Enol ether fragrance precursor

Abstract

The present invention relates to compounds of formula (I) as fragrance precursor compounds. In particular, the present invention relates to a method for releasing compounds of formula (II) ketones or aldehydes, formula (III) formates and / or formula (IV) alcohols by exposing the compounds of formula (I) to an environment that oxidizes them. Furthermore, the present invention relates to perfuming compositions and perfumed consumer products comprising at least one compound of formula (I).

Description

Technical Field

[0001] The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method for releasing compounds of formula (II) ketones or aldehydes, formula (III) formates and / or formula (IV) alcohols by exposing the compounds of formula (I) to an environment that oxidizes them. Furthermore, the present invention relates to perfuming compositions and perfumed consumer products comprising at least one compound of formula (I). Background Art

[0002] The perfume (daily fragrance) industry is particularly interested in compositions or additives that can simultaneously prolong or enhance the perfuming effect of a mixture of several aromatics over a certain period of time. For standard perfume raw materials, it is particularly necessary to obtain lasting performance, which is too volatile or has poor fragrance retention (substantivity) by itself, or is only deposited on the surface of the final application in small quantities. In addition, some perfume ingredients, especially aldehydes, are unstable and need to be protected before use to prevent their slow degradation. Persistent perfumes are desirable for various applications, such as fine or functional perfumes or cosmetic preparations. The washing and softening of textiles is a specific field in which it is always necessary to make the effect of active substances, especially perfumes or perfumed compositions, effective for a period of time after washing, softening and drying. In fact, it is known that many active substances particularly suitable for this type of application lack persistence (tenacity) on clothing, or are not retained on clothing during rinsing, with the result that their perfuming effect is only experienced briefly rather than very strongly. Considering the importance of this type of application in the perfume industry, research in this field has been continued, especially in order to find new and more effective solutions to the above-mentioned problems.

[0003] Surprisingly, it has been found that the enol ether compounds according to the present invention solve the above problems and can effectively release compounds of ketones or aldehydes of formula (II), formates of formula (III) and / or alcohols of formula (IV). As far as we know, only structural analogs are reported in the prior art, such as WO2014 / 180791 which discloses allyl ether derivatives. Summary of the invention

[0004] Olfactory perception is a complex and dynamic process, and controlling the release profile of volatile aroma compounds can maximize the impact of fragrance formulations and enrich the sensory experience. Fragrance profragrances, such as the compounds of the present invention, increase the control range and persistence of the release profile of highly volatile fragrance raw materials (PRMs).

[0005] Without wishing to be bound by any particular theory, the compounds of the present invention may achieve their effect on the olfactory properties of a perfuming composition by tethering the PRM to a molecular anchor and requiring a specific reaction mechanism under certain environmental conditions to release the PRM from this anchor point. In the present invention, when the fragrance pro-fragrance is exposed to oxygen in the ambient air, a binary release of the two PRMs is facilitated by oxidation.

[0006] A first object of the present invention is a method for releasing a compound selected from the group consisting of:

[0007] a) a ketone or aldehyde of formula (II),

[0008]

[0009] Wherein n represents an integer from 0 to 5;

[0010] R 1 Simultaneously or independently represent at least one substituent of an aromatic ring and are hydroxyl, C 1-6 Alkyl, C 1-6 Alkoxy or RCOO, ROCO groups, where R is a hydrogen atom or C 1-4 Alkyl; or two adjacent R 1 When combined together, it represents -O-(CH 2 ) m O-, where m is 1 or 2, or forms C 5-10 A saturated or unsaturated ring, optionally substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 Alkoxy;

[0011] R 2 represents hydrogen atom, C 1-6 Alkyl or C 6-10 Aryl, optionally substituted with hydroxyl, C 1-3 Alkyl, C 1-3 Alkoxy, RCOO or ROCO group, in which R is independently a hydrogen atom or a C 1-4 alkyl;

[0012] b) a formic acid ester of the formula (III),

[0013]

[0014] Where R 3 , R 4 and R 5 represents simultaneously or independently a hydrogen atom or a C optionally containing 1 to 3 oxygen atoms 1-18 Hydrocarbyl; or R 3 and R 4When combined together, it represents a C optionally containing 1 to 3 oxygen atoms. 3-18 a hydrocarbon group; and

[0015] c) an alcohol of formula (IV),

[0016]

[0017] Where R 3 , R 4 and R 5 has the same meaning as defined above;

[0018] wherein at least one of the compounds of formula (II), formula (III) or formula (IV) is an active compound,

[0019] Wherein the precursor compound comprises a compound of formula (I),

[0020]

[0021] Where n, R 1 , R 2 , R 3 , R 4 and R 5 has the same meaning as defined above

[0022] The process is carried out by exposing a precursor compound of formula (I) to an environment in which the compound is oxidized; ie ambient conditions.

[0023] The terms "active compound", "active volatile compound", "active volatile aldehyde, ketone, formate and / or alcohol" or similar are used herein to refer to an aldehyde, ketone, formate and / or alcohol compound which is capable of bringing a benefit or effect to its surroundings. In particular, the "active compound" is selected from the group consisting of a perfuming ingredient, a flavoring ingredient, a malodor counteracting ingredient or an insect repellent or attractant ingredient. Therefore, to be considered an "active compound" a compound must have at least one property which makes it useful as a perfuming ingredient, as a malodor counteracting ingredient, as a flavoring ingredient, and / or as an insect repellent or attractant.

[0024] The term "perfuming ingredient" is understood as a compound that is used as an active ingredient in a perfuming preparation or composition to impart a hedonic effect. In other words, to be considered a perfuming ingredient, such a compound must be recognized by a person skilled in the art of perfumery as being able to impart or change the smell of a composition in an active or pleasant manner, rather than just having a smell. The term "flavoring ingredient" is understood as being able to impart a taste sensation to a pallet of a taster. The term "malodor counteracting ingredient" is understood as being able to reduce the perception of malodors (i.e., odors that are unpleasant or offensive to the human nose). The term "attractant or repellent" is understood as a compound that has a positive or negative effect on insects. Examples of attractant or repellent ingredients can be found in references or other works of similar nature, for example: AMEl-Sayed, The Pherobase 2005, http: / / www.pherobase.net.

[0025] According to the above and below mentioned embodiments of the present invention, when the active compound is a perfuming ingredient, i.e., a perfuming aldehyde, ketone, formate and / or alcohol, the method according to the present invention is particularly useful. "Perfuming aldehydes, ketones, formate and / or alcohols" are compounds used in the perfume industry, i.e., compounds used as active ingredients in perfuming preparations or compositions to impart a hedonic effect. In other words, to be considered as perfuming aldehydes, ketones, formate and / or alcohols, they must be recognized by the technicians in the field of perfumery as being able to impart or modify the smell of the composition in an active or pleasant manner, rather than just having a smell. Perfuming aldehydes, ketones, formate and / or alcohols can be natural or synthetic. In any case, many of these auxiliary ingredients are listed in references such as S. Arctander's work Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated version or other works of similar nature, as well as in the rich patent literature in the field of perfumery.

[0026] The term "perfuming aldehydes, ketones, formates and / or alcohols" as described herein is also referred to as "perfuming compounds".

[0027] In fact, the present invention proceeds in exactly the same way, regardless of the exact nature of the active aldehyde, ketone, formates or alcohols. Therefore, it should be understood that even though the invention will be further described hereinafter with specific reference to "perfuming compounds", the following embodiments are also applicable to other active aldehydes, ketones, formates and / or alcohols (i.e., for example, "perfuming" may be replaced by "flavoring", "malodor counteracting", "insect attracting" or "insect repelling").

[0028] The term "hydrocarbon group" is to be understood as a group consisting of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e. a straight-chain or branched saturated hydrocarbon (e.g. an alkyl), a straight-chain or branched unsaturated hydrocarbon (e.g. an alkenyl or alkynyl), a saturated cyclic hydrocarbon (e.g. a cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. a cycloalkenyl or cycloalkynyl), or may be in the form of an aromatic hydrocarbon, i.e. an aryl, or may also be in the form of a mixture of the types of groups mentioned, for example, unless specifically restricted to only one type mentioned, a particular group may contain straight-chain alkyl, branched alkenyl (e.g. with one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties. Similarly, in all embodiments of the present invention, when referring to a group in the form of more than one type of topology (e.g. straight-chain, cyclic or branched) and / or saturation or unsaturation (e.g. alkyl, aromatic or alkenyl), it also means that it may contain groups having any of the topologies or saturated or unsaturated moieties as described above. Similarly, in all embodiments of the present invention, when referring to a group in a form of saturation or unsaturation (e.g., alkyl), it is meant that the group can be of any type of topology (e.g., straight chain, cyclic or branched) or have several parts with various topological structures. The term "arylalkyl" has the normal meaning of the art, i.e., it is an acyclic alkyl group in which one hydrogen atom is replaced by an aryl group. The term "alicyclic group" has the normal meaning of the art; i.e., it is an organic compound that is both aliphatic and cyclic, and it contains one or more all-carbon rings that can be saturated or unsaturated.

[0029] The expression "comprising 1 to 3 oxygen atoms" or similar expressions is understood to include functional groups such as ether, acetal, ester, aldehyde, ketone, carboxylate or alcohol.

[0030] The expression "substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 "Alkoxy" or similar expressions are understood to mean substituted with 1 to 4 hydroxyl groups, 1 to 6 C 1-3 Alkyl and / or 1 to 6 C 1-3 Alkoxy, especially substituted with 1 to 3 hydroxyl groups, 1 to 5 C 1-3 Alkyl and / or 1 to 3 C 1-3 Alkoxy.

[0031] According to any of the above embodiments, compounds of formula (I) and formula (II) are defined, wherein n is 0, 1 or 2. Preferably, n may be 0 or 1.

[0032] According to any embodiment, compounds of formula (I) and formula (II) are defined, wherein R 1 Simultaneously or independently represent a hydroxyl group, C 1-4 Alkyl or C 1-3 Alkoxy; or two adjacent R1 When combined together, it represents -O-CH 2 -O- group, -(CH 2 ) 4 -yl, -(CH) 4 Preferably, compounds of formula (I) and formula (II) are defined, wherein R 1 Simultaneously or independently represent methyl, ethyl, methoxy, ethoxy; or two adjacent R 1 When combined together, it represents -(CH 2 ) 4 - or -(CH) 4 -base.

[0033] According to any embodiment, compounds of formula (I) and formula (II) are defined, wherein R 2 represents hydrogen atom, C 1-3 Preferably, R 2 Can represent a hydrogen atom, a methyl group or a phenyl group.

[0034] According to any of the above embodiments, R 3 , R 4 and R 5 The group contains at least 5 carbon atoms.

[0035] According to any embodiment, the compound of formula (III) is derived from a C 5-18 The formula of the compound (R 3 )(R 4 )(R 5 )COH active alcohol.

[0036] According to any embodiment, the compound of formula (IV) is a compound having a molecular weight of 80 to 230 g / mol and is C 5-18 The formula of the compound (R 3 )(R 4 )(R 5 )COH active alcohol.

