EDIBLE COMPOSITION, STOCK SOLUTION AND METHOD TO COMPLEMENT THE TASTE OR TASTE OF EDIBLE PRODUCTS CH

专利摘要:
flavoring composition containing carboxylic acid-amino acid conjugates, use of said composition, as well as stock solution, edible composition and caloric or non-caloric drink containing such composition. the present invention relates to a flavoring composition comprising a compound of formula (i) corresponding to the formula and edible salts thereof, wherein r 1 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, r 1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid.
公开号:BR112014024157B1
申请号:R112014024157-0
申请日:2013-03-28
公开日:2020-12-15
发明作者:Harry Renes；Yili Wang；Feng Shi；Esther Van Ommeren；Susanna Magdalena Vorster；Adri De klerk
申请人:Givaudan Sa；
IPC主号:

专利说明:

[001] The present invention relates to certain acid-carboxylic-amino acid conjugates, flavoring compositions containing said conjugates, and their use in edible compositions.
[002] Many food flavoring ingredients are known in the art that exert their own flavor characteristics very pronounced on a food. Such ingredients can be of great value in niche areas of certain 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 flavoring ingredients that act as a complement or enhance the taste and taste characteristics of the edible compositions in which they are incorporated.
[004] The applicant has now found a group of compounds that can be used with flavoring ingredients that complement or enhance the taste and taste characteristics of edible compositions in which they are incorporated through a wide category of flavor applications.
[005] The present invention provides in first compounds from the aspect of formula (I) corresponding to the formula

[006] its edible salts and their use in edible compositions,
[007] where:
[008] R1 is an alkyl residue containing 6 to 20 carbon atoms, or alkene residue containing 9 to 25 carbon atoms with 1 to 6 double bonds, R1 together with the carbonyl group to which is attached an acid residue carboxylic.
[009] Edible salts include those typically used in the food and beverage industry and include chlorides, sulfate, phosphates, gluconates, sodium, citrates, carbonates, acetate and lactate.
[0010] The skilled person will appreciate that the amino acid residue in the compounds defined above is the proline residue (Pro).
[0011] From now on, referring to the amino acid or its residue, the abbreviation of three letters used above in parentheses can be used.
[0012] Carboxylic acids can also be represented by abbreviations. Hereinafter, carboxylic acid residues can be mentioned by the abbreviation Cn, "n" where it 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, it can be abbreviated as C18: 0 (because it contains null double bonds), while an 18-carbon acid which has a double bond - for example, acid oleic - 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: 1t.
[0013] In a given embodiment of the present invention, the carboxylic acid residue is a fatty acid residue.
[0014] The fatty acid residue can be the residue of a C8 to C22 acid graphic. The fatty acid can be mammalian or non-mammalian. A mammalian fatty acid is a natural or synthetic fatty acid that is identical in structure to one naturally produced in a mammal, including, but not limited to, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, icosatrienoic acid, arachidonic acid, icosapentenoic 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-icosenoic acid; and 12-transenicosenoic acid.
[0015] 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 cis or trans configuration.
[0016] More particularly, the preferred fatty acid residues are C16 to C18, and can be saturated or unsaturated.
[0017] The knowledgeable person will appreciate, however, that natural sources of these fatty acids, for example, almond oil, avocado oil, castor oil, coconut oil, corn oil, algae oil supply. , 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, safflower oil is predominantly a source of C18: 2 linoleic acid, however it can contain other fatty acids, such as linolenic acid (C18: 3) and palmitic acid (C16: 0), among others. Consequently, referring here to a compound containing a certain 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 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.
[0018] The compounds of formula (I) can also be represented using these abbreviations. For example, the compound of formula (I) consisting of a residue of a C18 carboxylic acid and a residue of the amino acid Proline (Pro) can be represented by the abbreviation C18-Pro. For simplicity, the compounds of formula (I) hereinafter can be represented in this abbreviated form.
[0019] As is evident from formula (I) above, the amine nitrogen atom in the amino acid residue is attached to a carbonyl carbon atom of the carboxylic acid residue to form an amide bond. Thus, the short form C18-Pro represents the compound of formula (I) in which the proline residue is connected via its nitrogen atom to the carbonyl carbon atom of a C18 carboxylic acid.
[0020] These compounds are particularly effective for improving the juiciness and authenticity typical of citruses. They find use particularly in powder for juices and soft drinks, and also in dairy applications, such as fruit-flavored milk, yogurt and ice cream.
[0021] The compounds include C8-Pro, c9-Pro, c10-Pro, c12-Pro, c14-Pro, c16-Pro, c18-Pro, c20-Pro and c22-Pro.
[0022] The compounds include C8-Pro, c9-Pro, c10-Pro, c12-Pro, c14-Pro, c16-Pro, c18-Pro, c20-Pro and c22-Pro, in which the carboxylic acid residue is saturated.
[0023] 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 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.
[0024] Particularly preferred compounds that carry the residue Pro, N-geranoil-Pro, N-palmitoyl-Pro, N-palmitenoil-Pro, Nestearoil-Pro, N-linoleoil-Pro and N-linolenoyl-Pro.
[0025] 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 guaranteed 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 condition 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.
[0026] In yet another embodiment, an amino acid alkylester can be reacted with a fatty acid chloride under basic condition in an aqueous-based solvent, such as a water / THF solvent system. After that, the ester can be hydrolyzed carefully without affecting the amide bond in the basic aqueous methanol solution.
[0027] In yet another embodiment, a fatty acid and an alkyl acid amino acid can be reacted in dioxane in the presence of DCC (dicyclohexylcarbodiimide) and 1-hydroxypyrrolidine-2,5-dione. The ester can be hydrolyzed carefully without affecting the amide bond in the diluted aqueous basic methanol solution.
