Enol ether properfume

Abstract

To provide a method, a perfuming composition and a perfumed consumer product for imparting 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 on the surface of the final application.SOLUTION: The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method of releasing a compound, namely, a carbonyl, a formate ester and / or an alcohol represented by specific formulas, by exposing the compound of formula (I) to an environment in which 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).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound of formula (I) as a propargyl compound. In particular, the present invention relates to a method for releasing a compound, i.e., a carbonyl of formula (II), a formate of formula (III) and / or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment in which it is oxidized. Furthermore, the present invention relates to perfumed compositions and perfumed consumer products comprising at least one compound of formula (I).

[0002] background The perfume industry is particularly interested in compositions or additives that can extend or enhance the fragrance effect of at least one fragrance ingredient for a certain period of time. It is particularly desirable to obtain persistence for standard fragrance ingredients that are themselves too volatile, have poor residual properties, or deposit only small amounts on the surface of the final application. Furthermore, some fragrance ingredients are unstable and need to be protected from slow degradation before use. Long-lasting fragrances are desirable for various applications, such as luxury or functional fragrance formulations or cosmetics. Textile washing and softening treatments are a particular area in which the effectiveness of active substances, particularly fragrances or fragrance compositions, must remain effective for a certain period of time after washing, softening, and drying. Indeed, many active substances particularly suited to this type of application are known to have poor adhesion to laundry or not remain on laundry during rinsing, resulting in a fragrance effect that can only be experienced for a short period of time and is not very strong. Given the importance of this type of application in the perfume industry, research in this field has been continuously conducted, particularly with the aim of finding new and more effective solutions to the aforementioned problems.

[0003] International Publication No. 2019243501 discloses enol ethers that can efficiently release carbonyl compounds, formate compounds, and alcohol compounds. However, these compounds may be partially hydrolyzed after several days under acidic conditions.

[0004] It has now surprisingly been found that the enol ether compounds according to the invention solve this problem by reducing the hydrolysis rate while still allowing efficient release of the compounds, i.e. the carbonyl of formula (II), the formate of formula (III) and / or the alcohol of formula (IV).

[0005] Detailed Description Olfaction is a complex and dynamic process, and controlling the release profile of volatile fragrance compounds can maximize the impact of fragrance formulations and enrich the sensory experience. Pro-fragrances, such as the compounds of the present invention, provide greater control and longevity in the release profile of highly volatile perfume raw materials (PRMs), while having better stability in acidic media.

[0006] Without intending to be limited to any particular theory, the compounds of the present invention may achieve their effect on the olfactory properties of a perfume composition by tethering a PRM to a molecular anchor and requiring a specific reaction mechanism under specific environmental conditions to release the volatile PRM from this anchor. In the present invention, upon exposure of the pro-fragrance to oxygen in the ambient air, oxidation prompts the release of one, two, or up to three PRMs.

[0007] The first subject of the present invention is a method for producing a medicament for the treatment of a malaria parasite comprising: a) Formula [ka] [In the formula, R 1 is C 1~15 Alkyl group, C 3~15 Alkenyl group, C 6~10 Aryl group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group or C 3~14 heterocycloalkyl groups, each of which is a hydroxy group, C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 2~15Alkenyloxy group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group, C 3~15 Heterocycloalkyl group, carboxylic acid group, C 1~4 Carboxylic acid ester group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1~4 optionally substituted with one or more carboxylic acid ester groups; R 2 is a hydrogen atom, C 1~6 represents an alkyl group or a phenyl group; or R 1 and R 2 Together, C 5~16 Cycloalkyl groups, C 5~16 Cycloalkenyl group, C 4~14 Heterocycloalkyl group or C 4~14 heterocycloalkenyl groups, each of which is C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, carboxylic acid groups and / or C 1~4 optionally substituted with one or more carboxylic acid ester groups, wherein the heteroatom represents one or more oxygen atoms, b) Formula [ka] [In the formula, R 3 is a hydrogen atom, C 1~10 Alkyl group, C3~10 Alkenyl group, benzyl group, 2-phenylethyl group, or one, two or three C 1~4 C optionally substituted with alkyl groups 5~8 represents a cycloalkyl group; R 4 is a hydrogen atom, C 1~6 Alkyl group, phenyl group, or CH2C(O)OR 3 represents a group; where R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group], c) formula [ka] [In the formula, R 3 , R 4 and R 5 has the same meaning as defined above] 1. A method for releasing a compound selected from the group consisting of: The precursor compound is of formula (I) [ka] [In the formula, R 1 , R 2 and R 3 , R 4 and R 5 has the same meaning as defined above] in the form of any one of its stereoisomers or a mixture thereof, The release is achieved by exposing the precursor compound of formula (I) to an environment in which the compound is oxidized, i.e., ambient conditions.

[0008] According to any one of the embodiments of the present invention, at least one of the compounds of formula (II), (III) or (IV) is the active compound.

[0009] By "active compound," "active volatile compound," "active volatile carbonyl, formate and / or alcohol" or similar terms is understood a carbonyl, formate and / or alcohol compound that can provide a benefit or effect to its surrounding environment. In particular, an "active compound" is selected from the group consisting of a perfuming ingredient, a flavoring ingredient, a malodor-counteracting ingredient, an antimicrobial ingredient, and an insect repellent or attractant ingredient. Thus, for a compound to be considered an "active compound," it must possess at least one property that makes it useful as a perfuming ingredient, a malodor-counteracting ingredient, a flavoring ingredient, an antimicrobial ingredient, and / or an insect repellent or attractant.

[0010] The term "perfuming ingredient" is understood to mean a compound used as an active ingredient in a perfume formulation or composition to impart a hedonic effect. In other words, a compound considered to be a perfuming ingredient should be recognized by those skilled in the perfumery arts as not only having an odor but also being able to impart or modulate the odor of a composition in a pleasant or pleasant way. Perfuming ingredients can impart additional benefits other than odor modulation or impartation, such as persistence, blooming, malodor neutralization, antimicrobial effect, antiviral effect, microbial stability, or pest control. The term "flavoring ingredient" is understood to mean an ingredient capable of imparting a taste to the taster's palette. The term "malodor neutralizing ingredient" is understood to mean an ingredient capable of reducing the perception of malodor, i.e., an unpleasant or unpleasant odor to the human nose. The term "antimicrobial ingredient" is understood to mean an ingredient capable of killing microorganisms or reducing or preventing their growth and / or accumulation, and includes antibacterial, antibiotic, antifungal, antiviral, and antiparasitic ingredients. The term "insect attractant or repellent" is understood to mean a compound that has a positive or negative effect on insects. Examples of insect attractant or repellent ingredients are described in references such as AM El-Sayed, The Pherobase 2005, http: / / www.pherobase.net or other works of a similar nature.

[0011] According to the above and below embodiments of the present invention, the method according to the present invention is particularly useful when the active compound is a perfuming ingredient, i.e., a perfuming carbonyl compound, a formate ester, and / or an alcohol. "Perfuming carbonyl compounds, formates, and / or alcohols" refer to compounds used in the perfume industry, i.e., compounds used as active ingredients in perfume formulations or compositions to impart a hedonic effect. In other words, to be considered perfuming, such carbonyl compounds, formates, and / or alcohols must be recognized by those skilled in the art of perfumery as not only possessing an odor but also being capable of imparting or modulating the odor of a composition in a pleasant or pleasant way. Perfuming carbonyl compounds, formates, and / or alcohols may be of natural or synthetic origin. Many of these perfuming carbonyl compounds, formates and / or alcohols are in any case listed in reference works such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or other works of a similar nature and in the abundant patent literature in the perfumery field.

[0012] The term "perfuming carbonyl compounds, formates and / or alcohols" as used herein is also referred to as "perfuming compounds".

[0013] Indeed, the present invention is practiced in exactly the same way regardless of the precise nature of the active carbonyl compound, formate ester, or alcohol. Thus, although the present invention is further described herein with specific reference to "perfuming compounds," it will be understood that the following embodiments are also applicable to other active carbonyl compounds, formates, and / or alcohols (i.e., the term "perfuming" can be replaced with, for example, "flavoring," "malodor-neutralizing," "antibacterial," "antimicrobial," "insect attractant," or "insect repellent").

[0014] The term "optionally" means that a group that is subject to optional substitution may or may not be substituted with a functional group. The term "one or more" means that the group is substituted with 1 to 7, preferably 1 to 5, and more preferably 1 to 3, functional groups.

[0015] The terms "alkyl" and "alkenyl" are understood to include branched and straight-chain alkyl and alkenyl groups. The terms "alkenyl," "cycloalkenyl," and "heterocycloalkenyl" are understood to include one, two, or three olefinic double bonds, preferably one or two olefinic double bonds. The terms "cycloalkyl," "cycloalkenyl," "heterocycloalkyl," "heterocycloalkenyl," and "heterocyclic" are understood to include monocyclic or fused, spiro, and / or bridged bicyclic or tricyclic cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, and heterocyclic groups, preferably monocyclic cycloalkyl, cycloalkenyl, heterocycloalkyl, and heterocycloalkenyl groups.

[0016] The term "carbonyl" refers to R 2 represents an aldehyde or a ketone depending on the meaning of the group; i.e., the carbonyl compound of formula (II) 2 When represents a hydrogen atom, it is an aldehyde, and R 2 C 1~6 If it represents an alkyl or phenyl group, it is a ketone.

[0017] The term "aryl" is understood to include any group that contains at least one aromatic group, such as a phenyl, indenyl, indanyl, benzodioxolyl, dihydrobenzodioxinyl, tetrahydronaphthalenyl or naphthalenyl group.

[0018] For clarity, expressions such as "any one of its stereoisomers or a mixture thereof" have the usual meaning as understood by those skilled in the art, i.e., that the compound of formula (I) may be a pure enantiomer or a diastereomer. In other words, the compound of formula (I) may have multiple stereocenters, each of which may have two different spatial configurations (e.g., R or S). The compound of formula (I) may be in the form of a pure enantiomer or a mixture of enantiomers or diastereomers. The compound of formula (I) may be in the form of a racemate or a scalemic mixture. Thus, the compound of formula (I) may be a single stereoisomer or in the form of a composition of matter comprising or consisting of various stereoisomers.

[0019] According to any one of the above embodiments of the present invention, the compound of formula (I) can be in the form of its E or Z isomer or a mixture thereof, for example, the present invention includes a composition of matter consisting of one or more compounds of formula (I) having the same chemical structure but different double bond configurations. In particular, compound (I) can be in the form of a mixture of E and Z isomers, wherein the E isomer accounts for at least 50%, even at least 60%, even at least 70%, or even at least 75% of the total mixture (i.e., the mixture E / Z is composed of 75 / 25 to 100 / 0). Alternatively, compound (I) can be in the form of a mixture of E and Z isomers, wherein the Z isomer accounts for at least 50%, even at least 60%, even at least 70%, or even at least 75% of the total mixture (i.e., the mixture E / Z is composed of 25 / 75 to 0 / 100), which is particularly the case when R 2 corresponds to the case of a hydrogen atom.

[0020] According to any one of the embodiments of the present invention, R 1 C 3~15 When alkenyl is used, the double bond is 1It is understood that the carbon atom bonded to the aryl group is not adjacent to the carbon atom bonded to the aryl group. That is, the compound of formula (II) is not an enone, and the compound of formula (I) is not a dienol ether.

[0021] According to a particular embodiment of the present invention, R 2 is a hydrogen atom, C 1~3 In particular, R 2 can represent a hydrogen atom, a methyl group or an ethyl group. More particularly, R 2 can represent a hydrogen atom or a methyl group.

[0022] According to a particular embodiment of the present invention, R 1 is C 1~12 Alkyl group, C 3~12 Alkenyl group, C 6~10 Aryl group, C 3~12 Cycloalkyl groups, C 5~12 Cycloalkenyl group or C 3~12 Each of these groups can represent a hydroxy group, C 1~10 Alkyl group, C 2~10 Alkenyl group, C 1~10 Alkoxy group, C 2~10 Alkenyloxy group, C 3~10 Cycloalkyl groups, C 5~10 Cycloalkenyl group, C 3~10 Heterocycloalkyl groups, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~6 Alkyl group, C 1~6 Optionally substituted with one or more alkoxy and / or hydroxy groups. In particular, R 1 is C 1~10 Alkyl group, C 3~10 Alkenyl group, C 3~11 Cycloalkyl group or C 5~11 Each of these groups can represent a cycloalkenyl group, 1~4 Alkyl group, C 1~4 Alkoxy group, C 3~8 Cycloalkyl groups, C5~8 Optionally substituted with one or more cycloalkenyl groups, C aryl groups and / or C aryloxy groups, each of which is selected from the group consisting of hydroxy groups, C 1~4 Alkyl groups and / or C 1~4 Optionally substituted with one or more alkoxy groups. In particular, R 1 is C 1~10 Alkyl group or C 3~10 Each of these groups may represent an alkenyl group, 1~4 Optionally substituted with one or more of alkoxy groups, 4-methoxyphenyl groups and / or phenyl groups. More particularly, R 1 can represent a nonyl group, a decyl group, a dec-9-en-1-yl group, a 4-phenylbutan-2-yl group or a phenylethyl group.

[0023] According to another particular embodiment of the invention, R 1 may represent a naphthyl or phenyl group, which may be joined by one or two R 1’ optionally substituted with a group, where R 1’ may simultaneously or independently be a hydroxy group, C 1~3 Alkyl group, C 1~3 Alkoxy group, R a COO group, R a represents an OCO group, where R a is a hydrogen atom, C 1~3 Alkyl group, C 2~3 Alkenyl group or two adjacent R 1’ together to form -O-(CH2) m -O- [wherein m is 1 or 2], or C 5~6 Forms a saturated or unsaturated ring. In particular, R 1 may represent a naphthyl or phenyl group, which may be joined by one or two R 1’ optionally substituted with a group, where R 1’ may simultaneously or independently be a hydroxy group, C 1~3 Alkyl group, C 1~3 Represents an alkoxy group, or two adjacent R 1’together to form -O-(CH2) m -O- [wherein m is 1 or 2], or C 5~6 Forming a saturated or unsaturated ring. More particularly, R 1 can represent a phenyl group, a naphthyl group, a 4-methoxyphenyl group or a 3,4-dimethoxyphenyl group.

[0024] According to a particular embodiment of the present invention, R 1 and R 2 Together, C 5~16 Cycloalkyl group or C 5~16 Cycloalkenyl groups can be formed, each of which is C 1~8 Alkyl group, C 1~8 Alkoxy group, C 3~8 Cycloalkyl groups, C 5~8 Optionally substituted with one or more cycloalkenyl and / or phenyl groups. In particular, R 1 and R 2 Together, C 5~8 Cycloalkyl group or C 5~8 Cycloalkenyl groups can be formed, each of which is C 1~6 Alkyl groups and / or C 1~3 Optionally substituted with one or more alkoxy groups. More particularly, R 1 and R 2 Together, 1 to 3 C 1~6 C optionally substituted with alkyl groups 5~6 A cycloalkyl group can be formed.

[0025] According to any one of the embodiments of the present invention, R 3 is C 1~8 Alkyl group, C 3~8 Alkenyl group, benzyl group, 2-phenylethyl group, or one, two or three C 1~3 C optionally substituted with alkyl groups 5~6 In particular, R 3 is C 1~8 Alkyl group, C 3~8In particular, R may represent an alkenyl group or a 2-isopropyl-5-methylcyclohexyl group. 3 is C 1~8 Alkyl group or C 3~8 In particular, R 3 is C 1~8 Alkyl group or C 3~6 It can represent an alkenyl group. More particularly, R 3 can represent a methyl group, a hexyl group, an octyl group, a 2-phenylethyl group, a 2-butyl (ie, sec-butyl) group, a 3-octyl group, or a hex-3-en-1-yl group.

[0026] According to any one of the embodiments of the present invention, R 4 is a hydrogen atom, C 1~3 It can represent an alkyl group or a phenyl group. In particular, R 4 is a hydrogen atom or C 1~3 It may represent an alkyl group. More particularly, R 4 can represent a hydrogen atom or a methyl group.

