# US 10,863,758 B2 · Fragrance and flavor compositions containing isomeric alkadienyl esters > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,863,758 B2 - Document ID: US10863758B2 - Status: Granted - Kind: B2 - Application number: 15/658,940 - Filed: 2017-07-25 - Published: 2018-02-01 - Granted: 2020-12-15 - Earliest claimed: 2016-07-29 - Assignees: Bedoukian Research, Inc. - Applicants: Bedoukian Research, Inc. - Inventors: Matthew Bedoukian - Web page: https://patentgrep.com/patent/US10863758B2 ## CPC - A23L 27/29: Fruit flavours - A23G 4/06: characterised by the composition {containing organic or inorganic compounds} - A23L 2/38: Other non-alcoholic beverages (drinks from legumes A23L11/60) - A23L 2/56: Flavouring or bittering agents (sweeteners A23L2/60) - A23L 27/202: {Aliphatic compounds} - C07C 69/007: Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom - C07C 69/145: of unsaturated alcohols - C07C 69/24: esterified with monohydroxylic compounds - C11B 9/0019: {carbocylic acids; Salts or esters thereof} - C12G 3/06: with flavouring ingredients - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F) - C12G: WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES (beer C12C); PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H ## Abstract A composition containing at least one isomeric alkadienyl ester in an amount effective to impart a fragrance or flavor to the composition. A fragrance or flavor composition containing at least one isomeric alkadienyl ester in an amount effective to impart a fragrance or flavor to the composition. A consumer product containing the fragrance or flavor composition having at least one isomeric alkadienyl ester in an amount effective to impart a fragrance or flavor to the composition. A method of imparting a fragrance or flavor to a consumer product by adding to the consumer product a fragrance or flavor composition containing at least one isomeric alkadienyl ester in an amount effective to impart a fragrance or flavor to the consumer product. ## Claims ### Claim 1 A composition comprising at least one isomeric 3,5-heptadienyl ester in an amount effective to impart a fragrance or flavor to the composition; wherein the at least one isomeric 3,5-heptadienyl ester is selected from the group consisting of 3,5-heptadienyl acetate, 3,5-heptadienyl propionate, 3,5-heptadienyl butyrate, 3,5-heptadienyl isobutyrate, 3,5-heptadienyl tiglate, and 3,5-heptadienyl alpha methyl butyrate; wherein the at least one isomeric 3,5-heptadienyl ester has from about 70 percent to about 99.5 percent of Z,E isomers, and from about 0.1 percent to about 30 percent of E,E isomers, based on the total Z and E isomers in the composition; wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance selected from the group consisting of at least one of natural, green, sweet, fruity, floral, fresh, watery, sea weed, marine, and ozonic notes, to the composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor selected from the group consisting of at least one of fresh, tropical, green, fruity, watermelon, berry, bakery, caramel, vegetable, and green bell pepper notes, to the composition. ### Claim 2 (depends on 1) The composition of claim 1 wherein the at least one isomeric 3,5-heptadienyl ester is Z,E-3,5-heptadienyl acetate, Z,E-3,5-heptadienyl propionate, Z,E-3,5-heptadienyl butyrate, Z,E-3,5-heptadienyl isobutyrate, Z,E-3,5-heptadienyl tiglate, or Z,E-3,5-heptadienyl alpha methyl butyrate. ### Claim 3 A fragrance or flavor composition comprising at least one isomeric 3,5-heptadienyl ester in an amount effective to impart a fragrance or flavor to the composition; wherein the at least one isomeric 3,5-heptadienyl ester is selected from the group consisting of 3,5-heptadienyl acetate, 3,5-heptadienyl propionate, 3,5-heptadienyl butyrate, 3,5-heptadienyl isobutyrate, 3,5-heptadienyl tiglate, and 3,5-heptadienyl alpha methyl butyrate; wherein the at least one isomeric 3,5-heptadienyl ester has from about 70 percent to about 99.5 percent of Z,E isomers, and from about 0.1 percent to about 30 percent of E,E isomers, based on the total Z and E isomers in the composition; wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance selected from the group consisting of at least one of natural, green, sweet, fruity, floral, fresh, watery, sea weed, marine, and ozonic notes, to the fragrance composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor selected from the group consisting of at least one of fresh, tropical, green, fruity, berry, bakery, caramel, vegetable, and green bell pepper notes, to the flavor composition. ### Claim 4 (depends on 3) The fragrance or flavor composition of claim 3 wherein the at least one isomeric 3,5-heptadienyl ester is Z,E-3,5-heptadienyl acetate, Z,E-3,5-heptadienyl propionate, Z,E-3,5-heptadienyl butyrate, Z,E-3,5-heptadienyl isobutyrate, 3,5-heptadienyl tiglate, or Z,E-3,5-heptadienyl alpha methyl butyrate. ### Claim 5 (depends on 3) A consumer product containing the fragrance or flavor composition of claim 3. ### Claim 6 (depends on 5) The consumer product of claim 5 selected from the group consisting of a candle, an air care product, a perfume, a cologne, a soap, a personal care product, a detergent, a fabric care product, and a household cleaning product. ### Claim 7 (depends on 5) The consumer product of claim 5 selected from the group consisting of a soap, a detergent, an air freshener, a room spray, a pomander, a candle, and a cosmetic comprising a cream, an ointment, a toilet water, a pre-shave lotion, an aftershave lotion, a talcum powder, a hair-care agent, a body deodorant, and an anti-perspirant. ### Claim 8 (depends on 5) The consumer product of claim 5 selected from the group consisting of an air care product, a perfume, and a cologne. ### Claim 9 (depends on 5) The consumer product of claim 5 selected from the group consisting of a beverage, a powder or semi-frozen/frozen concentrate for a drink, a candy, a sugarless candy, a chocolate, a chewing gum, a bubble gum, a condiment, a spice, a seasoning, a dry cereal, an oatmeal, a granola bar, an alcoholic beverage, an energy beverage, a juice, a tea, a coffee, a salsa, a gel bead, a film strip for halitosis, a lozenge, a cough drop, a throat lozenge, a throat spray, a toothpaste, and a mouth rinse. ### Claim 10 (depends on 5) The consumer product of claim 5 selected from the group consisting of a beverage, a dairy product, a confectionary, a cereal, a snack, and a soup. ### Claim 11 (depends on 5) The consumer product of claim 5 selected from the group consisting of a beverage, a chewing gum, and a bubble gum. ### Claim 12 (depends on 3) A method of imparting a fragrance or flavor to a consumer product comprising adding to the consumer product the fragrance or flavor composition of claim 3 in an amount effective to impart a fragrance or flavor to the consumer product. ### Claim 13 A composition comprising at least one isomeric 3,5-heptadienyl ester in an amount effective to impart a fragrance or flavor to the composition; wherein the at least one isomeric 3,5-heptadienyl ester is selected from the group consisting of Z,E-3,5-heptadienyl acetate, Z,E-3,5-heptadienyl propionate, Z,E-3,5-heptadienyl butyrate, Z,E-3,5-heptadienyl isobutyrate, 3,5-heptadienyl tiglate, and Z,E-3,5-heptadienyl alpha methyl butyrate, wherein the at least one isomeric 3,5-heptadienyl ester has from about 70 percent to about 99.5 percent of Z,E isomers, based on the total Z and E isomers in the composition; wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance selected from the group consisting of at least one of natural, green, sweet, fruity, floral, fresh, watery, sea weed, marine, and ozonic notes, to the composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor selected from the group consisting of at least one of fresh, tropical, green, fruity, watermelon, berry, bakery, caramel, vegetable, and green bell pepper notes to the composition. ### Claim 14 (depends on 13) The composition of claim 13 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount of at least about 1 ppm by weight, based on the total weight of the composition, to impart a fragrance to the composition. ### Claim 15 (depends on 13) The composition of claim 13 wherein the at least one isomeric 3,5-heptadienyl ester is combined with geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalool, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethyl-benzyl carbinol, trichloromethylphenyl carbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, alpha-hexylcinnam-aldehyde, 2-methyl-3-(p-tert-butylphenyl)-propanal, 2-methyl-3-(p-isopropylphenyl)-propanal, 3-(p-tert-butylphenyl)-propanal, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarbaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, n-decanal, n-dodecanal, 9-decen-1-ol, phenoxyethylisobutyrate, phenylacetaldehydedi-methylacetal, phenylacetaldehyde-diethylacetal, geranylnitrile, citronellylnitrile, cedrylacetate, 3-isocamphylcyclohexanol, cedrylmethyl ether, isolongifolanone, aubepinitrile, aubepine, heliotripine, coumarin, eugenol, vanillin, diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylionones, ironed, cis-3-hexenol and esters of the