[0028] In yet another modality, an anhydride (mixture) of a fatty acid is reacted with an amino acid in dioxane.
[0029] In yet another embodiment, an alkyl ester of fatty acid can be reacted with an amino acid in dioxane.
[0030] In yet another modality, an amino acid alkylester is reacted with a triglyceride, optionally in the presence of a cosolvent. The amino acid ester thus formed is then hydrolyzed according to a method described above.
[0031] In yet another modality, an amino acid is reacted with a triglyceride, optionally in the presence of a cosolvent.
[0032] 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 cosolvent and / or water.
[0033] In yet another embodiment, a fatty acid alkylester 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.
[0034] The compounds of formula (I) communicate remarkable organoleptic properties to edible compositions to which they are added. Especially, they impart a highly intense, authentic and harmonious taste, and a roundness and fullness to edible compositions containing them.
[0035] More particularly, the compounds can be incorporated into an edible product to communicate a remarkable taste, body and improved perception of fat; or an improved umami or salt taste; or a freshness and richness.They are particularly useful in applications low in fat, salt and umami. They are also useful in fat-free formulations such as drinks and oral care applications. They also find use in dairy applications and in vanilla, cocoa and chocolate.
[0036] This finding was considered the most surprising of all: when the applicant tasted the compounds in the diluted aqueous solution, they were either tasteless or they exhibited a disappointing, slightly fatty taste profile. As such, they appeared to be quite unsuitable for use in flavor applications. Only their combination with flavor co-ingredients and the judicious selection of their levels of use was it possible to discover the remarkable organoleptic properties of these compounds. Their effect on edible compositions was quite exceptional: instead of exerting a characteristic flavor profile on some foodstuffs or a drink, they actually complement, elevate or accentuate the essential or authentic flavor and the taste characteristics of the foods or drinks in which they 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.
Consequently, the invention provides, in another of its aspects, a method for imparting taste and / or taste to, or improving the taste and / or taste of, an edible composition, such method comprises the addition to said composition of a compound of formula (I) defined here.
[0038] The remarkable organoleptic effects are observed when the compounds of formula (I) are incorporated into an edible composition containing one or more flavor co-ingredients.
[0039] The flavor co-ingredients can be sugar, fats, salt (eg sodium chloride), MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.
[0040] In a given embodiment, sugar is 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.
[0041] In a given 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.
[0042] In a certain embodiment, the 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.
[0043] In a given modality, MSG is present in amounts from 0.001% to 2%, based on the total weight of an edible composition.
[0044] In a given 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.
[0045] In a given 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.
[0046] The types of organic acids include citric, malic, tartaric, fumaric, lactic, acetic, succinic. The types of edible compositions containing organic acids include drinks, such as soft drinks, still drinks, juices, powdered soft drinks, concentrated liquid, alcoholic drinks and functional drinks.
[0047] In a given embodiment, phosphorus is present in an amount of up to 0.5% by weight of an edible composition. Phosphorus is typically present as a phosphate or phosphoric acid.
[0048] In a given embodiment, the 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.
[0049] Despite its interesting organoleptic properties, however, the applicant found that the formulation of the compounds of formula (I) was not a common matter. The discovered potency of the compounds suggested that they can be used at very low levels for flavor applications and, therefore, 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 in a suitable vehicle, for example, a diluent, such as a solvent. However, the compounds are solids or viscous oils at room temperatures, and very limited in water solubility. The applicant has found that a stock solution of at least approximately 0.01%, more particularly the stock solution of approximately 0.01 - 1% of a compound of formula (I) has reached a balance as to acceptable solvent levels of ease handling and mixing, and the desire to limit the amount of the solvent that would have to be removed from the stock solution by further processing the compounds into flavoring compositions and edible products for reasons of lack of taste, efficiency, price and so on. The applicant has found that suitable solvents for the stock solution include ethanol, triacetin, glycerol and migliol.
[0050] To assist in the solubilization process, produce a stock solution and minimize the amount of the solvent, it is preferred to use compounds of formula (I) formed from a mixture of carboxylic acids, instead of a pure carboxylic acid.
[0051] Consequently, the invention provides in another of its aspects a stock solution of at least approximately 0.01%, more particularly approximately a stock solution of 0.01 - 1% of a compound of formula (I).
[0052] The stock solution may contain other materials such as vehicle materials and / or adjuvants more fully described below. In a given embodiment, the stock solution contains antioxidant selected from a group consisting of vitamin C, vitamin E, rosemary extract, anthracine, butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT). Antioxidants are preferably employed to prevent, or significantly reduce the generation of unpleasant volatile odors as a result of the 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 residue of fatty acid contains more than one double bond. The determination of an effective amount of antioxidant is within the reach of the skilled person, however amounts in the range of approximately 10 ppm to 1000 ppm based on the weight of the stock solution may be present.
[0053] In the preparation of the flavoring compositions of the present invention, the compounds of formula (I) can be used in any physical form. They can be used in pure form, in the form of a stock solution described above; or they can be used in the form of an emulsion; or they can be used in a powder form. If the compounds of formula (I) are presented in the form of a powder, the powder form can be produced by a dispersive evaporation process, such as a spray drying process, as are 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 comprising the compound of formula (I). Especially, 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 described more fully described below.
[0054] A powder comprising a compound of formula (I) forms another aspect of the present invention.
[0055] The compounds of formula (I) can be incorporated into an edible composition alone, or in the form of a flavor composition comprising one or more flavor co-ingredients.
[0056] A flavoring composition comprising a compound according to formula (I) forms another aspect of the present invention.
[0057] In an embodiment of the present invention, the flavor formulation comprises a compound of formula (I) and at least a co-ingredient of flavor.