[0027] According to any one of the embodiments of the present invention, R 5 is a hydrogen atom or R 4 is a methyl group, R 5 is a hydrogen atom or a methyl group.

[0028] According to a particular embodiment, at least one of the compounds of formula (II) and (IV) is an active compound. Furthermore, the compound of formula (II) is an active compound.

[0029] According to a particular embodiment, the carbonyl compound of formula (II) and / or the activated alcohol of formula (IV) are perfuming ingredients. It will also be clear to those skilled in the art that the compounds of formulae (II), (III) and (IV) according to the invention are essentially volatile compounds.

[0030] The carbonyl compound, formate ester and / or alcohol may advantageously be characterized by a vapor pressure of at least 1.0 Pa, as calculated using the software EPIwin v.3.10 (2000, available from the US Environmental Protection Agency). According to another embodiment, the vapor pressure of the ketone, formate ester and / or alcohol may be at least 5.0, or even at least 7.0 Pa.

[0031] According to a particular embodiment, the compound of formula (I) is non-volatile. The compound of formula (I) can be advantageously characterized by a vapor pressure of 0.01 Pa or less, as calculated using the software EPIwin v.3.10 (2000, available from the US Environmental Protection Agency). According to a preferred embodiment, the vapor pressure is 0.001 Pa or less.

[0032] According to a particular embodiment, the carbonyl compound of formula (II) is selected from the group consisting of acetophenone, p-methylacetophenone, p-methoxyacetophenone, benzophenone, 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one, 1-(naphthalen-2-yl)ethan-1-one, 1-(naphthalen-1-yl)ethan-1-one, 1-(p-tolyl)propan-1-one, 1-(1,1,2,3,3,6-hexamethyl-2,3-dihydro-1H-inden-5-yl)ethan-1-one, 1-(3,5,5,6,8 ... 1-(6-(tert-butyl)-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl)ethan-1-one, acetone, 3-hexanone, 4-nonanone, 5-undecanone, cyclohexanone, cyclopentanone, cyclooctan ... Chloheptanone, cyclooctanone, cyclodecanone, 2-butanone, 2-pentanone, 2-hexanone, 2-heptanone, 2-octanone, 2-nonanone, 2-decanone, 2-undecanone, 2-tridecanone, 2-pentadecanone, 3-heptanone, 3-octanone, 5-methyl-3-heptanone, 6-methyl-5-heptan-2-one, 2,6-dimethyl-7-octen-4-one, 2-(sec-butyl)cyclohexan-1-one, 2-(tert-butyl)cyclohexan-1-one, 4-(tert-butyl)cyclohexane -1-one, 4-(tert-pentyl)cyclohexan-1-one, 5-isopropyl-2-methylcyclohexan-1-one, 2-isopropyl-5-methylcyclohexan-1-one, 2,2,6-trimethylcyclohexan-1-one, 2,2,4-trimethylbicyclo[3.1.1]heptan-3-one, thujone, 2-ethyl-4,4-dimethylcyclohexan-1-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, plicatone, thujopsan-4-one, 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one, 4-phenyl-2-butanone, 4-(4-methoxyphenyl)-2-butanone, zingerone, 4-(1,3-benzodioxol-5-yl)-2-butanone, 2-cyclohexyl-4-methyl-2-pentanone, 1-(4-methyl-1-phenoxy)-2-propanone, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-one, 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one, (5-E / Z)-6,10-dimethylundeca-5,9-dien-2-one, Cyclopentadecanone, (Z)-cycloheptadecan-9-en-1-one, 3-methylcyclopentadecan-1-one, 3-methyl-5-cyclopentadecen-1-one, (Z)-cyclopentadec-4-en-1-one, 4,8-cyclododecadien-1-one, 7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, 7-propyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, 1-(5-propylbenzo[d][1,3]dioxol-2-yl)ethan-1-one, 4,4a,6,7,8,8a-hexamethylbenzo[d][1,3]dioxol-2-yl)ethan-1-one, Hydro-1,4-methanonaphthalen-5(1H)-one, 2-pentylcyclopentan-1-one, 2-hexylcyclopentan-1-one, 2-heptylcyclopentan-1-one, 2-(hex-5-en-1-yl)cyclopentan-1-one, 2,2,5-trimethyl-5-pentylcyclopentan-1-one, Iso-E-Super, 1-(5-isopropyl-2-methylcyclohex-2-en-1-yl)propan-1-one, 2,2,7,9-tetramethylspiro[5.5]undec-7-en-1-one, 1-(naphthalene) ... The ketone is selected from the group consisting of methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 4-(4-hydroxyphenyl)butan-2-one, and 1-(4-methoxyphenyl)propan-2-one.

[0033] In particular, the carbonyl compounds of formula (II) are acetophenone, p-methylacetophenone, p-methoxyacetophenone, 1-(naphthalen-2-yl)ethan-1-one, 2,3,3-trimethyl-2,3-dihydro-1H-inden-1-one, 2-nonanone, 2-decanone, 2-undecanone, 4-phenyl-2-butanone, 4-(4-methoxyphenyl)-2-butanone, 4-(tert-pentyl)cyclohexan-1-one, 4-(1,3-benzodioxol-5-yl)-2-butanone, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-one (dihydro-α-ionone), 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one, 2-pentylcyclopentan-1-one, 2-hexylcyclopentan-1-one, 2-hexylcyclohex ... The ketone is selected from the group consisting of cyclopentan-1-one, 2-heptylcyclopentan-1-one, 3-methylcyclopentadecan-1-one, cyclopentadecanone, 2,2,6-trimethylcyclohexanone, (4E / Z,8E / Z)-cyclododeca-4,8-dien-1-one, 2-(2-(4-methylcyclohex-3-en-1-yl)propyl)cyclopentan-1-one, 2-isopropyl-5-methylcyclohexan-1-one, 7-methyloctahydro-1,4-methanonaphthalen-6(2H)-one, 2-ethyl-4,4-dimethylcyclohexan-1-one, 2-(hex-5-en-1-yl)cyclopentan-1-one, 1-(4-methoxyphenyl)propan-2-one, and 2-(sec-butyl)cyclohexan-1-one.

[0034] According to certain embodiments, the carbonyl compound of formula (II) is benzaldehyde, 4-methylbenzaldehyde, 4-ethylbenzaldehyde, 4-isopropylbenzaldehyde, 4-(tert-butyl)benzaldehyde, 4-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, benzo[d][1,3]dioxole-5-carbaldehyde (heliotropin), vanillin, 3-ethoxy-4-hydroxybenzaldehyde, 2-hydroxy-4-methoxybenzaldehyde, 4-formyl-2-methoxyphenylacetate. ester, 4-formyl-2-methoxyphenyl isobutyrate, 3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, 2-ethylhexanal, 3,7-dimethyloctanal, 2-methyldecanal, 2-methylundecanal, 6-nonenal, 4-decenal, 5-octenal, 8-nonenal, 8-decenal, 9-decenal, 3-(3,3-dimethyl-2,3-dihydro- (1H-inden-5-yl)propanal, 9-undecenal, 10-undecenal, 3-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)propanal, 4-dodecenal, 8-isopropyl-6-methylbicyclo[2.2.2]oct-5-ene-2-carbaldehyde, 3-(4-(tert-butyl)phenyl)propanal, 3-(4-(tert-butyl)phenyl)-2-methylpropanal, 2-methyl-4-phenylbutanal, 3-methyl-5-phenylpentanal, 4-(4-hydrophenyl)- 4-methyl-5-(p-tolyl)pent-4-enal, 3,7-dimethyloct-6-enal, 2-phenylpropanal, phenylacetaldehyde, 3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropanal, 5-methoxyoctahydro-1H-4,7-methanoindene-1-carbaldehyde, 6-methoxyoctahydro-1H-4,7-methanoindene-1-carbaldehyde, 3-(3-isopropylphenyl)butanal, 3-(4-isobutyl-2-methylphenyl)propanal, 3,6-dimethylcyclohex-3-ene-1-carbaldehyde, 2-((3,7-dimethyl Oct-6-en-1-yl)oxy)acetaldehyde, 3-(4-ethylphenyl)-2,2-dimethylpropanal, 3,5,6-trimethylcyclohex-3-ene-1-carbaldehyde, 4-(4-methylpent-3-en-1-yl)cyclohex-3-ene-1-carbaldehyde, 3-phenylpropanal, 3-(4-isopropylphenyl)-2-methylpropanal, 8,8-dimethyl-1,2,3,4,6,7, 8,8a-Octahydronaphthalene-2-carbaldehyde, 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-enal, 3,5,5-trimethylhexanal, 2,6,10-trimethyl-9-undecenal, 3-(4-methoxyphenyl)-2-methylpropanal, 7-hydroxy-3,7-dimethyloctanal, 3-(4-isopropylphenyl)propanal, 2-(4-isopropylphenyl)propanal The aldehyde is selected from the group consisting of 3-(4-isopropylphenyl)acetaldehyde, 6-methoxy-2,6-dimethylheptanal, 3-(4-isopropylcyclohex-1-en-1-yl)propanal, 3-(4-isopropylcyclohexylidene)propanal, 3-(3-isopropylcyclohex-1-en-1-yl)propanal, and 3-(5-isopropylcyclohex-1-en-1-yl)propanal.

[0035] In particular, the carbonyl compounds of formula (II) are octanal, nonanal, decanal, undecanal, dodecanal, benzaldehyde, 4-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, benzo[d][1,3]dioxole-5-carbaldehyde, vanillin, 4-formyl-2-methoxylphenyl acetate, 2-methyldecanal, 2-methylundecanal, 2-phenylpropanal, 2-methyl-4-phenylbutanal, 2-(4-methyl-4-phenylbutanal, 2 ... The aldehyde is selected from the group consisting of 4-(4,4-dimethylcyclohex-1-en-1-yl)propanal, 4-(4-methylpent-3-en-1-yl)cyclohex-3-ene-1-carbaldehyde, and 3,7-dimethyloct-6-enal.

[0036] According to a particular embodiment, the formic acid ester of formula (III) is selected from the group consisting of methyl 2-(formyloxy)acetate, ethyl 2-(formyloxy)acetate, propyl 2-(formyloxy)acetate, isopropyl 2-(formyloxy)acetate, butyl 2-(formyloxy)acetate, pentyl 2-(formyloxy)acetate, hexyl 2-(formyloxy)acetate, hex-3-en-1-yl 2-(formyloxy)acetate, octyl 2-(formyloxy)acetate, octan-3-yl 2-(formyloxy)acetate, Acetate, phenethyl 2-(formyloxy)acetate, benzyl 2-(formyloxy)acetate, methyl 2-(formyloxy)propanoate, ethyl 2-(formyloxy)propanoate, propyl 2-(formyloxy)propanoate, isopropyl 2-(formyloxy)propanoate, butyl 2-(formyloxy)propanoate, sec-butyl 2-(formyloxy)propanoate, pentyl 2-(formyloxy)propanoate, hexyl 2-(formyloxy)propanoate, hex-3-en-1-yl 2-(formyloxy)propanoate, octyl 2-(formyloxy)propanoate, octan-3-yl 2-(formyloxy)propanoate, phenethyl 2-(formyloxy)propanoate, 3,7-dimethyloct-6-en-1-yl 2-(formyloxy)propanoate, 2-isopropyl-5-methylcyclohexyl 2-(formyloxy)propanoate, benzyl 2-(formyloxy)propanoate, methyl 2-(formyloxy)-2-methylpropanoate, ethyl 2-(formyloxy)-2-methylpropanoate ethylpropanoate, propyl 2-(formyloxy)-2-methylpropanoate, butyl 2-(formyloxy)-2-methylpropanoate, hexyl 2-(formyloxy)-2-methylpropanoate, hex-3-en-1-yl 2-(formyloxy)-2-methylpropanoate, methyl 2-(formyloxy)-2-phenylacetate, ethyl 2-(formyloxy)-2-phenylacetate, dimethyl 2-(formyloxy)succinate and diethyl 2-(formyloxy)succinate.

[0037] According to a particular embodiment, the alcohol of formula (IV) is methyl 2-hydroxypropanoate, ethyl 2-hydroxypropanoate, propyl 2-hydroxypropanoate, butyl 2-hydroxypropanoate, sec-butyl 2-hydroxypropanoate, isopropyl 2-hydroxypropanoate, octyl 2-hydroxypropanoate, octan-3-yl 2-hydroxypropanoate, hexyl 2-hydroxypropanoate, hex-3-en-1-yl 2-hydroxypropanoate, 3,7-dimethyloct-6-en-1-yl 2-hydroxypropanoate, phenethyl 2-hydroxypropanoate, benzyl 2-hydroxypropanoate, 2-hydroxy-2-methylpropanoate, 2-isopropyl-5-methylcyclohexyl 2-hydroxypropanoate, methyl 2-hydroxy-2-methylpropanoate, ethyl 2-hydroxy-2-methylpropanoate, propyl 2-hydroxy-2-methylpropanoate, butyl 2-hydroxy-2-methylpropanoate, hexyl 2-hydroxy-2-methylpropanoate, methyl glycolate, ethyl glycolate, butyl glycolate, hexyl glycolate, methyl 2-hydroxy-2-phenylacetate, ethyl 2-hydroxy-2-phenylacetate, dimethyl 2-hydroxysuccinate and diethyl 2-hydroxysuccinate.

