# US 10,119,097 B2 · Organic compounds

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- Number: US 10,119,097 B2
- Document ID: US10119097B2
- Status: Granted
- Kind: B2
- Application number: 15/516,828
- Filed: 2014-11-10
- Published: 2017-10-19
- Granted: 2018-11-06
- Earliest claimed: 2014-11-10
- Assignees: Givaudan SA
- Applicants: Givaudan SA
- Inventors: Corinne Baumgartner; Felix Flachsmann
- Web page: https://patentgrep.com/patent/US10119097B2

## CPC

- C11B 9/0061: {compounds containing a six-membered aromatic ring not condensed with another ring}
- C07C 43/205: the aromatic ring being a non-condensed ring
- C07C 43/215: having unsaturation outside the six-membered aromatic rings
- C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids}
- C11B 9/003: {the ring containing less than six carbon atoms}
- C11D 3/507: {Compounds releasing perfumes by thermal or chemical activation}
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

A fragrance precursor represented by the formula 1 wherein X and Y together represent a double bond to a carbon atom bearing R1 and R2, with R1═H, methyl, acetyl or C1-C3 alkoxycarbonyl (e.g. ethoxycarbonyl); and R2=phenyl optionally substituted with up to 3 (i.e. 0, 1, 2 or 3) groups selected from C1-C4 alkyl (e.g. methyl, ethyl, iso-propyl, tert-butyl), vinyl, hydroxy, C1-C3 alkoxy (e.g. ethoxy), and —O—CH2—O—, e.g. R2 is benzo[d][1,3]dioxol-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl or R2=naphthyl, (naphthyl)methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-pentamethyl-1,2,3,4-tetrahydronaphthalen-7-yl or R2=COR3, wherein R3 is H, C1-C10 alkoxy (e.g. ethoxy, 1-(3,3-dimethylcyclohexyl)ethoxy), C1-C4 alkyl (e.g. methyl, ethyl, propyl, iso-propyl, tert-butyl), e.g. R2 is formyl, acetyl, ethoxycarbonyl, 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl; or wherein X is OR4, with R4 being H or alkyl, and Y is OR5, with R5 being alkyl, useful as a perfume ingredient.

## Claims

### Claim 1

A fragrance precursor according to the formula 1
wherein
X and Y together represent a double bond to a carbon atom bearing R1 and R2,
R1 is H, methyl, acetyl or C1-C3 alkoxy carbonyl, and
R2 is phenyl optionally substituted with up to 3 groups selected from C1-C4 alkyl, vinyl, hydroxy, C1-C3 alkoxy, and —O—CH2—O—, or
R2 is naphthyl, (naphthyl)methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-pentamethyl-1,2,3,4-tetrahydronaphthalen-7-yl or
R2 is COR3, wherein R3 is H, C1-C10 alkoxy, or C1-C4 alkyl;
or wherein
X is OR4 , wherein R4 is H or alkyl, and
Y is OR5, wherein R5 is alkyl.

### Claim 2 (depends on 1)

A fragrance precursor according to claim 1 selected from the group consisting of:
ethyl 2-acetyl-5-(4-isobutyl-2-methylphenyl)pent-2-enoate, and,
4-isobutyl-1-(4-(4-methoxyphenyl)but-3-en-l-yl)-2-methylbenzene.

### Claim 3 (depends on 2)

A perfume composition comprising a fragrance precursor according to claim 2.

### Claim 4 (depends on 3)

The perfume ingredient according to claim 3 which is adapted to release an ingredient with muguet odour characteristics.

### Claim 5 (depends on 2)

A perfume composition comprising a fragrance precursor according to claim 2.

### Claim 6 (depends on 2)

A personal care or household care composition comprising a fragrance precursor according to claim 2.

### Claim 7 (depends on 2)

A method of imparting a muguet odour characteristic to a perfume composition comprising the step of: adding to said composition at least a fragrance precursor according to claim 2.

### Claim 8 (depends on 1)

A perfume ingredient comprising a fragrance precursor according to claim 1.

### Claim 9 (depends on 8)

The perfume ingredient according to claim 8 which is adapted to release an ingredient with muguet odour characteristics.

### Claim 10 (depends on 1)

A perfume composition comprising a fragrance precursor according to claim 1.

### Claim 11 (depends on 10)

A perfume composition according to claim 10 that is free of aryl-substituted propanals, that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality.

### Claim 12 (depends on 10)

A perfume composition according to claim 10 which further comprises 3-(4-isobutyl-2-methylphenyl) propanal.

### Claim 13 (depends on 10)

A perfume composition according to claim 10 comprising one or more additional fragrance ingredients.

### Claim 14 (depends on 10)

A perfume composition according to claim 10, which is adapted to release an ingredient with muguet odour characteristics.

### Claim 15 (depends on 1)

A personal care or household care composition comprising a fragrance precursor according to claim 1.

### Claim 16 (depends on 1)

A method of imparting a muguet odour characteristic to a perfume composition comprising the step of: adding to said composition at least a fragrance precursor according to claim 1.

### Claim 17 (depends on 1)

The fragrance precursor of claim 1, wherein R2 is benzo[d][1,3]dioxo-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl.

### Claim 18 (depends on 1)

The fragrance precursor of claim 1, wherein R2 is formyl, acetyl, ethoxycarbonyl, or 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl.