fat, Banana flavor (0.04%) C18:2 - gaba (0.25 ppm): banana fuller, more authentic, sweeter.
[0223] UHT milk 0% fat, Banana flavor (0.04%), C18:2 - gaba (0.5 ppm): fuller banana, authentic, creamy and sweet,
[0224] UHT milk 0% fat, Banana flavor (0.04%), C18:2 - gaba (1 ppm): creamy banana, creamy, sweet aftertaste.
[0225] UHT milk 3% fat, Banana flavor (0.04%): strong estery banana, eugenol type, spicy
[0226] UHT milk 3% fat, Banana flavor (0.04%), C18:2 - gaba (0.25 ppm): more authentic, less estery and rounder
[0227] UHT milk 3% fat, Banana flavor (0.04%), C18:2 - gaba (0.5 ppm): creamy banana
[0228] UHT milk 3% fat, Banana flavor (0.04%), C18:2 - gaba (1 ppm): creamy long-lasting and more authentic and more impactful. Flavored, unsweetened yogurt cream and different fat levels
[0229] In a Yogurt containing 0%, 1.5% and 3% fat, flavored flavor with a patented cream flavor dosed at 0.03%, C18:2-gaba was added at 2 ppm. The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0230] Yogurt 0% fat, cream flavor (0.03%): very acidic, metallic
[0231] Yogurt 0% fat, cream flavor (0.03%), C18:2-gaba 2 ppm: less acidic, light creamy aftertaste
[0232] Yogurt 1.5% fat, cream flavor (0.03%): moderate creamy yogurt
[0233] Yogurt 1.5% fat, cream flavor (0.03%), C18:2-gaba 2 ppm: very creamy, consistent, pleasant long-lasting, with a hint of whipped cream.
[0234] Yogurt 3% fat, cream flavor (0.03%): sour after taste, creamy
[0235] Yogurt 3% fat, cream flavor (0.03%), C18:2-gaba 2 ppm: less acidic, much creamier, very long-lasting creamy aftertaste. Yogurt sweetened with strawberry sugar
[0236] The base consisted of a yogurt base with 1.5% hard fat, sweetened with 8% sucrose by weight, flavored with a patented strawberry flavor @ 0.015%.
[0237] Base: fruity, strawberry
[0238] Base plus C18:2-gaba at 2ppm: very creamy and fresh strawberry
[0239] Base plus C18:0-gaba at 2ppm: whole juicy, gelatinous Strawberry yogurt Activa
[0240] In an Activa strawberry flavored yogurt, fat C18:2-gaba
[0241] Active: gelatinous, green and creamy strawberry,
[0242] Activia plus C18:2-gaba at 2 ppm: very creamy strawberry, whole and fresh Vanilla milk 3.0% fat
[0243] In a 3% fat milk drink, sweetened with 4% sucrose by weight, flavored with Vanillin @ 10 ppm and a Vanilla extract @ 0.03% C18:2-gaba, was added at 0, 5 or 2 ppm.
[0244] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0245] Base: Milk 3% fat, 4% sugar, vanilla 10 ppm, vanilla extract 0.03%
[0246] Base: vanillic sweet, very slightly grainy,
[0247] Base: C18:2-gaba 2 ppm: with grain flavor, grease, authentic, sweet, Chocolate milk with different fat content
[0248] In a C18:2-gaba chocolate milk with 1.8% and 3% fat was added at 0.5 and 1 ppm.
[0249] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0250] Chocolate milk 1.8% fat: cocoa powder flavor, sweet, slightly creamy,
[0251] C18:2-gaba chocolate milk with 1.8% fat at 0.5 ppm: stronger cocoa note, more chocolate vs cocoa
[0252] C18:2-gaba chocolate milk with 1.8% fat at 1 ppm: very creamy, chocolate, creamy long-lasting and cho-colate flavor.
[0253] Chocolate milk 3% fat: cocoa powder, sweet, creamy flavor
[0254] Chocolate milk C18:2-gaba with 3% fat at 0.5 ppm: very creamy cocoa note, highlighted.
[0255] Chocolate milk C18:2-gaba with 3% fat at 1 ppm: very creamy, long lasting, sweet, taste almost similar to cho-colate ice cream. Soy milk
[0256] In a soy milk sweetened with 5% sucrose by weight, flavored with a patented milk flavor at a dosage of 0.1%, C18:2-gaba was added at 2 ppm
[0257] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0258] Soy milk, 5% sucrose, milk flavor @ 0.1%: sweet, dry, green, soy flavor
[0259] Soymilk, 5% sucrose, milk flavor @ 0.1%, C18:2- gaba at 2ppm: clean, creamy, good soy taste masking, creamy and milky. Caloric & Non-Calorie Drinks
[0260] Test on beverage products containing carbohydrate sweeteners such as Sucrose, High Fructose Corn Syrup, Fructose and Glucose; or high intensity non-nutritive sweeteners such as Aspartame Acesulfame K, Sucralose, Cyclamate, Na+ Saccharin, Neotame, Rebaudioside A and/or other stevia-based sweeteners.