[0038] According to certain embodiments, the compound of formula (I) is methyl 2-((2-methylundec-1-en-1-yl)oxy)acetate, methyl 2-((2-methylundec-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-((2-methylundec-1-en-1-yl)oxy)propanoate, methyl 2-((2-methyl-4-phenylbut-1-en-1-yl)oxy)propanoate, octyl 2-methyl-4-phenylbut-1-en-1-yl ... methyl 2-((2-methylundec-1-en-1-yl)oxy)propanoate, hex-3-en-1-yl 2-((2-methylundec-1-en-1-yl)oxy)propanoate, methyl 2-(dodec-1-en-1-yloxy)propanoate, methyl 2-((3-methyl-5-phenylpent-1-en-1-yl)oxy)propanoate, methyl 2-(styryloxy)propanoate, methyl 2 -Methyl-2-(styryloxy)propanoate, methyl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate, hexyl-2-((2-phenylprop-1-en-1-yl)oxy)propanoate, hex-3-en-1-yl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate, methyl 2-((2-methyldec-1-en-1-yl)oxy), methyl 2-( (3-(4-methoxyphenyl)-2-methylprop-1-en-1-yl)oxy)propanoate, methyl 2-((2-ethylhex-1-en-1-yl)oxy)propanoate, methyl 2-((4-(4-methoxyphenyl)-2-methylbut-1-en-1-yl)oxy)propanoate, methyl 2-((2-pentylcyclopentylindene)methoxy)propanoate, methyl 2-((2-ethyl-4,4-dimethylcyclohexylindene)methoxy)propanoate, methyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate, methyl 2-((2-(naphthalen-2-yl)prop-1-en-1-yl)oxy)propanoate, methyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-((2- methyl dec-1-en-1-yl)oxy)propanoate, methyl 2-((3-(4-methoxyphenyl)-2-methylprop-1-en-1-yl)oxy)-2-methylpropanoate, methyl 2-methyl-2-((2-phenylprop-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-((2-methyl-4-phenylbut-1-en-1-yl)oxy)propanoate, Methyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)-2-methylpropanoate, methyl 2-methyl-2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-((2-pentylcyclopentylindene)methoxy)propanoate, methyl 2-(undeca-1,10-dien-1-yloxy)propanoate, methyl 2-(tridec-1-en-1-yloxy)propanoate, methyl 2-(dodeca-1,11-dien-1-yloxy)propanoate, methyl 2-((3-methyldodec-1-en-1-yl)oxy)propanoate, methyl 2-((4-phenylpent-1-en-1-yl)oxy)propanoate, methyl 2-((4-methoxystyryl)oxy)propanoate, methyl 2-((3,4-Dimethoxystyryl)oxy)propanoate, methyl 2-methyl-2-(tridec-1-en-1-yloxy)propanoate, methyl 2-methyl-2-((3-methyldodec-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-(tridec-1-en-1-yloxy)propanoate, phenethyl 2-(styryloxy)propanoate, (Z)-Hexa-3 -en-1-yl 2-(styryloxy)propanoate, octan-3-yl 2-(styryloxy)propanoate, (Z)-hex-3-en-1-yl 2-((4-methoxystyryl)oxy)propanoate, phenethyl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate, octan-3-yl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate propanoate, phenethyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate, sec-butyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate, (Z)-hex-3-en-1-yl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate, phenethyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate, sec-butyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate, phenethyl 2-((2-(naphthalen-2-yl)vinyl)oxy)propanoate, 2-isopropyl-5-methylcyclohexyl 2-((2-methylundec-1-en-1-yl)oxy)propanoate, 3,7-dimethyloct-6-en-1-yl 2-((2-methylundec-1-en-1-yl)oxy)propanoate, ethyl 2-((2-pentylcyclopentylindene)methoxy)propanoate, (Z)-hex-3-en-1-yl 2-((2-pentylcyclopentylindene)methoxy)propanoate, methyl 2-((2-heptylcyclopentylindene)methoxy)propanoate, methyl 2-(non-1-en-1-yloxy)propanoate, methyl 2-(undec-1-en-1-yl)oxy -yloxy)propanoate, (Z)-hex-3-en-1-yl 2-(dodec-1-en-1-yloxy)propanoate, methyl 2-(dodec-1-en-1-yloxy)-2-methylpropanoate, methyl 2-methyl-2-(undec-1-en-1-yloxy)propanoate, methyl 2-methyl-2-((3-phenylprop-1-en-1-yl)oxy)propanoate, methyl 2-methyl-2-((2-(naphthalen-2-yl)prop-1-en-1-yl)oxy)propanoate methyl 2-((4-hydroxy-3-methoxystyryl)oxy)-2-methylpropanoate, hexyl 2-((4-hydroxy-3-methoxystyryl)oxy)-2-methylpropanoate, octyl 2-((4-hydroxy-3-methoxystyryl)oxy)-2-methylpropanoate, methyl 2-((3,4-dimethoxystyryl)oxy)-2-methylpropanoate, methyl 2-((4-acetoxy-3-methoxystyryl)oxy)-2-methylpropanoate, methyl 2-methyl-2- ((3-methylundec-1-en-1-yl)oxy)propanoate, (Z)-hex-3-en-1-yl 2-((3-methyldodec-1-en-1-yl)oxy)propanoate, methyl 2-(dodeca-1,10-dien-1-yloxy)propanoate, methyl 2-(dodeca-1,10-dien-1-yloxy)-2-methylpropanoate, methyl 2-methyl-2-((3-methyl-5-phenylpent-1-en-1-yl)oxy)propanoate, methyl 2-((2-(benzo[d][1,3]dioxol-5-yl)vinyl)oxy)-2-methylpropanoate and methyl 2-((4-methoxystyryl)oxy)-2-methylpropanoate.

[0039] According to any one of the above embodiments, the carbonyl compound of formula (II), the formate of formula (III), and the alcohol of formula (IV) are released from the precursor compound of formula (I) by oxidation of the precursor compound of formula (I) under ambient conditions. Furthermore, the precursor compound of formula (I) is oxidized under ambient conditions in the absence of a catalyst. For clarity, expressions such as "ambient conditions" have the usual meaning understood by those skilled in the art, i.e., the oxidation occurs at room temperature, in air, and under atmospheric pressure. In other words, the environment in which the compound is oxidized is air. It is understood here that the compound of formula (I) is oxidized in ambient air. In particular, it is understood that the compound of formula (I) does not require a pure oxygen environment, heat, or a catalyst for oxidation.

[0040] Without intending to be limited to any particular theory, the rate at which the precursor compound of formula (I) is oxidized may be greater than, equal to, or less than the evaporation rate of the respective carbonyl compound of formula (II), formate ester of formula (III), or alcohol of formula (IV).

[0041] In some embodiments, the rate at which the precursor compound of formula (I) is oxidized, and thereby the individual carbonyl compound of formula (II), formate ester of formula (III), or alcohol of formula (IV) is released, enhances or prolongs the diffusion effect and / or perception of the characteristic fragrance of the at least one carbonyl compound of formula (II), at least one formate ester of formula (III), and / or at least one alcohol of formula (IV) as defined above.

[0042] In one embodiment, 100% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 90% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 80% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 70% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 60% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 50% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 40% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 30% of the compounds of Formula (I) are oxidized in ambient air in a period ranging from 24 to 48 hours. Alternatively, 20% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 10% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 9% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 8% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 7% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 6% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 5% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 4% of the compounds of formula (I) are oxidized in ambient air over a period ranging from 24 to 48 hours. Alternatively, 3% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours, alternatively, 2% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours, or alternatively, 1% of the compound of formula (I) is oxidized in ambient air for a period ranging from 24 to 48 hours.

[0043] The present invention also relates to microcapsules containing at least one compound of formula (I). In one embodiment, at least one compound of formula (I) is encapsulated in a core-shell microcapsule, in which the at least one compound of formula (I) is contained in a core surrounded by a shell. In one embodiment, the shell of the microcapsule protects the compound of formula (I) from the environment. The shell is composed of a material capable of releasing at least one compound of formula (I) and / or compounds of formulas (II), (III), and / or (IV). In one embodiment, the shell is composed of a material capable of releasing the compound of formula (I) and / or compounds of formulas (II), (III), and / or (IV) upon rupture of the shell and / or by diffusion through the shell. Those skilled in the art are familiar with methods for producing such microcapsules. Therefore, microcapsules containing at least one compound of formula (I) are one subject of the present invention.

[0044] In a preferred embodiment, encapsulation of a compound of formula (I) can provide an environment within the capsule that can oxidize all or a portion of the compound of formula (I), thereby releasing the respective ketone of formula (II), formate of formula (III), or alcohol of formula (IV) within the capsule. In a preferred embodiment, the shell of the microcapsule can act as a permeability barrier, thereby preventing leakage of the respective carbonyl compound of formula (II), formate of formula (III), or alcohol of formula (IV) from the capsule.

[0045] According to certain embodiments, the shell of the microcapsules comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e., polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof. The shell may also be of organic-inorganic type, such as a hybrid shell composed of at least two types of inorganic particles crosslinked together, or even a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0046] According to certain embodiments, core-shell microcapsules may also be derived by using different or two or more encapsulation methods.

[0047] In preferred embodiments, the shells of the microcapsules may each independently be selected from the group of aminoplast, polyamide, polyester, polyurea, and polyurethane shells and mixtures thereof.

[0048] In certain embodiments, the shell of the microcapsules comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde, or crosslinked melamine formaldehyde or melamine glioxal.

[0049] In certain embodiments, the microcapsule shell is a polyurea system, which is composed of, for example, but not limited to, an isocyanate-based monomer and an amine-containing crosslinker, such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules include a polyurea wall that is the reaction product of the polymerization of at least one polyisocyanate containing at least two isocyanate functional groups with at least one reactant selected from the group consisting of an amine (e.g., a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of the amine can be omitted.

[0050] In certain embodiments, the colloidal stabilizer comprises an aqueous solution of 0.1-0.4% polyvinyl alcohol, 0.6-1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages are by weight relative to the total weight of the colloidal stabilizer). In certain embodiments, the emulsifier is an anionic or amphiphilic biopolymer, which may be selected from the group consisting of, for example, gum arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0051] In certain embodiments, the shell of the microcapsules is polyurethane-based, which is comprised of, for example, but not limited to, polyisocyanates and polyols, polyamides, polyesters, and the like.

[0052] In certain embodiments, the microcapsules have a polymeric shell resulting from complex coacervation, where the shell is optionally crosslinked.

[0053] In certain embodiments of core-shell microcapsules, the core-shell microcapsules comprise an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), and a composite shell comprising a first material and a second material, wherein the first material is a coacervate and the second material is a polymeric material, wherein the first material and the second material are different.

[0054] In certain embodiments, the weight ratio of the first material to the second material is comprised between 50:50 and 99.9:0.1.

[0055] In certain embodiments, the coacervate comprises a first polyelectrolyte, preferably selected from proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate, cellulose derivatives guar gum, pectinate, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or even a vegetable gum such as acacia gum (gum arabic), most preferably gum arabic.

[0056] The first material of the coacervate can be hardened chemically using a suitable cross-linking agent such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin, or enzymatically using an enzyme such as transglutaminase.

[0057] The second polymeric material may be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount of less than 3 wt. %, preferably less than 1 wt. %, based on the total weight of the microcapsule slurry.

[0058] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In certain embodiments, the microcapsule wall material can comprise any suitable resin, including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, and the like, among others. Suitable resins include the reaction products of aldehydes and amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include methylolmelamine, methylated methylolmelamine, iminomelamine, and mixtures thereof. Suitable ureas include dimethylolurea, methylated dimethylolurea, urea resorcinol, and mixtures thereof. Suitable materials for production can be obtained from one or more of the following companies: Solutia Inc. (St. Louis, MO, USA), Cytec Industries (West Paterson, NJ, USA), and Sigma-Aldrich (St. Louis, MO, USA).

[0059] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules comprise: an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - optionally an inner shell composed of a polymer of a multifunctional monomer; a biopolymer shell comprising proteins, wherein at least one protein is cross-linked; and Includes:

[0060] According to a particular embodiment, the protein is selected in the group consisting of milk proteins, caseinates such as sodium or calcium caseinate, casein, whey protein, protein hydrolysates, gelatin, gluten, pea protein, soy protein, silk protein and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate. According to a particular embodiment, the protein comprises sodium caseinate and a globular protein, preferably selected in the group consisting of whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable protein and mixtures thereof.

[0061] The protein is preferably a mixture of sodium caseinate and whey protein.

[0062] According to certain embodiments, the biopolymer shell comprises cross-linked proteins selected in the group consisting of sodium caseinate and / or whey protein.

[0063] According to certain embodiments, the microcapsule slurry comprises: an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - a polymer of a polyfunctional monomer; preferably an inner shell composed of a polyisocyanate having at least two isocyanate functional groups; - a biopolymer shell comprising a protein, wherein at least one protein is cross-linked; wherein the protein preferably comprises a mixture comprising sodium caseinate and a globular protein, preferably whey protein; - optionally at least one outer inorganic layer; The microcapsule comprises at least one microcapsule comprising:

[0064] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0065] The weight ratio of sodium caseinate to whey protein is preferably 0.01-100, more preferably 0.1-10, and even more preferably 0.2-5.

[0066] In certain embodiments, the microcapsules are 1) mixing perfume oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) dispersing or dissolving an aminoplast resin and optionally a stabilizer in water to form an aqueous phase; 3) mixing the oil phase and the water phase to produce an oil-in-water dispersion having an average droplet size of 1 to 100 microns; 4) A curing step is carried out to form the walls of the microcapsules; 5) optionally drying the final dispersion to obtain dry core-shell microcapsules; and a method for preparing a core-shell microcapsule comprising:

[0067] In certain embodiments, the core-shell microcapsules are formaldehyde-free. A typical method for preparing a formaldehyde-free aminoplast-containing microcapsule slurry includes: 1) The following: a. a polyamine component in the form of melamine or in the form of a mixture of melamine with at least one C1-C4 compound containing two NH2 functional groups; b. Glyoxal and C 4~6 an aldehyde component in the form of a mixture of 2,2-dialkoxyethanal and, optionally, glyoxalate, said mixture comprising glyoxal / C 4~6 The molar ratio of 2,2-dialkoxyethanal is 1 / 1 to 10 / 1; and c. Protonic acid catalyst; preparing an oligomeric composition comprising or obtainable by reacting together the reaction product of 2) preparing an oil-in-water dispersion having a droplet size of 1 to 600 microns, the oil-in-water dispersion comprising: a. Oil; b.Aqueous medium; c. at least the oligomeric composition obtained in step 1; d. Below: i.C4~C 12 Aromatic or aliphatic di- or tri-isocyanates and their biuret, triuret, trimer, trimethylolpropane adducts and mixtures thereof; and / or ii.Formula: Q-(oxiran-2-ylmethyl) n di- or tri-oxirane compounds of the formula: [wherein n is 2 or 3, and Q is a C2-C6 group optionally containing 2 to 6 nitrogen and / or oxygen atoms]; at least one cross-linking agent selected from: e. Optionally, a C1-C4 compound containing two NH2 functional groups; and 3) heating the dispersion; 4) cooling the dispersion; Includes.

[0068] The above method is described in more detail in WO 2013 / 068255.

[0069] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules comprise: an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - below: Acyl chloride a first amino compound, and Secondary amino compounds a polyamide shell comprising or obtainable from and a polyamide-containing core-shell type polyamide microcapsule comprising:

[0070] According to certain embodiments, the polyamide-containing core-shell microcapsules comprise: an oily core comprising a hydrophobic active substance, preferably comprising at least one compound of formula (I); below: acyl chloride, preferably in an amount of 5 to 98%, preferably 20 to 98%, more preferably 30 to 85% w / w, a first amino compound, preferably in an amount comprised between 1 and 50% w / w, preferably between 7 and 40% w / w, a second amino compound, preferably in an amount comprised between 1 and 50% w / w, preferably between 2 and 25% w / w, a stabilizer, preferably a biopolymer, preferably in an amount comprised between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%; a polyamide shell comprising or obtainable from Includes:

[0071] According to certain embodiments, the polyamide-containing core-shell microcapsules comprise: an oily core comprising a hydrophobic active substance, preferably at least one compound of formula (I), - below: Acyl chloride a first amino compound, which is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof; a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, and a biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and / or mixtures thereof; a polyamide shell comprising or obtainable from Includes:

[0072] The first amino compound may be different from the second amino compound.

[0073] Typically, the method for producing polyamide-based microcapsules includes the steps of: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry; Including, adding a stabilizer to the oil phase and / or the water phase; At least one second amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0074] In certain embodiments, the shell of the microcapsule is polyurea- or polyurethane-based. Examples of polyurea-based and methods for producing polyurea-based microcapsule slurries are described, for example, in WO 2007 / 004166, EP 2300146, and EP 2579976. Typically, the method for producing polyurea- or polyurethane-based microcapsule slurries includes: a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding an oil phase to an aqueous phase to form an oil-in-water dispersion, the average droplet size being comprised between 1 and 500 μm, preferably between 5 and 50 μm; d) applying conditions sufficient to induce interfacial polymerization to form microcapsules in the form of a slurry; Includes.

[0075] In certain embodiments, the microcapsules may be in the form of a powder, which can be obtained in particular by subjecting the microcapsule slurry to drying, such as spray drying, to provide the microcapsules as such, i.e., in powder form. It is understood that any standard method known to those skilled in the art for carrying out such drying can also be applied. In particular, the slurry can be spray-dried, preferably in the presence of a polymeric carrier such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, gum arabic, vegetable gum, pectin, xanthan, alginate, carrageenan, or cellulose derivative, to provide the microcapsules in powder form.

[0076] However, as disclosed in WO 2017 / 134179, other drying methods may also be mentioned, such as extrusion, plating, spray granulation, fluidized bed, or even drying at room temperature using materials (carriers, desiccants) that meet certain criteria.

[0077] In another aspect, the present invention relates to a method for imparting, enhancing, improving or modulating the odor characteristics of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition, the air or the article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined above. As used herein, the term "surface" may refer to the skin, hair, textile or hard surface of a user to which a perfuming composition consisting of or comprising at least one compound of formula (I) is applied.

[0078] In another aspect, the present invention relates to a method for enhancing or prolonging the diffusion effect of the characteristic fragrance of at least one carbonyl compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV) as defined above, on a surface or into the air surrounding a perfuming composition, by treating the surface or the air with at least one compound (I) as defined above, or a composition or article comprising at least one compound (I), under conditions allowing the release over time of at least one carbonyl compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV).

