Mixtures with enriched E-isomers of unsaturated macrocyclic musk compounds

Abstract

Herein described are novel mixtures, containing or consisting of a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00001##
wherein it applies that one of the four wavy lines denotes a double bond and the remaining wavy lines denote a single bond, respectively, and X is selected from CH.sub.2 and CH.sub.2CH.sub.2,
and the first compound (E) is trans-configurated and the second compound (Z) is cis-configurated, wherein the weight ratio of compound (E) to compound (Z) in the mixture is in the range of 75:25, preferably of 80:20, to 90:10,
uses of such mixtures, methods for producing such mixtures as well as products containing such mixtures.

Claims

1. A fragrance substance mixture comprising: (a) a first compound (E) and a second compound (Z), both having the same chemical formula, wherein the first compound (E) and the second compound (Z) are individually selected from the group consisting of cyclohexadec-8-en-1-one and cyclopentadec-4-en-1-one, and wherein the first compound (E) is trans-configurated and the second compound (Z) is cis-configurated, and wherein the weight ratio of the first compound (E) to the second compound (Z) is from 4:1 to 9:1; and (b) one or several additional fragrance substances; wherein the fragrance substance mixture does not comprise compounds of formula (I) except for the first compound (E) and the second compound (Z) of (a), ##STR00008## wherein one of the four wavy lines denotes a double bond and the remaining wavy lines denote a single bond, respectively, and X is selected from CH.sub.2 and CH.sub.2CH.sub.2.

2. A fragrance substance mixture according to claim 1, wherein the one or several additional fragrance substances is or are selected from the groups consisting of alcohols, aldehydes, ketones, ethers, esters, and carboxylates.

3. A fragrance substance mixture according to claim 1, wherein the one or several additional fragrance substances has or have a molar mass in the range of 150 to 285 g/mol.

4. A fragrance substance mixture according to claim 1, wherein the weight ratio of the total mass of fragrance substances that do not correspond to the first compound (E) and the second compound (Z) to the total mass of the first compound (E) and the second compound (Z) is higher than or equal to 4:1.

5. A fragrance substance mixture according to claim 1 producible by a method comprising the following steps: (i) providing a base mixture comprising the first compound (E) and the second compound (Z), wherein the weight ratio of the first compound (E) to the second compound (Z) in the base mixture is lower than 9:1, (ii) performing an acid-catalyzed isomerization on the second compound (Z) contained in the base mixture, so that a mixture is obtained, wherein the weight ratio of the first compound (E) to the second compound (Z) is in the range of 4:1 to 9:1; and (iii) incorporating into the mixture one or several additional fragrance substances.

6. A fragrance substance mixture according to claim 1, wherein the amount of the first compound (E) and the second compound (Z) is sufficient (a) to mask or reduce one or several unpleasant olfactory impression(s) of another fragrance substance in the fragrance substance mixture, and/or (b) to enhance one or several pleasant olfactory impression(s) of another fragrance substance in the fragrance substance mixture.

7. A fragrance substance mixture according to claim 1, wherein the total amount of the first compound (E) and the second compound (Z) with regard to the total weight of the fragrance substance mixture is 1 wt. % or less.

8. A fragrance substance mixture of claim 1, wherein the fragrance substance mixture comprises cyclohexadec-8-en-1-one and cyclopentadec-4-en-1-one.

9. A fragrance substance mixture according to claim 1, wherein the one or several additional fragrance substances has or have a molar mass in the range of 210 g/mol or less.

10. A fragrance substance mixture according to claim 1, wherein the ratio of the total mass of fragrance substances that do not correspond to the first compound (E) and second compound (Z) to the total mass of compound(s) of the first compound (E) and second compound (Z) is higher than or equal to 9:1.

11. A fragrance substance mixture according to claim 1, wherein the ratio of the total mass of fragrance substances that do not correspond to the first compound (E) and the second compound (Z) to the total mass of compound(s) of the first compound (E) and the second compound (Z) is higher than or equal to 19:1.

12. A fragrance substance mixture according to claim 1, wherein (a) is cyclohexadec-8-en-1-one.

13. A fragrance substance mixture according to claim 1, wherein (a) is cyclopentadec-4-en-1-one.

14. A fragrance substance mixture according to claim 1, wherein the one or several additional fragrance substances is or are selected from the groups consisting of ketones and esters.