[0037] According to any embodiment, compounds of formula (I), formula (III) and formula (IV) are defined, wherein R 3 represents a C optionally containing 1 to 3 oxygen atoms 2-18 Preferably, compounds of formula (I), formula (III) and formula (IV) are defined, wherein R 3 Can represent C 4-10 Straight-chain, branched or cyclic alkyl, alkenyl or diene group, phenyl, benzyl, C 7-16 Arylalkyl or styryl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3Alkoxy, phenoxymethyl or C 8-15 A saturated or unsaturated alicyclic group, which optionally contains an ether functional group. 3 Can represent C 4-10 Straight-chain, branched or cyclic alkyl or alkenyl, phenyl, benzyl, or C 7-10 Arylalkyl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3 Alkoxy, phenoxymethyl or C 8-15 A saturated or unsaturated alicyclic group, which optionally contains an ether functional group. 3 Can represent C 4-10 Straight-chain, branched or cyclic alkyl or alkenyl, phenyl, benzyl, or C 7-10 Arylalkyl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3 More preferably, R 3 Can represent C 4-10 Straight-chain, branched or cyclic alkyl or alkenyl, phenyl, benzyl or phenoxymethyl.

[0038] According to any embodiment, R 4 and R 5 can represent hydrogen atoms or C 1-6 Alkyl or C 2-6 Preferably, R 4 and R 5 can represent hydrogen atoms or C 1-6 Preferably, R 4 and R 5 can represent hydrogen atoms or C 1-3 Preferably, R 4 Can represent hydrogen atoms or C 1-3 Alkyl, and R 5 Can represent a hydrogen atom or a methyl group. Even more preferably, R 4 can represent a hydrogen atom or a methyl group, and R 5 Can represent a hydrogen atom or a methyl group.

[0039] According to any embodiment, when R 3 and R 4 When combined together, it can represent C 5-12 A straight-chain or branched alkanediyl or alkenediyl, or C 5-12 Preferably, when R 3 and R 4 When combined together, it can represent C 8-12 Even more preferably, when R 3 and R4 When combined together, it can represent C 8-12 A straight-chain or branched alkanediyl group.

[0040] According to any embodiment, the aldehyde or ketone of formula (II), the formic ester of formula (III) and / or the active alcohol of formula (IV) are perfuming ingredients. For a person skilled in the art, it is obvious that the compounds of the present invention are inherently volatile compounds. According to any embodiment, at least one of the compounds of formula (II), formula (III) or formula (IV) is a perfuming ingredient. Preferably, at least two of the compounds of formula (II), formula (III) or formula (IV) are perfuming ingredients.

[0041] The aldehydes, ketones, formates and / or alcohols may advantageously be characterized by a vapor pressure higher than 1.0 Pa, calculated using the software EPIwin v.3.10 (2000, available from the U.S. Environmental Protection Agency). According to another embodiment, the vapor pressure of the aldehydes, ketones, formates and / or alcohols may be higher than 5.0, or even higher than 7.0 Pa. In some embodiments, the vapor pressure of the aldehydes, ketones, formates and / or alcohols may be lower than 1.0 Pa.

[0042] In one embodiment, the compound of formula (I) is non-volatile. The compound of formula (I) can advantageously be characterized by a vapor pressure below 0.01 Pa, as calculated using the software EPIwin v.3.10 (2000, available from the U.S. Environmental Protection Agency). According to one embodiment, the vapor pressure is below 0.001 Pa.

[0043] According to any embodiment, the ketone or aldehyde of formula (II) is selected from the group consisting of benzaldehyde, 4-methylbenzaldehyde, 4-ethylbenzaldehyde, 4-isopropylbenzaldehyde, 4-(tert-butyl)benzaldehyde, 4-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, benzo[d][1,3]dioxole-5-carbaldehyde, vanillin, 3-ethoxy-4-hydroxybenzaldehyde, 4-formyl-2-methoxyphenyl acetate, 4-formyl-2-methoxyphenyl isobutyrate, 3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde, acetophenone, propiophenone, 2-methyl-1-phenylpropan-1-one, p-methylacetophenone, p-isopropylacetophenone, p-tert-butylacetophenone, p-methoxyacetophenone, diphenylacetophenone, 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one, 1-(naphthalen-2-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-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one -yl)ethan-1-one, 1-(6-tert-butyl-1,1-dimethyl-4-indanyl)-1-ethanone, (3-isopropyl-1,1,2,6-tetramethyl-5-indanyl)-1-ethanone, 4-tert-butyl-2,6-dimethyl-1-phenylacetophenone and 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthyl)-1-ethanone.

[0044] According to any embodiment, the ketone or aldehyde of formula (II) is selected from the group consisting of: acetophenone, benzaldehyde, benzophenone, p-methylacetophenone, p-methoxyacetophenone, 1-(naphthalen-2-yl)ethan-1-one, 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one, propiophenone, 1-phenylbutan-1-one and 2-methyl-1-phenylpropan-1-one.

[0045] According to any embodiment, the formic acid ester of formula (III) is selected from the group consisting of phenylethyl formate, 3,7-dimethyloct-6-en-1-yl formate, 2-phenoxyethyl formate, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hex-3-yl formate, oct-3-yl formate, (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexyl formate, 1-((2-(tert-butyl)cyclohexyl)oxy)but-2-yl formate, 2,6-dimethyloct-7-en-2-yl formate, 3,7-dimethyloct-7-en-2-yl formate, 3-Methyloctyl formate, 2-methyl-1-phenylpropan-2-yl formate, 2,6-dimethylhept-2-yl formate, methyl formate, ethyl formate, propyl formate, isopropyl formate, butyl formate, pentyl formate, 2-methylbutyl formate, 3-methylbutyl formate, butyl-2-formate, 2-methylpropyl formate, cyclohexyl formate, hexyl formate, heptyl formate, octyl formate, nonyl formate, decyl formate, 3-octyl formate, benzyl formate, 3,7-dimethyloct-6-enyl formate, cinnamyl formate, 4-methoxybenzyl formate, (E)-3,7-dimethyl formate Oct-2,6-dien-1-yl formate, (Z)-3,7-dimethyloct-2,6-dien-1-yl formate, 2-hexenyl formate, 3-hexenyl formate, 3,5,5-trimethylhexyl formate, 2-phenylethyl formate, 2-(phenoxy)ethyl formate, 3-phenylpropyl formate, 3-methylbut-2-enyl formate, bornyl formate, isobornyl formate, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-yl formate, cedryl formate, cyclododecyl formate, decahydronaphthalen-2-yl formate , menthyl formate, 1-phenylethyl formate, 5-methyl-2-(prop-1-en-2-yl)cyclohexyl formate, 3a,4,5,6,7,7a-hexahydro-1H-4,7-dimethanoinden-5-yl formate, 3a,4,5,6,7,7a-hexahydro-1H-4,7-dimethanoinden-6-yl formate, 1-(3,3-dimethylcyclohexyl)ethyl formate, 2-methyl-1-phenylprop-2-yl formate and 3,7-dimethylocta-1,6-dien-3-yl formate and 2,6-dimethylocta-2,7-dien-1-yl formate.

[0046] According to any embodiment, the formate (III) is selected from the group consisting of phenylethyl formate, 3-hexenyl formate, octyl formate, decyl formate, 3,7-dimethyloct-6-en-1-yl formate, 2-phenoxyethyl formate, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hex-3-yl formate, hexyl formate, benzyl formate, oct-3-yl formate, (1RS,2 SR,5RS)-2-isopropyl-5-methylcyclohexyl ester, cyclododecyl formate, 1-(3,3-dimethylcyclohexyl)ethyl formate, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-yl formate, 2,6-dimethyloct-7-en-2-yl formate, 3,7-dimethyloct-3-yl formate, 2-methyl-1-phenylpropan-2-yl formate, 2,6-dimethylhept-2-yl formate.

[0047] According to any embodiment, the alcohol is selected from the group consisting of 2-phenylethan-1-ol, octan-1-ol, hex-3-en-1-ol, 3,7-dimethyloct-6-en-1-ol, decan-1-ol, 2-phenoxyethan-1-ol, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-ol, octan-3-ol, (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexan-1-ol, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethyl Octanol, 2-methyl-1-phenylpropan-2-ol, 2,6-dimethylheptan-2-ol, methanol, ethanol, propan-1-ol, propan-2-ol, butan-1-ol, pentan-1-ol, 2-methylbutan-1-ol, 3-methylbutan-1-ol, butan-2-ol, 2-methylpropan-1-ol, cyclohexanol, hexan-1-ol, heptan-1-ol, nonan-1-ol, phenylmethanol, 3,7-dimethyloct-6-en-1-ol, 3-phenylprop-2-en-1-ol, (4-methoxyphenyl)methanol, (E)-3,7-dimethyloct-2,6-dien-1-ol, (Z)-3,7-di methylocta-2,6-dien-1-ol, hex-2-en-1-ol, 3,5,5-trimethylhexan-1-ol, 3-phenylpropan-1-ol, 3-methylbut-2-en-1-ol, 1,7,7-trimethylbicyclo[2.2.1]hept-2-ol, 1,7,7-trimethylbicyclo[2.2.1]hept-2-ol, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol, (3S,3aR,6R,7S,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene-3-ol, cyclododecanol, decanol Hydronaphthalen-2-ol, 2-isopropyl-5-methylcyclohexan-1-ol, 1-phenylethan-1-ol, 5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-ol, 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-ol, 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-6-ol, 1-(3,3-dimethylcyclohexyl)ethan-1-ol, 2-methyl-1-phenylpropan-2-ol, 3,7-dimethylocta-1,6-dien-3-ol and 2,6-dimethylocta-2,7-dien-1-ol.

[0048] According to any embodiment, the alcohol is selected from the group consisting of: 2-phenylethan-1-ol, octan-1-ol, hex-3-en-1-ol, hept-1-ol, nonan-1-ol, decan-1-ol, 2-phenoxyethan-1-ol, 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-ol, hexan-1-ol, phenylmethanol, octan-3-ol, 3,7-dimethyloct-6-en-1 -ol, (1RS,2SR,5RS)-2-isopropyl-5-methylcyclohexan-1-ol, cyclododecanol, 1-(3,3-dimethylcyclohexyl)ethan-1-ol, 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol, 2,6-dimethyloct-7-en-2-ol, 3,7-dimethyloctan-3-ol, 2-methyl-1-phenylpropan-2-ol and 2,6-dimethylheptan-2-ol.