[0058] In a given embodiment of the present invention, the flavoring composition comprises:
[0059] a compound according to formula (I);
[0060] at least one flavor co-ingredient;
[0061] optionally a vehicle material; and
[0062] optionally, at least one adjuvant.
[0063] The term "flavor co-ingredient" is an ingredient that is capable of contributing or communicating or modifying, in a positive or pleasant way, the taste of an edible composition.
[0064] In any case, flavor co-ingredients can be used in a composition according to the present invention, including flavors, but not limited to natural, artificial flavors, spices, condiments, and so on. The flavor co-ingredients include synthetic essential oils and aromatic seasoning and / or oils, oil-resins, essences, distillates, and derivatives of plant extracts, leaves, flowers, fruits, and so on, and combinations comprising at least one of the foregoing .
[0065] Essential oils include peppermint oil, decannel oil, pirola oil (methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bay oil, anise, eucalyptus oil, thyme oil, cedar leaf oil, nutmeg oil, pepper, 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 include lemon, orange, mistletoe, grapefruit, yazu, sudachi, and fruit essences include apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon, apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango, mangostin, pomegranate , papaya and so on.
[0066] Examples of additional flavors communicated by a flavoring flavor 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 asaftida flavor, an ajowan flavor, an anise flavor, an angelica flavor, a fennel flavor, a pepper flavor, a cinnamon flavor, a chamomile flavor, a mustard flavor, a flavor cardamom flavor, caraway flavor, cumin flavor, clove flavor, spicy flavor, coriander flavor, sassafras flavor, flavored flavor, Zanthoxyli Fructus flavor, perilla flavor, fruit flavor juniper, a taste of ginger, a taste of star anise, a taste of horseradish, a taste of thyme, a taste of tarragon, a taste of dill, a taste of capsicum, a taste of nutmeg, a taste of basil , a marjoram flavor, a rosemary flavor, a bay leaf flavor, and a wasabi (horseradish horseradish); a nutty flavor such as an almond flavor, a hazelnut flavor, a macadamia nut 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, such as an onion flavor, a garlic flavor, a cabbage flavor, a carrot flavor, a celery flavor, mushroom flavor, and a tomato flavor.
[0067] In some embodiments, it said that flavoring co-ingredients include aldehydes and esters such as cinnamyl acetate, cinnamaldehyde, diethyl acetate, dihydrocarbyl acetate, eugenyl format 49, p-methylamisole, and so on can be used. Additional examples of aldehyde condiments include acetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde (licorice, anise), cinnamic aldehyde (cinnamon), citral, that is, alpha-citral (lemon, mistletoe), neral , that is, beta-citral (lemon, mistletoe), decanal (orange, lemon), ethyl vanilla (vanilla, cream), that is, heliotrope. Piperonal (vanilla, cream), vanilla (vanilla, cream), alpha-amyl cinnamaldehyde (spicy fruit flavors), butyraldehyde (butter, cheese), valeraldehyde (butter, cheese), citronella (modifies, many types), decanal (citrus fruits), c-8 aldehyde (citrus fruits), C-9 aldehyde (citrus fruits), C-12 aldehyde (citrus fruits), 2-ethyl butyraldehyde (soft fruits), hexenal, that is, trans-2 (soft 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 so on.
[0068] Additional examples of another coedredient flavor can be found in "Chemicals Used in Food Processing", publication 1274, pages 63-258, by the National Academy of Sciences.
[0069] Flavor co-ingredients can also include salt flavors, umami flavors, and flavored 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-methoxyphenyl) -3- (pyridineyl-2) propanone-1, arginine, potassium chloride, ammonium chloride, succinic acid, N- (2-methoxy-4-methyl benzyl) -N '- (2- (pyridinyl-2) ethyl) oxalamide, N- (heptanyl-4) benzo (D) (1,3) dioxol-5-carboxamide, N- (2,4-dimethoxybenzyl) -N '- (2- (pyridinyl-2) ethyl) oxalamide, N- (2-methoxy-4-methylbenzyl) -N'-2 (2- (5-methyl pyridinyl- 2) ethyl) oxalamide, cyclopropyl-E, Z-2,6-nonadienamide.
[0070] Particularly, the modalities of the present invention, the flavor ingredient is selected from the compounds and compositions disclosed in WO2005102701, WO2006009425, WO2005096843, WO2006046853 and WO2005096844, all of which references are incorporated herein by reference in their entirety.
[0071] Flavor co-ingredients can include known flavor flavors, umami flavors, and flavored 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 aminobutyric acid, allyl cysteine, 1- (2-hydroxy-4-methoxyphenyl) -3- (pyridineyl-2) propanone-1, arginine, potassium chloride, ammonium chloride, succinic acid, N- (2-methoxy-4-methyl benzyl) -N '- (2- (pyridinyl-2) ethyl) oxalamide, N- (heptanyl-4) benzo (D) (1,3) dioxol-5-carboxamide, N- (2,4-dimethoxybenzyl) -N '- (2- (pyridinyl-2) ethyl) oxalamide, N- (2-methoxy-4-methyl benzyl) -N'-2 (2- (5-methyl-pyridinyl- 2) ethyl) oxalamide, cyclopropyl-E, Z-2,6-nonadienamide.
[0072] The carrier material can be used in compositions according to the invention to encapsulate or trap other components of the composition in a matrix. The role of the carrier material can simply be that of a processing aid or a bulking agent, or it could be employed to protect or conserve other components from the effects of moisture or oxygen or any other aggressive means. The carrier material could also act as a means of controlling the flavor release of edible compositions.
[0073] The carrier materials may include mono-, di-otherisaccharines, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohols, proteins or pectin. Examples of certain 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 modified starch, hydrogenated starch hydrolyzate, succinylated or hydrolyzed starch, agar, carrageenan, arabic gum, accacia gum, tragacanth, alginates, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose, derivatives and mixtures of the same . Naturally, those skilled in the art appreciate that the materials cited are given here as an example and should not be construed as limiting the invention.
