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 mixture comprising a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00008## 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.

2. A mixture according to claim 1, wherein the mixture comprises one or several compounds comprises a cyclohexadecen-1-one.

3. A mixture according to claim 1, wherein the mixture is a fragrance substance mixture.

4. A mixture according to claim 3, wherein the additional or one, several or all of the additional fragrance substances is or are selected from the groups consisting of alcohols, aldehydes, ketones, ethers, esters and carboxylates.

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

6. A mixture according to claim 3, wherein the ratio of the total mass of fragrance substances that do not correspond to formula (I) to the total mass of compound(s) of formula (I) is higher than or equal to 80:20.

7. A mixture according to claim 1 producible by a method comprising the following steps: (i) providing a base mixture comprising a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00009## 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 base mixture is lower than 90:10, (ii) performing an acid-catalyzed isomerization on compound (Z) contained in the base mixture, so that a mixture is obtained, wherein the weight ratio of compound (E) to compound (Z) is in the range of 75:25.

8. A method for producing a mixture comprising a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00010## 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, comprising the following steps: (i) providing a base mixture comprising a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00011## 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 base mixture is lower than 90:10, (ii) performing an acid-catalyzed isomerization on compound (Z) contained in the base mixture, so that a mixture is obtained, wherein the weight ratio of compound (E) to compound (Z) is in the range of 75:25.

9. A fragrance substance mixture according to claim 3, wherein the amount of compound (E) and compound (Z) is sufficient (a) to mask or reduce the or one or several unpleasant olfactory impression(s) of another fragrance substance in the fragrance substance mixture, and/or (b) to enhance the one or several pleasant olfactory impression(s) of another fragrance substance in the fragrance substance mixture.

10. A fragrance substance mixture according to claim 3, wherein the total amount of compounds of formula (I) with regard to the total weight of the fragrance substance mixture is 1 wt. % or less.

11. A perfumed product comprising a mixture according to claim 1 in a sensorially effective amount.

12. A perfumed product according to claim 11, wherein the product is selected from the group consisting of perfume extraits, eau de parfums, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, acidic, alkaline and neutral detergents, textile fresheners, ironing aids, liquid detergents, powdery detergents, laundry pretreatment agents, fabric softeners, laundry soaps, laundry tablets, disinfectants, surface disinfectants, air improvers, aerosol sprays, waxes and polishes, personal care agents, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, products for decorative cosmetic, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

13. A method for producing a perfumed product comprising the following steps: i) providing a mixture of a first compound (E) and a second compound (Z), wherein compounds (E) and (Z) are compounds of formula (I) with identical constitutional formula ##STR00012## 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, ii) providing one or several further components of the perfumed product to be produced, and iii) contacting or mixing the further components provided in step ii) with a sensorially effective amount of the components provided in step i).

14. A method (a) for masking or reducing one or several unpleasant olfactory impressions of one or several unpleasantly smelling substances comprising combining the one or several unpleasantly smelling substances with a mixture of claim 1, and/or (b) for enhancing one or several pleasant olfactory impressions of one or several pleasantly smelling substances comprising combining the one or several pleasantly smelling substances with a mixture of claim 1.

15. The method of claim 14, wherein the one or several unpleasantly smelling substances and/or the one or several unpleasantly smelling substances is or are selected from the group consisting of alcohols, aldehydes, ketones, ethers, esters and carboxylates, and/or has or have a molar mass in the range of 150 to 285 g/mol.

16. A mixture of claim 1, wherein the weight ratio of compound (E) to compound (Z) in the mixture is in the range of 80:20 to 90:10.

17. A mixture of claim 2, wherein the mixture comprises one or several compounds comprising cyclohexadec-8-en-1-one, and cyclopentadec-4-en-1-one.

18. A mixture according to claim 5, wherein the one, several or all of the additional fragrance substances has or have a molar mass in the range of 210 g/mol or less

19. A mixture according to claim 6, wherein the ratio of the total mass of fragrance substances that do not correspond to formula (I) to the total mass of compound(s) of formula (I) is higher than or equal to 90:10.

20. A mixture according to claim 6, wherein the ratio of the total mass of fragrance substances that do not correspond to formula (I) to the total mass of compound(s) of formula (I) is higher than or equal to 95:5.

Description

EXAMPLES

Example 1: Perfume Oil P1 Ketones

[0105]

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

[0106] A wooden accentuated composition with soft-floral elements of violets and lilies results, rounded off with aromatic components of tonka beans and cinnamon bark.

[0107] 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

[0108]

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

[0109] The scent is refreshing-citric, green-fruity, pear-like, smells aromatic of wild berries and has a subtle rounding of tropical wood.

[0110] 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))

[0111] 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.

[0112] 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).

Isomerization Results:

[0113]

TABLE-US-00003 Structure MW GC-% educt GC-% isomerization Globanone [00006] 236 67% E 31% Z 77% E 21% Z Exaltenone [00007] 222 3% E 95% Z 82% E 16% Z

[0114] 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).