# US 2021/0228459 A1 · Esters and ethers of 3-methyl-pentane-diol and unsaturated derivatives thereof and their use as aroma chemical

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- Number: US 2021/0228459 A1
- Document ID: US20210228459A1
- Status: Published application
- Kind: A1
- Application number: 17/051,092
- Filed: 2019-04-26
- Published: 2021-07-29
- Earliest claimed: 2018-04-27
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Miriam BRU ROIG; Manuel DANZ; Ralf PELZER; Florian GARLICHS
- Web page: https://patentgrep.com/patent/US20210228459A1

## CPC

- A61K 8/375: {the alcohol moiety containing more than one hydroxy group}
- A23L 27/2026: {Hydroxy compounds}
- A61K 8/33: containing oxygen
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61Q 19/10: Washing or bathing preparations
- C07C 41/09: by dehydration of compounds containing hydroxy groups
- C07C 43/15: containing only non-aromatic carbon-to-carbon double bonds
- C07C 43/1785: {having more than one ether bound}
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 69/08: of dihydroxylic compounds
- C07C 69/16: of dihydroxylic compounds
- C07C 69/28: esterified with dihydroxylic compounds
- C11B 9/0015: {containing oxygen as the only heteroatom}
- C11B 9/0019: {carbocylic acids; Salts or esters thereof}
- C11D 3/2068: {Ethers}
- C11D 3/2093: {Esters; Carbonates}
- C11D 3/50: Perfumes
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- C11D 2111/12: Soft surfaces, e.g. textile
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

The present invention relates to the use of esters and/or ethers of 3-methyl-pentane-diol and unsaturated derivates thereof as aroma chemicals, to aroma chemical compositions comprising at least one ester of 3-methyl-pentan-diol and/or unsaturated derivates thereof and/or at least one ether of 3-methyl-pentan-diol and/or unsaturated derivates thereof and to a method for preparing an aroma chemical composition, in particular a fragranced composition, specifically a fragranced ready-to-use composition, which comprises incorporating at least one ester of 3-methyl-pentane-diol and/or one or more unsaturated derivates thereof and/or at least one ether 3-methyl-pentane-diol and/or one or more unsaturated derivates thereof into a composition, in particular into a ready-to-use composition. The present invention further relates to specific ethers of 3-methyl-pentane-diol and unsaturated derivates thereof and to specific esters of 3-methyl-pentane-diol, to specific mixtures of such compounds and to unsaturated derivates thereof and a method for their preparation.

## Claims

### Claim 1

The use of a compound of formula (I)
wherein
one of the symbols designates a single bond and the other designates a double bond or a single bond,
R1 is hydrogen, C1-C4-alkyl or —(C═O)—R3,
R2 is hydrogen, C1-C4-alkyl or —(C═O)—R4,
R3 is hydrogen or C1-C4-alkyl, and
R4 is hydrogen or C1-C4-alkyl,
or of a stereoisomer thereof, or of a mixture of stereoisomers thereof, or of a mixture of different compounds of formula (I)
as an aroma chemical,
with the proviso that if R1 is hydrogen, R2 is different from hydrogen.

### Claim 2 (depends on 1)

The use according to claim 1, where in formula (I)
R1 is C1-C4-alkyl,
R2 is hydrogen or C1-C4-alkyl.

### Claim 3 (depends on 1)

The use according to claim 1, where the compound of formula (I) has at least one of the following features a), b) and/or c)
a) R1 and R2 are identical,
b) R1 and R2 are C1-C3-alkyl,
c) R1 and R2 are methyl or ethyl, preferably methyl.

### Claim 4 (depends on 1)

The use according to claim 1, where in formula (I)
R1 is —(C═O)—R3, and
R2 is hydrogen, —(C═O)—R4 or C1-C4-alkyl.

### Claim 5 (depends on 4)

The use according to claim 4, where the compound of formula (I) has at least one of the following features d), e), f) and/or g)
d) R2 is —(C═O)—R4,
e) R3 and R4 are identical,
f) R3 and R4 are hydrogen or C1-C4-alkyl,
g) R3 and R4 are hydrogen or C1-C3-alkyl, preferably hydrogen, methyl or ethyl.

### Claim 6 (depends on 1)

The use according to claim 1, where R1 and R2 are identical and are either both C1-C4-alkyl, or R1 is —(C═O)—R3 and R2 is —(C═O)—R4, where R3 and R4 are identical and are hydrogen or C1-C4-alkyl.

### Claim 7 (depends on 1)

The use according to claim 1, of a mixture containing two or three isomers of a compound of formula I, where the isomers are of the formulae (I.1), (I.2) and (I.3),

### Claim 8 (depends on 1)

The use according to claim 1, for imparting an olfactory impression.

### Claim 9 (depends on 8)

The use according to claim 8, as a fragrance.