Description

EXAMPLES

Example 1: Perfume Oil P1 Ketones

(1) TABLE-US-00001 Component wt. proportion HEXENYL BENZOATE CIS-3 5 PHENYL ACETALDEHYDE 3 DIMETHYL ACETAL LINALYL ACETATE 70 APRIFLOREN 20 LILIAL 30 FLOROSA 20 MAJANTOL 20 MUGETANOL 5 LINALOOL 35 ROSE OXIDE 5 PHENYLETHYL ALCOHOL 50 ROSAPHEN 50 GERANYL ACETATE 20 BENZYL ACETATE 50 HEDIONE 120 YLANG OIL TYPE BASE 5 ISOBUTYL SALICYLATE 18 DIHYDRO IONONE BETA 20 IONONE ALPHA 35 IONONE BETA 25 ISORALDEINE 70 100 ANISALDEHYDE 20 HELIOTROPIN 30 METHYL CINNAMATE 15 COUMARIN 20 CEDRYL ACETATE 20 ISO E SUPER 120 TIMBEROL 5 PATOULIOEL 5 BRAHMANOL 10 950

(2) A wooden accentuated composition with soft-floral elements of violets and lilies results, rounded off with aromatic components of tonka beans and cinnamon bark.

(3) An addition of 10% (with respect to the total weight of the fragrance substances of the group of ketones contained in the judged fragrance substance mixture) of an isomer mixture of cyclohexadec-8-en-1-one (here: 80% trans-cyclohexadec-8-en-1-one: 20% cis-cyclohexadec-8-en-1-one) makes the composition more harmonious, reduces the spice notes and makes it appear of higher value, cosmetic and elegant.

Example 2: Perfume Oil P2 Esters

(4) TABLE-US-00002 Component wt. proportion ALDEHYDE C 12 LAURIN 4 VERTOCITRAL 5 STYROLYL ACETATE 12 MINTONATE 10 DIHYDROMYRCENOL 45 LINALYL ACETATE 75 AGRUNITRILE 10 ORANGE OIL 50 METHYL ANTHRANILATE 5 ISOBORNYL ACETATE 10 HEXYL ACETATE 10 ALDEHYDE C 14 SO CALLED 45 ALDEHYDE C 18 SO CALLED 10 MANZANATE 10 ALLYL CAPRONATE 5 ALLYL CYCLOHEXYL PROPIONATE 5 ALLYL HEPTYLATE 5 DEWFRUIT TYPE BASE 10 LILIAL 30 PHENYLETHYL ACETATE 20 PHENYLETHYL ALCOHOL 50 CITRONELLYL ACEATE 20 DAMASCONE DELTA 10 BENZYL ACETATE 30 HEDIONE 75 HEXYL CINNAMIC ALDEHYDE 75 ALPHA BENZYL SALICYLATE 30 HEXYL SALICYLATE 60 MYSORE ACETATE 30 ISORALDEINE 70 30 AGRUMEX HC 25 HERBAFLORAT 75 HERBYL PROPIONATE 35 AMBROCENIDE 10% IN DPG 4 YSAMBER K 25 950

(5) The scent is refreshing-citric, green-fruity, pear-like, smells aromatic of wild berries and has a subtle rounding of tropical wood.

(6) The addition of up to 10%, preferably less than 10% (with respect to the total weight of the fragrance substances of the group of esters contained in the judged fragrance substance mixture) of an isomer mixture of cyclohexadec-8-en-1-one (here: 90% trans-cyclohexadec-8-en-1-one: 10% cis-cyclohexadec-8-en-1-one) gives rise to a mild, aromatic and very near-natural fruitiness. Slightly overaccentuated chemical undertones are reduced. The relative strength of the aroma sensation is enhanced in a pleasant way.

Example 3: Production of a Mixture According to the Invention (Enrichment of E-Isomer by Means of Isomerization (e.g. By Using Globanone or Exaltenone))

(7) 45 g Globanone (cyclohexadec-8-en-1-one) (here: 67% (E) and 31% (Z)) are dissolved in 225 ml isopropanol and 3.0 g nitric acid (65%) are added. Subsequently, it is stirred for 8 h at room temperature.

(8) Workup: Soda is added to the batch, it is concentrated on a rotary evaporator and distilled by means of Kugelrohr distillation. It can be proceeded in a corresponding manner starting from an isomer mixture of cyclopentadec-4-en-1-one (exaltenone)instead of an isomer mixture of cyclohexadec-8-en-1-one(see the table listed below for details).

(9) Isomerization Results:

(10) TABLE-US-00003 Structure MW GC-% educt GC-% isomerization Globanone 236 67% E 31% Z 77% E 21% Z Exaltenone 222 3% E 95% Z 82% E 16% Z

(11) Further enrichments of E-isomer are possible, for example, by means of fractional distillation (e.g.: 80% E:20% Z and 90% E:10% Z).