Search

EP-4734932-A1 - ORGANIC COMPOUNDS AND THEIR USE FOR GENERATING A FRAGRANT ALCOHOL

EP4734932A1EP 4734932 A1EP4734932 A1EP 4734932A1EP-4734932-A1

Abstract

Compound of formula (I) being an ether or an ester as precursor for generating a fragrant alcohol according to formula (II); its use as fragrance precursor, and fragrance compositions and consumer products comprising the compound.

Inventors

  • FLACHSMANN, FELIX
  • ZHOU, LIJUN
  • CHARPENTIER, Julie

Assignees

  • Givaudan SA

Dates

Publication Date
20260506
Application Date
20240626

Claims (10)

  1. 1 . A compound of formula (I) wherein - is indicating a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 is independently selected from the group consisting of H, Me and Et; R 2 is selected from the group consisting of H, Me and Et, or forms together with the carbon atoms C2 and C3 a 3 membered ring; and X is selected from the group consisting of aryl bearing up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl and alkyl alkenoate; benzyl bearing a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, (C=O)Ph at the benzylic position; propan-2-yl substituted with phenyl, naphthalen-1-yl or naphthalen-2-yl at position 2; dimethyl 2-malonate and diethyl 2-malonate; and alkanoyl (C(O)-R 10 ), with R 10 selected from linear or branched C 4 to Ci 8 alkyl, linear or branched C 4 to Ci 8 alkenyl with one or two double bonds, linear or branched C 4 to Ci 8 ether and oxoalkyl, and hydroxyphenyl, with the proviso that the compound is not nona-2,6-dien-1-yl palmitate as precursor for generating a fragrant alcohol of formula (II)
  2. 2. The compound of formula (I) according to claim 1 , wherein the fragrant alcohol of formula (II) that is released from the compound of formula (I) is selected from the group consisting of 3,7-dimethylnon-6-en-1-ol, 2,4,7-trimethyloct-6-en-1-ol, 6-nonenol, 6-ethyl-3- methyloct-6-en-1-ol, (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methanol, and 2,6- nonadienol.
  3. 3. The compound of formula (I) according to claim 1 or 2, wherein X is selected from the group consisting of aryl bearing up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl and alkyl alkenoate; benzyl bearing a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, (C=O)Ph at the benzylic position; propan-2-yl substituted with phenyl, naphthalen-1-yl or naphthalen-2-yl at position 2; dimethyl 2-malonate and diethyl 2-malonate; and wherein the fragrant alcohol of formula (II) that is released from the compound of formula (I) is selected from the group consisting of 3,7-dimethylnon-6-en-1-ol, 2,4,7- trimethyloct-6-en-1-ol, 6-nonenol, 6-ethyl-3-methyloct-6-en-1-ol, (1-methyl-2-(5- methylhex-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol.
  4. 4. Use of a compound of formula (I) according to any of claims 1 through 3 as precursor for generating a fragrant alcohol of formula (II) according to claim 1.
  5. 5. A fragrance composition comprising at least one compound of formula (I) according to any of claims 1 through 3.
  6. 6. A consumer product comprising at least one compound of formula (I) according any of claims 1 through 3 and a consumer product base.
  7. 7. A method to release a fragrant alcohol of formula (II) as defined in any of claims 1 through 3, wherein a compound of formula (I) as defined in any of claims 1 through 3is exposed to ambient air and/or humidity.
  8. 8. A method of manufacturing a consumer product, comprising the steps of a) provision of a compound of formula (I) according to any of claims 1 through 3, or a fragrance composition according to claim 5; and b) admixing it to a consumer product base.
  9. 9. Use of a compound of formula (I) according to any of claims 1 through 3 or a fragrance composition according to claim 5 in consumer products.
  10. 10. A method to confer, enhance, improve or modify the hedonic properties of a fragrance composition or a consumer product, which method comprises adding to said composition or consumer product at least one compound of formula (I) according to any of claims 1 through 3.

