Perfuming ingredients with lily of the valley note

Patent metadata

Field	Value
Publication number	US-12110472-B2
Application number	US-201817292836-A
Country	US
Kind code	B2
Filing date	Nov 13, 2018
Priority date	Nov 13, 2018
Publication date	Oct 8, 2024
Grant date	Oct 8, 2024

Abstract

The present invention primarily relates to the use of 3-(4-isobutyl-2-methyl-cyclohexyl)pro-panal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-meth-ylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-1-yl)propanal as perfuming ingredients. Moreover, the present invention relates to perfume compositions and perfumed products comprising the before mentioned perfuming ingredients. Still more particularly, the invention relates to a method for producing said perfumed products and a method of imparting and/or increasing i) floral and/or ii) green and/or iii) lily of the valley odor characteristics to perfumed products. This invention also relates to 3-(4-isobutyl-2-methyl-cyclohexyl)propanal, 3-(4-Isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, 3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal, or 3-(4-isobutyl-6-methyl-cyclohexen-yl)propanal and a process for the preparation of said compounds.

First claim

The invention claimed is:

1. A compound selected from the group consisting of:

3-(4-isobutyl-2-methyl-cyclohexyl)propanal,

3-(4-isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal, and

3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal.

2. The compound of claim 1 , wherein the compound is:

3-(4-isobutyl-2-methyl-cyclohexyl)propanal.

3. The compound of claim 1 , wherein the compound is:

3-(4-isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal.

4. The compound of claim 1 , wherein the compound is:

3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal.

5. A perfume composition comprising one or more compounds of claim 1 and one or more fragrance ingredients, and optionally, 3-(4-isobutyl-2-methylcyclohex-1-en-1-yl)propanal.

6. A perfumed product comprising the perfume composition of claim 5 .

7. The perfumed product of claim 6 , wherein the perfumed product is selected from perfume extraits, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, detergents, textile fresheners, ironing aids, liquid detergents, powdery detergents, laundry pretreatment agents, fabric softeners, laundry soaps, laundry tablets, disinfectants, air fresheners, aerosol sprays, waxes, polishes, personal care agents, hand creams, hand lotions, foot creams, foot lotions, depilatory creams, depilatory lotions, aftershave creams, aftershave lotions, tanning creams, tanning lotions, hair care products, deodorants, antiperspirants, decorative cosmetics, candles, lamp oils, incense sticks, insecticides, repellents, and fuels.

8. A method for imparting a fragrance to a composition comprising adding one or more compounds of claim 1 to the composition.

9. The method of claim 8 , wherein the fragrance has a floral odor characteristic, a green odor characteristic, a lily of the valley odor characteristic, or a combination thereof.

10. The method of claim 9 , wherein the fragrance additionally has a sweet odor characteristic, a creamy odor characteristic, or a combination thereof.

11. The method of claim 8 , wherein the compound is:

3-(4-isobutyl-2-methyl-cyclohexyl)propanal.

12. The method of claim 8 , wherein the compound is:

3-(4-isobutyl-6-methyl-cyclohexa-1,5-dien-1-yl)propanal.

13. The method of claim 8 , wherein the compound is:

3-(4-isobutyl-6-methylene-cyclohexen-1-yl)propanal.

14. A method for imparting or increasing a fragrance to a product to obtain a perfumed product, the method comprising adding a sensorially effective amount of the perfume composition of claim 5 to the product and obtaining the perfumed product.

15. The method of claim 14 , wherein the fragrance has a floral odor characteristic, a green odor characteristic, a lily of the valley odor characteristic, or a combination thereof.

16. The method of claim 14 , wherein the perfumed product is selected from perfume extraits, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, detergents, textile fresheners, ironing aids, liquid detergents, powdery detergents, laundry pretreatment agents, fabric softeners, laundry soaps, laundry tablets, disinfectants, air fresheners, aerosol sprays, waxes, polishes, personal care agents, hand creams, hand lotions, foot creams, foot lotions, depilatory creams, depilatory lotions, aftershave creams, aftershave lotions, tanning creams, tanning lotions, hair care products, deodorants, antiperspirants, decorative cosmetics, candles, lamp oils, incense sticks, insecticides, repellents, and fuels.

17. A method for producing a perfumed product comprising:
(i) providing one or more compounds of claim 1 ;
(ii) providing one or more additional components of the perfumed product; and
(iii) contacting or mixing the one or more additional components of the perfumed product with a sensorially effective amount of the one or more compounds.

18. A process for preparing a compound of claim 1 comprising one or more of reaction steps (i)-(xii):

wherein R′ is an alkyl group, and R″ and R′″ are independently an alkyl group or may be connected via an alkyl group to form a ring.

19. The process of claim 18 , wherein R′ is ethyl.

20. The process of claim 18 , wherein R″ and R′″ are independently methyl or ethyl, or may be a connected ethane-1,2-diyl or a propane-1,2-diyl to form a ring.

Assignees

• Symrise Ag

Inventors

• Hölscher Bernd
• Chandrasekaran Vijayanand
• Ohrmann Eva

Classifications

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07C67/31

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C45/65

  by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups · CPC title

• C07C45/515

  the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group (cyclic acetals or ketals C07C45/59, C07C45/60) · CPC title

• C07C41/48

  Preparation of compounds having [IMAGE cpc-sch-C07C-0958.gif] groups · CPC title