[0079] Furthermore, the present invention provides i) at least one compound of formula (I) as defined above; and ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; iii) optionally at least one flavor adjuvant; The present invention relates to a perfume composition comprising:

[0080] By "perfume carrier" is meant herein a material that is substantially neutral from the perfumery point of view, i.e. a material that does not significantly alter the organoleptic properties of the perfuming ingredients. Said carrier may be liquid or solid.

[0081] The liquid carrier may include, but is not limited to, emulsifying systems, i.e., solvents and surfactant systems, or solvents commonly used in perfumery.It is not possible to provide a complete detailed description of the nature and types of solvents commonly used in perfumery.However, the most commonly used, but not limited to, solvents such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate, or mixtures thereof. For compositions comprising both a fragrance carrier and a fragrance base, suitable fragrance carriers other than those specified above may be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (supplier: Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (supplier: Dow Chemical Company), or hydrogenated castor oil such as those known under the trademark Cremophor® RH 40 (supplier: BASF).

[0082] A solid carrier refers to a material to which a perfume composition or some components of the perfume composition can be chemically or physically bound. Generally, such solid carriers are used to stabilize the composition or to control the evaporation rate of the composition or some components. The use of solid carriers is currently useful in the art, and those skilled in the art know how to achieve the desired effect. However, non-limiting examples of solid carriers include absorbent rubber or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood materials, organic or inorganic gels, clays, gypsum talc, or zeolites.

[0083] Other non-limiting examples of solid carriers can include encapsulating materials.Examples of such materials can include wall-forming materials and plasticizing materials, such as monosaccharides, disaccharides or trisaccharides, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, protein or pectin, or even the materials listed in references such as H. Scherz, Hydrokolloides: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996.Encapsulation is a process well known to those skilled in the art, and can be carried out using techniques such as spray drying, coagulation or even extrusion, and can also consist of coating encapsulation, including coacervation and complex coacervation techniques.

[0084] Non-limiting examples of solid carriers include core-shell capsules with aminoplast, polyamide, polyester, polyurea or polyurethane type resins or mixtures thereof (all of which are well known to those skilled in the art) using techniques such as phase separation processes induced by polymerization, interfacial polymerization, coacervation or all of which are described in the prior art, optionally in the presence of polymeric stabilizers or cationic copolymers.

[0085] The resins can be prepared by polycondensation of aldehydes (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid, or glycolaldehyde, and mixtures thereof) with amines, such as urea, benzoguanamine, glycoluril, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and mixtures thereof. Alternatively, preformed resin alkylolated polyamines, such as those commercially available under the trademarks Urac® (supplied by Cytec Technology Corp), Cymel® (supplied by Cytec Technology Corp), Urecoll®, or Luracoll® (supplied by BASF), may be used.

[0086] Other resins are produced by polycondensation of polyols, such as glycerol, with polyisocyanates, such as the trimer of hexamethylene diisocyanate, isophorone diisocyanate or xylene diisocyanate, or the biuret of hexamethylene diisocyanate, or the trimethylolpropane adduct of the trimer of xylene diisocyanate (known under the trademark Takenate®, supplier: Mitsui Chemicals, Inc.), among which the trimethylolpropane adduct of the trimer of xylene diisocyanate and the biuret of hexamethylene diisocyanate are mentioned.

[0087] Representative examples of important literature related to the encapsulation of perfumes by polycondensation of amino resins, i.e., melamine-based resins, with aldehydes include, for example, the articles published by K. Dietrich et al. in Acta Polymerica, vol. 40, pp. 243, 325, and 683, 1989, and vol. 41, pp. 91, 1990. These articles already describe the various parameters affecting the production of such core-shell microcapsules by prior art methods, and these parameters are further detailed and exemplified in the patent literature. U.S. Pat. No. 4,396,670 to Wiggins Teape Group Limited is a relevant pioneering example of such literature. Since then, many other authors have written extensively in this field, and it would be impossible to cover all published developments here, but a general knowledge of encapsulation technology is of great importance. Representative examples of recent related literature disclosing the appropriate use of such microcapsules include, for example, the article by H.Y. Lee et al. in Journal of Microencapsulation, 2002, vol. 19, pp. 559-569, WO 01 / 41915, or even the article by S.Bone et al. in Chimia, 2011, vol. 65, pp. 177-181.

[0088] The term "perfume base" means a composition comprising at least one perfuming co-ingredient.

[0089] Perfuming co-ingredients are not compounds according to the present invention. Furthermore, the term "perfuming co-ingredient" refers to a compound used in a perfuming formulation or composition to impart a hedonic effect. In other words, to be considered perfuming, such a co-ingredient must be recognized by those skilled in the art as not only having an odor but also being able to impart or modulate the odor of the composition in a pleasant or pleasant way.

[0090] A more detailed description of the nature and type of perfuming co-ingredients present in the base is not warranted here, but in any case they cannot be described in exhaustive detail and those skilled in the art can select them based on their general knowledge and depending on the application and the desired organoleptic effect. Generally, these perfuming co-ingredients belong to different chemical classes such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and said perfuming co-ingredients may be of natural or synthetic origin.

[0091] In particular, perfuming co-ingredients commonly used in perfume formulations, e.g. - aldehyde-forming ingredients: decanal, dodecanal, 2-methylundecanal, 10-undecenal, octanal, nonanal and / or nonenal; - Aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene; - Balsamic ingredients: coumarin, ethyl vanillin and / or vanillin; - Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; - Floral ingredients: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-t-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone, methyl-2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanethanol, 2,6,6-trimethyl-3- Cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis-dihydrodiphenyl ether Methyl jasmonate, 3-methyl-5-phenyl-1-pentanol, vergyl proprionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; - Fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, 3-methyl-5-cyclo pentadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,7,8,8-hexamethylcyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl]ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopentene- 1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; Other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal Examples include:

[0092] The perfume base according to the invention is not limited to the above-mentioned perfuming co-ingredients, many of which are in any case listed in reference works such as the book "Perfume and Flavor Chemicals" by S. Arctander, 1969, Montclair, New Jersey, USA, or its more recent versions, or other works of a similar nature, and in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may be compounds known to release in a controlled manner various types of perfuming compounds, also known as pro-perfumes or pro-fragrances.Non-limiting examples of suitable pro-perfumes or pro-fragrances include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one, 2-phenanthroline ... Nylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy- 4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenethoxyprop-1 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene or mixtures thereof.

[0093] The term "perfume adjuvant" refers to ingredients that may impart further additional benefits such as color, specific light resistance, chemical stability, etc. The nature and type of adjuvants commonly used in perfumed bases cannot be described in exhaustive detail, but it must be mentioned that such ingredients are well known to those skilled in the art. However, specific, non-limiting examples include viscosity agents (e.g., surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light and / or buffers or chelating agents, e.g., BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0094] It is understood that a person skilled in the art is entirely capable of designing the optimum formulation for obtaining the desired effect by mixing the above-mentioned components of the perfuming composition not only by applying standard knowledge in the art but also by trial and error methods.

[0095] The composition of the present invention, which consists of at least one compound of formula (I) of the present invention and at least one perfume carrier, represents a particular embodiment of the present invention, and also represents a perfume composition comprising at least one compound of formula (I) of the present invention, at least one perfume carrier, at least one perfume base, and optionally at least one perfume adjuvant.

[0096] It is useful to mention here that the possibility of having more than one compound of formula (I) of the invention or other precursors of the same type in the above-mentioned compositions is important, since it allows the perfumer to prepare accords and fragrances with the odor tones of the various compounds of the invention, thus generating novel building blocks for creative purposes.

[0097] For the sake of clarity, it is also understood that mixtures obtained directly from chemical synthesis, which may contain the compounds of the invention as starting materials, intermediates or final products, such as reaction media without appropriate purification, cannot be considered perfuming compositions according to the invention, unless said mixture provides the compounds of the invention in a form suitable for perfumery.Unless otherwise stated, unpurified reaction mixtures are generally excluded from the present invention.

[0098] Furthermore, the compounds of formula (I) of the present invention can also be advantageously used in the field of modern perfumery, i.e. in all fields of fine perfumery or functional perfumery, to provide or modulate in a desirable way the odor of consumer products to which the compounds of formula (I) are added. The present invention therefore also relates to perfumed consumer products comprising at least one compound of formula (I) as defined above or a perfumed composition as defined above.

[0099] For clarity, it should be mentioned that the term "perfumed consumer product" means a consumer product that is expected to provide at least a pleasant perfume effect to the surface to which the consumer product is applied (e.g., skin, hair, textile, or hard surface). In other words, a perfumed consumer product according to the present invention is a perfumed consumer product comprising a functional formulation, optionally an additional benefit agent depending on the desired consumer product, such as a conditioner, detergent, or air freshener, and an olfactorily effective amount of at least one compound of the present invention. For clarity, the perfumed consumer product is a non-edible product.

[0100] The nature and type of ingredients of the scented consumer product are not warranted to be described in more detail here, but in any case they cannot be described in exhaustive detail and the skilled person can select them on the basis of his general knowledge and depending on the nature of the product and the desired effect.

[0101] In one embodiment, the scented consumer product is a perfume, a fabric care product, a body care product, a cosmetic, a skin care product, an air care product, or a home care product.

[0102] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, splash perfumes or eau de parfums, colognes, shave or aftershave lotions; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid fragrances, fabric refreshers, ironing water, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g. shampoos, coloring formulations or hairsprays, color care products, hair styling products, dental care products), disinfectants, intimate care products; cosmetics (e.g. skin creams or lotions, vanishing creams or deodorants or antiperspirants (e.g. sprays or roll-ons), depilatories, tanning products). or tanning or after-sun products, nail products, skin cleansers, cosmetics); or skin care products (such as soaps, shower mousses, shower oils or gels or bath mousses, bath oils or gels, or hygiene or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powdered air fresheners that can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or in public spaces (hall, hotel, mall, etc.); or home care products, such as mould removers, furniture care products, wipes, dishwashing detergents or hard surface (e.g. floor, bathroom, hygiene or window) cleaners; leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0103] Typical examples of fabric detergent or softener compositions that can incorporate the compounds of the present invention are described in WO 97 / 34986 or U.S. Patent Nos. 4,137,180 and 5,236,615 or EP 799885. Other typical detergent and softening compositions that can be used are described in Ullmann's Encyclopedia of Industrial Chemistry, Vol. 20, Wiley-VCH, Weinheim, pp. 355-540 (2012); Flick, Advanced Cleaning Product Formulations, Noye Publication, Park Ridge, New Jersey (1989); Showell, Surfactant Science Series, Vol. 71: Powdered Detergents, Marcel Dekker, New York (1988); Proceedings of the World Conference on Detergents (4th, 1998, Montreux, Switzerland), AOCS print and other publications.

[0104] The proportions in which the compounds according to the invention can be incorporated into the various articles or compositions mentioned above vary within wide ranges of values, depending on the nature of the article or composition to be perfumed and the desired olfactory effect, and, in the case of mixing the compounds according to the invention with perfuming co-ingredients, solvents or additives commonly used in the art, also on the nature of the co-ingredients in a given composition.

[0105] For example, typical concentrations of the compounds of the invention are on the order of 0.001 to 10% or more by weight based on the weight of the composition incorporating the compounds of the invention, and in the case of flavored consumable products, typical concentrations of the compounds of the invention are on the order of 0.0001 to 5% or more by weight based on the weight of the consumable product incorporating the compounds of the invention.

[0106] Furthermore, the present invention relates to compounds of formula (I). Another subject of the invention is therefore compounds of formula (I) [ka] [In the formula, R 1 is C 2~15 Alkyl group, C 3~15 Alkenyl group, C 6~10 Aryl group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group or C 3~14 heterocycloalkyl groups, each of which is a hydroxy group, C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 2~15 Alkenyloxy group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group, C 3~15 Heterocycloalkyl group, carboxylic acid group, C 1~4 Carboxylic acid ester group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1~4 optionally substituted with one or more carboxylic acid ester groups; R 2 is a hydrogen atom, C 1~3 represents an alkyl group or a phenyl group; or R 1 and R 2 Together, C 5~16 Cycloalkyl groups, C 5~16 Cycloalkenyl group, C 4~14 Heterocycloalkyl group or C 4~14 heterocycloalkenyl groups, each of which is C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 3~15 Cycloalkyl groups, C5~15 Cycloalkenyl group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, carboxylic acid groups and / or C 1~4 optionally substituted with one or more carboxylic acid ester groups, wherein the heteroatom represents one or more oxygen atoms; R 3 is a hydrogen atom, C 1~10 Alkyl group, C 3~10 alkenyl group, benzyl group, 2-phenylethyl group, or 1, 2 or 3 C 1~4 C optionally substituted with alkyl groups 5~8 represents a cycloalkyl group; R 4 is a hydrogen atom, a methyl group, a phenyl group, or CH2C(O)OR 3 represents a group; where R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group, with the proviso that R 2 , R 4 and R 5 is a hydrogen atom, R 1 is not an unsubstituted phenyl group] in the form of any one of its stereoisomers or mixtures thereof, with the proviso that methyl 2-((2,2-diphenylvinyl)oxy)acetate and ethyl 2-((3-phenylprop-1-en-1-yl)oxy)acetate are excluded.

[0107] In a further aspect, the present invention provides a method for treating a cancer cell comprising: a) Formula [ka] [In the formula, R 1 is C 1~15 Alkyl group, C 3~15 Alkenyl group, C6~10 Aryl group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group or C 3~14 heterocycloalkyl groups, each of which is a hydroxy group, C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 2~15 Alkenyloxy group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group, C 3~15 Heterocycloalkyl group, carboxylic acid group, C 1~4 Carboxylic acid ester group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C 1~4 optionally substituted with one or more carboxylic acid ester groups; R 2 is a hydrogen atom, C 1~6 represents an alkyl group or a phenyl group; or R 1 and R 2 Together, C 5~16 Cycloalkyl groups, C 5~16 Cycloalkenyl group, C 4~14 Heterocycloalkyl group or C 4~14 heterocycloalkenyl groups, each of which is C 1~15 Alkyl group, C 2~15 Alkenyl group, C 1~15 Alkoxy group, C 3~15 Cycloalkyl groups, C 5~15 Cycloalkenyl group, C 6~10 Aryl groups and / or C 6~10 aryloxy groups, each of which is optionally substituted by one or more of 1~8 Alkyl group, C 1~8 Alkoxy groups, carboxylic acid groups and / or C 1~4optionally substituted with one or more carboxylic acid ester groups, wherein the heteroatom represents one or more oxygen atoms, b) Formula [ka] [In the formula, R 3 is a hydrogen atom, C 1~10 Alkyl group, C 3~10 Alkenyl group, benzyl group, 2-phenylethyl group, or one, two or three C 1~4 C optionally substituted with alkyl groups 5~8 represents a cycloalkyl group; R 4 is a hydrogen atom, C 1~6 Alkyl group, phenyl group, or CH2C(O)OR 3 represents a group; where R 3 has the same meaning as defined above; R 5 represents a hydrogen atom or a methyl group], c) formula [ka] [In the formula, R 3 , R 4 and R 5 has the same meaning as defined above] Use of a precursor compound for releasing a compound selected from the group consisting of: At least one of the compounds of formula (II), (III) or (IV) is an active compound; The precursor compound is of formula (I) [ka] [In the formula, R 1 , R 2 and R 3 , R 4 and R 5 has the same meaning as defined above] in the form of any one of its stereoisomers or a mixture thereof, It also relates to a use wherein the release is effected by exposing the precursor compound of formula (I) to an environment in which the compound is oxidized, ie ambient conditions.

[0108] In a further aspect, the present invention relates to the use of at least one compound of formula (I) as defined above for imparting, enhancing, improving or modulating the odor characteristics of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, which method comprises adding to the composition or article, or contacting or treating the surface with an effective amount of at least one compound of formula (I) as defined above. As used herein, the term "surface" may refer to the skin, hair, textile or hard surface of a user to which a perfuming composition consisting of or comprising at least one compound of formula (I) is applied.