### Claim 10 (depends on 1)

The use of a compound of formula (I) or of a stereoisomer thereof or of a mixture of stereoisomers thereof or of a mixture of different compounds of formula (I) as defined in claim 1, for modifying the scent character of a fragranced composition, in particular of a fragranced ready-to-use composition.

### Claim 11 (depends on 1)

The use according to claim 1, in a composition selected from the group consisting of perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

### Claim 12 (depends on 1)

Composition comprising at least one compound of formula (I), a stereoisomer thereof or a mixture of stereoisomers thereof, as defined in claim 1, and at least one further component selected from the group consisting of aroma chemicals different from compounds (I) and non-aroma chemical carriers.

### Claim 13 (depends on 12)

The composition according to claim 12, selected from the group consisting of perfume compositions, body care compositions, products for oral and dental hygiene, hygiene articles, cleaning compositions, textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.

### Claim 14 (depends on 1)

A method of preparing an aroma chemical composition, in particular a fragranced composition, specifically a fragranced ready-to-use composition, comprising incorporating at least one compound of formula (I), a stereoisomer thereof or a mixture of stereoisomers thereof, as defined in claim 1, into such a composition, specifically into a ready-to-use composition.

### Claim 15

A compound of the general formula (I)
wherein
one of the symbols designates a single bond and the other designates a double bond or a single bond,
R1 is hydrogen, C1-C4-alkyl or —(C═O)—R3,
R2 is hydrogen, C1-C4-alkyl or —(C═O)—R4,
R3 is hydrogen or C1-C4-alkyl, and
R4 is hydrogen or C1-C4-alkyl,
a stereoisomer thereof, a mixture of stereoisomers thereof, or a mixture of different compounds of formula (I),
with the proviso that if R1 is hydrogen R2 is different from hydrogen,
except for the following compounds and mixtures:
(5-acetoxy-3-methylene-pentyl) acetate,
[(E)-5-acetoxy-3-methyl-pent-3-enyl] acetate,
[(Z)-5-acetoxy-3-methyl-pent-3-enyl] acetate,
(5-acetoxy-3-methyl-pentyl) acetate,
[(E)-5-formyloxy-3-methyl-pent-3-enyl] formate,
[(Z)-5-formyloxy-3-methyl-pent-3-enyl] formate,
(3-methyl-5-propanoyloxy-pentyl) propanoate,
[5-(2,2-dimethylpropanoyloxy)-3-methyl-pentyl] 2,2-dimethylpropanoate,
1,5-dimethoxy-3-methylene-pentane,
(E)-1,5-dimethoxy-3-methyl-pent-2-ene,
(Z)-1,5-dimethoxy-3-methyl-pent-2-ene,
1,5-dimethoxy-3-methyl-pentane,
(Z)-1,5-diethoxy-3-methyl-pent-2-ene,
1,5-diethoxy-3-methyl-pentane,
(E)-1,5-diisopropoxy-3-methyl-pent-2-ene,
(Z)-1,5-diisopropoxy-3-methyl-pent-2-ene,
1,5-dibutoxy-3-methylene-pentane,
(E)-1,5-dibutoxy-3-methyl-pent-2-ene,
(Z)-1,5-dibutoxy-3-methyl-pent-2-ene,
5-isopropoxy-3-methyl-1-pentanol,
5-sec-butoxy-3-methyl-1-pentanol,
1-acetoxy-5-isopropoxy-3-methyl-2-pentene,
(5-hydroxy-3-methyl-pentyl) 3-methylbutanoate,
[3-methyl-5-(3-methylbutanoyloxy)pentyl] 3-methylbutanoate,
(5-hydroxy-3-methylene-pentyl) acetate,
[(E)-5-hydroxy-3-methyl-pent-2-enyl] acetate,
[(Z)-5-hydroxy-3-methyl-pent-2-enyl] acetate,
(5-hydroxy-3-methyl-pentyl) formate,
mixture of [(E)-5-acetoxy-3-methyl-pent-3-enyl] acetate and [(Z)-5-acetoxy-3-methyl-pent-3-enyl] acetate,
mixture of [(E)-3-methyl-5-propanoyloxy-pent-3-enyl] propanoate and [(Z)-3-methyl-5-propanoyloxy-pent-3-enyl] propanoate,
mixture of (E)-1,5-dimethoxy-3-methyl-pent-2-ene and (Z)-1,5-dimethoxy-3-methyl-pent-2-ene,
mixture of (E)-1,5-diethoxy-3-methyl-pent-2-ene and (Z)-1,5-diethoxy-3-methyl-pent-2-ene,
mixture of (E)-3-methyl-1,5-dipropoxy-pent-2-ene and (Z)-3-methyl-1,5-dipropoxy-pent-2-ene,
mixture of (E)-1,5-dibutoxy-3-methyl-pent-2-ene and (Z)-1,5-dibutoxy-3-methyl-pent-2-ene, and
mixture of (5-hydroxy-3-methylene-pentyl) acetate, [(E)-5-hydroxy-3-methyl-pent-2-enyl]acetate and [(Z)-5-hydroxy-3-methyl-pent-2-enyl] acetate.