[0074] By "flavor adjuvant" is meant an ingredient capable of imparting the added added benefit to compositions of the present invention, such as a color, resistance to light, chemical stability and so on. Suitable adjuvants include solvents (include water, alcohol, ethanol, triacetin, oils, fats, vegetable oil and migliol), binders, diluents, disintegrating agents, lubricants, coloring agents, preservatives, antioxidants, emulsifiers, stabilizers, agents anti-caking agent, and so on. In a given embodiment, the flavor composition comprises an antioxidant. Said antioxidants may include vitamin C, vitamin E, rosemary extract, anthracine, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).
[0075] Examples of such flavoring decomposition carriers or adjuvants can be found in, for example, "Perfume and Flavor Materials of Natural Origin", S. Arctander, editor, Elizabeth, N.J., 1960; in "Perfume and Flavor Chemicals", S.Arctander, editor, volume. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in Flavors, E. Ziegler and H. Ziegler (editor)., Wiley-VCH Weinheim, 1998, and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (editor)., 1st edition, The Cosmetic, Toiletry and Fragrance Association, Inc, Washington, 1988.
[0076] Other suitable and desirable ingredients of flavoring compositions are described in standard texts, such as "Handbook of Industrial Chemical Additives", editor M. and I. Ash, 2nd edition, (Sinapse 2000).
[0077] The flavoring compositions according to the present invention can be supplied in any suitable physical form. For example, they can be in the form of oils, emulsions or dispersions in an organic liquid or water liquid suitable for use in edible compositions, or in solid form, such as powder.
[0078] If flavoring compositions are to be 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.
Accordingly, in another aspect of the present invention, a method of forming a powder composition is provided, comprising the steps of providing a liquid composition, comprising a compound of formula (I) and one or more optional ingredients selected from at least one flavor co-ingredient, a carrier material and an adjuvant, and dispersively evaporate said liquid composition to form a powder composition.
[0080] In this way, a compound of the formula (I) or a flavoring composition comprising said composition can be presented in a powder form.
[0081] The liquid composition used in the preparation of a powder can be in the form of a solution, emulsion, dispersion or slurry. The liquid can contain water, and / or an organic liquid, such as ethanol, glycerol, triacetin, migliol (MCT) which is acceptable for use in edible compositions.
[0082] The powder compositions according to the present invention can be prepared according to methods and apparatus known in the art of powder production on an industrial scale. A particularly suitable method is spray drying. The spray drying apparatus and techniques are well known in the art and do not need any 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 the powder compositions of the present invention and are incorporated herein by reference in its integrity.
[0083] The manner in which the compounds of formula (I) are incorporated into powder flavoring compositions of the present invention is not critical. For example, the compounds can be added to the liquid composition described above and subjected to dispersive evaporation and processed together with all other components of the flavoring composition. Alternatively, the compounds can be added to the flavor composition after it has been formed as a powder.
[0084] Many of the flavor co-ingredients described here are volatile and / or may be sensitive to oxidative degradation, particularly when subjected to high temperatures, and under humidity conditions. Consequently, certain problems can arise when subjecting 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, mistletoe and grapefruit, and Fruit essences include apple, pear, peach, strawberry, raspberry, cherry, plum, pineapple, apricot and so on. The volatile components of these flavor co-ingredients can include, but are not limited to, acetaldehyde, dimethyl sulfite, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate. Flavor co-ingredients containing aldehydes or volatile esters include, for example, cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarbyl 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, mistletoe); neral, that is, beta citral (lemon, mistletoe); decanal (orange, lemon); ethyl vanilla (vanilla, cream); heliotropin, that is, piperonal (vanilla, cream); vanilla (vanilla, cream); alpha-amyl cinnamaldehyde (spicy fruit flavors); butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); the citronelal (modifies, many types); decanal (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethyl butyraldehyde (soft fruits); hexenal, that is, trans-2 (soft 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 thereof.
[0085] The applicant surprisingly found that, with the inclusion of a compound of the formula (I) in a powdered flavoring composition, it was possible to maintain the flavor quality of the flavoring composition converted into the powdered form by a dispersive evaporation process.
Consequently, the invention provides in another of its aspects a method of maintaining the flavor quality of a powdered flavoring composition comprising the step of including in said powdered flavoring composition, a compound of the formula (I).
[0087] As stated above, the compounds of formula (I) or flavoring compositions containing such compounds can be incorporated into edible compositions, and an edible composition containing such compound or the flavoring composition forms another aspect of the present invention.
[0088] The term "edible composition" refers to products for consumption by a patient, typically via the oral cavity (although consumption can occur via non-oral means such as inhalation), with at least one of the goals of satisfaction, nutrition , or health and well-being benefits. Edible compositions can be present in any form including, but not limited to, liquids, solids, semi-solids, lozenges, capsules, lozenges, strips, powder, gels, gums, pastes, sludges, syrups, aerosols and sprays. The term also refers to, for example, nutritional and dietary supplements. Edible compositions include compositions that are placed within the oral cavity for a period of time before being discarded, but not swallowed. It can be put in the mouth before it is consumed, 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 the manner described here by the addition of compounds of formula (I) or whose taste is so modified by processing such that it is enriched in a compound of formula (I).
[0089] In a given modality, the term "edible compositions" refers to products consumed by a patient, typically via the oral cavity (although consumption can occur via non-oral means such as inhalation), with one of the goals of satisfaction or nutrition.
[0090] In a more specific modality, the term "edible compositions" refers to products consumed by a patient, typically via the oral cavity (although consumption can occur via non-oral means, such as inhalation), with the aim satisfaction. Even more particularly, the term refers to food and drink.
[0091] In a given embodiment, the term "edible composition" does not refer to pharmaceutical compositions.
[0092] In another embodiment, the term "edible composition" does not refer to nutritional supplements.
[0093] Widely, the edible composition includes, but is not limited to, foodstuffs of all kinds, sweet products, baked products, sweet products, flavored products, fermented products, dairy products, drinks and oral care products.
[0094] Examples of foodstuffs include, but are not limited to, frozen snacks, sweet and flavored snacks, fruit snacks, chips / fries, extruded snacks, corn tortilla / chips, popcorn, salted bagels, nuts , other sweet and flavored snacks, snack bars, granola bars, breakfast counters, energy bars, fruit bars, other snack bars, meal replacement products, weight loss products, convalescent drinks, ready meals , canned ready meals, frozen ready meals, dry ready meals, chilled ready meals, dinner mixes, frozen pizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup, frozen soup, uht soup, frozen soup , pasta, canned pasta, dry pasta, frozen / fresh pasta, noodles, plain noodles, instant noodles, instant noodle cups / bowls, instant noodle bags, quick noodles chilled, snack noodles, dried food, dessert mixes, sauces, desserts and condiments, herbs and spices, extensions, bottling and preserves, honey, chocolate extensions, nut based extensions, and yeast based extensions.
[0095] Examples of confectionery products include, but are not limited to, gum (which includes sugared gum, sugar-free gum, functional gum and gum), stuffed confectionery, chocolate and other chocolate sweets, medicated sweets, lozenges , tablets, lozenges, mint, standard mint, energy mint, chewing candies, hard candies, boiled candies, breath and other oral care films or strips, cane candies, lollipops, gums, jellies, chocolate candy, caramel, hard and soft baked products, milk candies, adulation, licorice, jelly candies, gum drops, jelly seeds, walnuts, melted candies, combinations of one or more of the above, and edible flavoring compositions that incorporate one or more more of the above.
[0096] Examples of baked products include, but are not limited to, alfajores, bread, packaged / industrial bread, unpackaged / artisan bread, sweets, cakes, packaged / industrial cakes, unpacked / artisanal cakes, cookies, chocolate covered cookies, waffer cookies, stuffed cookies, flavored cookies and crackers, bread substitutes.
[0097] Examples of sweet products include, but are not limited to, breakfast cereals, ready-to-eat cereals, family breakfast cereals, flakes, müsli, other ready-to-eat cereals, breakfast cereals children, hot cereal.
[0098] Examples of flavored products include, but are not limited to, savory snacks (chips, chips, walnuts, toasted tortilla, salted bagels, cheese snacks, corn snacks, potato snacks, popcorn ready for consume, microwave popcorn, bacon shells, nuts, crackers, snack crackers, breakfast cereals, meats, meat jelly, smoked meats (ham, bacon), lunch / snack meats (dogs- hot, cold cuts, sausage), tomato products, margarine, peanut butter, soup (light, canned, creamy, instant, UHT), canned vegetables, pasta sauces.
[0099] Examples of dairy products include, but are not limited to, cheese, cheese sauces, cheese-based products, ice cream, impulse ice cream, single portion milk ice cream, single portion ice cream, multi-packaged milk ice cream, popsicle multi-packaged, ice cream to go, milk ice cream to go, ice cream desserts, artisan ice cream, home ice cream, frozen yogurt, artisan ice cream, dairy products, milk, fresh / pasteurized milk, fresh / pasteurized whole milk, fresh / pasteurized semi-skimmed milk , long life / uht milk, long life / uht milk, long life semi-skim milk / uht, long life skim milk / uht, goat milk, condensed / evaporated milk, condensed / evaporated milk powder, flavored condensed milk, functional and other condensed milk, flavored milk drinks, flavored dairy drinks, milk drinks flavored with fruit juice, soy milk, fermented milk drinks, dairy drinks ferme nts, coffee bleaches, powdered milk, flavored powdered milk drinks, cream, yogurt, whole natural yogurt, flavored yogurt, fruit flavored yogurt, pro-biotic yogurt, drinking yogurt, regular drink yogurt, yogurt for pro-biotic drinking, chilled and stable desserts for storage, milk-based desserts, soy-based desserts.
[00100] Examples of drinks include, but are not limited to, flavored water, soft drinks, fruit drinks, coffee-based drinks, tea-based drinks, juice-based drinks (includes fruit and vegetables), milk-based drinks, gel drinks, carbonated or still drinks, powdered drinks, alcoholic or non-alcoholic drinks.
[00101] 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, grain and grain products, fruits and products fruits.
[00102] In a given modality, the consumable product is soy sauce selected from the group, consisting of cheese, soup, hot and cold sauces, fruits, vegetables, ketchups, tea, coffee, snacks such as fries or extruded snacks.
[00103] The compounds of formula (I), when added to a flavoring composition and / or an edible composition, act on the composition to complete its flavor and / or taste to make it more delicious and authentic. The effects can be temporary or related to intensity, for example, the compounds can act to improve, strengthen, slow down, refine a flavor, or produce more salivation. The compounds of formula (I) can also affect the temporary profile of a flavor, this that is, they can affect the initial impact of a flavor, the body of a flavor, or its permanence effect.
[00104] The compounds of formula (I) can modify any aspect of the temporary taste or taste profile of an edible composition. Especially, the compounds improve the taste and communicate more creamy and fatty sensations.
[00105] Compounds of formula (I) or flavoring compositions containing them can be added to edible compositions in large quantities for transport. The amount will depend on the nature of the edible composition to be palatable and the desired effect, as well as on the nature of the ingredients present in said flavoring composition. In order to obtain the notable beneficial effects attributed to the presence of the compounds of the formula (I), the flavoring composition must be employed in quantities such that the compounds of the formula (I) are present in quantities of one part per billion to 10 parts per million based on the total weight of the edible composition. While higher amounts than that can be used, the beneficial effects are considerably less evident and undesirable outside the notes can become more and more evident.