[0109] In a further aspect, the present invention relates to the use of at least one compound of formula (I) as defined above to enhance or prolong the diffusion effect and / or perception of the characteristic fragrance of at least one carbonyl compound of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV) as defined above on a surface, wherein the surface is treated with at least one compound of formula (I) as defined above or with a composition or article comprising at least one compound of formula (I) under conditions allowing the release over time of at least one carbonyl compound of formula (II), at least one formate ester of formula (III) and / or at least one active alcohol of formula (IV).

[0110] Compounds of formula (I) may be prepared by standard methods known in the art, as described below.

[0111] Example The invention will now be described in further detail by the following examples, in which abbreviations have their usual meaning in the art and temperatures are given in degrees Celsius (°C). NMR spectra were obtained using a 400 MHz ( 1 H) and 100MHz ( 13 Bruker Avance II Ultrashield 400 plus, 500MHz (C) 1 H) and 125MHz ( 13 Bruker Avance III 500 or 600MHz ( 1 H) and 150MHz ( 13 The spectra were acquired using a Bruker Avance III 600 cryoprobe operating at 1000 Hz (C). The spectra were internally referenced to tetramethylsilane at 0.0 ppm. 1 H NMR signal shifts are expressed in δ ppm and coupling constants (J) are expressed in Hz according to the following multiplets: s singlet; d doublet; t triplet; q quartet; m multiplet; b broad (indicating unspecified bonds) and were interpreted using Bruker Topspin software. 13 C NMR data are expressed as chemical shifts δ ppm and hybridizations from DEPT 90 and DEPT 135 experiments, denoting: C quaternary; CH methine; CH methylene; CH methyl.

[0112] Example 1 Preparation of a compound according to formula (I) releasing a carbonyl compound of formula (II) Compound 1. Methyl 2-((2-methylundec-1-en-1-yl)oxy)acetate: The dimethyl acetal of 2-methylundecanal (10.0 g, 43.4 mmol), methyl glycolate (7.82 g, 87 mmol), and KHSO4 (0.06 g, 0.43 mmol) were added to a 25 ml round-bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated at 150 °C (oil bath) for 40 min while free methanol distilled from the reaction vessel. Additional methyl glycolate (3.87 g, 43 mmol) was added, and the mixture was heated at 190 °C (oil bath) for 1 h. The mixture was placed under vacuum (5 Torr), and heating was continued at 190 °C (oil bath) for 2.5 h while excess methyl glycolate distilled from the reaction flask. The title compound (5.4 g, 48% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 110 °C, 4 Pa) as a colorless oil (E / Z = 58:42).

[0113] [ka]

[0114] Compound 2. Methyl (S)-2-((2-methylundec-1-en-1-yl)oxy)propanoate: The dimethyl acetal of 2-methylundecanal (8 g, 34.7 mmol), (S)-methyl lactate (7.29 g, 70 mmol), and KHSO (0.048 g, 0.35 mmol) were added to a 25 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 150 °C (oil bath) for 1 h while free methanol distilled from the reaction vessel. After removing the Vigreux column, the mixture was heated at 190 °C for 2 h while excess methyl lactate distilled from the reaction flask. The title compound (6.4 g, 68% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 105 °C, 3 Pa) as a colorless oil (E / Z = 57:43).

[0115] [ka]

[0116] Compound 3. Methyl 2-methyl-2-((2-methylundec-1-en-1-yl)oxy)propanoate: Dimethyl acetal of 2-methylundecanal (9.2 g, 39.9 mmol), methyl 2-hydroxyisobutyrate (19.5 g, 165 mmol), and KHSO (0.058 g, 0.42 mmol) were added to a 25 ml round-bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated at 190 °C (oil bath) for 2 h while methanol and excess methyl 2-hydroxyisobutyrate were distilled from the reaction flask. After adding NaCO (0.5 g), the title compound (6.4 g, 56% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 113 °C, 3.3 Pa) as a colorless oil (E / Z = 67:33).

[0117] [ka]

[0118] Compound 4. Methyl (S)-2-((2-methyl-4-phenylbut-1-en-1-yl)oxy)propanoate: Dimethyl acetal of 2-methyl-4-phenylbutanal (10.4 g, 49.9 mmol), (S)-methyl lactate (10.4 g, 99.9 mmol), and KHSO (0.068 g, 0.5 mmol) were added to a 25 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 150 °C (oil bath) for 2 h while free methanol distilled from the reaction vessel. After removing the Vigreux column, the mixture was heated at 190 °C for 1 h while excess methyl lactate distilled from the reaction flask. The title compound (8.5 g, 68% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 120 °C, 4 Pa) as a colorless oil (E / Z = 60:40).

[0119] [ka]

[0120] Compound 5. Octyl (S)-2-((2-methylundec-1-en-1-yl)oxy)propanoate: Methyl (S)-2-((2-methylundec-1-en-1-yl)oxy)propanoate (compound 2, 8.2 g, 30.2 mmol), octanol (15.7 g, 121 mmol), DMAP (3.69 g, 30.2 mmol), and cyclohexane (100 mL) were added to a round-bottom flask (250 mL) equipped with a Dean-Stark trap. The mixture was heated at reflux for 1 day. The mixture was concentrated in vacuo, and the residue was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 → 90:10) to afford 9.36 g (25.4 mmol, 84% yield) of the title compound as a colorless oil (E / Z = 61:39).

[0121] [ka]

[0122] Compound 6. (Z)-hex-3-en-1-yl (S)-2-((2-methylundec-1-en-1-yl)oxy)propanoate: A mixture of methyl (S)-2-((2-methylundec-1-en-1-yl)oxy)propanoate (compound 2, 5.26 g, 19.4 mmol), (Z)-hex-3-en-1-ol (33 g, 329 mmol), and DBU (2.1 g, 13.8 mmol) was heated at 120 °C (oil bath) for 9 h. The mixture was diluted with ethyl ether and washed with water. The organic phase was dried over NaSO, filtered, and concentrated in vacuo. Excess (Z)-hex-3-en-1-ol was removed by short-path vacuum distillation, and the residue was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 to 90:10) to give 3.2 g (9.4 mmol, 48% yield) of the title compound as a pale yellow oil (E / Z = 58:42).

[0123] [ka]

[0124] Compound 7. Methyl (S)-2-(dodec-1-en-1-yloxy)propanoate: Dimethyl acetal of 2-dodecanal (11.5 g, 49.9 mmol), (S)-methyl lactate (13.3 g, 128 mmol), and KHSO4 (0.031 g, 0.46 mmol) were added to a 35 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 150 °C (oil bath) for 1.5 h while the free methanol was distilled from the reaction vessel. The reaction mixture was subjected to short-path vacuum distillation to obtain a fraction containing the enol ether (128–138 °C, 3.3 Pa). This fraction was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 → 90:10) followed by Kugelrohr distillation to obtain 2.0 g (7.4 mmol, 15% yield) of the title compound as a pale yellow oil (E / Z = 37:63).

[0125] [ka]

[0126] Compound 8. (±)-Methyl 2-((3-methyl-5-phenylpent-1-en-1-yl)oxy)propanoate: Dimethyl acetal of 5-phenyl-3-methylpentanal (9 g, 40.8 mmol), (±)-methyl lactate (16.9 g, 162 mmol), and KHSO4 (0.17 g, 1.24 mmol) were added to a 35 ml round-bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated at 140 °C (oil bath) while the free methanol was distilled from the reaction vessel. After 1 h, the reaction vessel was placed under vacuum (60 kPa) and the pressure was reduced to 40 kPa while the methyl lactate was distilled from the flask. After 1 h, the pressure was gradually reduced to 40 Pa over 1.5 h. After this time, 0.5 g of Na2CO3 was added to the flask, and the title compound (4.73 g, 45% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 115–117 °C, 1 Pa) as a colorless oil (mixture of diastereomers, E / Z = 50:50).

[0127] [ka]

[0128] Compound 9. Methyl (S)-2-(styryloxy)propanoate: Dimethyl acetal of phenylacetaldehyde (18.3 g, 110 mmol), (S)-methyl lactate (28.6 g, 275 mmol), and KHSO (0.075 g, 0.50 mmol) were added to a 50 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 150 °C (oil bath) for 1 h while free methanol distilled from the reaction vessel. After removing the Vigreux column, the mixture was heated at 190 °C for 1 h while excess methyl lactate distilled from the reaction flask. The title compound (10.7 g, 47% yield) was isolated from the remaining reaction mixture by short-path vacuum distillation (bp 114 °C, 15 Pa) as a colorless oil (E / Z = 50:50).

[0129] [ka]

[0130] Compound 10. Methyl 2-methyl-2-(styryloxy)propanoate: Dimethyl acetal of phenylacetaldehyde (9.9 g, 59.6 mmol), methyl 2-hydroxy-2-isobutyrate (14.3 g, 121 mmol), and KHSO (0.087 g, 0.64 mmol) were added to a 25 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 170 °C for 1 h and 190 °C (oil bath) for 1 h while the free methanol was distilled from the reaction vessel. The mixture was then heated at 150 °C under vacuum (0.7 kPa) for 1 h. After adding NaCO (0.5 g), the title compound (3.7 g, 28% yield) was isolated from the reaction flask by fractional distillation (bp 92 °C, 4 Pa) as a colorless oil (E / Z = 41:59).

[0131] [ka]

[0132] Compound 11. Methyl (S)-2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Dimethyl acetal of 2-phenylpropanal (7.23 g, 40.1 mmol), (S)-methyl lactate (8.46 g, 81.2 mmol), and KHSO (0.052 g, 0.38 mmol) were added to a 25 ml round-bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was heated at 120 °C (oil bath) for 1 h while free methanol was distilled from the reaction vessel. The mixture was heated at 190 °C for 1 h while excess methyl lactate was distilled from the reaction flask. The title compound (6.4 g, 72% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 112 °C, 3 Pa) as a colorless oil (E / Z = 83:17).

[0133] [ka]

[0134] Compound 12. Hexyl (S)-2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Methyl (S)-2-((2-phenylprop-1-en-1-yl)oxy)propanoate (compound 11, 5.0 g, 22.7 mmol), hexanol (9.3 g, 90.8 mmol), DMAP (0.84 g, 6.9 mmol), and cyclohexane (75 mL) were added to a round-bottom flask (150 mL) equipped with a Dean-Stark trap. The mixture was heated at reflux for 1 day. The mixture was diluted with ethyl ether and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 → 85:15) to afford 4.9 g (16.8 mmol, 74% yield) of the title compound as a colorless oil (E / Z = 83:17).

[0135] [ka]

[0136] Compound 13. (Z)-hex-3-en-1-yl (S)-2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Methyl (S)-2-((2-phenylprop-1-en-1-yl)oxy)propanoate (Compound 11, 5.0 g, 22.7 mmol), (Z)-hex-3-en-1-ol (9.1 g, 90.9 mmol), DMAP (0.84 g, 6.9 mmol), and cyclohexane (75 mL) were added to a round-bottom flask (150 mL) equipped with a Dean-Stark trap. The mixture was heated at reflux for 28 h. The reaction mixture was concentrated in vacuo and filtered through a pad of silica gel. After removal of the solvent, the crude product was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 → 80:20) to afford 2.7 g (9.3 mmol, 41% yield) of the title compound as a pale yellow oil (E / Z = 82:18).

[0137] [ka]

[0138] Compound 14. (±)-Methyl 2-((2-methyldec-1-en-1-yl)oxy)propanoate: Dimethyl acetal of 2-methyldecanal (8.0 g, 37 mmol), (±)-methyl lactate (7.7 g, 74 mmol), and KHSO (0.15 g, 1.10 mmol) were added to a 25 ml round-bottom flask equipped with a Vigreux column (10 cm), a distillation head, and a nitrogen bubbler. The mixture was heated at 150-160 °C (oil bath) for 1 h while free methanol was distilled from the reaction vessel. After removing the Vigreux column, the mixture was heated at 180-190 °C for 1 h while excess methyl lactate was distilled from the reaction flask. The reaction mixture was then heated under vacuum (1.3 kPa) at 150 °C for 1 h to remove residual methyl lactate. The title compound (8.57 g, 90% yield) was isolated from the reaction flask by short-path vacuum distillation (bp 86-90° C., 1 Pa) as a colorless oil (E / Z=60:40).

[0139] [ka]

[0140] Compound 15. (±)-Methyl 2-((3-(4-methoxyphenyl)-2-methylprop-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 14, starting from the dimethyl acetal of 3-(4-methoxyphenyl)-2-methylpropanal (8 g, 35.7 mmol), (±)-methyl lactate (7.4 g, 71.3 mmol), and KHSO (0.15 g, 1.1 mmol), the title compound (7.59 g, 80% yield) was isolated as a colorless oil by short-path vacuum distillation (bp 117-120 °C, 1 Pa) (E / Z = 57:43).

[0141] [ka]

[0142] Compound 16. (±)-Methyl 2-((2-ethylhex-1-en-1-yl)oxy)propanoate: The title compound was prepared according to the procedure described for compound 14, except that the reaction mixture was heated at 180°C (oil bath) for 1 hour, and then the reaction mixture was heated under vacuum (12-1.3 kPa) at 140°C for 1 hour. Starting from dimethyl acetal of 2-ethylhexanal (10 g, 57.4 mmol), (±)-methyl lactate (14.9 g, 143 mmol), and KHSO (0.23 g, 1.72 mmol), the title compound (7.43 g, 60% yield) was isolated by short-path vacuum distillation (bp 90-93°C, 53 Pa) as a colorless oil (isomer ratio = 53:47).

[0143] [ka]

[0144] Compound 17. (±)-Methyl 2-((4-(4-methoxyphenyl)-2-methylbut-1-en-1-yl)oxy)propanoate: General procedure: Methoxymethyltriphenylphosphonium chloride (15.1 g, 44.1 mmol) and the ketone (29.4 mmol) were added to 120 mL of toluene. Potassium t-butoxide (5.27 g, 47 mmol) was added to the stirred slurry in four portions, 15 minutes apart. The mixture was stirred for 4 hours, at which point it turned deep red. It was then poured into 500 mL of water and extracted with EtOAc (250 mL x 3). The organic phases were combined, dried over NaSO, filtered, and concentrated to a granular solid. The resulting methyl enol ether product was isolated by flash chromatography (silica gel, hexane) followed by bulb-to-bulb distillation. Alternatively, the solid was washed with hexane and filtered. The filtrate was concentrated to give the crude methyl enol ether, which was purified by fractional distillation. This methyl enol ether (30–40 mmol) was then combined with (±)-methyl lactate (2–2.5 equiv.) and KHSO4 (3 mol%) in a round-bottom flask (25–35 mL) equipped with a distillation head and nitrogen bubbler. The mixture was heated at 150–160 °C (oil bath) for 1 h while the free methanol distilled from the reaction vessel. The mixture was then heated at 180 °C for 1 h while the methyl lactate continued to distill from the reaction flask. The reaction mixture was then heated under vacuum (1.3 kPa) at 150–160 °C for 1 h to remove any remaining methyl lactate. The resulting enol ether was isolated from the reaction flask by short-path vacuum distillation.

[0145] Following this general procedure, the title compound was isolated by short-path distillation (bp 128-132 °C, 1 Pa) of the crude reaction mixture using the methyl enol ether prepared from 4-(4-methoxyphenyl)butan-2-one in 61% yield as a colorless liquid (E / Z = 57:43).

[0146] [ka]

[0147] Compound 18. (±)-Methyl 2-((2-pentylcyclopentylidene)methoxy)propanoate: Following the procedure described for compound 17, starting from the methyl enol ether prepared from 2-pentylcyclopentanone, the title compound was isolated by short-path distillation (bp 85-88 °C, 1 Pa) of the crude reaction mixture in 74% yield as a colorless liquid (mixture of diastereomers, E / Z = 57:43).

[0148] [ka]

[0149] Compound 19. (±)-Methyl 2-((2-ethyl-4,4-dimethylcyclohexylidene)methoxy)propanoate: Following the procedure described for compound 17, starting from the methyl enol ether prepared from 2-ethyl-4,4-dimethylcyclohexanone, the title compound was isolated by short-path distillation (bp 86-88 °C, 1 Pa) of the crude reaction mixture in 71% yield as a colorless liquid (mixture of diastereomers, E / Z = 80:20).