[0261] Sweetener in beverage applications ranges from 0-20%. Examples:
[0262] Carbonated soda: < 1% to 15% sweetener
[0263] Soft drinks (non-alcoholic): < 1% to 15% sweetener
[0264] Juices; < 1% to 15% sweetener
[0265] Powdered soft drinks: < 1% to 20% sweetener
[0266] Liquid concentrates: < 1% to 20% sweetener
[0267] Alcoholic beverages: < 1% to 40% sweetener
[0268] Functional beverages: < 1% to 20% sweetener
[0269] Coffee-based beverages: < 1% to 15% sweetener
[0270] Tea based beverages: < 1% to 15% sweetener Test on coffee 3 in 1
[0271] In a Nestle 3-in-1 coffee beverage (market product) sweetened with sucrose and containing cream with fat C18:2-gaba was added.
[0272] Samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste, abundance, salivation, sweetness, juiciness, richness, longevity and fat.
[0273] The base is a 3-in-1 Coffee drink (market product) sweetened with sucrose and containing cream with fat
[0274] Basis: coffee, sweet, moderate dairy
[0275] Base plus C18:2-baby at 1ppm: very pleasant taste effect, creamy as if coffee cream is added, sweeter. Taste Test
[0276] In a powdered Tang orange flavored soft drink (market product) sweetened with sucrose plus high intensity sweetener and containing citric acid and C18:2-gaba.
[0277] All samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, taste & body, enhancement, richness, juiciness, longevity, salivation, sweetness, masking unpleasant high intensity sweetener notes.
[0278] The base is Tang Orange flavor
[0279] Base: sweet, orange, licorice and unpleasant notes of long-lasting high intensity sweetener, bitter, weak
[0280] Base plus C18:2-gaba at 0.5 ppm: enhances sweet juicy orange notes, enhanced taste. Additionally, the unpleasant notes of the high-intensity sweetener have been suppressed. Mango flavored soft drink containing different levels of juice.
[0281] In a smooth Mango flavored drink, sweetened with 8% sucrose and containing 0.1% citric acid and 1%, 4% and 6% clear mango juice flavored with a patented Mango flavor @ 0.05% , C18:2-gaba was added as such.
[0282] All samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, juicy taste, enhancement, richness, juiciness, longevity, salivation, sweetness.
[0283] In a smooth Mango flavored drink, sweetened with 8% sucrose & containing 0.1% citric acid and 1% clear mango juice flavored with patented Mango flavor @ 0.05%, C18:2-gaba was added as such.
[0284] The base is water, 8% sucrose, 0.1% citric acid, 1% clear mango juice (very low% juice), flavored with Mango flavor, dosed at 0.05% Base: sweet , fruity, mango, weak
[0285] Base plus C18:2-gaba at 1ppm: Very juicy mango, authentic, similar to greasy peel, much more palatable, long-lasting mango flavor, taste is close to whole juice
[0286] In a smooth Mango flavored drink, sweetened with 8% sucrose & containing 0.1% citric acid and 4% flavored clear mango juice with Mango flavor @ 0.05%, C18:2-gaba & C18 :2-Pro have been added, as such (separate) and in combination.
[0287] The base is water, 8% sucrose, 0.1% citric acid, 4% clear mango juice (30% reduced juice), flavored with Mango flavor, dosed at 0.05% Base: sweet , fruity, mango, little taste
[0288] Base plus C18:2-gaba at 1 ppm: Very thick juicy mango, authentic, similar to greasy peel, hard-sour mango flavor, more palatable than whole juice,
[0289] A smooth Mango flavored drink, sweetened with 8% sucrose & containing 0.1% citric acid and 6% light mango juice flavor with Mango flavor @ 0.05%, C18:2-gaba
[0290] The base is water, 8% sucrose, 0.1% citric acid, 6% clear mango juice (whole juice), flavored with Mango flavor, dosed at 0.05%. Base: Sweet, fruity, mango, full flavour.
[0291] Base plus C18:2-baby at 1ppm: Very thick juicy mango, authentic, similar to greasy rind, hard-sour mango flavor, rich. Test on Alcoholic Drinks Test on Baileys Cream Liqueur:
[0292] In Baileys (Market Product) C18:2-gaba cream liquor was added at 1 ppm.
