# US 7,323,606 B2 · Aromachemicals > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,323,606 B2 - Document ID: US7323606B2 - Status: Granted - Kind: B2 - Application number: 11/356,300 - Filed: 2006-02-17 - Published: 2006-09-21 - Granted: 2008-01-29 - Earliest claimed: 2006-02-17 - Assignees: Flexitral, Inc. - Inventors: Luca Turin - Web page: https://patentgrep.com/patent/US7323606B2 ## CPC - C11D 3/50: Perfumes - A23L 27/203: {Alicyclic compounds} - C07C 33/05: Alcohols containing rings other than six-membered aromatic rings - C07C 69/007: Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom - C11B 9/003: {the ring containing less than six carbon atoms} - C11D 3/2037: {Terpenes} - C11D 3/2093: {Esters; Carbonates} - C07C 2601/02: with a three-membered ring - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - 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) ## Abstract The present invention provides a compound having one of the following formulae: R and R1 are each independently H or C1-5 alkyl provided that in formula (I) when R is methyl, R1 is H or C2-5 alkyl. R2 has from 1 to about 12 carbon atoms and is a straight or branched aliphatic group, or a cyclic, heterocyclic or aromatic group. R3 and R4 are each independently H or CH3. Mixtures of these compounds, methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavoring and in articles of manufacture is also provided. ## Claims ### Claim 1 A compound having one of the following formulae: wherein R and R1 are each independently H or C1-5 alkyl provided that in formula (I) when R is methyl, R1 is H or C2-5 alkyl; R2 has from 1 to 12 carbon atoms and is a straight or branched chain aliphatic group, or a cyclic; heterocyclic or aromatic group; and R3 and R4 are each independently H or CH3. ### Claim 2 (depends on 1) A compound according to claim 1 of formula (I), wherein R is methyl and R1 is ethyl. ### Claim 3 (depends on 1) A compound according to claim 1 of formula (II), wherein R, R1 and R2 are each methyl. ### Claim 4 (depends on 1) A method of producing a compound of formula (I) as defined in claim 1, which comprises cyclopropanating a parent compound of formula: wherein R and R1 are as defined for formula (I). ### Claim 5 (depends on 1) A method of producing a compound of formula (II) as defined in claim 1, which comprises cyclopropanating a parent compound of formula: wherein R and R1 are as defined for formula (II) to produce a product of formula: and esterifying that product to produce a compound of formula (II). ### Claim 6 (depends on 1) A method for treating a substrate to impart flavorant/fragrance releasing characteristics thereto comprising treating the substrate with a compound as defined in claim 1. ### Claim 7 (depends on 1) A composition having aroma, fragrance or odor releasing characteristics containing a compound or mixture of compounds as defined in claim 1. ### Claim 8 (depends on 7) A composition according to claim 7, wherein the compound or mixture of compounds is present in an amount of at least 30 percent by weight. ### Claim 9 (depends on 8) A composition according to claim 8, wherein the compound or mixture of compounds is present in an amount of at least 60 percent by weight. ### Claim 10 (depends on 7) A composition according to claim 7 in the form of a perfume, fragrance or cologne, a soap, a bath or shower gel, a shampoo or other hair care product, a cosmetic preparation, a body odorant, deodorant or antiperspirant, an air freshener, a liquid or solid fabric detergent or softener, bleach product, disinfectant or an all-purpose household or industrial cleaner. ### Claim 11 (depends on 10) A composition according to claim 10, in the form of a liquid or solid fabric detergent. ### Claim 12 (depends on 10) A composition according to claim 10, in the form of a bleach product. ### Claim 13 (depends on 10) A composition according to claim 10, in the form of a disinfectant product. ### Claim 14 (depends on 10) A composition according to claim 10, in the form of a body odorant, deodorant or antiperspirant product. ### Claim 15 (depends on 7) A composition according to claim 7, in the form of a beverage. ### Claim 16 (depends on 7) A composition according to claim 7, in the form of a flavoring product. ### Claim 17 (depends on 7) A composition according to claim 7, in the form of a food. ### Claim 18 (depends on 7) A composition according to claim 7, in the form of a chewing gum. ### Claim 19 (depends on 7) A composition according to claim 7, in the form of a pharmaceutical product. ### Claim 20 (depends on 7) A composition according to claim 7, in the form of an orally-deliverable matrix material. ### Claim 21 (depends on 1) A method to modify a taste or flavor property of a composition, which comprises adding thereto a flavor effective amount of a compound or mixture of compounds as defined in claim 1. ### Claim 22 (depends on 21) A method according to claim 21, wherein said composition, is in the form of a beverage, a flavoring, a food, a chewing gum, a pharmaceutical or an orally deliverable matrix. ### Claim 23 (depends on 1) A method to modify an aroma, fragrance or odor characteristics of a composition, which comprises adding thereto an aroma, fragrance or odor effective amount of a compound or mixture of compounds as defined in claim 1. ### Claim 24 (depends on 23) A method according to claim 23 wherein said composition, is in the form of a perfume, a body odorant, deodorant or antiperspirant, a detergent, a bleach product or a disinfectant.