[0150] [ka]

[0151] Compound 20. (±)-Methyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 17, starting from the methyl enol ether prepared from acetanisole, the title compound was isolated by short-path distillation (bp 126–129 °C, 1 Pa) of the crude reaction mixture as a colorless liquid in 65% yield (E / Z = 78:22).

[0152] [ka]

[0153] Compound 21. (±)-methyl 2-((2-(naphthalen-2-yl)prop-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 17, starting from the methyl enol ether prepared from 1-(naphthalen-2-yl)ethan-1-one, the title compound was isolated by silica gel flash chromatography in 71% yield as a white solid (E / Z=94:6).

[0154] [ka]

[0155] Compound 22. (±)-Methyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 17, starting from the methyl enol ether prepared from p-methylacetophenone, the title compound was isolated by short-path distillation (bp 98–104 °C, 1 Pa) of the crude reaction mixture as a colorless liquid in 79% yield (E / Z = 82:18).

[0156] [ka]

[0157] Compound 23. Methyl 2-methyl-2-((2-methyldec-1-en-1-yl)oxy)propanoate: General Procedure: Dimethyl acetal (40 mmol), methyl 2-hydroxyisobutyrate (120 mmol), and KHSO4 (1.2 mmol) were added to a 25-35 ml round-bottom flask equipped with a Vigreux column (10 cm), distillation head, and nitrogen bubbler. The reaction flask was placed in a 150 °C oil bath, which was immediately heated to 180 °C. Methanol and excess 2-hydroxyisobutyrate were distilled from the reaction vessel. After 1 h, the Vigreux column was removed, and heating was continued for an additional 0.5-1 h. The resulting enol ether was isolated from the reaction flask by short-path vacuum distillation.

[0158] Following the general procedure described above, starting with dimethyl acetal of 2-methyldecanal (8 g, 37 mmol), methyl 2-hydroxyisobutyrate (17.4 g, 148 mmol), and KHSO (0.15 g, 1.10 mmol), the title compound (5.0 g, 50% yield) was isolated by short-path vacuum distillation (bp 96-100 °C, 2 Pa) as a colorless oil (E / Z=62:38).

[0159] [ka]

[0160] Compound 24. Methyl 2-((3-(4-methoxyphenyl)-2-methylprop-1-en-1-yl)oxy)-2-methylpropanoate: Following the procedure described for compound 23, starting from the dimethyl acetal of 3-(4-methoxyphenyl)-2-methylpropanal (6 g, 26.8 mmol), methyl 2-hydroxyisobutyrate (9.48 g, 80.3 mmol), and KHSO (0.11 g, 0.8 mmol), the title compound (6.47 g, 87% yield) was isolated as a colorless oil by short-path vacuum distillation (bp 122-125 °C, 1 Pa) (E / Z = 60:40).

[0161] [ka]

[0162] Compound 25. Methyl 2-methyl-2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 23, starting from dimethyl acetal of 2-phenylpropanal (10 g, 55.5 mmol), methyl 2-hydroxyisobutyrate (19.7 g, 166 mmol), and KHSO (0.23 g, 1.7 mmol), the title compound (11.0 g, 85% yield) was isolated as a colorless oil by short-path vacuum distillation (bp 88-92 °C, 1.3 Pa) (E / Z = 85:15).

[0163] [ka]

[0164] Compound 26. Methyl 2-methyl-2-((2-methyl-4-phenylbut-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 23, starting from dimethyl acetal of 2-methyl-4-phenylbutanal (9 g, 43.2 mmol), methyl 2-hydroxyisobutyrate (15.3 g, 130 mmol), and KHSO (0.18 g, 1.3 mmol), the title compound (9.28 g, 82% yield) was isolated by short-path vacuum distillation (bp 88-91 °C, 1 Pa) as a colorless oil (E / Z=58:42).

[0165] [ka]

[0166] Compound 27. Methyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)-2-methylpropanoate: General procedure: Methoxymethyltriphenylphosphonium chloride (15.1 g, 44.1 mmol) and the ketone (29.4 mmol) were added to 120 mL of toluene. Potassium t-butoxide (5.27 g, 47 mmol) was added to the stirred slurry in four portions, 15 minutes apart. The mixture was stirred for 4 hours, at which point it turned deep red. It was then poured into 500 mL of water and extracted with EtOAc (250 mL x 3). The organic phases were combined, dried over NaSO, filtered, and concentrated to a granular solid. The resulting methyl enol ether product was isolated by flash chromatography (silica gel, hexane) followed by bulb-to-bulb distillation. Alternatively, the solid was washed with hexane and filtered. The filtrate was concentrated to give the crude methyl enol ether, which was purified by fractional distillation. Next, the methyl enol ether (30–40 mmol) was combined with methyl 2-hydroxyisobutyrate (3 equiv.) and KHSO4 (3 mol%) in a round-bottom flask (25–35 mL) equipped with a Vigreux column (10 cm), distillation head, and nitrogen bubbler. The reaction flask was placed in a 150 °C oil bath, which was then heated to 180 °C. Methanol and excess 2-hydroxyisobutyrate were distilled from the reaction vessel. After 1 h, the Vigreux column was removed, and heating was continued for an additional 0.5–1 h. The resulting enol ether was isolated from the reaction flask by short-path vacuum distillation.

[0167] Following this general procedure, the title compound was isolated by short-path distillation (bp 118-121 °C, 1.2 Pa) of the crude reaction mixture using the methyl enol ether prepared from acetanisole in 78% yield as a colorless liquid (E / Z = 78:22).

[0168] [ka]

[0169] Compound 28. (±)-Methyl 2-methyl-2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate methyl: Following the procedure described for compound 27, starting from the methyl enol ether prepared from p-methylacetophenone, the title compound was isolated by short-path distillation (bp 94–98 °C, 1 Pa) of the crude reaction mixture as a colorless liquid in 81% yield (E / Z = 83:17).

[0170] [ka]

[0171] Compound 29. (±)-Methyl 2-methyl-2-((2-pentylcyclopentylidene)methoxy)propanoate: Following the procedure described for compound 27, starting from the methyl enol ether prepared from 2-pentylcyclopentanone, the title compound was isolated by short-path distillation (bp 90-92 °C, 1 Pa) of the crude reaction mixture as a colorless liquid in 84% yield (E / Z = 68:32).

[0172] [ka]

[0173] Compound 30. (±)-Methyl 2-(undeca-1,10-dien-1-yloxy)propanoate: Following the procedure described for compound 8, starting from dimethyl acetal of 10-undecenal (12 g, 56 mmol), (±)-methyl lactate (23.3 g, 224 mmol), and KHSO (0.23 g, 1.7 mmol), the title compound (4.53 g, 32% yield) was isolated as a colorless oil by short-path distillation (bp 92–96°C, 1.3 Pa) (E / Z=43:57).

[0174] [ka]

[0175] Compound 31. (±)-Methyl 2-(tridec-1-en-1-yloxy)propanoate: The title compound was prepared according to the procedure described for compound 8, starting with the dimethyl acetal of tridecanal (7.0 g, 28.6 mmol), (±)-methyl lactate (11.9 g, 115 mmol), and KHSO (0.12 g, 0.86 mmol). The crude reaction mixture was poured into saturated aqueous NaHCO and extracted with ethyl acetate. The organic phase was dried over MgSO, filtered, and concentrated. The crude product was subjected to silica gel flash chromatography (hexane / EtOAc 100:0 to 95:5) followed by bulb-to-bottom distillation to afford the title compound (1.4 g, 17% yield) as a colorless liquid (E / Z=50:50).

[0176] [ka]

[0177] Compound 32. (±)-Methyl 2-(dodeca-1,11-dien-1-yloxy)propanoate: General procedure: Methoxymethyltriphenylphosphonium chloride (15.1 g, 44.1 mmol) and aldehyde (29.4 mmol) were added to 120 mL of toluene. Potassium t-butoxide (5.27 g, 47 mmol) was added to the stirred slurry in four portions, 15 minutes apart. The mixture was stirred for 4 hours, at which point it turned deep red. It was then poured into 500 mL of water and extracted with EtOAc (250 mL x 3). The organic phases were combined, dried over NaSO, filtered, and concentrated to a granular solid. The resulting methyl enol ether product was isolated by flash chromatography (silica gel, hexane) followed by bulb-to-bulb distillation. Alternatively, the solid was washed with hexane and filtered. The filtrate was concentrated to give the crude methyl enol ether, which was purified by fractional distillation. Next, this methyl enol ether (30–40 mmol) was combined with (±)-methyl lactate (3–4 equivalents) and KHSO (0.03 equivalents) in a round-bottom flask (25–35 mL) equipped with a distillation head and nitrogen bubbler. This mixture was heated at 140 °C (oil bath) while the free methanol distilled from the reaction vessel. After 1 h, the reaction vessel was placed under vacuum (60 kPa) and the pressure reduced to 40 kPa while the methyl lactate distilled from the flask. After 1 h, the pressure was gradually reduced to 40 Pa over 1–1.5 h. 0.5 g of NaCO was then added, and the resulting enol ether was isolated from the reaction flask by short-path vacuum distillation.

[0178] Following this general procedure, using the methyl enol ether prepared from 10-undecanal (8.0 g, 40.7 mmol), (±)-methyl lactate (17 g, 163 mmol), and KHSO4 (0.17 g, 1.22 mmol), the title compound (4.21 g, 38% yield) was isolated as a colorless oil after successive short-path distillations (bp 94-96 °C, 1 Pa) (E / Z = 43:57).

[0179] [ka]

[0180] Compound 33. (±)-Methyl 2-((3-methyldodec-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 32, using the methyl enol ether prepared from 2-methylundecanal (9.0 g, 42.4 mmol), (±)-methyl lactate (17.6 g, 170 mmol), and KHSO4 (0.17 g, 1.27 mmol), the title compound (5.52 g, 45% yield) was isolated after successive short-path distillations (bp 93-98 °C, 1 Pa) as a colorless oil (mixture of diastereomers, E / Z = 40:60).

[0181] [ka]

[0182] Compound 34. (±)-Methyl 2-((4-phenylpent-1-en-1-yl)oxy)propanoate: Following the procedure described for compound 32, the title compound (3.58 g, 31% yield) was isolated by short-path distillation (bp 108-110 °C, 1.3 Pa) as a colorless oil (mixture of diastereomers, E / Z = 43:57) using the methyl enol ether prepared from 3-phenylbutanal (8.0 g, 45.4 mmol), (±)-methyl lactate (16.5 g, 159 mmol), and KHSO (0.19 g, 1.36 mmol).

[0183] [ka]

[0184] Compound 35. (±)-Methyl 2-((4-methoxystyryl)oxy)propanoate: Following the procedure described for compound 32, the title compound (3.96 g, 32% yield) was isolated as a colorless oil by short-path distillation (bp 128-131 °C, 1 Pa) using the methyl enol ether prepared from p-anisaldehyde (8.5 g, 51.8 mmol), (±)-methyl lactate (16.2 g, 155 mmol), and KHSO (0.21 g, 1.55 mmol) (E / Z=47:53).

[0185] [ka]

[0186] Compound 36. (±)-Methyl 2-((3,4-dimethoxystyryl)oxy)propanoate: The title compound was prepared using the methyl enol ether prepared from 3,4-dimethoxybenzaldehyde (7.5 g, 38.6 mmol), (±)-methyl lactate (16.1 g, 154 mmol), and KHSO (0.16 g, 1.16 mmol) according to the procedure described for compound 32. The crude reaction mixture was poured into saturated aqueous NaHCO and extracted with ethyl acetate. The organic phase was dried over MgSO, filtered, and concentrated. The crude product was filtered through a silica gel pad (hexane / EtOAc 50:50) and then subjected to bulb distillation (200 °C, 2.7 Pa) to give the title compound (1.3 g, 13% yield) as a colorless liquid (E / Z = 41:59).

[0187] [ka]

[0188] Compound 37. (±)-Methyl 2-methyl-2-((3-methyldodec-1-en-1-yl)oxy)propanoate: Starting from the methyl enol ether prepared from 2-methylundecanal (8.0 g, 37.7 mmol), methyl 2-hydroxyisobutyrate (17.8 g, 151 mmol), and KHSO (0.26 g, 1.88 mmol) according to the procedure described for compound 32 (reaction mixture heated at 150 °C), the title compound (3.95 g, 35% yield) was isolated by short-path distillation (bp 118-122 °C, 1 Pa) as a colorless liquid (E / Z = 32:68).

[0189] [ka]

[0190] Compound 38. (±)-Methyl 2-methyl-2-(tridec-1-en-1-yloxy)propanoate: Following the procedure described for compound 8 (reaction mixture heated for 4.5 h), starting from dimethyl acetal of tridecanal (9.0 g, 36.8 mmol), methyl 2-hydroxyisobutyrate (15.2 g, 129 mmol), and KHSO (0.15 g, 1.1 mmol), the title compound (1.79 g, 16% yield) was isolated by short-path distillation (bp 122–126 °C, 1.2 Pa) as a colorless liquid (E / Z=33:67).

[0191] [ka]

[0192] Compound 39. (±)-(Z)-Hex-3-en-1-yl 2-(styryloxy)propanoate: General procedure: A mixture of the enol ether derived from methyl lactate (10–20 mmol), alcohol (3–10 equiv.), and DBU (1 equiv.) was added to a round-bottom flask equipped with a distillation head and nitrogen bubbler. The mixture was typically heated at 150°C (oil bath) for 3 h, followed by 180°C for 1 h, while methanol was distilled off. The transesterification product was isolated by silica gel flash chromatography of the crude reaction mixture (hexane / EtOAc).

[0193] Following this general procedure, using compound (±)-9 (4 g, 19.4 mmol) and cis-3-hexen-1-ol (19.4 g, 194 mmol), the title compound (3.0 g, 57% yield) was isolated by silica gel flash chromatography as a pale yellow liquid (E / Z=53:47).

[0194] [ka]

[0195] Compound 40. (±)-Phenethyl 2-(styryloxy)propanoate: Following the general procedure described for compound 39, compound (±)-9 (4 g, 19.4 mmol) and 2-phenylethanol (7.11 g, 58.2 mmol) were used to isolate the title compound (0.75 g, 13% yield) by silica gel flash chromatography as a pale yellow liquid (E / Z=53:47).

[0196] [ka]

[0197] Compound 41. (±)-Octan-3-yl 2-(styryloxy)propanoate: Following the general procedure described for compound 39, compound (±)-9 (2.2 g, 10.7 mmol) and 3-octanol (5.56 g, 42.7 mmol) were used to isolate the title compound (1.63 g, 50% yield) by silica gel flash chromatography as a pale yellow liquid (mixture of diastereomers, E / Z=47:53).

[0198] [ka]

[0199] Compound 42. (±)-(Z)-hex-3-en-1-yl 2-((4-methoxystyryl)oxy)propanoate: Following the general procedure described for compound 39, compound 35 (2.5 g, 10.6 mmol) and cis-3-hexen-1-ol (6.36 g, 63.5 mmol) were used to isolate the title compound (2.0 g, 62% yield) as a pale yellow liquid by silica gel flash chromatography (E / Z=45:55).

[0200] [ka]

[0201] Compound 43. (±)-phenethyl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound (±)-11 (5.0 g, 22.7 mmol) and 2-phenylethanol (8.32 g, 68.1 mmol) were used to isolate the title compound (1.8 g, 26% yield) as a pale yellow liquid by silica gel flash chromatography (E / Z=85:15).

[0202] Following the general procedure described for compound 39, starting from compound (±)-11 and 2-phenylethanol (X equivalents), the title compound was isolated by silica gel flash chromatography in 31% yield as a colorless liquid (E / Z=85:15).

