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US-12624309-B2 - Enol ether properfume

US12624309B2US 12624309 B2US12624309 B2US 12624309B2US-12624309-B2

Abstract

The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment wherein it is oxidized. Moreover, the present invention relates to a perfuming composition and a perfumed consumer product comprising at least one compound of formula (I).

Inventors

  • Gary Bernard Womack

Assignees

  • FIRMENICH SA

Dates

Publication Date
20260512
Application Date
20210610
Priority Date
20200625

Claims (20)

  1. 1 . A method to release from a precursor compound, compounds selected from the group consisting of a) a carbonyl compound of formula wherein R 1 is a C 1-15 alkyl, C 3-15 alkenyl, C 6-10 aryl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 2-15 alkenyloxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 3-15 heterocycloalkyl, carboxylic acid, C 1-4 carboxylic ester, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group; R 2 represents a hydrogen atom, a C 1-6 alkyl or phenyl group; or R 1 and R 2 , when taken together, form a C 5-16 cycloalkyl, C 5-16 cycloalkenyl, C 4-14 heterocycloalkyl or C 4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom; b) a formate ester of formula R 3 represents a hydrogen atom, a C 1-10 alkyl group, a C 3-10 alkenyl group, a benzyl group, a 2-phenylethyl group or a C 5-8 cycloalkyl group optionally substituted by one, two or three C 1-4 alkyl groups; R 4 represents a hydrogen atom, a C 1-6 alkyl, a phenyl or a CH 2 C(O)OR 3 group; wherein R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group; c) an alcohol of formula wherein R 3 , R 4 and R 5 have the same meaning as defined above; wherein the precursor compound comprises a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R 1 , R 2 , R 3 , R 4 and R 5 have the same meaning as defined above; by exposing the precursor compound of formula (I) to an environment wherein the compound is oxidized.
  2. 2 . The method according to claim 1 , wherein R 2 is a hydrogen atom or a C 1-3 alkyl group.
  3. 3 . The method according to claim 1 , wherein R 4 is a hydrogen atom or a C 1-3 alkyl group.
  4. 4 . The method according to claim 1 , wherein R 5 is a hydrogen atom or when R 4 is a methyl group, R 5 is a hydrogen atom or methyl group.
  5. 5 . The method according to claim 1 , wherein R 1 is a C 1-10 alkyl, C 3-10 alkenyl, C 3-11 cycloalkyl or C 5-11 cycloalkenyl group, each optionally substituted with one or more of a C 1-4 alkyl, C 1-4 alkoxy, C 3-8 cycloalkyl, C 5-8 cycloalkenyl, C 6 aryl and/or C 6 aryloxy group, each optionally substituted with one or more of a C 1-4 alkyl, hydroxy and/or C 1-4 alkoxy group.
  6. 6 . The method according to claim 1 , wherein R 1 is a naphthyl group or a phenyl group optionally substituted by one or two R 1′ group wherein R 1′ , simultaneously or independently, represents a hydroxy group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a R a COO group, a R a OCO group wherein R a is a hydrogen atom, a C 1-3 alkyl group, a C 2-3 alkenyl group, or two adjacent R 1′ , when taken together, represent a —O—(CH 2 ) m —O— wherein m is 1 or 2 or form a C 5-6 saturated or unsaturated ring.
  7. 7 . The method according to claim 1 , wherein the compound of formula (II) and/or (IV) are a perfuming ingredient.
  8. 8 . The method according to claim 1 , wherein the environment wherein the compound is oxidized is air.
  9. 9 . A method to confer, enhance, improve or modify the odor properties of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition, the air, or article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined in claim 1 .
  10. 10 . A method for intensifying or prolonging the diffusion effect of the characteristic fragrance of at least one carbonyl compound of formula (II): wherein R 1 is a C 1-15 alkyl, C 3-15 alkenyl, C 6-10 aryl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 2-15 alkenyloxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 3-15 heterocycloalkyl, carboxylic acid, C 1-4 carboxylic ester, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group; R 2 represents a hydrogen atom, a C 1-6 alkyl or phenyl group; or R 1 and R 2 , when taken together, form a C 5-16 cycloalkyl, C 5-16 cycloalkenyl, C 4-14 heterocycloalkyl or C 4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom, and/or of at least one active formate ester of formula (III): wherein R 3 