[00106] Interesting organoleptic effects, for example, salt, alcohol or coolant-raising effects, in edible compositions containing salt or alcohol or coolant compounds can be achieved when the compounds of formula (I) are used at levels from 1 to 100 ppb.
[00107] Interesting organoleptic effects, for example, elevation of umami effects, in edible compositions containing umami flavorings can be achieved when the compounds of formula (I) are used at levels of 100 to 250 ppb.
[00108] Interesting organoleptic effects, particularly the taste-enhancing effects in edible compositions, can be achieved when the compounds of formula (I) are used at levels of 250 to 500 ppb.
[00109] Interesting organoleptic effects, intensifying effects, for example, greases in edible compositions containing fats, can be achieved when the compounds of formula (I) are used at levels of 500 to 1000 ppb.
[00110] It is particularly advantageous to incorporate compounds of the formula (I) into edible compositions that are formed under high temperature conditions, such as cooking, frying or that are processed by heat treatments such as pasteurization or under UHT conditions. Under high processing or preparation temperatures, volatile flavoring ingredients may be lost or degraded with the consequence that the flavor intensity may be reduced and the essential and authentic flavor characteristics may be reduced. Such edible products include dairy products, snacks, baked goods, powdered soft drinks and similar dry mixes, and so on, fats and seasonings, mayonnaise, desserts, soups and broths, and drinks.
[00111] A particularly preferred class of the edible composition according to the present invention are powdered soft drinks and similar dry mixing applications. Dry mixing applications are known in the art and products included in powder form that are intended to be reconstituted before consumption. They include powdered soups, powdered cake mixes, powdered chocolate drinks, instant coffees, condiments and fondants, and so on.
[00112] Dry powder formed by dispersive evaporation processes, such as spray drying, represents a very convenient vehicle for releasing essential oil quality flavors to edible compositions.
[00113] Unfortunately, essential oils, and particularly citrus essential oils, can be particularly sensitive to dispersive evaporation processes, especially processes performed at high temperatures. Essential oils tend to evaporate or degrade to form products that have unpleasant odors. Powdered flavoring compositions, particularly those containing citrus oils, may be of poor quality and exhibit a relatively short expiration date as a result.
[00114] Surprisingly, the incorporation of compounds of formula (I) or flavoring compositions containing them in powder compositions, results in powder compositions that expose the impact and authenticity of the essential oils used in their preparation, essentially maintaining essential oil quality in powder flavor formulations.
[00115] Consequently, the invention provides in another aspect a powdered flavoring composition comprising a compound according to formula (I) and at least one additional flavor co-ingredient.
[00116] In another aspect of the invention there is provided a powdered composition for refreshment or other composition comprising dry compound a compound according to formula (I).
[00117] In still another aspect of the present invention there is provided a powdered composition for refreshment or other composition comprising a dry flavor powder composition comprising a compound of formula (I).
[00118] In yet another aspect of the present invention there is provided a method of forming a powdered flavoring composition comprising the step of incorporating into said composition a compound according to formula (I).
[00119] In a given embodiment the compound of formula (I) can be added to the powdered flavoring composition formed, or it can be added to the flavoring composition before forming the powder.
[00120] Another particularly preferred class of the edible composition according to the present invention is snacks. Snacks are a well-known category of product for people versed in the food industry. These products are described above and include, without restriction, savory donuts, corn chips, chips, baked goods, extruded products, tortilla chips and so on. Even more particularly, the low-fat snack compositions to which the invention relates. Low-fat snack compositions contain less than 30% by weight fat, more particularly between 5 to 25% by weight fat.
[00121] A problem with reducing fat in a snack composition is the loss in taste and texture. Fats play an important role in the way the dough behaves during processing and greatly affect the quality, flavor and texture of ready-to-eat products. As the fat content in snack products is reduced or replaced with other ingredients (for example, non-digestible fat, protein, fiber, gums), adverse organoleptic effects (for example, lack of taste, drying, lack of crispness and lack of flavor) are increased.The adverse organoleptic effects result in products that have reduced taste.
[00122] Considerable efforts have been spent on inventing flavoring compositions to overcome the problems associated with low-fat snack products. The flavors can be applied to a snack as topics in the form of dry powder and / or as liquids (for example, oil-based, water-based). Another approach was to add flavor to the dough.
[00123] Despite these various approaches that have been taken to improve consumer appeal and lack of taste in snacks and particularly low fat snacks, there is still a need for improved low fat snacks having toppings applied to them with visual appeal, flavor , and texture of high fat snacks.
[00124] Compounds according to formula (I) or flavoring compositions containing them can be incorporated into snacks to communicate an effective flavor and a palate with remarkable roundness and fullness. In addition, the effects of taste and taste can be achieved even in low-fat snacks.
[00125] Consequently, the invention provides in another of its aspects a snack comprising a flavoring composition as described above. In a particular embodiment of the invention the snack has a fat content of approximately 40% or less by weight, based on the total weight of the snack, more particularly approximately 30% or less, still more particularly 25% or less, more particularly still approximately 10% or less, even more particularly approximately 5% or less, even more particularly approximately 3% or less.
[00126] 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.
[00127] Another particularly preferred class of the edible composition according to the present invention is alcoholic beverages.
[00128] The applicant surprisingly found that, composing according to formula (I) incorporated in an alcoholic drink, it had the effect of increasing the alcohol impact of the drink.
[00129] Consequently, the invention provides in another of its aspects an alcoholic beverage comprising a compound according to formula (I).