[0049] According to any embodiment, the compound of formula (I) is selected from the group consisting of: (1-(octyloxy)prop-1-en-2-yl)benzene, (1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)benzene, (1-(decyloxy)prop-1-en-2-yl)benzene, (1-phenylethoxyprop-1-en-2-yl)benzene, (1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)benzene, (1-(2-phenoxyethoxy)prop-1-en-2-yl)benzene, (1-((1-((1R,6S)-2,2,6-trimethylcyclohexyl)hex-3-yl)oxy)prop-1-en-2-yl)benzene 1-en-2-yl)benzene, (1-(hexyloxy)prop-1-en-2-yl)benzene, (1-(benzyloxy)prop-1-en-2-yl)benzene, (1-(oct-3-yloxy)prop-1-en-2-yl)benzene, (1-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)prop-1-en-2-yl)benzene, ((2-phenylprop-1-en-1-yl)oxy)cyclododecane, (1-(1-(3,3-dimethylcyclohexyl)ethoxy)prop-1-en-2-yl)benzene, (1-((1-((2-(tert-butyl)cyclohexyl)oxy)but-2-yl)oxy)prop-1-en-2-yl)benzene, (1-((2,6-dimethyl 1-en-2-yl)benzene, (1-((3,7-dimethyloct-3-yl)oxy)prop-1-en-2-yl)benzene, (1-((2-methyl-1-phenylprop-2-yl)oxy)prop-1-en-2-yl)benzene, (1-((2,6-dimethylhept-2-yl)oxy)prop-1-en-2-yl)benzene, (2-(((Z)-hex-3-en-1-yl)oxy)vinyl)benzene, (2-phenylethoxyvinyl)benzene, (2-((3,7-dimethyloct-6-en-1-yl)oxy)vinyl)benzene, (2-(oct-3-yloxy)vinyl)benzene, (2-(2-phenoxyethoxy)vinyl 1-(((Z)-hex-3-en-1-yloxy)prop-1-en-2-yl)-4-methylbenzene, 1-(1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)-4-methylbenzene, 1-(1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)-4-methylbenzene, 1-(1-(((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)-4-methylbenzene, 1-methyl-4-(1-(2-phenoxyethoxy)prop-1-en-2-yl)benzene, 6-(1-phenoxyprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene, 6-(1-(hexyloxy)prop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene, 6-(1-(octyloxy)prop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene, 6-(1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene 6-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene, 6-(1-(2-phenoxyethoxy)prop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene, 2-(1-phenylethoxyprop-1-en-2-yl)naphthalene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, 2-(1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)naphthalene , 2-(1-(pentyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(hexyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(octyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(2-phenoxyethoxy)prop-1-en-2-yl)naphthalene, 2-(1-(heptyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(nonyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(decyloxy)prop-1-en-2-yl)naphthalene, 2-(1-(oct-3-yloxy)prop-1-en-2-yl)naphthalene, 1-(1-( ((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)-4-methoxybenzene, 1-methoxy-4-(1-(octyloxy)prop-1-en-2-yl)benzene, 1-methoxy-4-(1-phenoxyprop-1-en-2-yl)benzene, 1-(1-(hexyloxy)prop-1-en-2-yl)-4-methoxybenzene, 1-methoxy-4-(1-(2-phenoxyethoxy)prop-1-en-2-yl)benzene and 1-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)-4-methoxybenzene. ,

[0050] In one embodiment, at least two of the compounds of Formula (II), Formula (III) or Formula (IV) are active compounds.

[0051] In another embodiment, the compound of Formula (II), Formula (III) or Formula (IV) is the active compound.

[0052] According to any embodiment, the ketone or aldehyde 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. Even, the precursor compound of formula (I) is oxidized under ambient conditions and without any catalyst. For the sake of clarity, the normal meaning understood by those skilled in the art is represented by the expression "ambient conditions" or similar terms, that is, oxidation occurs at room temperature in air, sunlight and atmospheric pressure. In other words, the environment in which the compound is oxidized is air. It can be understood from this that the compound of formula (I) is oxidized in ambient air. In particular, it should be understood that the compound of formula (I) does not require a pure oxygen environment, heat or catalyst to oxidize.

[0053] Without wishing to be bound by any particular theory, the rate at which the precursor compound of formula (I) is oxidized may be greater than, equal to, or slower than the rate at which the respective ketone or aldehyde of formula (II), the respective formate of formula (III), or the respective alcohol of formula (IV) evaporates.

[0054] In some embodiments, the rate at which the precursor compound of formula (I) is oxidized, and thereby the rate at which the respective ketone or aldehyde of formula (II), the respective formate of formula (III), or the respective alcohol of formula (IV) is released, enhances or prolongs the diffusion effect and / or the perceived characteristic aroma of at least one active aldehyde or ketone of formula (II), at least one active formate of formula (III), and / or at least one active alcohol of formula (IV) as defined above.

[0055] In one embodiment, 100% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 90% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 80% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 70% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 60% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 50% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 40% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 30% of the compound of formula (I) is oxidized within a period of 24 to 48 hours in ambient air. Alternatively, 20% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 10% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 9% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 8% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 7% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 6% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 5% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 4% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 3% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 2% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 1% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours.

[0056] In one embodiment, the compound of formula (I) is encapsulated. At least one compound of formula (I) can be encapsulated in microcapsules. In one embodiment, at least one compound of formula (I) is encapsulated in core-shell microcapsules, wherein the compound of formula (I) is contained in a core surrounded by a shell. The shell of the microcapsule protects the compound of formula (I) from environmental influences. The shell is made of a material capable of releasing the compound of formula (I) and / or the active compound of formula (II), formula (III) and / or formula (IV). In one embodiment, the shell is made of a material capable of releasing the compound of formula (I) and / or the active compound of formula (II), formula (III) and / or formula (IV) when the shell is broken and / or by diffusion through the shell. Those skilled in the art are familiar with the method for preparing the microcapsules.

[0057] The nature of the polymer shell from the microcapsules of the present invention can vary. As non-limiting examples, the shell can be aminoplast-based, polyurea-based or polyurethane-based. The shell can also be composite, i.e., organic-inorganic, such as a composite shell composed of at least two cross-linked inorganic particles, or a shell produced by the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0058] According to one embodiment, the shell comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine-formaldehyde or melamine-glyoxal.

[0059] According to another embodiment, the shell is polyurea-based, made from, for example but not limited to, isocyanate-based monomers and amine-containing crosslinking agents such as guanidine carbonate and / or guanazole. Preferred polyurea-based microcapsules comprise: a polyurea wall, which is a polymeric reaction product between at least one polyisocyanate containing at least two isocyanate functional groups and at least one reactant selected from amines (e.g., water-soluble guanidine salts and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of amines can be omitted.

[0060] According to a specific embodiment, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% of a cationic copolymer of vinyl pyrrolidone and quaternized vinyl imidazole (all percentages are defined relative to the total weight of the colloidal stabilizer). According to another embodiment, the emulsifier is an anionic or amphiphilic biopolymer, preferably selected from gum arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0061] According to another embodiment, the shell is polyurethane based, made from, for example but not limited to, polyisocyanates and polyols, polyamides, polyesters, and the like.

[0062] The preparation of aqueous dispersion / slurry of core-shell microcapsules is well known to those skilled in the art. On the one hand, the microcapsule wall material can include any suitable resin and especially include melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction product of aldehydes and amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril and their mixtures. Suitable melamines include methylol melamine, methylated methylol melamine, imino melamine and their mixtures. Suitable ureas include dimethylol urea, methylated dimethylol urea, urea-resorcinol and their mixtures. Suitable manufacturing materials can be obtained from one or more of Solutia Inc. (St Louis, Missouri USA), Cytec Industries (West Paterson, New Jersey USA), Sigma-Aldrich (St.Louis, Missouri USA).

[0063] According to a specific embodiment, the core-shell microcapsules are formaldehyde-free capsules. A typical method for preparing an aminoplast-free formaldehyde-free microcapsule slurry comprises the following steps: 1) preparing an oligomeric composition comprising the reaction product of the following ingredients, or an oligomeric composition obtained by reacting the following ingredients together:

[0064] a) in the form of melamine or melamine and at least one 2 Functional group C 1 -C 4 a polyamine component in the form of a mixture of compounds;

[0065] b) Glyoxal, C 4-6 The aldehyde component is in the form of a mixture of 2,2-dialkoxyacetaldehyde and optionally glyoxylate, the glyoxal / C 4-6 The molar ratio of 2,2-dialkoxyethanol is 1 / 1 to 10 / 1; and

[0066] c) protonic acid catalyst;

[0067] 2) preparing an oil-in-water dispersion, wherein the droplet size is 1 to 600 μm, and comprising:

[0068] i.Oil;

[0069] ii. Water medium

[0070] iii. at least one oligomeric composition as obtained in step 1;

[0071] iv. at least one cross-linking agent selected from the group consisting of:

[0072] A)C 4 -C 12 Aromatic or aliphatic di- or triisocyanates and their biuret, triuret, trimer, trimethylolpropane adducts and mixtures thereof; and / or

[0073] B) a di- or tri-oxirane compound of the formula

[0074] A-(Oxiran-2-ylmethyl) n

[0075] wherein n represents 2 or 3, and l represents a C optionally containing 2 to 6 nitrogen and / or oxygen atoms 2 -C 6 Group;

[0076] v.Optionally, contains two NH 2 Functional group C 1 -C 4 Compounds;

[0077] 3) heating the dispersion;

[0078] 4) Cooling the dispersion.

[0079] This method is described in more detail in WO 2013 / 068255, the contents of which are incorporated herein by reference.

[0080] According to another embodiment, the shell of the microcapsule is polyurea-based or polyurethane-based. Examples of methods for preparing polyurea-based and polyurethane-based microcapsule slurries are described, for example, in WO2007 / 004166, EP2300146, EP2579976, the contents of which are also incorporated herein by reference. A method generally used to prepare a polyurea-based or polyurethane-based microcapsule slurry comprises the following steps:

[0081] a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase;

[0082] b) preparing an aqueous solution of an emulsifier or a colloid stabilizer to form an aqueous phase;

[0083] c) adding the oil phase to the water phase to form an oil-in-water dispersion, wherein the average droplet size is 1 to 500 μm, preferably 5 to 50 μm;

[0084] d) applying conditions sufficient to initiate interfacial polymerization and form microcapsules in the form of a slurry.

[0085] In some forms, encapsulation of the compound of formula (I) can provide an environment within the capsule where all or a portion of the compound of formula (I) can be oxidized, thereby releasing the respective ketone or aldehyde of formula (II), the respective formate of formula (III), or the respective alcohol of formula (IV) into the capsule. In some embodiments, the shell of the microcapsule can act as a permeation barrier to prevent the respective ketone or aldehyde of formula (II), the respective formate of formula (III), or the respective alcohol of formula (IV) from leaking out of the capsule.

[0086] Examples of microcapsules suitable for use in the present invention include, but are not limited to, microcapsules disclosed in International Patent Application Publication No. WO 2007 / 026307 A2. Other examples include microcapsules disclosed in International Patent Application Publication No. WO 2014 / 029695 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2006 / 006003 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2006 / 018964 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2007 / 096790 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2009 / 153695 A1. Additional examples include microcapsules disclosed in European Patent No. EP2379047.

[0087] Examples of methods for encapsulating compounds of formula (I) include, but are not limited to, microcapsules disclosed in International Patent Application Publication No. WO 2007 / 026307 A2. Other examples include microcapsules disclosed in International Patent Application Publication No. WO 2014 / 029695 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2006 / 006003 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2006 / 018964 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2007 / 096790 A1. Additional examples include microcapsules disclosed in International Patent Application Publication No. WO 2009 / 153695 A1. Additional examples include microcapsules disclosed in European Patent No. EP2379047.