[0293] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, alcohol impact, taste, abundance, salivation, sweetness, bitterness, richness, longevity and fat. Base is Baileys cream liqueur.
[0294] Base: alcoholic, cream, cocoa
[0295] Base plus C18:2-gaba at 1ppm: Strongly enhanced alcohol effect, more cocoa, very creamy and long-lasting aftertaste. Test on Heineken beer:
[0296] In Heineken beer (Market Product) C18:2-gaba was added at 0.5 ppm.
[0297] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, alcohol impact, malt flavor, hop flavor, taste, abundance, salivation, sweetness, bitterness, richness, longevity and fat. The base is Heineken beer
[0298] Base: Bitter, hop-like, fruity, malty, alcoholic
[0299] Base plus C18:2-bab at 0.5ppm: more loupe, more bitter, more malt and stronger alcohol impact. Test in Orange Breezer:
[0300] In Orange Breezer (Market Product) C18:2-gaba was added at 1 ppm.
[0301] The samples were evaluated by expert tasters. The tasters were asked to describe the samples focusing on authentic taste, alcohol impact, juiciness, taste, abundance, salivation, sweetness, bitterness, richness, longevity and fat. The base is Orange Breezer
[0302] Base: Bitter, orange, soapy, burning, alcoholic
[0303] Base plus C18:2-gaba at 0.5 ppm: orange more alcoholic, sweeter, juicier, less soapy Test with drinks containing 0.01% to 7% organic acids Test 18:2 with organic acids in a drink.
[0304] In a solution containing water, 7% sucrose by weight, and different organic acids, C18:2-gaba was added at 1 ppm. We observed taste effects on acid perception in addition of C18:2-gaba. 7% sucrose plus 0.121% tartaric acid by weight
[0305] The base is water, 7% Sucrose by weight, 0.121% by weight tartaric acid
[0306] Base: sharp acid aftertaste, astringent
[0307] Base plus C18:2-gaba at 1 ppm, decreased sharp acid perception, full-body taste, stronger, more immediate salivation (front impact), and an impression of the flesh of the fruit (grape, apple, banana taste , pear) 7% sucrose plus 0.1081% malic acid by weight
[0308] The base is water, 7% sucrose by weight, malic acid 0.1081% by weight
[0309] Base: acidic, green, slightly astringent
[0310] Base plus C18:2-gaba at 1 ppm, decreased sharp acid perception, produces fuller body, palate, strong salivation, and an impression of the flesh and skin notes of the fruit (apple) 7% Sucrose plus citric acid a 0.1% by weight
[0311] Base is water, 7% sucrose by weight, 0.1% by weight citric acid Base: fresh sharp, acid
[0312] Base plus C18:2-gaba at 1 ppm, decreased sharp acid perception, full body taste, strong salivation, and an impression of the juicy notes of citrus fruit (orange, lemon) 7% sucrose plus fumaric acid at 0, 0936% by weight
[0313] Base is water, 7% sucrose by weight, fumaric acid 0.0936% by weight Base: moldy, acidic, astringent
[0314] Base plus C18:2-gaba at 1ppm: decreased sharp acid perception, full body taste effects, higher sweet effects, and an impression of the full notes characteristic of sweet red & vanilla flavor types (vanilla, chocolate, raspberry, cherry, especially benzaldehyde) Test in low salt Kikkoman soy sauce
[0315] Base is Kikkoman soy sauce
[0316] Base: dark roast taste, umami,
[0317] Base plus C18:2-baby at 0.5 ppm: much saltier, sweeter and longer lasting. Test in Eru Prestige
[0318] Base is Eru prestige
[0319] Base: Yesy, cheese bite, slightly bitter
[0320] Base plus C18:2-gaba at 0.5 ppm, very salty, much more cheese bite, umami, prolonged, long lasting. Test in menthol fondant (1%)
[0321] Base is Fondant 65%, Sugar Syrup 34% and a patented menthol flavor at 1%
[0322] Base: Refreshing, menthol, sweet,
[0323] Base plus C18:2-gaba at 2 ppm: menthol impact enhanced, stronger, refreshing, sweeter, lasting, fresh. Calve salad dressing with low fat content:
[0324] Base is Calve salad dressing (market product)
[0325] Base: acidic, rancid, watery
[0326] Base plus C18:2-gaba at 0.5ppm plus fuller, creamy, rich, less acidic. 60% reduced fat mayonnaise Calve Base is 60% reduced fat mayonnaise (Market Product)
[0327] Base: rancid, acidic, null,
[0328] Base plus C18:2-baby at 0.5 ppm whole, rich, creamy, more like egg yolk. Comparison in a mango juice drink
[0329] Base is 8% sucrose, 0.1% citric acid, 0.18 g clear mango juice, and a patented 0.05% mango flavor.