[0203] [ka]

[0204] Compound 44. (±)-Octan-3-yl 2-((2-phenylprop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound (±)-11 (5.0 g, 22.7 mmol) and 3-octanol (8.67 g, 68.1 mmol) were used to isolate the title compound (1.82 g, 25% yield) by silica gel flash chromatography as a pale yellow liquid (mixture of diastereomers, E / Z=93:7).

[0205] [ka]

[0206] Compound 45. (±)-phenethyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound 22 (3.0 g, 12.8 mmol) and 2-phenylethanol (9.39 g, 76.8 mmol) were used to isolate the title compound (1.3 g, 31% yield) by silica gel flash chromatography as a pale yellow liquid (E / Z=78:22).

[0207] [ka]

[0208] Compound 46. (±)-sec-butyl 2-((2-(p-tolyl)prop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound 22 (2.0 g, 8.54 mmol) and 2-butanol (3.8 g, 51.2 mmol) were used to isolate the title compound (1.0 g, 42% yield) by silica gel flash chromatography as a colorless liquid (mixture of diastereomers, E / Z=81:19).

[0209] [ka]

[0210] Compound 47. (±)-(Z)-hex-3-en-1-yl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound 20 (3.0 g, 12.1 mmol) and cis-3-hexen-1-ol (7.3 g, 72.9 mmol) were used to isolate the title compound (1.9 g, 49% yield) as a pale yellow liquid by silica gel flash chromatography (E / Z=73:27).

[0211] [ka]

[0212] Compound 48. (±)-phenethyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound 20 (2.6 g, 10.4 mmol) and 2-phenylethanol (7.6 g, 62.3 mmol) were used to isolate the title compound (0.52 g, 15% yield) by silica gel flash chromatography as a pale yellow liquid (E / Z=79:21).

[0213] [ka]

[0214] Compound 49. (±)-sec-butyl 2-((2-(4-methoxyphenyl)prop-1-en-1-yl)oxy)propanoate: Following the general procedure described for compound 39, compound 20 (2.0 g, 8.0 mmol) and 2-butanol (3.55 g, 47.9 mmol) were used to isolate the title compound (0.7 g, 30% yield) by silica gel flash chromatography as a colorless liquid (mixture of diastereomers, E / Z=87:13).

[0215] [ka]

[0216] Compound 50. (±)-phenethyl 2-((2-(naphthalen-2-yl)vinyl)oxy)propanoate: Following the general procedure described for compound 39, a mixture of compound 21 (5.5 g, 20.3 mmol), 2-phenylethanol (24.9 g, 203 mmol), and DBU (0.92 g, 6.0 mmol) was heated at 150 °C for 2 h. The reaction mixture was diluted with dichloromethane and washed with water. The organic phase was dried over MgSO, filtered, and concentrated. The title compound (3.48 g, 47% yield) was isolated by silica gel flash chromatography as a viscous pale yellow oil (E / Z = 81:19).

[0217] [ka]

[0218] Compound 51. 1-(2-(((Z)-hex-3-en-1-yl)oxy)vinyl)-4-methoxybenzene (example of comparative hydrolysis): Following the procedure described for compound 32, using the methyl enol ether prepared from p-anisaldehyde (8.0 g, 48.7 mmol), cis-3-hexen-1-ol (14.6 g, 146 mmol), and KHSO4 (0.2 g, 1.46 mmol), the title compound (1.87 g, 17% yield) was isolated as a colorless oil after two successive short-path distillations (bp 118-121 °C, 1.1 Pa) (E / Z = 47:53).

[0219] [ka]

[0220] Example 2 Hydrolysis of compounds according to formula (I) and comparative compounds The acid-catalyzed hydrolysis of compounds 10, 25, 27, 28, 39, 40, 41, 42, 44, 46, 47, and 49 was measured and compared to the hydrolysis of enol ethers derived from the same aldehydes but using alkyl alcohols (see table below). Acid-catalyzed hydrolysis results in the loss of the enol ether, which is an indicator of long-term storage stability in acidic consumer products. Each enol ether was dissolved in a 4:1 mixture of THF / 1M HCl, and the percentage remaining relative to an internal standard was measured over time.

[0221] To a 15 mL vial, 125 mg of the enol ether, 60 mg of hexadecane, and 10 mL of THF (purged with N2 and containing 2500 ppm BHT) were added. After mixing, 2 mL of this solution was removed with a volumetric pipette and used to obtain a time-zero measurement. 2 mL of 1 M HCl was mixed with the remaining 8 mL of THF solution. This mixture was dispensed into 5 mL vials (1 mL per vial). These vials were gently flushed with nitrogen and fitted with screw caps wrapped in parafilm. These vials were stored at room temperature until analysis. For analysis, 2 mL of ethyl acetate was added to the vial and mixed. After phase separation, the upper phase was collected and washed with saturated sodium carbonate (1 mL). A sample of the organic phase was analyzed by GC-FID. For the time-zero sample, 0.5 mL of deionized water was added to 2 mL of the original THF solution. 1 mL of this solution was added to a 5 mL vial, diluted with 2 mL of ethyl acetate, and mixed. The upper phase was collected and washed with saturated sodium carbonate (1 mL). The upper phase was then analyzed by GC-FID. The remaining percentage of enol ether was determined by dividing the peak area ratio of the enol ether to the internal standard by the ratio measured at time zero.

[0222] [Table 1-1] [Table 1-2]

[0223] The table above compares the hydrolysis rates of enol ethers prepared from alkyl alcohols or α-hydroxy esters: phenylacetaldehyde, 2-(4-methoxyphenyl)acetaldehyde, 2-phenylpropanal, 2-(p-tolyl)propanal, and 2-(4-methoxyphenyl)propanal. After 504 hours (21 days), only 39.5% and 4.5% of the phenylacetaldehyde enol ethers prepared from 2-phenylethanol (item 5) and 3-octanol (item 6) remained, while the enol ethers prepared from α-hydroxy esters remained at 70.8%, 53.0%, 53.0%, and 88.4% (items 1–4). At the same time point, 46.8% of the enol ether of p-methoxyphenylacetaldehyde derived from an α-hydroxy ester (entry 7) remained, while only 14.6% of the enol ether derived from cis-3-hexen-1-ol (entry 8) remained. For enol ethers prepared from 2-phenylpropanal, improved hydrolytic stability was observed for compounds 25 and 44 (entries 9 and 10) compared with enol ethers prepared from primary (entry 11), secondary (entry 12), or tertiary alkyl alcohols (entry 13). Slower rates of hydrolysis were also observed for the enol ethers of α-hydroxy esters, 2-(p-tolyl)propanal (entries 14 and 15) and 2-(4-methoxyphenyl)propanal (entries 17–19), compared with the corresponding enol ethers derived from 2-phenylethanol (entries 16 and 20). The table shows that enol ethers made from α-hydroxy esters hydrolyze more slowly than the corresponding enol ethers made from alkyl alcohols, and therefore, the enol ethers of the present invention are expected to be more stable in acidic consumer products such as liquid fabric softeners.

[0224] Example 3 Headspace analysis of fabric softener applications containing compounds of formula (I) of the present invention A model liquid fabric softener was prepared by mixing 12.3 wt% TEA-esterquat (Stepantex® VL 90A), 0.4 wt% 10% aqueous calcium chloride, 0.04 wt% Proxcel GXL, and 87.2 wt% deionized water. Enol ether (0.075 mmol) was weighed into a vial and dissolved in 0.25 mL of acetone. Liquid fabric softener (4.5 g) was added to the vial, and the mixture was mixed by hand shaking. Reference samples were similarly prepared using 0.075 mmol of each released volatile. The fabric softener sample was rinsed into a 3 L beaker with deionized water, filling the beaker to a total volume of 1.5 L. Five grams of cotton sample fabric (approximately 12.5 x 12.5 cm, weighing 270 g / m²) was added to the beaker. 2 Testfabrics (Product 403, West Pittston, PA) was added and stirred by hand for 3 minutes. After an additional 2 minutes of settling, the sample fabrics were removed and the excess water was squeezed out by hand. The fabrics were then hung to dry overnight (15-16 hours) at room temperature. These sample fabrics were then subjected to dynamic headspace analysis.

[0225] Each sample fabric was placed in a thermostated (25°C) headspace sampling cell (approximately 160 mL capacity). An air sampling pump was used to pass a constant flow of air (200 mL / min) through the sampling cell, then through a cartridge containing 100 mg of Tenax®. Before entering the sample cell, the air was drawn through activated carbon packing and then through a saturated aqueous NaCl solution to maintain a constant relative humidity of 75%. Headspace samples were collected continuously in 30-minute intervals over 2.5 hours. The cartridges were thermally desorbed using a Gerstel TDU 3.5 equipped with a cryofocusing unit at -30°C and transferred to an Agilent 8890 gas chromatograph equipped with an HP1 capillary column (30 m, 0.25 mm internal diameter, 0.25 μm film thickness) and coupled to an Agilent 5977B mass spectrometer. TDU temperature settings for desorption: 40°C to 70°C (30°C / min), held for 4 minutes, then heated to 260°C (400°C / min), held for 5 minutes. CIS settings (Tenax® packed liner): cryofocused at -30°C, then heated to 300°C at 12°C / min, held for 4 minutes (heater mode: standard). PTV inlet settings: pressure 7.7 psi, total flow 99 ml / min, septum purge flow 3 ml / min, run in standard flow mode. Inlet mode was set to solvent vent, split vent purge flow was set to 95 ml / min, and vent flow was set to 50 ml / min. GC oven temperature profile: 52°C to 110°C at 20°C / min (held for 2 minutes), then ramped to 210°C (20°C / min). The amount of each fragrance volatile recovered (reported as ng / L air) was determined using an external standard calibration curve for each chemical. At least five acetone solutions were prepared with analyte concentrations ranging from 0.05 g / L to 5 g / L. These solutions were injected (0.2 μL) onto Tenax® cartridges and desorbed as described above. Each solution was analyzed in triplicate. The calibration curve was forced through the origin.

[0226] [Table 2]

[0227] Example 4 Headspace analysis of the application of leave-on hair conditioners containing compounds of formula (I) of the present invention A model rinse-off hair conditioner was prepared by a commonly known method with the following composition (wt %): Deionized water 95.50% Salcare SC 91 (Supplier: BASF) 1.00% Aculyn(TM) 46 (Supplier: Dow) 1.00% Wacker-Belsil® DMS 6038 (supplier: Wacker) 0.50% Phenonip(TM) (Supplied by Clariant) 0.50% Mirasil® ADM-E (supplier: Elkem) 1.50%

[0228] A 25 wt% solution of the enol ether in acetone was dispersed in a leave-on hair conditioner to yield a sample containing 0.16 mmol of precursor. The sample was thoroughly mixed and allowed to soak for 2 hours. A reference sample containing an equimolar amount of the target ketone was similarly prepared. Hair swatches (10 g) were rinsed with warm tap water (37°C) for 30 seconds and then gently combed to straighten the hair. Each hair conditioner sample (1 g) was applied to the hair swatch and massaged into the hair to ensure thorough dispersion. The swatches were then hung and allowed to dry overnight (15-16 hours) at room temperature. The hair swatches were then subjected to dynamic headspace analysis as described in Example 3, except that the headspace sampling cell was thermostated at 35°C.

[0229] [Table 3]

[0230] Example 5 Headspace analysis of rinse-off hair conditioner applications containing compounds of formula (I) of the present invention A model rinse-off hair conditioner was prepared by a commonly known method with the following composition (wt %): Deionized water 92.54% Chlorhexidine dihydrochloride 0.05% Natrosol® 250 H (supplied by Hercules) 1.00% Dehyquart(R) C 4046 (Supplier: Cognis) 0.20% Mirasil® ADM-E (supplier: Rhodia) 1.20% Genamin® KDM (supplied by Clariant) 1.00% Crodamol® SS (supplier: Croda) 0.50% Crodacol® C90 (supplier: Croda) 3.01% Myristyl alcohol (supplied by Aldrich) 0.20% Nipagin (registered trademark) M (supplied by Nipa) 0.30%

[0231] A 25 wt% solution of enol ether in acetone was dispersed in rinse-off hair conditioner to obtain a sample containing 0.16 mmol of precursor. A reference sample containing an equimolar amount of the desired aldehyde was also prepared. These samples were soaked at room temperature for 2 hours. A hair swatch (10 g) was wetted with warm tap water (approximately 37°C) and the excess water was gently squeezed off. 1.0 g of rinse-off conditioner was applied along the hair swatch and gently massaged into the hair for 1 minute. The hair swatch was then immersed in a 3 L beaker of warm tap water (approximately 37°C) and rubbed up and down three times, then side to side three times. After squeezing out the excess water, another 1 g sample of hair conditioner was applied and the process was repeated. After gently squeezing out the excess water, the hair swatch was hung and allowed to dry at room temperature overnight (15-16 hours). The hair swatches were then subjected to dynamic headspace analysis as described in Example 3, except that the headspace sampling cell was thermostated at 35°C.

[0232] [Table 4]

[0233] Example 6 Perfume oil production Non-limiting examples of typical perfume oils are prepared by mixing the following perfuming co-ingredients: [Table 5]

[0234] Example 7 Preparation of clear isotropic shampoo formulations containing compounds of formula (I) of the present invention A typical unscented, clear, isotropic shampoo formulation is shown in Table 5. This unscented shampoo formulation is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are mixed separately by adding them one after the other, with good mixing after each addition. This premix is ​​added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Premix Phase B and Premix Phase C are then added with stirring (Monomuls® 90L-12 is heated to melt in Texapon® NSO IS). Phases D and E are added with stirring. The pH is adjusted to 5.5-6.0 with citric acid solution.

[0235] [Table 6]

[0236] Next, a perfume oil (e.g., as described in Example 6, in an amount of 0.1 to 0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) of the present invention, such as compound 37, 33 or 18 (0.05 to 0.50% by weight, based on the total weight of the unscented shampoo formulation), are added to the unscented shampoo formulation described in Table 5 under gentle shaking to obtain a scented shampoo formulation.

[0237] Example 8 Preparation of pearlescent shampoo formulations containing compounds of formula (I) of the present invention A typical fragrance-free pearlescent shampoo formulation is shown in Table 6. This fragrance-free shampoo formulation is made by dispersing tetrasodium EDTA, guar hydroxypropyltrimonium chloride, and polyquaternium-10 in water. Once Phase A is homogeneous, NaOH (10% aqueous solution, Phase B) is added. Next, the premixed Phase C is added, and the mixture is heated to 75°C. Phase D ingredients are added and mixed until the mixture is homogeneous. The mixture is cooled. At 45°C, Phase E ingredients are added with mixing. The final viscosity is adjusted with NaCl (25% aqueous solution), and the pH is adjusted to 5.5-6.0 with NaOH (10% aqueous solution).

[0238] [Table 7]

[0239] Next, a perfume oil (e.g., as described in Example 6, in an amount of 0.1 to 0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.05 to 0.50% by weight, based on the total weight of the unscented shampoo formulation) are added to the unscented pearlescent shampoo formulation described in Table 6 under gentle shaking to obtain a scented pearlescent shampoo formulation.

[0240] Example 9 Preparation of rinse-off hair conditioner formulations containing compounds of formula (I) of the present invention A typical unscented rinse-off hair conditioner formulation is shown in Table 7. This unscented rinse-off hair conditioner formulation is prepared by mixing the ingredients of Phase A until a uniform mixture is obtained. The Tylose® is completely dissolved. The mixture is then heated to 70-75°C. The ingredients of Phase B are combined and melted at 70-75°C. The ingredients of Phase B are then added to Phase A with good mixing, and mixing is continued until the temperature of the mixture reaches 60°C. The ingredients of Phase C are then added with mixing, and mixing is continued until the mixture cools to 40°C. The pH is adjusted to 3.5-4.0 with citric acid solution.

[0241] [Table 8]

[0242] A perfume oil (e.g., as described in Example 6, in an amount of 0.2 to 1.0% by weight, based on the total weight of the unscented conditioner formulation) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.05 to 0.5% by weight, based on the total weight of the unscented conditioner formulation) are then added to the unscented rinse-off hair conditioner formulation described in Table 7 under gentle shaking to obtain a perfumed rinse-off hair conditioner formulation.