[0088] Another object of the invention is a method or process for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition or article an effective amount of at least one compound of formula (I) as defined above 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 user's skin, hair, fabric or hard surface to which a perfume composition comprising or containing at least one compound of formula (I) is applied.

[0089] Another object of the present invention is a method for enhancing or prolonging the diffusion and / or perception of the characteristic aroma of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive 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 preparation comprising at least one compound of formula (I), under conditions suitable to allow release of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive alcohol of formula (IV) over time.

[0090] Furthermore, the present invention relates to a perfuming composition comprising:

[0091] i) at least one compound of formula (I) as defined above;

[0092] ii) an ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and

[0093] iii) optionally, at least one flavor adjuvant.

[0094] By "perfume carrier" it is meant here a material which is practically neutral from a perfume point of view, ie which does not significantly alter the organoleptic properties of the perfuming ingredient. The carrier may be liquid or solid.

[0095] As liquid carrier, there may be cited, as non-limiting examples, emulsifying systems, i.e. solvents and surfactant systems, or solvents commonly used in perfumes. A detailed description of the properties and types of solvents commonly used in perfumes is not exhaustive. However, there may be cited, as non-limiting examples, solvents such as butylene glycol or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriol triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetoxyprop-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethanol, triethyl citrate or mixtures thereof, which are the most commonly used. For compositions comprising both a perfume carrier and a perfume base, in addition to those described in detail above, other suitable perfume carriers may also be ethanol, a water / ethanol mixture, limonene or other terpenes, isoparaffins, such as those sold under the trademark Those known as (source: Exxon Chemical), or glycol ethers and glycol ether esters, such as those sold under the trademark Those known as castor oil (source: Dow Chemical Company), or hydrogenated castor oil, such as those sold under the trademark RH 40 Those known per se (source: BASF).

[0096] Solid carrier refers to a kind of material, and some composition of perfuming composition or perfuming composition can be combined with it chemically or physically.Usually, use such solid carrier to stabilize composition, or control the evaporation rate of composition or some composition.Solid carrier is what uses in this field at present, and those skilled in the art know how to reach the desired effect.Yet, as the non-limiting example of solid carrier, can enumerate absorption gum or polymer or inorganic material, for example porous polymer, cyclodextrin, wood-based material, organic or inorganic gel, clay, gypsum, talcum or zeolite.

[0097] As other non-limiting examples of solid carriers, encapsulating materials can be cited. Examples of such materials may include wall-forming materials and plasticizing materials, such as monosaccharides, disaccharides or trisaccharides, natural or modified starch, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, or in references such as H.Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Materials listed in Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a process well known to the person skilled in the art and may be performed, for example, using techniques such as spray drying, agglomeration or extrusion; or consist of coating encapsulation including coacervation and complex coacervation techniques.

[0098] As non-limiting examples of solid supports, one may in particular cite core-shell capsules using resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or mixtures thereof (all said resins being well known to a person skilled in the art), by a phase separation process initiated using techniques such as polymerization, interfacial polymerization, coacervation or these techniques together (all said techniques having been described in the prior art), and optionally in the presence of polymeric stabilizers or cationic copolymers.

[0099] The resins may be produced by polycondensation of aldehydes such as formaldehyde, 2,2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof with amines such as urea, benzoguanamine, glycoluryl, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and the like and mixtures thereof. Alternatively, preformed resins may be used, such as those sold under the trademark (Source: Cytec Technology Corp.), (Source: Cytec Technology Corp.), or (Source: BASF) Those that are commercially available.

[0100] Other resins are obtained by mixing a polyol such as glycerol with a polyisocyanate such as a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate, or a biuret of hexamethylene diisocyanate, or a trimer of xylylene diisocyanate and trimethylolpropane (known under the trade name Known sources: those produced by the polycondensation of xylylene diisocyanate (source: Mitsui Chemicals), wherein the trimer of xylylene diisocyanate with trimethylolpropane and the biuret of hexamethylene diisocyanate.

[0101] Some research literature related to the encapsulation of spices by condensation of amino resins, i.e. melamine-based resins, with aldehydes includes articles such as Acta Polymerica, 1989, vol. 40, pages 243, 325 and 683 and 1990, vol. 41, page 91 published by K. Dietrich et al. These articles have described various parameters affecting the preparation of such core-shell microcapsules according to prior art methods, which are also further detailed and exemplified in patent literature. US 4'396'670 of Wiggins Teape Group Limited is a relevant early example of the latter. Since then, many other authors have enriched the literature in this field, and it is impossible to cover all the published progress here, but general knowledge of encapsulation technology is very important. More recent targeted publications also involve the suitable use of such microcapsules, such as the articles Journal of Microencapsulation, 2002, vol. 19, pages 559-569 by HY Lee et al., International Patent Publication WO01 / 41915 or S. et al., Chimia, 2011, vol. 65, pages 177-181.

[0102] The term "perfume base" is to be understood as a composition comprising at least one perfuming co-ingredient.

[0103] Said perfuming co-ingredients are not compounds according to the invention. Furthermore, the term "perfuming co-ingredient" is to be understood as a compound which is used in perfuming preparations or compositions to impart a hedonic effect. In other words, to be considered a perfuming co-ingredient such a co-ingredient must be recognized by a person skilled in the art as being able to impart or modify the odor of a composition in an active or pleasant manner, rather than merely possessing an odor.

[0104] The nature and types of perfuming co-ingredients present in the base do not warrant a more detailed description here, which is in any case non-exhaustive and a person skilled in the art will be able to choose them according to his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and they may be of natural or synthetic origin.

[0105] In particular, one may cite perfuming co-ingredients known to have similar olfactory notes, for example:

[0106] In particular, one may cite the perfuming auxiliary ingredients usually used in perfume formulations, for example:

[0107] - Aldehyde aroma components: decanal, dodecanal, 2-methylundecane, 10-undecenal, octanal and / or nonenal;

[0108] - aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, menthol and / or alpha-pinene;

[0109] - balsamic ingredients: coumarin, ethyl vanillin and / or vanillin;

[0110] - Citrus aroma ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthenadiene;

[0111] -Floral fragrance ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethyl alcohol, 3-(4-tert-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, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, tricyclodecenyl acetate, geraniol, p-menthen-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, methyl homo-dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, (S)-2-(1,1-dimethylpropoxy)propyl propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amyl cinnamaldehyde, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate and / or a mixture of methylionone isomers;

[0112] -Fruit aroma ingredients: γ-undecalactone, 4-decanoic acid ethyl ester, hexyl acetate, 2-methylbutyric acid ethyl ester, γ-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate and / or diethyl 1,4-cyclohexanedicarboxylate;

[0113] - Green aroma ingredients: 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styroyl acetate, (2-methylbutoxy) allyl 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;

[0114] - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, pentadecenolide, 3-methyl-5-cyclopentadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[G]-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, pentadecenolide and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate;

[0115] - Woody components: 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-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;

[0116] -Other ingredients (e.g. ambery, powdery, spicy or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal and / or 3-(3-isopropyl-1-phenyl)butanal.

[0117] The perfume base according to the invention may not be limited to the above mentioned perfuming co-ingredients, and many other such co-ingredients are anyway listed in references such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or its updated editions, or other works of similar nature, as well as a large number of patent documents in the field of perfumery. It should also be understood that the co-ingredients may also be compounds known to release various types of perfuming compounds in a controlled manner.

[0118] The term "perfume adjuvant" is understood as an ingredient capable of imparting additional additional benefits such as color, specific light fastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming compositions is not exhaustive, but it must be mentioned that said ingredients are well known to the person skilled in the art. As specific non-limiting examples the following may be cited: viscous agents (e.g. surfactants, thickeners, gelling and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light or buffers or chelating agents, such as BHT), colorants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti-irritant), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof.

[0119] It will be appreciated that a person skilled in the art is fully capable of designing the best formulation for the desired effect simply by applying standard knowledge in the field and mixing the above-mentioned components of the perfuming composition by trial and error.

[0120] Besides perfuming compositions comprising at least one compound of formula (I), at least one perfume carrier, at least one perfume base and optionally at least one perfume adjuvant, perfuming compositions consisting of at least one compound of formula (I) and at least one perfume carrier also constitute a particular embodiment of the present invention.

[0121] It is useful here to mention that the possibility of having more than one compound of the invention or other precursors of similar type in the above compositions is important, since this enables the perfumer to prepare blends or fragrances having odor notes of different compounds of the invention, thereby creating new building blocks for creative purposes.

[0122] For the sake of clarity, it is also to be understood that any mixture resulting directly from a chemical synthesis in which the composition of matter of the invention is used as starting material, intermediate or end product, such as a reaction medium without sufficient purification, cannot be considered as a perfuming composition according to the invention, as long as said mixture does not provide the compounds of the invention in a form suitable for use in perfumery. Therefore, unpurified reaction mixtures are generally excluded from the present invention, unless otherwise stated.

[0123] Furthermore, the compounds of the invention can also be advantageously used in all areas of modern perfumery, i.e. fine perfumery or functional perfumery, to actively impart or modify the smell of a consumer product to which compound (I) is added. The invention therefore also relates to a perfumed consumer product comprising at least one compound of formula (I) as defined above or a perfumed composition as defined above.

[0124] For the sake of clarity, it has to be mentioned that a "perfumed consumer product" is understood to be a consumer product that delivers at least one pleasant perfuming effect to the surface to which it is applied (e.g. skin, hair, fabric or household surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product comprising a functional formulation and optionally additional benefit agents corresponding to a desired consumer product (e.g. a conditioner, detergent or air freshener), and an olfactory effective amount of at least one compound of the invention. For the sake of clarity, the perfumed consumer product is a non-edible product.

[0125] The nature and types of ingredients of the perfumed consumer product do not warrant a more detailed description here, which is in any case non-exhaustive, the skilled person being able to choose them on the basis of his general knowledge and according to the characteristics of the product in question and the desired effect.

[0126] In one embodiment, the perfumed consumer product is a perfume, a fabric care product, a body care product, a cosmetic preparation, a skin care product, an air care product or a home care product.

[0127] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, splashes or eau de perfums, colognes or shaving lotions or aftershaves; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, fabric refreshers, ironing water, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g. shampoos, coloring preparations or hair sprays, color care products, hair styling products, dental care products), disinfectants, intimate care products; cosmetic preparations (e.g. skin creams or lotions, vanishing creams, or body deodorants (deodorants) or antiperspirants (e.g. sprays or roll-ons), depilatories, suntan preparations, sunscreens or aftersun products , nail products, skin cleansing products, cosmetics); or skin care products (e.g. soaps, bath mousses, bath oils or shower gels, or hygiene products or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powder air fresheners, which can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (lobbies, hotels, shopping malls, etc.); or home care products, such as mildew removers, furniture care agents, wipes, dishwashing detergents or detergents for hard surfaces (e.g. floors, bathrooms, sanitary ware or window cleaning); leather care products; car care products, such as polishes, waxes or plastic cleaners.

[0128] 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. Pat. Nos. 4,137,180 and 5,236,615 or EP 799 885. Other typical detergent and softener compositions that can be used are described in, for example, Ullmann's Encyclopedia of Industrial Chemistry, vol. 20, Wiley-VCH, Weinheim, p. 355-540 (2012); Flick, Advanced Cleaning Product Formulations, Noye Publication, Park Ridge, New Jersey (1989); Showell, in 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.