Description

ORGANIC COMPOUNDS AND THEIR USE FOR GENERATING A FRAGRANT ALCOHOL TECHNICAL FIELD The present invention relates generally to fragrance precursors, which are able to release fragrant alcohols. The invention also relates to perfume preparations and consumer products containing said precursors. The invention further relates to methods of making said perfume precursors, perfume preparations and consumer products, as well as the use of said perfume precursors and perfume preparations in consumer products, such as personal care and household care products. BACKGROUND Perfumed consumer products such as personal care, cleaning or laundry products comprising fragrances are well-known in the art. However, it is known that fragrances can be altered through degradation caused by interaction with air or when incorporated in certain consumer product bases, where alkalinity, acidity, the presence of oxidizing agents, such as hypochlorite salts, or other base components may lead to chemical degradation of the fragrance. In addition, volatile fragrances tend to be dissipated with time. Furthermore, when used in the perfumed consumer products mentioned above, the deposition of the fragrance on a treated substrate is diminished by the washing and/or rinsing procedure. Nevertheless, it is desired by consumers to have products that can be stored overtime and still giving a constant perfume impression. In particular, the impact of volatile components is to be retained. Furthermore, it is desired that such products create a long-lasting pleasing fragrance slowly emitting from the treated substrate over time. To address these needs, fragrance precursors can be used, which are substances that are essentially odorless themselves, but which, in particular circumstances, will decompose to release the fragrant molecule. There are several classes of known precursors which release fragrant molecules upon activation, such as hydrolysis, temperature change, oxygen, action of light and enzymes. For example, WO2012085287 reports a group of precursors able to release a fragrance by spontaneous air oxidation. In W02007143873 another group of precursors is described which can be cleaved by hydrolysis. All precursors do show different stability, and they release the fragrant molecule under different conditions. There is still need to provide precursors able to release fragrant alcohols over an extended time period and which can be easily incorporated into a variety of consumer products. SUMMARY In accordance with a first aspect of the present invention there is provided a compound of formula (I) wherein - is indicating a carbon-carbon single or double bond between C2 and C3; R1, R3, R4, R5 and R6 is independently selected from the group consisting of H, Me and Et; R2 is selected from the group consisting of H, Me and Et, or forms together with the carbon atoms C2 and C3 a 3 membered ring; and X is selected from the group consisting of aryl bearing up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl and alkyl alkenoate; benzyl bearing a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, (C=O)Ph at the benzylic position; propan-2-yl substituted with phenyl, naphthalen-1-yl or naphthalen-2-yl at position 2; dimethyl 2-malonate and diethyl 2-malonate; and alkanoyl (C(O)-R10), with R10 selected from linear or branched C4 to Ci8 alkyl, linear or branched C4 to Cis alkenyl with one or two double bonds, linear or branched C4 to Ci8 ether and oxoalkyl, and hydroxyphenyl, with the proviso that the compound is not nona-2,6-dien-1-yl palmitate, as precursor for generating a fragrant alcohol of formula (II) In accordance with a second aspect of the present invention there is provided a use of a compound of formula (I) as fragrance precursor which is capable of releasing fragrant alcohols of formula (II) over an extended time period. In accordance with a third aspect of the present invention there are provided fragrance compositions and consumer products comprising said compounds of formula (I). In accordance with a fourth aspect of the present invention there is provided a method to release a fragrant alcohol of formula (II). In accordance with a fifth aspect of the present invention there are provided methods of making said perfume precursors, perfume preparations and consumer products. In accordance with a sixth aspect of the present invention there is provided the use of said perfume precursors of formula (I) and perfume preparations in consumer products, such as fabric care, personal care and household care products. In accordance with a seventh aspect of the present invention there is provided a method to confer, enhance, improve or modify the hedonic properties of a fragrance composition or a consumer product. Certain embodiments of any aspect of the present invention may provide one or more of the followin