represents a hydrogen atom, a C 1-10 alkyl group, a C 3-10 alkenyl group, a benzyl group, a 2-phenylethyl group or a C 5-8 cycloalkyl group optionally substituted by one, two or three C 1-4 alkyl groups; R 4 represents a hydrogen atom, a C 1-6 alkyl, a phenyl or a CH 2 C(O)OR 3 group; wherein R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group, and/or of at least one active alcohol of formula (IV): wherein R 3 , R 4 and R 5 have the same meaning as defined above, on a surface or the air surrounding the perfuming composition, wherein the surface, or the air is treated with at least one compound (I) as defined in claim 1 , or with a composition or article containing at least one compound (I), under conditions susceptible of allowing the release of at least one ketone or aldehyde formula (II), of at least one formate ester of formula (III) and/or of at least one alcohol of formula (IV) over time.
  11. 11 . A perfuming composition comprising i) at least one compound of formula (I), as defined claim 1 ; ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and iii) optionally at least one perfumery adjuvant.
  12. 12 . A perfumed consumer product comprising at least one compound of formula (I), as defined in claim 1 .
  13. 13 . The perfumed consumer product according to claim 12 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.
  14. 14 . The perfumed consumer product according to claim 13 , characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a hair conditioning product, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, an oil or gel, or a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furniture care product, a wipe, a dish detergent or hard-surface detergent, a leather care product, a car care product.
  15. 15 . A compound of formula in the form of any one of its stereoisomers or a mixture thereof and wherein R 1 is a C 2-15 alkyl, C 3-15 alkenyl, C 6-10 aryl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 2-15 alkenyloxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 3-15 heterocycloalkyl, carboxylic acid, C 1-4 carboxylic ester, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group; R 2 represents a hydrogen atom, a C 1-3 alkyl or a phenyl group; or R 1 and R 2 , when taken together, form a C 5-16 cycloalkyl, C 5-16 cycloalkenyl, C 4-14 heterocycloalkyl or C 4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom; R 3 represents a C 1-10 alkyl group, a C 3-10 alkenyl group, a benzyl group, a 2-phenylethyl group or a C 5-8 cycloalkyl group optionally substituted by one, two or three C 1-4 alkyl groups; R 4 represents a hydrogen atom or a methyl, phenyl or CH 2 C(O)OR 3 group; wherein R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group; and provided that when R 2 , R 4 and R 5 are a hydrogen atom, R 1 is not an unsubstituted phenyl group; and provided that methyl 2-((2,2-diphenylvinyl) oxy) acetate and ethyl 2-((3-phenylprop-1-en-1-yl) oxy) acetate are excluded.
  16. 16 . The method according to claim 1 , wherein: R 2 is a hydrogen atom or a methyl group; and/or R 4 is a hydrogen atom and or a methyl group; and/or R 5 is a hydrogen atom or when R 4 is a methyl group, R 5 is a hydrogen atom or methyl group.
  17. 17 . The method according to claim 16 , wherein R 1 is a C 1-10 alkyl, C 3-10 alkenyl, C 3-11 cycloalkyl or C 5-11 cycloalkenyl group, each optionally substituted with one or more of a C 1-4 alkyl, C 1-4 alkoxy, C 3-8 cycloalkyl, C 5-8 cycloalkenyl, C 6 aryl and/or C 6 aryloxy group, each optionally substituted with one or more of a C 1-4 alkyl, hydroxy and/or C 1-4 alkoxy group.
  18. 18 . The method according to claim 16 , wherein R 1 is a naphthyl group or a phenyl group optionally substituted by one or two R 1′ group wherein R 1′ , simultaneously or independently, represents a hydroxy group, a C 1-3 alkyl group, a C 1-3 alkoxy group, a R a COO group, a R a OCO group wherein R a is a hydrogen atom, a C 1-3 alkyl group, a C 2-3 alkenyl group, or two adjacent R 1′ , when taken together, represent a —O—(CH 2 ) m —O— wherein m is 1 or 2 or form a C 5-6 saturated or unsaturated ring.
  19. 19 . A method to confer, enhance, improve or modify the odor properties of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition, the air, or article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined in claim 16 .
  20. 20 . A perfumed consumer product comprising at least one compound of formula (I), as defined in claim 16 .