[0129] The proportions in which the compounds according to the invention can be incorporated into the various preparations or compositions described above vary within wide ranges of values. These values ​​depend on the nature of the preparation to be perfumed and the desired organoleptic effect, as well as on the nature of the co-ingredients in a given base, when the compounds according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

[0130] For example, based on the weight of the composition into which it is incorporated, the typical concentration of the compounds of the present invention is 0.001% to 10% by weight, or even more. When these compounds are used directly for the fragrance or flavoring of the above-mentioned various consumer products, concentrations lower than these, such as 0.001% to 5% by weight, can be used.

[0131] Furthermore, the present invention relates to compounds of formula (I),

[0132]

[0133] Wherein n represents an integer from 0 to 5;

[0134] R 1 Simultaneously or independently represent at least one substituent of an aromatic ring and are hydroxyl, C 1-6 Alkyl, C 1-6 Alkoxy or RCOO, ROCO groups, where R is a hydrogen atom or C 1-4 Alkyl; or two adjacent R 1 When combined together, it represents -O-(CH 2 ) m O-, where m is 1 or 2, or forms C 5-10 A saturated or unsaturated ring, optionally substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 Alkoxy;

[0135] R 2 represents hydrogen atom, C 1-6 alkyl;

[0136] R 3 Represents C 4-10 Straight-chain, branched or cyclic alkyl, alkenyl or diene group, benzyl or C 7-16 Arylalkyl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3 Alkoxy, phenoxymethyl or C 8-15 a saturated or unsaturated alicyclic group, which optionally contains an ether function; R 4 and R 5 represents hydrogen or C 1-6 Alkyl or C 2-6 alkenyl; or R3 and R 4 Together they represent C 5-12 A straight-chain or branched alkanediyl or alkenediyl, or C 5-12 Alicyclic group.

[0137] The proviso is that (2-((3-methylbut-2-en-1-yl)oxy)vinyl)benzene, (1-(isopentyloxy)prop-1-en-2-yl)benzene, (2-(pentyloxy)vinyl)benzene, (1-(dodecyloxy)prop-1-en-2-yl)benzene, (2-(hexyloxy)vinyl)benzene, (2-(heptyloxy)vinyl)benzene, (2-(octyloxy)vinyl)benzene, (1-(2-cyclohexylethoxy)prop-1-en-2-yl)benzene benzene, (1-(2-(cyclohexylethoxy)prop-1-en-2-yl)benzene and 1-methyl-4-(1-((2-phenylcyclohexyl)oxy)prop-1-en-2-yl)benzene.

[0138] Exemplary embodiments of the compounds of formula (I) are described above.

[0139] The present invention also relates to the use of at least one compound of formula (I),

[0140]

[0141] Where n, R 1 , R 2 , R 3 , R 4 and R 5 has the same meaning as defined above,

[0142] For releasing a compound selected from the group consisting of:

[0143] a) a ketone or aldehyde of formula (II),

[0144]

[0145] Wherein n represents an integer from 0 to 5;

[0146] R 1 Simultaneously or independently represent at least one substituent of an aromatic ring and are hydroxyl, C 1-6 Alkyl, C 1-6 Alkoxy or RCOO, ROCO groups, where R is a hydrogen atom or C 1-4 Alkyl; or two adjacent R1 When combined together, it represents -O-(CH 2 ) m O-, where m is 1 or 2, or forms C 5-10 A saturated or unsaturated ring, optionally substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 Alkoxy;

[0147] R 2 represents hydrogen atom, C 1-6 Alkyl or C 6-10 Aryl, optionally substituted with hydroxyl, C 1-3 Alkyl, C 1-3 Alkoxy, RCOO or ROCO group, in which R is independently a hydrogen atom or a C 1-4 alkyl;

[0148] b) a formic acid ester of the formula (III),

[0149]

[0150] Where R 3 , R 4 and R 5 represents simultaneously or independently a hydrogen atom or a C optionally containing 1 to 3 oxygen atoms 1-18 Hydrocarbyl; or R 3 and R 4 When combined together, it represents a C optionally containing 1 to 3 oxygen atoms. 3-18 a hydrocarbon group; and

[0151] c) an alcohol of formula (IV),

[0152]

[0153] Where R 3 , R 4 and R 5 has the same meaning as defined above;

[0154] At least one of the compounds of formula (II), formula (III) or formula (IV) is an active compound.

[0155] In one embodiment, the invention relates to the use of at least one compound of formula (I) as defined above for imparting, enhancing, improving or modifying the odor characteristics of a perfuming composition, the air surrounding the perfuming composition, a surface or a perfumed article, comprising adding to the composition or article an effective amount of at least one compound of formula (I) as defined above 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 user's skin, hair, fabric or hard surface to which a perfume composition comprising or containing at least one compound of formula (I) is applied.

[0156] In another embodiment, the present invention relates to the use of at least one compound of formula (I) as defined above for the diffusion and / or perception of the characteristic aroma of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive 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 preparation comprising at least one compound of formula (I), under conditions suitable to allow release of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive alcohol of formula (IV) over time.

[0157] In some aspects, embodiments of the uses correspond to embodiments of the methods according to the invention. DETAILED DESCRIPTION

[0158] Example

[0159] 1. Preparation of Compounds

[0160] The following compounds have been prepared and characterized. Only the mass spectral data (EI, 70 eV), major fragment ions and relative abundances and NMR data of the E-isomer (usually the major isomer) are provided. 3 As solvent, recorded at 500 or 600 MHz 1 H NMR spectrum. Chemical shifts δ are expressed in ppm relative to TMS as a standard, and coupling constants J are expressed in Hz.

[0161] Example 1. (1-(Octyloxy)prop-1-en-2-yl)benzene: A mixture of hydratropicaldehyde (10 g, 74.5 mmol), octanol (24.3 g, 186 mmol), TsOH (0.28 g, 1.49 mmol) and toluene (100 mL) was heated to reflux for 1 hour while removing the reaction water using a Dean-Stark trap. After the mixture was cooled, it was diluted with EtOAc and saturated with NaHCO3 The organic phase was washed with Na 2 SO 4 Drying, filtration and concentration gave crude dioctyl acetal. About one quarter of this material (19.3 mmol) was mixed with KHSO 4 (0.5 g, 3.67 mmol) were mixed and heated under vacuum (30 Torr) using a Kugelrohr distillation apparatus. After 2.5 hours at 140°C and another 2.5 hours at 160°C, GC analysis indicated that most of the acetal had been converted to the enol ether. Kugelrohr distillation (145°C, 80 mTorr) gave 3.46 g of the enol ether (14.0 mmol, 73% yield) as a colorless liquid (E / Z=81:19). 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.88 (t, J = 7.1 Hz, 3H), 1.21-1.44 (m, 10H), 1.66 (pentet, J = 6.7 Hz, 2H), 2.00 (d, J = 1.3 Hz, 3H), 3.83 (t, J = 6.7 Hz, 2H), 6.46 (q, J = 1.3 Hz, 1H), 7.12-7.17 (m, 1H), 7.24-7.32 (m, 4H).

[0162] Examples 2-7. Using a Kugelrohr distillation apparatus, dimethyl acetal of diphenylpropanal (4 g, 22.1 mmol), alcohol (66 mmol) and KHSO were heated at 100-120°C under vacuum (100-300 Torr). 4 (33 mg, 0.22 mmol) for 1 to 2 hours to achieve the exchange of methoxy groups with alcohols while removing the released methanol. Thereafter, the temperature is increased (120 to 140° C.) and the pressure is reduced (25 to 50 mTorr) to complete the elimination reaction to form the enol ether while removing excess alcohol. The enol ether is then distilled from the reaction mixture (160 to 180° C., 25 to 50 mTorr). If desired, the product can be further purified by a second Kugelrohr distillation.

[0163] Example 2. (1-(((Z)-hex-3-en-1-yl)oxy)prop-1-en-2-yl)benzene: Starting from (Z)-3-hexen-1-ol, the title compound was isolated as a colorless oil in 37% yield (E / Z = 80:20).

[0164] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 0.97 (t, J = 7.5 Hz, 3H), 1.99 (d, J = 1.3 Hz, 3H), 2.07 (pentet, J = 7.3 Hz, 2H), 2.41 (q, J = 7.0 Hz, 2H), 3.83 (t, J = 7.0 Hz, 2H), 5.33-5.40 (m, 1H), 5.47-5.54 (m, 1H), 6.46 (q, J = 1.3 Hz, 1H), 7.12-7.17 (m, 1H), 7.24-7.32 (m, 4H).

[0165] Example 3. (1-(Decyloxy)prop-1-en-2-yl)benzene: Starting from decanol, the title compound was isolated as a colorless oil in 75% yield (E / Z=81:19).

[0166] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.88 (t, J = 7.0 Hz, 3H), 1.20-1.43 (m, 14H), 1.66 (pentet, J = 6.8 Hz, 2H), 2.00 (d, J = 1.4 Hz, 3H), 3.82 (t, J = 6.7 Hz, 2H), 6.46 (q, J = 1.4 Hz, 1H), 7.12-7.17 (m, 1H), 7.23-7.32 (m, 4H).

[0167] Example 4. (1-Phenethoxyprop-1-en-2-yl)benzene: Starting from 2-phenylethanol, the title compound was isolated as a colorless oil in a yield of 66% (E / Z=81:19).

[0168] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 1.98 (d, J = 1.4 Hz, 3H), 2.96 (t, J = 7.0 Hz, 2H), 4.03 (t, J = 7.0 Hz, 2H), 6.44 (q, J = 1.4 Hz, 1H), 7.13-7.18 (m, 1H), 7.19-7.31 (m, 9H).

[0169] Example 5. (1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)benzene: Starting from citronellol, the title compound was isolated as a colorless oil in a yield of 64% (E / Z=83:17).

[0170] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 0.93 (d, J = 6.7 Hz, 3H), 1.15-1.24 (m, 1H), 1.32-1.41 (m, 1H), 1.44-1.52 (m, 1H), 1.57-1.64 (m, 1H), 1.60 (s, 3H), 1.68 (d, J = 1.3 Hz, 3H), 1.68-1.76 (m, 1H), 1.92-2.07 (m, 2H), 1.99 (d, J = 1.3 Hz, 3H), 3.82-2.92 (m, 2H), 5.10 (t, J = 7.4 Hz, 1H), 6.46 (q, J = 1.3 Hz, 1H), 7.12-7.17 (m, 1H), 7.23-7.33 (m, 4H).

[0171] Example 6. (1-(2-Phenoxyethoxy)prop-1-en-2-yl)benzene: Starting from 2-phenoxyethan-1-ol, the title compound was isolated as a white solid in 77% yield (E / Z=80:20). 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 1.99 (d, J = 1.4 Hz, 3H), 4.1 (s, 4H), 6.53 (q, J = 1.4 Hz, 1H), 6.87-6.96 (m, 3H), 7.13-7.18 (m, 1H), 7.22-7.31 (m, 6H).