[00130] In yet another aspect of the invention there is provided a method of producing an increased alcoholic impression in an alcoholic beverage by incorporating a compound according to formula (I) into the said beverage.
[00131] The compounds of formula (I) can be incorporated into the alcoholic drink of dita in quantities of 1 ppb to 1 ppm.
[00132] Another preferred class of edible compositions is products ingested in the form of tablets, capsules, powder, multiparticulates and so on, which may include pharmaceutical and nutraceutical products.
[00133] Certain groups of people have problems swallowing pills or capsules, powder, multiparticulates and so on. This problem can be particularly pronounced in certain consumer groups, such as children and the very elderly or the weak. The applicant surprisingly found that it composes according to formula (I), when taken in the oral cavity they produce a pronounced salivating effect. Incorporating the compounds in these dosage forms, particularly as the part of a coating around said dosage forms, can ease the swallowing process of certain consumers, particularly children and the very elderly or the weak.
Consequently, in another aspect the invention provides an orally administrable dosage form, particularly in the form of tablet, powder or multiparticulate capsules comprising a compound according to formula (I).
[00135] Another preferred class of the edible composition is baked goods. The compounds of formula (I) can be incorporated topically or in the dough. Can be incorporated at levels of 1 ppb to 1 ppm, the compounds of formula (I) provide less dry and more juicy baked products.
[00136] Another preferred class of edible compositions is caloric or non-calorie drinks 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, 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.
[00137] Incorporated at levels of 1 ppb to 10 ppm, the compounds of formula (I) communicate said drinks containing sweeteners at levels of less than 1% and up to approximately 20%, a sweetness and a positive taste that resembles sugar.
[00138] Other preferred edible compositions are flavored compositions, particularly those that are soy-based or fish-based.
[00139] Incorporated at levels of 1 ppb to 10 ppm, in a soy-based composition (such as soy sauce) or a fish-based composition (such as fish sauce) containing from 5 to 40% salt, the compositions are rated as exhibiting strong umami tastes that are long lasting and rich.
[00140] Another preferred edible composition is a cloudy drink composition.
[00141] Certain drinks, such as juices, have relatively higher turbidity and thus have an opaque appearance. It is often desired that the drink has a relatively high turbidity. This could be desirable to provide a more natural look to drinks with a low juice content, or it could be for reasons related to sedimentation disguise or "touch" (where essential oil or dye rises to the surface of a reservoir during storage ). Cloudy drinks are usually formed using a turbid agent. The clouding agents are usually supplied in the form of emulsions, or the clouding agent may be the part of a powdered drink which, upon reconstitution, will form an emulsion which provides a permanent clouding to the drink.
[00142] The compounds of formula (I), in addition to their remarkable organoleptic properties, can lend stability to turbid agents and to drink compositions containing them.
[00143] Consequently, the invention provides in another of its aspects a composition comprising a cloudy drink composition and a compound of the formula (I).
[00144] In a given embodiment of the invention, a flavoring composition as defined herein can be provided in the form of an emulsion. This emulsion composition can be particularly useful in cloudy beverage applications, especially in which it is intended to employ a turbid agent.
[00145] In yet another aspect of the invention there is provided a composition comprising a cloudy drink, a turbid agent and a compound of the formula (I).
[00146] Other preferred edible compositions are those compositions that are formed by a maturation process.
[00147] In food processing, it often happens that a food has to remain for an extended period of time and under well-defined conditions to obtain the food with the required and approved quality. A commonly used term for this process is maturing. Maturation is well known in the processing of 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 removing water, or removing out of grade) that have beneficial effects on food. Examples of this are chocolate scoop and the drying of noodles, vegetables and fruits. Transformations that improve food quality are induced by chemical conversions, or enzymatically catalyzed conversions or fermentative transformations. All of these conversions are slow and therefore expensive; they are also not fully predictable or controllable.
[00148] The compounds of formula (I), taking into account their remarkable property of adding to the authentic taste 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 taste quality of the matured product.
[00149] Consequently, in another aspect of the invention there is provided a method of ripening a cheese selected from the group consisting of product, meat, soy sauce and wine, beer, sausage, sauerkraut, tempeh and tofu, comprising the stage of ripening the product in the presence of a compound according to formula (I).
[00150] In another aspect of the invention there is provided a method of chocolate scooping, said method comprising the step of adding to chocolate a compound according to formula (I), or flavoring composition containing it.
[00151] Now follows a series of non-limiting examples that serve to illustrate the invention. Synthesis examples 1.General structure

[00152] R1 = is a straight chain hydrocarbon group that has 9 to 21 carbon atoms and containing zero to three double bonds
[00153] or
[00154] R1 is a [(1E) -2,6-dimethylpta-1,5-dienyl-1] group.
[00155] Several compounds that belong to that general formula were synthesized according to one of the two procedures described below. 2. Synthesis. Via A: (DCC method).
[00156] In a 250 ml round bottom flask, the fatty acid (3.93 mmols) was mixed with 1-hydroxypyrrolidine-2,5-dione (0.498 g, 4.32 mmols) in dioxane (50 ml) to produce a colorless solution. The solution was cooled to 10 ° C and DCC (0.892 g, 4.32 mmols) was added with 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 mmols) in a 2% solution of sodium bicarbonate (0.363 g, 4.32 mmols) in water. The reaction mixture was stirred for 4 hours at 50 ° C. Dioxane was evaporated and the aqueous residue was further diluted with water, acidified with a dilute 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, eluting with DCM / methanol. 1 g of the 85-90% pure product can be obtained. 2.2Via B (DCC method with protection group). Step 1:
[00157] To a solution of an O-methylated amino acid (16.51 mmols) in DCM (100 ml) was added to triethylamine (1.519 g, 15.01 mmols) at minus 15 ° C. Fatty acid (0.01 mmol) was added with stirring. A solution of DCC (15.01 mmols) in 10 ml of DCM was added dropwise at 0 ° C. The reaction mixture was stirred at 0 ° C for one hour and stirring was 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, with eluent DCM / methanol. The intermediate ester compound can be isolated in a purity of 95%. Step 2:
[00158] The O-methylated N-acyl-amino acid (4.91 mmol) was dissolved in a mixture of Ethanol (8.00 ml) and water (8 ml). To this mixture was added a solution of 32% sodium hydroxide (2.453 g, 19.63 mmols) and the mixture was stirred at room temperature for three hours. The mixture was allowed to stand for 14 hours.