### Claim 16 (depends on 15)

The compound of claim 15, where none of R1 and R2 is hydrogen.

### Claim 17 (depends on 15)

The compound of claim 15, where R1 and R2 are identical and are either both C1-C4-alkyl or R1 is —(C═O)—R3 and R2 is —(C═O)—R4, where R3 and R4 are identical and are hydrogen or C1-C4-alkyl, preferably hydrogen, methyl or ethyl.

### Claim 18 (depends on 1, 2, 3, 4, 5, 6)

A composition comprising a mixture of at least two compounds selected from the group consisting of isomers of formulae (I.1), (I.2) and (I.3),
wherein R1 and R2 have one of the meanings as defined in claims 1 to 6, comprising each of the compounds present in the mixture in an amount of from 1-99% by weight, with the proviso that the weight of the compounds of formulae (I.1), (I.2) and (I.3) present in said mixture adds up to 100%;
except for following mixtures:
mixture of [(E)-5-acetoxy-3-methyl-pent-3-enyl] acetate and [(Z)-5-acetoxy-3-methyl-pent-3-enyl] acetate,
mixture of [(E)-3-methyl-5-propanoyloxy-pent-3-enyl] propanoate and [(Z)-3-methyl-5-propanoyloxy-pent-3-enyl] propanoate,
mixture of (E)-1,5-dimethoxy-3-methyl-pent-2-ene and (Z)-1,5-dimethoxy-3-methyl-pent-2-ene,
mixture of (E)-1,5-diethoxy-3-methyl-pent-2-ene and (Z)-1,5-diethoxy-3-methyl-pent-2-ene,
mixture of (E)-3-methyl-1,5-dipropoxy-pent-2-ene and (Z)-3-methyl-1,5-dipropoxy-pent-2-ene,
mixture of (E)-1,5-dibutoxy-3-methyl-pent-2-ene and (Z)-1,5-dibutoxy-3-methyl-pent-2-ene and
mixture of (5-hydroxy-3-methylene-pentyl) acetate, [(E)-5-hydroxy-3-methyl-pent-2-enyl]acetate and [(Z)-5-hydroxy-3-methyl-pent-2-enyl] acetate.

### Claim 19 (depends on 18)

The composition according to claim 18, containing the compound of formula (I.1) and either one of the compounds of formulae (I.2) and (I.3) or both compounds of formulae (I.2) and (I.3); and in particular containing all three compounds (I.1), (I.2) and (I.3).

### Claim 20 (depends on 18)

The composition according to claim 18, wherein
R1 and R2 are C1-C4-alkyl, or
R1 is —(C═O)—R3, R2 is —(C═O)—R4, and R3 and R4 are C1-C4-alkyl.

### Claim 21 (depends on 18)

The composition according to claim 18, where in all compounds of formulae (I.1), (I.2) and (I.3) present in the mixture all radicals R1 and R2 are identical and are either C1-C4-alkyl, or all radicals R1 are —(C═O)—R3, all radicals R2 are —(C═O)—R4, and all radicals R3 and R4 are identical and are hydrogen or C1-C4-alkyl.

### Claim 22 (depends on 18)

The composition according to claim 18, comprising a mixture which is selected from the group consisting of
mixtures of (5-formyloxy-3-methylene-pentyl) formate, [(E)-5-formyloxy-3-methyl-pent-3-enyl] formate and [(Z)-5-formyloxy-3-methyl-pent-3-enyl] formate;
mixtures of (5-acetoxy-3-methylene-pentyl) acetate, [(E)-5-acetoxy-3-methyl-pent-3-enyl]acetate and [(Z)-5-acetoxy-3-methyl-pent-3-enyl] acetate;
mixtures of (3-methylene-5-propanoyloxy-pentyl) propanoate, [(E)-3-methyl-5-propanoyloxy-pent-3-enyl] propanoate and [(Z)-3-methyl-5-propanoyloxy-pent-3-enyl]propanoate,
mixtures of 1,5-dimethoxy-3-methylene-pentane, (E)-1,5-dimethoxy-3-methyl-pent-2-ene and (Z)-1,5-dimethoxy-3-methyl-pent-2-ene,
mixtures of 1,5-diethoxy-3-methylene-pentane, (E)-1,5-diethoxy-3-methyl-pent-2-ene and (Z)-1,5-diethoxy-3-methyl-pent-2-ene, and
mixtures of 1,5-di-n-butoxy-3-methylene-pentane, (E)-1,5-di-n-butoxy-3-methyl-pent-2-ene and (Z)-1,5-di-n-butoxy-3-methyl-pent-2-ene.

### Claim 23 (depends on 18)

The composition according to claim 18, where in case that the mixture contains all three compounds of formulae (I.1), (I.2) and (I.3) the ratio of (I.1):(I.2):(I.3) is in the range of from 90:5:5 to 10:45:45.