[0172] Example 7. (1-((1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-yl)oxy)prop-1-en-2-yl)benzene: from 1-((1RS,6SR)-2,2,6-trimethylcyclohexyl)hexan-3-ol ( Firmenich), the title compound was isolated as a colorless oil in 35% yield (E / Z=83:17).

[0173] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.47-.056 (m, 1H), 0.73-0.96 (Me signal, 13H), 1.00-1.74 (m, 14H), 2.00 (s, vinyl Me, 3H), 3.58-3.71 (m, 1H), 6.52 (s, 1H), 7.11-7.16 (m, 1H), 7.23-7.31 (m, 4H).

[0174] Examples 8-14. A toluene solution (100 ml) of diphenylpropanal (5 g, 37.3 mmol), alcohol (0.5-2 equivalents) and TsOH (142 mg, 0.75 mmol) was refluxed for 2 hours. The reaction water was removed using a Dean-Stark trap. The mixture was stopped from being heated and then Na 2 CO 3 (0.7 g, 6.6 mmol). The reaction mixture was diluted with EtOAc and washed with water, saturated NaHCO 3 The organic phase was washed with Na 2 SO 4 Dry, filter and concentrate. Unless otherwise stated, the residue is subjected to Kugelrohr distillation to first remove excess alcohol (typical conditions, 70-80°C, 20 mTorr) and then obtain the enol ether (typical conditions, 120-140°C, 20 mTorr).

[0175] Example 8. (1-(Hexyloxy)prop-1-en-2-yl)benzene: Starting from hexanol (0.5 equiv.), the title compound was isolated as a colorless oil in 58% yield (E / Z = 85:15) by silica gel flash chromatography (hexanes) followed by Kugelrohr distillation.

[0176] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.90 (t, J = 7.0 Hz, 3H), 1.26-1.44 (m, 6H), 1.66 (quintet, J = 6.8 Hz, 2H), 2.00 (d, J = 1.4 Hz, 3H), 3.83 (t, J = 6.8 Hz, 2H), 6.46 (q, J = 1.4 Hz, 1H), 7.12-7.17 (m, 1H), 7.24-7.32 (m, 4H).

[0177] Example 9. (1-(Benzyloxy)prop-1-en-2-yl)benzene: Starting from benzyl alcohol (0.9 equiv.), the title compound was isolated as a colorless oil in 54% yield (E / Z = 83:17) by silica gel flash chromatography (hexanes) followed by Kugelrohr distillation.

[0178] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 2.04 (d, J = 1.4 Hz, 3H), 4.86 (s, 2H), 6.53 (q, J = 1.4 Hz, 1H), 7.11-7.16 (m, 1H), 7.21-7.36 (m, 9H).

[0179] Example 10. (1-(Oct-3-yloxy)prop-1-en-2-yl)benzene: Starting from 3-octanol (2 equiv.), the title compound was isolated as a colorless oil in 75% yield (E / Z = 85:15).

[0180] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.89 (t, J = 7.0 Hz, 3H), 0.94 (t, J = 7.5 Hz, 3H), 1.23-1.64 (m, 10H), 2.00 (d, J = 1.3 Hz, 3H), 3.62 (quintet, J = 6.0 Hz, 1H), 6.52 (q, J = 1.3 Hz, 1H), 7.10-7.15 (m, 1H), 7.22-7.32 (m, 4H).

[0181] Example 11. (1-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)prop-1-en-2-yl)benzene: Starting from (-)-menthol (2 equiv.), the title compound was isolated as a colorless oil in 86% yield (E / Z = 88:12).

[0182] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.81 (d, J = 7.0 Hz, 3H), 0.86-0.93 (m, 1H), 0.92 (d, J = 6.6 Hz, 3H), 0.93 (d, J = 7.0 Hz, 3H), 0.97-1.11 (m, 2H), 1.34-1.46 (m, 2H), 1.63-1.70 (m, 2H), 1.99 (d, J = 1.3 Hz, 3H), 2.02-2.10 (m, 1H), 2.14-2.24 (m, 1H), 3.50 (dt, J = 4.3, 10.7 Hz, 1H), 6.56 (q, J = 1.3 Hz, 1H), 7.11-7.16 (m, 1H), 7.24-7.32 (m, 4H).

[0183] Example 12. ((2-phenylprop-1-en-1-yl)oxy)cyclododecane: Starting from cyclododecanol (1 equiv), the title compound was isolated by silica gel flash chromatography (hexanes) as a white solid in 47% yield (E / Z=85:15).

[0184] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 1.26-1.51 (m, 18H), 1.54-1.63 (m, 2H), 1.69-1.79 (m, 2H), 1.99 (d, J = 1.3 Hz, 3H), 3.86 (m, 1H), 6.52 (q, J = 1.3 Hz, 1H), 7.12-7.16 (m, 1H), 7.24-7.32 (m, 4H).

[0185] Example 13. (1-(1-(3,3-dimethylcyclohexyl)ethoxy)prop-1-en-2-yl)benzene: Starting from 1-(3,3-dimethylcyclohexyl)ethan-1-ol (1 equiv), the title compound was isolated as a colorless oil in 84% yield (E / Z = 88:12).

[0186] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.90 (s, 3H), 0.92 (s, 3H), 0.92-1.12 (m, 3H), 1.19 (d, J = 6.4 Hz, 3H), 1.31-1.84 (m, 6H), 2.00 (d, J = 1.3 Hz, 3H), 3.58 (quintet, J = 6.2 Hz, 1H), 6.49 (q, J = 1.3 Hz, 1H), 7.12-7.16 (m, 1H), 7.23-7.32 (m, 4H).

[0187] Example 14. Starting from 1-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol (1 equiv.), the title compound was isolated as a colorless oil in 56% yield (mixture of diastereomers).

[0188] 1 H NMR (CDCl 3 , 500 MHz, E-isomer, 4 diastereomers): δ 0.90, 0.92, 0.94, 0.97 (all s, 9H), 0.95-1.02 (m, 4), 1.04-1.84 (m, 9H), 1.97-2.00 (overlapping with Me signal, 3H), 1.99-2.15 (m, 1H), 3.01-3.11, 3.25-3.40, 3.51-3.83 (all m, 4H), 6.55, 6.57, 6.60, 6.66 (all q, J = 1.3 Hz, 1H), 7.10-7.16 (m, 1H), 7.22-7.32 (m, 4H).

[0189] Examples 15-18. A pentane solution (100 ml) of diphenylpropanal (5 g, 37.2 mmol), a tertiary alcohol (74.4 mmol) and TsOH (0.28 g, 1.47 mmol) was heated to reflux for 22 hours. The reaction water was removed using a Dean-Stark trap. The mixture was stopped from being heated and then Na 2 CO 3 (0.7 g, 6.6 mmol). The reaction mixture was diluted with EtOAc and washed with water, saturated NaHCO 3 The organic phase was washed with Na 2 SO 4 Dry, filter and concentrate. The residue is first subjected to Kugelrohr distillation to remove excess tertiary alcohol and then to remove the enol ether.

[0190] Example 15. (1-((2,6-dimethyloct-7-en-2-yl)oxy)prop-1-en-2-yl)benzene: Starting from 2,6-dimethyloct-7-en-2-yl (dihydromyrcenol), the title compound was isolated as a colorless oil in 81% yield (E / Z = 85:15).

[0191] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.98 (d, J = 6.7 Hz, 3H), 1.22-1.32 (m, 2H), 1.28 (s, 6H), 1.32-1.43 (m, 2H), 1.51-1.60 (m, 2H), 1.99 (d, J = 1.4 Hz, 3H), 2.12 (m, 1H), 4.90 (ddd, J = 0.9, 1.9, 10.3 Hz, 1H), 4.95 (ddd, J = 1.3, 1.9, 17.3 Hz, 1H), 5.68 (ddd, J = 7.5, 10.3 17.3 Hz, 1H), 6.66 (q, J = 1.4 Hz, 1H), 7.12-7.17 (m, 1H), 7.24-7.33 (m, 4H).

[0192] Example 16. (1-((3,7-dimethyloctan-3-yl)oxy)prop-1-en-2-yl)benzene: Starting from 3,7-dimethyloctan-3-ol (tetrahydrolinalool), the title compound was isolated as a colorless oil in 74% yield (E / Z = 87:13).

[0193] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 0.87 (d, J = 6.7 Hz, 6H), 0.9 (t, J = 7.5 Hz, 3H), 1.17 (m, 2H), 1.23 (s, 3H), 1.34 (m, 2H), 1.48-1.67 (m, 5H), 2.00 (d, J = 1.3 Hz, 3H), 6.65 (q, J = 1.3 Hz, 1H), 7.09-7.16 (m, 1H), 7.23-7.33 (m, 4H).

[0194] Example 17. (1-((2-methyl-1-phenylpropan-2-yl)oxy)prop-1-en-2-yl)benzene: Starting from 2-methyl-1-phenylpropan-2-ol, the title compound was isolated as a colorless oil in a yield of 63% (E / Z=87:13).

[0195] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 1.28 (s, 6H), 2.00 (d, J = 1.4 Hz, 3H), 2.88 (s, 2H), 6.75 (q, J = 1.4 Hz, 1H), 7.12-7.33 (m, 10H).

[0196] Example 18. (1-((2,6-dimethylhept-2-yl)oxy)prop-1-en-2-yl)benzene: Starting from 2,6-dimethylhept-2-ol, the title compound was isolated as a colorless oil in 69% yield (E / Z = 87:13).

[0197] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.88 (d, J = 6.7 Hz, 6H), 1.14-1.20 (m, 2H), 1.29 (s, 6H), 1.34-1.42 (m, 2H), 1.50-1.59 (m, 3H), 2.00 (d, J = 1.4 Hz, 3H), 6.67 (q, J = 1.4 Hz, 1H), 7.12-7.18 (m, 1H), 7.24-7.33 (m, 4H).

[0198] Examples 19-21: Using a Kugelrohr distillation apparatus, dimethyl acetal of phenylacetaldehyde (5 g, 30.1 mmol), alcohol (120 mmol) and KHSO 4A mixture of (51 mg, 0.375 mmol) was heated at 90-120°C for 2-3 hours under vacuum (200-300 Torr) to exchange the methoxy groups with the added alcohol while removing the released methanol. Thereafter, the temperature was raised (130-140°C) and the pressure was lowered (25-30 mTorr) to complete the elimination reaction to form the enol ether. Under these conditions, the resulting enol ether and alcohol were distilled from the reaction mixture. The distillate was then subjected to another bulb-to-bulb distillation to first remove the excess alcohol and then the enol ether.

[0199] Example 19. (2-(((Z)-hex-3-en-1-yl)oxy)vinyl)benzene): Starting from (Z)-3-hexen-1-ol, the title compound was isolated as a colorless oil in a yield of 36% (E / Z = 55:45). 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.98 (t, J = 7.5 Hz, 3H), 2.07 (quintet, J = 7.5 Hz, 2H), 2.45 (q, J = 6.9 Hz, 2H), 3.80 (t, J = 6.9 Hz, 2H), 5.33-5.41 (m, 1H), 5.48-5.55 (m, 1H), 5.83 (d, J = 13.0 Hz, 1H), 6.97 (d, J = 13.0 Hz, 1H), 7.08-7.13 (m, 1H), 7.17-7.28 (m, 4H).

[0200] Example 20. (2-Phenylethoxyvinyl)benzene: Starting from 2-phenylethanol, the title compound was isolated as a colorless oil in 36% yield (E / Z = 53:47).

[0201] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 2.98 (t, J = 7.0 Hz, 2H), 4.00 (t, J = 7.0 Hz, 2H), 5.82 (d, J = 13.0 Hz, 1H), 6.96 (d, J = 13.0 Hz, 1H), 7.07-7.31 (m, 10H).

[0202] Example 21. (2-((3,7-dimethyloctyl)oxy)vinyl)benzene: Starting from citronellol, the title compound was isolated as a colorless oil in 48% yield (E / Z = 48:52).

[0203] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 0.94 (d, J = 6.7 Hz, 3H), 1.16-1.42 (m, 1H), 1.33-1.42 (m, 1H), 1.46-1.56 (m, 1H), 1.60 (s, 3H), 1.60-1.71 (m, 1H), 1.68 (d, 1.1 Hz, 3H), 1.71-1.18 (m, 1H), 1.92-2.08 (m, 2H), 3.79-3.89 (m, 2H), 5.07-5.13 (m, 1H), 5.82 (d, J = 13.0 Hz, 1H), 6.98 (d, J = 13.0 Hz, 1H), 7.08-7.14 (m, 1H), 7.19-7.29 (m, 4H).

[0204] Examples 22-23. Dimethyl acetal of phenylacetaldehyde (14.9 g, 90 mmol), alcohol (225 mmol) and KHSO 4 The enol ether and alcohol were distilled from the reaction flask. The enol ether-rich fractions were combined and distilled to give the pure enol ether.

[0205] Example 22. (2-(Oct-3-yloxy)vinyl)benzene: Starting from 3-octanol, the title compound was isolated by fractional distillation (Vigreux column, bp 105°C, 25 mTorr) as a colorless oil in 27% yield (E / Z = 37:63).

[0206] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 0.89 (t, J = 7.0 Hz, 3H), 0.94 (t, J = 7.5 Hz, 3H), 1.24-1.48 (m, 6H), 1.49-1.70 (m, 4H), 3.70 (quintet, J = 6.1 Hz, 1H), 5.91 (d, J = 12.7 Hz, 1H), 6.88 (d, J = 12.7 Hz, 1H), 7.07-7.13 (m, 1H), 7.17-7.30 (m, 4H).

[0207] Example 23. (2-(2-phenoxyethoxy)vinyl)benzene: Starting from 2-phenoxyethan-1-ol, the title compound was isolated by Kugelrohr distillation (170° C., 25 mTorr) as a white solid in 46% yield (E / Z=52:48).

[0208] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 4.20 (s, 4H), 5.89 (d, J = 13.0 Hz, 1H), 6.87-6.98 (m, 3H), 7.05 (d, J = 13.0 Hz, 1H), 7.10-7.15 (m, 1H), 7.20-7.31 (m, 6H).

[0209] Example 24. (Z)-(2-(Hex-3-en-1-yloxy)ethene-1,1-diyl)diphenyl: The dimethyl acetal of diphenylacetaldehyde was prepared by mixing the aldehyde (14.1 g, 71.6 mmol) with trimethyl orthoformate (3 eq.), TsOH (1.2 mol%), and methanol (100 mL) for 17 h. The Na 2 CO 3 (2.5 g) was added to neutralize the acid. After concentration, the remaining residue was subjected to short-path distillation (105-108 ° C, 25 mTorr) to obtain 15 g (62 mmol, 86% yield) of dimethyl acetal. Acetal (5.81 g, 24 mmol) was then mixed with Z-hex-3-en-1-ol (2 equivalents) and KHSO in a round-bottom flask (15 mL) equipped with a distillation head and a nitrogen bubbler. 4 (1 mol%) were combined. The mixture was heated (150°C oil bath) while distilling off the released methanol for 1 hour. The mixture was then placed under vacuum (7 Torr) and heated at 180°C while allowing excess alcohol to distill off from the flask (2 hours). Na 2 CO 3 (0.5 g), and 5.5 g (19.8 mmol, 82% yield) of the title compound were isolated from the reaction flask by distillation as a colorless oil (bp 152-155°C, 25 mTorr).

[0210] 1 H NMR (CDCl 3, 600 MHz): δ 0.95 (t, J = 7.5 Hz, 3H), 2.06 (quintet, J = 7.5 Hz, 2H), 2.45 (q, J = 7.1 Hz, 2H), 3.91 (t, J = 7.0 Hz, 2H), 5.36 (dt, J = 7.3, 10.8 Hz, 1H), 5.52 (dt, J = 7.3, 10.8 Hz, 1H), 6.49 (s, 1H), 7.18-7.24 (m, 4H), 7.25-7.32 (m, 4H), 7.39-7.42 (m, 2H).

[0211] Example 25. (2-Phenylethoxyethylene-1,1-diyl)diphenyl: A mixture of diphenylacetaldehyde (4.94 g, 25.2 mmol), 2-phenylethanol (7.78 g, 64.4 mmol), TsOH (0.097 g, 0.51 mmol) and toluene (100 mL) was heated at reflux for 2 h while removing the reaction water using a Dean-Stark trap. After the mixture was cooled, it was diluted with EtOAc and heated with saturated NaHCO 3 The organic phase was washed with Na 2 SO 4 Dry, filter and concentrate. The crude acetal is then reacted with KHSO 4 (1 g, 7.34 mmol) were mixed and heated under vacuum (50 Torr) using a Kugelrohr distillation apparatus. After 1 hour at 160°C, GC analysis showed that most of the acetal had been converted to the enol ether and excess 2-phenylethanol had been removed. Kugelrohr distillation (180-190°C, 50 mTorr) gave 4.24 g of the title compound (14.1 mmol, 56% yield) as a colorless liquid.

[0212] 1 H NMR (CDCl 3 ,500MHz): δ2.97(t,J=7.0Hz,2H),4.09(t,J=7.0Hz,2H),6.45(s,1H),7.14-7.35(m,15H).

[0213] Examples 26-29. Methoxymethyltriphenylphosphonium chloride (15.1 g, 44.1 mmol) and aryl ketone (29.4 mmol) were added to 120 ml of toluene. Potassium tert-butoxide (5.27 g, 47 mmol) was added to the stirred slurry in four portions every 15 minutes. The mixture was stirred for 4 hours and turned dark red. It was then poured into 500 ml of water and extracted with EtOAc (3×250 mL). The organic phases were combined and purified by Na 2 SO 4The mixture was dried, filtered and concentrated. The resulting methyl enol ether product was isolated by flash chromatography (silica gel, hexane) followed by Kugelrohr distillation. The methyl enol ether (30 mmol) was then mixed with 2-phenylethanol (2 eq.) and KHSO in a round bottom flask (15 mL) equipped with a distillation head and a nitrogen bubbler. 4 (1 mol%) were combined. The mixture was heated (oil bath at 150°C) while distilling off the released methanol (vapor temperature 64°C) until the vapor temperature dropped (typically 40 minutes). The mixture was then placed under vacuum (300 mTorr) and heated at 190°C while allowing excess 2-phenylethanol to distill off from the flask (typically 2 hours). Na 2 CO 3 After addition of 1% iodine (0.4 g), the resulting enol ether was isolated from the reaction flask by vacuum distillation or by flash chromatography on silica gel followed by Kugelrohr distillation.

[0214] Example 26. 1-Methyl-4-(1-phenoxyprop-1-en-2-yl)benzene: The title compound was isolated from the methyl enol ether by short path distillation of the crude reaction mixture (bp 143-145°C, 30 mTorr) as a colorless oil in 73% yield (E / Z=82:18).

[0215] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 1.97 (d, J = 1.2 Hz, 3H), 2.31 (s, 3H), 2.97 (t, J = 7.1 Hz, 2H), 4.03 (t, J = 7.1 Hz, 2H), 6.42 (q, J = 1.2 Hz, 1H), 7.07-7.32 (m, 9H).

[0216] Example 27. 1-Methoxy-4-(1-phenoxyprop-1-en-2-yl)benzene: The title compound was isolated from the methyl enol ether by short path distillation of the crude reaction mixture (bp 156-158°C, 30 mTorr) as a white solid in 84% yield (E / Z=78:23).

[0217] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 1.96 (d, J = 1.2 Hz, 3H), 2.98 (t, J = 7.1 Hz, 2H), 3.78 (s, 3H), 4.03 (t, J = 7.1 Hz, 2H), 6.36 (q, J = 1.2 Hz, 1H), 6.81-6.85 (m, 2H), 7.18-7.32 (m, 7H).

[0218] Example 28. 2-(1-Phenethoxyprop-1-en-2-yl)naphthalene: The title compound was isolated from the methyl enol ether by flash chromatography followed by Kugelrohr distillation to afford a white solid in 89% yield (E / Z=80:20).

[0219] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 2.09 (d, J = 1.2 Hz, 3H), 3.00 (t, J = 7.0 Hz, 2H), 4.10 (t, J = 7.0 Hz, 2H), 6.62 (q, J = 1.2 Hz, 1H), 7.19-7.48 (m, 8H), 7.64 (s, 1H), 7.72 (d, J = 8.7 Hz, 1H), 7.74-7.78 (m, 2H).

[0220] Example 29. 6-(1-(1-phenoxyprop-1-en-2-yl)-1,2,3,4-tetrahydronaphthalene: The title compound was isolated by flash chromatography followed by Kugelrohr distillation to give a colorless oil in 82% yield (E / Z=80:20).

[0221] 1 H NMR (CDCl 3 , 600 MHz, E-isomer): δ 1.75-1.81 (m, 4H), 1.96 (d, J = 1.3 Hz, 3H), 2.70-2.78 (m, 4H), 2.97 (t, J = 7.1 Hz, 2H), 4.03 (t, J = 7.1 Hz, 2H), 6.40 (q, J = 1.3 Hz, 1H), 6.95-7.03 (m, 3H), 7.20-7.33 (m, 5H).

[0222] Example 30. (1-Phenethoxybut-1-en-2-yl)benzene: The title compound was prepared in 59% yield by the method described in Examples 2-7 using the methyl enol ether of 2-phenylbutyraldehyde prepared from acetophenone as described in Examples 26-29 and 2-phenylethanol. It was isolated by Kugelrohr distillation as a colorless oil in 59% yield (E / Z=74:26).

[0223] 1 H NMR (CDCl 3, 500 MHz, E-isomer): δ 0.99 (t, J = 7.5 Hz, 3H), 2.52 (q, J = 7.5 Hz, 2H), 2.95 (t, J = 7.1 Hz, 2H), 4.01 (t, J = 7.1 Hz, 2H), 6.30 (s, 1H), 7.12-7.31 (m, 10H).