[00159] After 14 hours the mixture was acidified with a concentrated hydrochloric acid solution (1.612 ml, 19.63 mmols), diluted with water and extracted with mtbe. The organic layer was separated, dried and evaporated. 1.3 g of yellow solid medium residue were obtained. NMR confirmed the structure of the title compound, 95% purity 2.3 Via C (acid chloride).
[00160] An amino acid (20 mmols) was dissolved in a solution of sodium hydroxide (54.5 mmols) in water (40 ml).
[00161] Tetrahydrofuran (60 ml) was added. The fatty acid chloride (18.18 mmols) was added dropwise at room temperature. Stirring was continued for two hours. The mixture was diluted with water, acidified with a 37% hydrochloric acid solution (2.99 ml, 36.4 mmols) and extracted with ethyl acetate.
[00162] The organic layers were combined, dried and evaporated.
[00163] The residue contains approximately 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). 2.4 All synthesized compounds. Table 1: List of synthesized compounds.
3. NMR data (example) 3.1 Structure of 4 Proline-C18: 2

[00164] 1H NMR (600 MHz, CHLOROPHORMUM-d) δ ppm 0.78 - 0.85 (m, 3 H, HC (18)) 1.18 - 1.33 (m, 14 H, HC (4, 5, 6, 7, 15, 16, 17) 1.54 - 1.65 (m, 2 H, HC (3)) 1.84 - 1.92 (m, 1 H, H_C (22)) 1, 92 - 2.03 (m, 6 H, H_C (8, 14, 23)) 2.26 - 2.32 (m, 2 H, HC (2)) 2.44 (ddd, J = 12.29, 6.10, 2.92 Hz, 1 H, HC (22)) 2.70 (t, J of Hz = 6.70, 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).
[00165] 13C NMR (150 MHz, CHLOROPHORMUM-d) δ ppm 14.07 (C (18)) 22.57 (C (17)) 24.48 (C (3)) 24.79 C (23)) 25.62 (C11)) 27.05 (C (22)) 27.17 (C (8)) 27.19 (C (14)) 29.10 C (6)) 29.27 (C (4, 15)) 29.34 (C (5)) 29.60 C (7)) 31.51 C ((16)) 34.45 C (2)) 47.98 C (24)) 60.25 (C (21)) 128.07 (C (12)) 128.07 (C (10)) 130.00 (C (9)) 130.24 C (13)) 171.87 (C (1)) 175, 87 (C20)). Application Examples. Proline Derivative Tests.
[00166] Samples were evaluated by expert tasters.The tasters were asked to describe the samples that focus on authentic taste, taste, fullness, salty, salivation, umami, sweetness, juiciness, richness, long life and grease. Comparison on a mango juice drink
[00167] The base is water, 8% sucrose, 0.1% citric acid, 1% mango juice, appropriate 0.05% mango flavor.
[00168] Base: the mango fruit.
[00169] Base plus C16: 0-pro at 1 ppm too ripe, like orange, long lasting taste.
[00170] Base plus C18: 1-pro in 1 ppm sweet orange albedo. Orange Drink Test
[00171] The base is water, 7% sugar, 0.1% citric acid, appropriate orange flavor 0.06%.
[00172] Base: orange, relative to the fruit, slightly sweet.
[00173] Base plus C18: 2-pro at 1 ppm: very juicy, authentic orange. Lemon Drink Test
[00174] The base is water, 7% sucrose, 0.15% citric acid, appropriate lemon flavor.
[00175] Base: floral, citral, lemon
[00176] Base plus C18: 2-pro at 1 ppm: very juicy, more citral like, very authentic. Broth test
[00177] The base is the broth Maggi a lozenge in 500 ml of hot water.
[00178] Base: salty, umami, powdery
[00179] Base plus C16: 0-pro at 1 ppm: more salty, fuller, darker, more like meat.
[00180] Base plus C18: 1-pro at 1 ppm: full, plus umami, long lasting.

权利要求:
Claims (4)
[0001]
1. Edible composition, characterized by the fact that it comprises a compound selected from the group consisting of N-geranoil-Pro, N-palmitenoil-Pro, N-stearoil-Pro, N-oleoil-Pro, N-linoleoil-Pro and N- linolenoil-Pro, in which the compound complements the taste or taste characteristics of the edible composition when the compound is incorporated in an amount of 1 ppb to 10 ppm within the edible composition.
[0002]
2. Stock solution, characterized by the fact that it comprises 0.01 to 1% by weight of a compound as defined in claim 1, comprising a solvent selected from the group consisting of ethanol, triacetin, glycerol and migliol (MCT) or mixtures of themselves.
[0003]
3. Method to complement the flavor or taste characteristics of edible products, characterized by the fact that it comprises the step of incorporating the compound, as defined in claim 1.
[0004]
4. Edible composition according to claim 1, characterized by the fact that it also comprises at least one flavor co-ingredient.

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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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2020-05-05| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2020-08-18| B09A| Decision: intention to grant|

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2020-12-15| 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/US2013/034378|WO2013149022A1|2012-03-30|2013-03-28|N-acyl proline derivatives as food flavouring compounds|

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