[0330] Base: fruity mango
[0331] Base plus C18:2 boast at 2 ppm: similar to pink fat peel, juicy, authentic
[0332] Base: fruity mango
[0333] Base plus C18:2-baby at 2 ppm nice juicy hard browns whole, almost a little salty Comparison in broth
[0334] Base is Maggi beef broth 1 tablet in 500 ml of hot water
[0335] Base: salty, umami, powder
[0336] Base plus C18:2-baby at 2 ppm salty, savory, whole Strawberry drink comparison
[0337] Base is 7% sucrose, 0.1% citric acid, and a proprietary strawberry flavor @0.015%
[0338] Base: sweet, fruity, strawberry estery
[0339] Base plus C18:2-baby at 2 ppm fatty taste, creamy, fruity and juicy strawberry
[0340] Base plus C18:0-gaba at 0.5 ppm creamy, fruity, slow and moderately long-lasting sucu Test in a strawberry yogurt
[0341] Base: Yogurt 1.5% whole yoghurt, 8% sucrose, patented strawberry flavor @ 0.015% of
[0342] Base: fruity, strawberry
[0343] Base plus C18:2-gaba at 2ppm, creamy authentic strawberry, fruity, stronger strawberry, ripe, long-lasting, juicy, Vanilla milk test:
[0344] Base: Milk 0.15% fat, sweetened with 4% sucrose by weight, flavored with patented Vaniline flavor @ 10 ppm + ext. of Vanilla @ 0.03%
[0345] Base: vanillic sweet, slightly grainy flavor,
[0346] Base plus C18:2-gaba at 2 ppm: greasy, authentic vanilla lasting, vanilla bean taste is enhanced Test in chocolate flavored drink:
[0347] Base: Water, 4% sucrose, 0.03% patented chocolate flavor
[0348] Base: sweet vanillic, cocoa
[0349] Base plus C18:2-gaba at 2 ppm: wholemeal, sweeter, more vanillic milk chocolate is enhanced, very long-lasting Test in pear flavored drink:
[0350] Base: water, 7% sugar, 0.1% citric acid, patented pear flavor 0.025%
[0351] Base: nice pear, fruity estery, green
[0352] Base plus C18:2-gaba at 1ppm: long lasting, juicy and greasy rind very authentic type, like eating fruit instead of drinking a drink Test in peach flavored drink:
[0353] Base is water, 8% sugar, 0.1% citric acid, and patented peach flavor at 0.05%
[0354] Base: fruity peach
[0355] Base plus C18:2-gaba at 1 ppm: fruity, long-lasting peach, juicy and greasy rind very authentic type Test in Pineapple flavored drink:
[0356] Base is water, 8% sugar, 0.1% citric acid and 0.03% patented pineapple flavor
[0357] Base: pineapple jam, gelatinous
[0358] Base plus C18:2-gaba at 1 ppm very ripe, gelatinous, long lasting and sweet

权利要求:
Claims (6)
[0001]
1. Edible or beverage composition, characterized by the fact that it comprises a compound corresponding to formula (I)
[0002]
2. Edible composition or beverage according to claim 1, characterized in that the carboxylic acid residue has 10, 12, 14, 16 or 18 carbon atoms, saturated or unsaturated with one or two double bonds.
[0003]
3. Edible or beverage composition according to claim 1 or 2, characterized in that the carboxylic acid residue has 18 carbon atoms and has two double bonds.
[0004]
4. Edible or beverage composition according to any one of claims 1 to 4, characterized in that it comprises an ingredient selected from the group consisting of sugars, fats, salt, MSG, calcium ions, phosphate ions , organic acids, proteins, purines and mixtures thereof.
[0005]
5. Standard solution, characterized in that it comprises 0.01 to 1% by weight of the compound of formula (I) as defined in claim 1.
[0006]
6. Standard solution according to claim 5, characterized in that it comprises a solvent selected from the group consisting of ethanol, triacetin, glycerol and migliol or mixtures thereof.

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

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

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2020-05-05| B07A| Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]|

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2021-04-06| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2021-06-22| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|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/US2013/034335|WO2013148991A1|2012-03-30|2013-03-28|N-acyl derivatives of gamma amino - butyric acid and and beta alanine as food flavouring compounds|

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