Description

This present application is a U.S. national phase entry under 35 U.S.C. § 371 of PCT Application No. PCT/EP2021/065606, filed Jun. 10, 2021, which claims priority to U.S. Provisional Application No. 63/038, 160, filed Jun. 12, 2020, and European Patent Application No. 20182200.4, filed Jun. 25, 2020. The entire contents of these applications are explicitly incorporated herein by this reference. TECHNICAL FIELD The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment wherein it is oxidized. Moreover, the present invention relates to a perfuming composition and a perfumed consumer product comprising at least one compound of formula (I). BACKGROUND The perfume industry has a particular interest for compositions or additives which are capable of prolonging or enhancing the perfuming effect of at least one perfuming ingredient for a certain period of time. It is particularly desirable to obtain long-lasting properties for standard perfumery raw materials which are too volatile or have a poor substantivity by themselves, or which are only deposited in a small amount onto the surface of the final application. Furthermore, some of the perfumery ingredients are unstable and need to be protected against slow degradation prior to their use. Long-lasting perfumes are desirable for various applications, as for example fine or functional perfumery or cosmetic preparations. The washing and softening of textiles are particular fields in which there is a constant need to enable the effect of active substances, in particular perfumes, or perfuming compositions, to be effective for a certain period of time after washing, softening and drying. Indeed, many active substances which are particularly suitable for this type of application are known to lack tenacity on laundry, or do not remain on the laundry when rinsed, with the result that their perfuming effect is experienced only briefly and not very intensely. Given the importance of this type of application in the perfume industry, research in this field has been sustained, in particular with the aim of finding new, and more effective solutions to the aforementioned problems. WO 2019243501 discloses enol ether capable of efficiently releasing a carbonyl compound, a formate ester compound and an alcohol compound. However, said compounds, under acidic conditions, may be partly hydrolyzed after several days. It has now been surprisingly found that enol ether compounds according to the present invention solve the above-mentioned problem by reducing the rate of hydrolysis while still being able of efficiently releasing a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV). DETAILED DESCRIPTION Olfaction is a complex and dynamic process and controlling the release profile of volatile fragrance compounds may maximize the impact of fragrance formulations and enrich the sensorial experience. Profragrances, such as the compounds of the present invention add a dimension of control and long-lastingness to the release profile of highly volatile perfumery raw materials (PRMs) while having better stability in acidic media. Without intending to be limited to any particular theory, the compounds of the present invention may achieve their effect on the olfactive properties of a perfuming composition by tethering the PRM to a molecular anchor and requiring a specific reaction mechanism under certain environmental conditions to release the volatile PRM from this anchor. In the present invention, the release of one, two or up to three PRMs is prompted by oxidation when the profragrance is exposed to the oxygen in ambient air. The first object of the present invention is a method to release from a precursor compound, compounds selected from the group consisting of a) a carbonyl compound of formula whereinR1 is a C1-15 alkyl, C3-15 alkenyl, C6-10 aryl, C3-15 cycloalkyl, C5-15 cycloalkenyl or C3-14 heterocycloalkyl group, each optionally substituted with one or more of a hydroxy, C1-15 alkyl, C2-15 alkenyl, C1-15 alkoxy, C2-15 alkenyloxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C3-15 heterocycloalkyl, carboxylic acid, C1-4 carboxylic ester, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, hydroxy, carboxylic acid and/or C1-4 carboxylic ester group;R2 represents a hydrogen atom, a C1-6 alkyl or phenyl group; orR1 and R2, when taken together, form a C5-16 cycloalkyl, C5-16 cycloalkenyl, C4-14 heterocycloalkyl or C4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C1-15 alkyl, C2-15 alkenyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C6-10 aryl and/or C6-10 aryloxy group, each optional