[0243] Example 10 Preparation of structured shower gel formulations containing compounds of formula (I) of the present invention A typical unscented structured shower gel formulation is shown in Table 8. A scented structured shower gel is produced by adding, under gentle shaking, a perfume oil (e.g., as described in Example 6, in an amount of 0.1 to 1.5% by weight, based on the total weight of the structured shower gel) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.05 to 0.50% by weight, based on the total weight of the structured shower gel) to the unscented structured shower gel formulation of Table 8.

[0244] [Table 9]

[0245] Example 11 Preparation of clear shower gel formulations containing compounds of formula (I) of the present invention A typical unscented clear shower gel formulation is shown in Table 9. A clear, scented shower gel is produced by adding, under gentle shaking, a perfume oil (e.g., as described in Example 6, in an amount of 0.5 to 1.5% by weight, based on the total weight of the clear shower gel) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.05 to 0.50% by weight, based on the total weight of the clear shower gel) to the unscented clear shower gel formulation of Table 9.

[0246] [Table 10]

[0247] Example 12 Preparation of a milky shower gel formulation containing a compound of formula (I) of the present invention A typical unscented milky shower gel formulation is shown in Table 10. A milky scented shower gel is produced by adding perfume oil (e.g., as described in Example 6, in an amount of 0.1-1.5% by weight, based on the total weight of the milky shower gel) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.05-0.50% by weight, based on the total weight of the milky shower gel) to the unscented milky shower gel formulation of Table 10 under gentle shaking.

[0248] [Table 11]

[0249] Example 13 Preparation of anhydrous antiperspirant spray formulations containing compounds of formula (I) of the present invention A typical fragrance-free anhydrous antiperspirant spray formulation is shown in Table 11. The anhydrous antiperspirant spray formulation is prepared in a high-speed mixer. Silica and quaternium-18-hectorite are added to the isopropyl myristate and cyclomethicone mixture. Once fully swollen, aluminum chlorohydrate is added in small portions with stirring until the mixture is homogeneous and lump-free.

[0250] [Table 12]

[0251] Next, a perfume oil (e.g., as described in Example 6, 0.85% by weight based on the total weight of the antiperspirant spray formulation) and at least one compound of formula (I) of the present invention, such as compound 37, 33, or 18 (0.15% by weight based on the total weight of the antiperspirant spray formulation), are added to the unscented antiperspirant spray formulation of Table 11 to obtain a scented formulation.

[0252] Example 14 Preparation of deodorant spray emulsion formulations containing compounds of formula (I) of the present invention A typical deodorant spray emulsion formulation is prepared by mixing and dissolving all ingredients according to the order in Table 12. Next, perfume oil (e.g., as described in Example 6, 1.35% by weight based on the total weight of the deodorant spray formulation) and at least one compound of formula (I) of the present invention, such as compounds 37, 33, or 18 (0.10-0.20% by weight based on the total weight of the deodorant spray formulation), are added under gentle shaking. The mixture is then filled into an aerosol can, and the propellant is added by crimping. Aerosol filling: 40% active solution, 60% propane / butane (2.5 bar).

[0253] [Table 13]

[0254] Example 15 Preparation of deodorant stick formulations containing compounds of formula (I) of the present invention A typical fragrance-free deodorant stick formulation is shown in Table 13. This deodorant stick formulation is obtained by weighing all ingredients of Part A and heating to 70-75°C. Ceteareth-25 is added after the other ingredients of Part A are mixed and heated. Stearic acid is added after the Ceteareth-25 has dissolved. Part B is prepared by dissolving triclosan in 1,2-propylene glycol. Evaporated water is replaced. Part B is then poured into Part A slowly under mixing.

[0255] [Table 14]

[0256] Next, under gentle shaking, perfume oil (e.g., as described in Example 6, 0.85% by weight based on the total weight of the deodorant stick formulation) and at least one compound of formula (I) of the present invention, such as compounds 37, 33 or 18 (0.10-0.20% by weight based on the total weight of the deodorant stick formulation) are added to obtain a perfumed deodorant stick formulation. After cooling, the plastic bag is placed in a bucket and sealed for storage. The mold is filled at approximately 70°C.

[0257] Example 16 Preparation of deodorant roll-on formulations containing compounds of formula (I) of the present invention A typical fragrance-free deodorant roll-on formulation is shown in Table 14. Part A is made by sprinkling hydroxyethyl cellulose in small amounts into water while rapidly stirring with a turbine until the hydroxyethyl cellulose is completely swollen and forms a clear gel. Part B is slowly poured into Part A and stirring is continued until the entire mixture is homogeneous. Part C is then added.

[0258] [Table 15]

[0259] A perfumed deodorant roll-on formulation is then obtained by adding, under gentle shaking, perfume oil (e.g., as described in Example 6, in an amount of 0.85% by weight relative to the total weight of the deodorant stick formulation) and at least one compound of formula (I) of the present invention, such as, for example, compound 37, 33 or 18 (0.10-0.20% by weight relative to the total weight of the deodorant stick formulation).

[0260] Example 17 Preparation of a day cream base O / W emulsion containing a compound of formula (I) of the present invention A typical day cream base O / W emulsion formulation containing a compound of formula (I) of the present invention is shown in Table 15. Phases A and B are heated separately to 70-75°C, then Phase A is added to Phase B and a vacuum is applied. The mixture is stirred and cooled to 55°C over 15 minutes. After cooling to room temperature, phenoxyethanol (and) piroctone olamine (part C) are added when the mixture reaches 45°C. The mixture is stirred for 5 minutes, after which sodium carbomer (part D), perfume oil (e.g., as described in Example 6), and at least one compound of formula (I) of the present invention (part E) are added. The mixture is stirred for 3 minutes, after which stirring is stopped for 15 minutes. When the temperature of the mixture reaches 30°C, stirring is resumed for an additional 15 minutes until the cream is homogeneous, glossy, and lump-free. If necessary, adjust the pH to 6.70-7.20 with Glydant®, Phenoni® p, or Nipaguard® PO5, or to 6.30-7.00 with Nikkoguard®.

[0261] [Table 16]

[0262] Example 18 Preparation of liquid detergent formulations containing compounds of formula (I) of the present invention A typical liquid detergent formulation is prepared by mixing the components set forth in Table 16. Then, perfume oil (e.g., as described in Example 6, 0.3-0.8% by weight based on the total weight of the liquid detergent) and at least one compound of formula (I) of the present invention, such as compound 37, 33 or 18 (0.05-1.0% by weight based on the total weight of the liquid detergent) are added to the unscented liquid detergent formulation of Table 16 under gentle shaking.

[0263] [Table 17]

[0264] Example 19 Preparation of Hand Dishwashing Detergent Formulations Containing Compounds of Formula (I) of the Present Invention A typical unscented hand dish detergent formulation is shown in Table 17. This unscented hand dish detergent is made by combining water, sodium hydroxide, and diethanolamide. Linear alkylbenzene sulfonic acid is then added. After neutralization, the remaining ingredients are added and the pH is adjusted to 7-8 as needed.

[0265] [Table 18]

[0266] Next, a perfume oil (e.g., 0.85 wt. % based on the total weight of the hand dish detergent formulation, as described in Example 6) and at least one compound of formula (I) of the present invention, such as compound 37, 33 or 18 (0.10-0.20 wt. % based on the total weight of the dish detergent formulation), are added to the unscented hand dish detergent formulation of Table 17 under gentle shaking to obtain a scented hand dish detergent formulation.

Claims

1. below: a) Formula 【Chemical 1】 [In the formula, R １ is C １～１５ Alkyl group, C ３～１５ Alkenyl group, C ６～１０ Aryl group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group or C ３～１４ heterocycloalkyl groups, each of which is a hydroxy group, C １～１５ Alkyl group, C ２～１５ Alkenyl group, C １～１５ Alkoxy group, C ２～１５ Alkenyloxy group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group, C ３～１５ Heterocycloalkyl group, carboxylic acid group, C １～４ Carboxylic acid ester group, C ６～１０ aryl group and / or C ６～１０ aryloxy groups, each of which is optionally substituted by one or more of １～８ Alkyl group, C １～８ Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C １～４ optionally substituted with one or more carboxylic acid ester groups; R ２ is a hydrogen atom, C １～６ represents an alkyl group or a phenyl group; or R １ and R ２ Together, C ５～１６ Cycloalkyl group, C ５～１６ Cycloalkenyl group, C ４～１４ Heterocycloalkyl group or C ４～１４ heterocycloalkenyl groups, each of which is C １～１５ Alkyl group, C ２～１５ Alkenyl group, C １～１５ Alkoxy group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group, C ６～１０ aryl group and / or C ６～１０ aryloxy groups, each of which is optionally substituted by one or more of １～８ Alkyl group, C １～８ Alkoxy groups, carboxylic acid groups and / or C １～４ optionally substituted with one or more carboxylic acid ester groups, wherein the heteroatoms represent one or more oxygen atoms, b) Formula 【Chemistry 2】 [In the formula, R ３ is a hydrogen atom, C １～１０ Alkyl group, C ３～１０ an alkenyl group, a benzyl group, a 2-phenylethyl group, or one, two or three C １～４ C optionally substituted with alkyl groups ５～８ represents a cycloalkyl group; R ４ is a hydrogen atom, C １～６ Alkyl group, phenyl group, or CH ２ C(O)OR ３ represents a group; ３ has the same meaning as defined above; R ５ represents a hydrogen atom or a methyl group], c) Formula 【Chemistry 3】 [In the formula, R ３ , R ４ and R ５ has the same meaning as defined above] 1. A method for releasing a compound selected from the group consisting of: The precursor compound has the formula (I) 【Chemistry 4】 [In the formula, R １ , R ２ , R ３ , R ４ and R ５ has the same meaning as defined above] in the form of any one of its stereoisomers or a mixture thereof, The releasing is effected by exposing the precursor compound of formula (I) to an environment in which the compound is oxidized.

2. R ２ is a hydrogen atom, C １～３ 2. The method of claim 1, wherein the alkyl group represents an alkyl group, preferably a hydrogen atom or a methyl group.

3. R ４ is a hydrogen atom or C １～３ 3. The method according to claim 1 or 2, wherein the alkyl group represents an alkyl group, preferably a hydrogen atom or a methyl group.

4. R ５ is a hydrogen atom or R ４ is a methyl group, R ５ The method according to any one of claims 1 to 3, wherein is a hydrogen atom or a methyl group.

5. R １ is C １～１０ Alkyl group, C ３～１０ Alkenyl group, C ３～１１ Cycloalkyl group or C ５～１１ cycloalkenyl groups, each of which is C １～４ Alkyl group, C １～４ Alkoxy group, C ３～８ Cycloalkyl group, C ５～８ Cycloalkenyl group, C ６ aryl group and / or C ６ aryloxy groups, each of which is optionally substituted by one or more of １～４ alkyl group, hydroxy group and / or C １～４ 5. The method of claim 1, wherein the hydroxyl group is optionally substituted with one or more alkoxy groups.

6. R １ is a naphthyl or phenyl group, and the group is １’ optionally substituted with a group, where R １’ may simultaneously or independently represent a hydroxy group, C １～３ Alkyl group, C １～３ Alkoxy group, R ａ COO group, R ａ represents an OCO group, where R ａ is a hydrogen atom, C １～３ Alkyl group, C ２～３ alkenyl group, or two adjacent R １’ Together, -O-(CH ２ ) ｍ -O- [wherein m is 1 or 2], or C ５～６ 5. The method according to claim 1, wherein a saturated or unsaturated ring is formed.

7. 7. The method according to claim 1, wherein the compounds of formula (II) and / or (IV) are perfuming ingredients.

8. 8. The method of claim 1, wherein the environment in which the compound is oxidized is air.

9. 10. A method for imparting, enhancing, improving or modulating the odor characteristics of a perfumed composition, the air surrounding said perfumed composition, a surface or a perfumed article, said method comprising adding to said composition, said air or said article an effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 8, or contacting said surface with said effective amount or treating said surface with said effective amount.

10. 10. A method for enhancing or prolonging the diffusion effect of the characteristic fragrance of at least one carbonyl compound of formula (II), at least one active formate ester of formula (III) and / or at least one active alcohol of formula (IV) as defined in any one of claims 1 to 8, into a surface or into the air surrounding a perfuming composition, comprising treating said surface or said air with at least one compound (I) as defined in any one of claims 1 to 8, or a composition or article comprising at least one compound (I), under conditions allowing the release over time of at least one ketone or aldehyde of formula (II), at least one formate ester of formula (III) and / or at least one alcohol of formula (IV).

11. i) at least one compound of formula (I) as defined in any one of claims 1 to 8; and ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; iii) optionally at least one flavor adjuvant; A fragrance composition comprising:

12. A scented consumer product comprising at least one compound of formula (I) as defined in any one of claims 1 to 8 or a scenting composition according to claim 11.

13. 13. The scented consumer product of claim 12, wherein the scented consumer product is a perfume, a fabric care product, a body care product, a cosmetic, a skin care product, an air care product, or a home care product.

14. 14. The scented consumer product of claim 13, wherein the scented consumer product is a fine perfume, a splash or eau de perfume, a cologne, a shave or aftershave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, ironing water, paper, bleach, a carpet cleaner, a curtain care product, a shampoo, a coloring formulation, a color care product, a hair styling product, a dental care product, a disinfectant, an intimate care product, a hairspray, a hair conditioning product, a vanishing cream, a deodorant or antiperspirant, a depilatory, a tanning or sun product, a nail product, a skin cleanser, a cosmetic product, a scented 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" powder air freshener, a mold remover, a furniture care product, a wipe, a dish detergent or hard surface cleaner, a leather care product, a car care product.

15. formula 【Chemistry 5】 [In the formula, R １ is C ２～１５ Alkyl group, C ３～１５ Alkenyl group, C ６～１０ Aryl group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group or C ３～１４ heterocycloalkyl groups, each of which is a hydroxy group, C １～１５ Alkyl group, C ２～１５ Alkenyl group, C １～１５ Alkoxy group, C ２～１５ Alkenyloxy group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group, C ３～１５ Heterocycloalkyl group, carboxylic acid group, C １～４ Carboxylic acid ester group, C ６～１０ aryl group and / or C ６～１０ aryloxy groups, each of which is optionally substituted by one or more of １～８ Alkyl group, C １～８ Alkoxy groups, hydroxy groups, carboxylic acid groups and / or C １～４ optionally substituted with one or more carboxylic acid ester groups; R ２ is a hydrogen atom, C １～３ represents an alkyl group or a phenyl group; or R １ and R ２ Together, C ５～１６ Cycloalkyl group, C ５～１６ Cycloalkenyl group, C ４～１４ Heterocycloalkyl group or C ４～１４ heterocycloalkenyl groups, each of which is １～１５ Alkyl group, C ２～１５ Alkenyl group, C １～１５ Alkoxy group, C ３～１５ Cycloalkyl group, C ５～１５ Cycloalkenyl group, C ６～１０ aryl group and / or C ６～１０ aryloxy groups, each of which is optionally substituted by one or more of １～８ Alkyl group, C １～８ Alkoxy groups, carboxylic acid groups and / or C １～４ optionally substituted with one or more carboxylic acid ester groups, wherein the heteroatom represents one or more oxygen atoms; R ３ is C １～１０ Alkyl group, C ３～１０ an alkenyl group, a benzyl group, a 2-phenylethyl group, or one, two or three C １～４ C optionally substituted with alkyl groups ５～８ represents a cycloalkyl group; R ４ is a hydrogen atom, a methyl group, a phenyl group, or CH ２ C(O)OR ３ represents a group; ３ has the same meaning as defined above; R ５ represents a hydrogen atom or a methyl group, with the proviso that R ２ , R ４ and R ５ is a hydrogen atom, R １ is not an unsubstituted phenyl group] in the form of any one of its stereoisomers or mixtures thereof, with the proviso that methyl 2-((2,2-diphenylvinyl)oxy)acetate and ethyl 2-((3-phenylprop-1-en-1-yl)oxy)acetate are excluded.

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