latter, indan-musks, tetraline-musks, isochromane-musks, macrocyclic ketones, macrolactone-musks, ethylene brassylate, or aromatic nitromusks, to impart a fragrance to the composition. ### Claim 16 (depends on 13) The composition of claim 13 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount from about 0.01 ppm to about 1% by weight, based on the total weight of the composition, to impart a fragrance to the composition. ### Claim 17 (depends on 13) The composition of claim 13 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount from about 0.1 ppb to about 100 ppm by weight, based on the total weight of the composition, to impart a flavor to the composition. ### Claim 18 (depends on 13) The composition of claim 13 wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance of natural, green, hyacinth, violet leaf notes dominated by fresh watery, sea weed, marine or ozonic notes to the composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor of fresh, fruity, watermelon or green bell pepper notes to the composition. ### Claim 19 A fragrance or flavor composition comprising at least one isomeric 3,5-heptadienyl ester in an amount effective to impart a fragrance or flavor to the composition; wherein the at least one isomeric 3,5-heptadienyl ester is selected from the group consisting of Z,E-3,5-heptadienyl acetate, Z,E-3,5-heptadienyl propionate, Z,E-3,5-heptadienyl butyrate, Z,E-3,5-heptadienyl isobutyrate, 3,5-heptadienyl tiglate, and Z,E-3,5-heptadienyl alpha methyl butyrate; wherein the at least one isomeric 3,5-heptadienyl ester has from about 70 percent to about 99.5 percent of Z,E isomers, based on the total Z and E isomers in the composition; wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance selected from the group consisting of at least one of natural, green, sweet, fruity, floral, fresh, watery, sea weed, marine, and ozonic notes, to the fragrance composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor selected from the group consisting of at least one of fresh, tropical, green, fruity, watermelon, berry, bakery, caramel, vegetable, and green bell pepper notes, to the flavor composition. ### Claim 20 (depends on 19) The fragrance or flavor composition of claim 19 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount of at least about 1 ppm by weight, based on the total weight of the composition, to impart a fragrance or flavor to the composition. ### Claim 21 (depends on 19) The fragrance or flavor composition of claim 19 wherein the at least one isomeric 3,5-heptadienyl ester is combined with geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalool, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethyl-benzyl carbinol, trichloromethylphenyl carbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, alpha-hexylcinnam-aldehyde, 2-methyl-3-(p-tert-butylphenyl)-propanal, 2-methyl-3-(p-isopropylphenyl)-propanal, 3-(p-tert-butylphenyl)-propanal, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarbaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, n-decanal, n-dodecanal, 9-decen-1-ol, phenoxyethylisobutyrate, phenylacetaldehydedi-methylacetal, phenylacetaldehyde-diethylacetal, geranylnitrile, citronellylnitrile, cedrylacetate, 3-isocamphylcyclohexanol, cedrylmethyl ether, isolongifolanone, aubepinitrile, aubepine, heliotripine, coumarin, eugenol, vanillin, diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylionones, irones, cis-3-hexenol and esters of the latter, indan-musks, tetraline-musks, isochromane-musks, macrocyclic ketones, macrolactone-musks, ethylene brassylate, or aromatic nitromusks, to impart a fragrance to the composition. ### Claim 22 (depends on 19) The fragrance or flavor composition of claim 19 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount from about 0.01 ppm to about 1% by weight, based on the total weight of the composition, to impart a fragrance to the composition. ### Claim 23 (depends on 19) The fragrance or flavor composition of claim 19 wherein the at least one isomeric 3,5-heptadienyl ester is present in an amount from about 0.1 ppb to about 100 ppm by weight, based on the total weight of the composition, to impart a flavor to the composition. ### Claim 24 (depends on 19) The fragrance or flavor composition of claim 19 wherein the at least one isomeric 3,5-heptadienyl ester imparts a fragrance of natural, green, hyacinth, violet leaf notes dominated by fresh watery, sea weed, marine or ozonic notes to the composition; or wherein the at least one isomeric 3,5-heptadienyl ester imparts a flavor of fresh, fruity, watermelon or green bell pepper notes to the composition.