[0224] Example 31. (3-methyl-1-phenethoxybut-1-en-2-yl)benzene: The title compound was prepared by the method described in Examples 2 to 7 using the methyl enol ether of 3-methyl-2-phenylbutyraldehyde prepared from isobutylphenyl ketone as described in Examples 26 to 29, and 2-phenylethanol. It was isolated by flash chromatography on silica gel as a colorless oil in a yield of 24% (E / Z=55:45). 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 1.11 (d, J = 7.1 Hz, 6H), 2.95 (t, J = 7.1 Hz, 2H), 3.02 (quintet, J = 7.1 Hz, 1H), 3.97 (t, J = 7.1 Hz, 2H), 5.98 (s, 1H), 7.10-7.31 (m, 10H).

[0225] Example 32. 1-Methoxy-4-(1-(octyloxy)prop-1-en-2-yl)benzene: The title compound was prepared by the method described in Examples 2-7 using the methyl enol ether of 2-(4-methoxyphenyl)propanal prepared from p-methoxyacetophenone as described in Examples 26-29, and octanol. The title compound was isolated by Kugelrohr distillation as a colorless oil in a yield of 69% (E / Z = 76:24).

[0226] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ 0.88 (t, J = 7.0 Hz, 3H), 1.22-1.43 (m, 10H), 1.65 (quintet, J = 6.8 Hz, 2H), 1.97 (d, J = 1.3 Hz, 3H), 3.77 (s, 3H), 3.80 (t, J = 6.8 Hz, 2H), 6.37 (q, J = 1.3 Hz, 1H), 6.80-6.84 (m, 2H), 7.19-7.24 (m, 2H).

[0227] Example 33. 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene: The methyl enol ether of 2-(naphthalen-2-yl)propanal (25.2 mmol), prepared from 1-(naphthalen-2-yl)ethan-1-one as described in Examples 26-29, was reacted with citronellol (2 equiv.) and KHSO 4 The mixture was heated at 165°C for 90 minutes while the excess citronellol was distilled off from the flask. The reaction mixture was washed with CH 2 Cl 2 Dilute and then wash with saturated NaHCO 3 Wash the organic phase with Na 2 SO 4 Dry, filter and concentrate.The residue was purified by flash chromatography on silica gel (hexane / EtOAc, 98:2) to give 5.23 g (16.2 mmol, 64% yield) of the title compound as a light yellow oil (E / Z = 88:22).

[0228] 1 H NMR (CDCl 3 , 500 MHz, E-isomer): δ0.95 (d, J=6.6 Hz, 3H), 1.15-1.27 (m, 1H), 1.34-1.43 (m, 1H), 1.45-1.56 (m, 1H), 1.61-1.67 (m, 1H), 1.61 (s, 3H), 1.68 (s, 3H), 1.70-1.79 (m, 1H), 1.93-2.08 (m, 2H), 2.1 0(d,J=1.3Hz,3H),3.86-2.98(m,2H),5.11(t,J=7.1Hz,1H),6.65(q,J=1.3Hz,1H),7.34-7.4 5(m,2H),7.49(dd,J=8.7,1.9Hz,1H),7.67(s,1H),7.72(d,J=8.7Hz,1H),7.74-7.80(m,2H).

[0229] 2. Headspace analysis in fabric softener applications

[0230] Model liquid fabric softener is prepared by mixing 12.3 wt % of TEA-esterquat (VL 90A), 0.4 wt % of 10% calcium chloride aqueous solution, 0.04 wt % of Proxcel GXL, and 87.2 wt % of deionized water. Enol ether (0.075 mmol) is weighed into a vial and dissolved in 0.25 mL of acetone. Liquid fabric softener (4.5 g) is added into the vial and the mixture is shaken by hand to mix. Reference samples are prepared in the same manner using each 0.075 mmol of released volatiles. Fabric softener samples are rinsed into a 3 L beaker with deionized water, and the beaker is filled with a total volume of 1.5 L. Three 5 g cotton samples (approximately 12.5 x 12.5 cm, weight 270 g / m 2 , Item 403 from Testfabrics, West Pittston, PA) was added to the beaker and manually stirred for 3 minutes. After standing for another 2 minutes, the sample was taken out and the excess water was squeezed out by hand. The cloth was hung to dry overnight (15-16 hours) at room temperature. The sample was then subjected to dynamic headspace analysis.

[0231] Each sample was placed in a headspace sampling cell (about 160 mL volume) at a constant temperature (25°C). Using an air sampling pump, a constant air flow (200 mL / min) was passed through the sampling cell and then through a 100 mg headspace sampler. Before entering the sample cell, the air was drawn through an activated carbon plug and then through a saturated NaCl solution to maintain a constant relative humidity of 75%. After 1 and 2 hours, the air was washed with clean The cartridge was replaced with the spent cartridge for 15 minutes to collect the headspace sample. The column was thermally desorbed using a Perkin Elmer TurboMatrix 650 thermal desorber (30 m, 0.25 mm ID, 0.25 μm membrane) connected to an Agilent 6890 gas chromatograph equipped with an Agilent 5975C mass spectrometer and a Varian VF-1 ms capillary column. The desorber parameters were: valve temperature 250°C, transfer line 250°C, purge time 1 minute, desorption temperature 240°C, desorption time 5 minutes, desorption flow 20 mL / min, trap at 40°C / sec from -30°C to 250°C, trap hold time 4 minutes, outlet split 48 mL / min, column flow rate 1 mL / min. The GC oven temperature profile was increased from 60°C (1 minute) to 210°C and then to 250°C (2 minutes) at a rate of 20°C / min. For the analysis of (Z)-3-hexen-1-ol, the initial oven temperature was 52 °C (2 min). The amount of each aroma volatile collected (reported as ng / L air) was determined using external calibration of various chemicals. At least five acetone solutions were prepared with concentrations ranging from 0.05 g / L to 5 g / L of the analyte. The solutions were injected (0.2 μL) into the The solution was analyzed in triplicate. The calibration curve was forced through the origin.

[0232] Dynamic headspace concentrations (ng / L) of perfume raw materials prepared from line-dried cotton cloth treated with a fabric softener containing an enol ether fragrance precursor compared to the corresponding reference (data for 60-75 and 120-135 minute headspace samples, respectively).

[0233]

[0234]

[0235]

[0236] These data show that when applied to cotton from a fabric softener, the compounds of formula (I) release more perfume ingredients (aryl carbonyl compounds, formates and alcohols) than the corresponding reference samples. This indicates that the compounds of the invention produce the desired sustained release effect.

[0237] 3. Olfactory evaluation using leave-in hair conditioners

[0238] A model rinse-off hair conditioner was prepared with the following composition (wt %):

[0239]

[0240] A 25% enol ether solution in isopropyl myristate or a 25% enol ether solution in acetone was dispersed in a leave-in hair conditioner to provide samples containing 0.15% or 0.25% by weight of the precursor, respectively. Reference samples of equimolar levels of the expected aldehyde or ketone and formate were prepared in the same manner. The samples were macerated at room temperature for one day. The hair samples (10 grams) were rinsed in warm tap water (37°C) for 30 seconds and then gently combed to straighten the hair. The hair conditioner samples (1 g) were applied to the samples separately and then massaged into the hair to thoroughly disperse them. The samples were hung and dried at room temperature. After 6 hours and 24 hours, they were olfactorily evaluated by a panel for their odor intensity. The panelists were asked to rate the perceived odor intensity on a scale of 1 (barely noticeable) to 7 (very strong). Table 1 summarizes the data obtained from the panel evaluation.

[0241] Table 1: Olfactory evaluation using leave-in hair conditioners

[0242]

[0243]

[0244] These data show that the compound of formula (I) produces a higher odor intensity on the hair compared to the corresponding reference sample at 6 hours and 24 hours after application from a leave-on hair conditioner. This shows that the compounds of the invention produce the desired sustained release effect.

[0245] 4. Olfactory evaluation using rinse-off hair conditioners

[0246] A model rinse-off hair conditioner was prepared with the following composition (wt %).

[0247]

[0248] A 25% solution of the enol ether in isopropyl myristate was dispersed in a rinse-off hair conditioner to provide a conditioner containing 0.25 or 0.15% by weight of the precursor. Reference samples containing equimolar levels of the expected aldehyde or ketone and formate were prepared in the same manner. The samples were macerated at room temperature for one day. The hair samples (10 grams) were moistened with warm tap water (about 37° C.) and washed with an unperfumed milky shampoo. Shampoo (1 mL) was applied along the length of each hair sample using a syringe. The sample was massaged with fingertips for 30 seconds to disperse the shampoo and form a good foam. Rinse with warm tap water for 30 seconds, then gently squeeze out the excess water. Rinse the hair sample with a rinse-off hair conditioner (1.0 g) and gently massage it into the hair for 1 minute. The sample was then immersed in a 2-liter beaker with tap water, moved up and down 3 times, and then moved left and right 3 times. It was then rinsed with tap water for 30 seconds while detangling the hair with the fingertips. After gently squeezing out excess water, the samples were hung and dried at room temperature. After 6 hours and 24 hours, the samples were evaluated by the panel for odor intensity. The panelists were asked to rate the perceived odor intensity on a scale of 1 (barely perceptible) to 7 (very strong). Table 2 summarizes the data obtained from the panel evaluations.

[0249] Table 2: Olfactory Evaluation Using Rinse-Off Hair Conditioners

[0250]

[0251]

[0252] These data show that the compound of formula (I) produces a higher odor intensity on the hair compared to the corresponding reference sample at 6 hours and 24 hours after application from a rinse-off hair conditioner. This shows that the compounds of the invention produce the desired sustained release effect.

[0253] 5. Olfactory evaluation of pearlescent shampoo

[0254] A pearlescent shampoo was prepared in a generally known manner with the following composition (wt%).

[0255]

[0256] A 25% enol ether solution in isopropyl myristate was dispersed in pearlescent shampoo to provide a sample containing 0.15% by weight of the precursor. Reference samples containing equimolar levels of the expected ketone and formate were prepared in the same manner. The samples were macerated at room temperature for one day. The hair samples (10 grams) were moistened with warm tap water (about 37°C) and then washed with a milky shampoo. Shampoo (1 gram) was applied with a syringe along the length of each hair sample. The sample was massaged with fingertips for 30 seconds to disperse the shampoo and form a good foam. Rinse with warm tap water for 30 seconds and then gently squeeze out the excess water. The sample was then washed again with pearlescent shampoo for 30 seconds and rinsed with warm tap water for 30 seconds. After gently squeezing out excess water, the sample was hung and dried at room temperature. After 6 hours and 24 hours, the odor intensity of the sample was evaluated by the panel. Panel members were asked to score the perceived odor intensity on a scale of 1 (hardly perceptible) to 7 (very strong). Table 3 summarizes the data obtained from the panel evaluation.

[0257] Table 3: Olfactory evaluation in pearlescent shampoo

[0258]

[0259] These data show that the compound of formula (I) produces a higher odour intensity on the hair than the corresponding reference sample at 6 hours and 24 hours after application from the shampoo. This indicates that the compounds of the invention produce the desired sustained release effect.

[0260] 6. Olfactory evaluation using antiperspirant / deodorant sticks

[0261] A model antiperspirant was prepared in a generally known manner with the following composition (wt %).

[0262]

[0263] Samples containing 0.15 wt. % of enol ether fragrance precursors were prepared by dispersing a 15:20 mixture of enol ether and isopropyl myristate in a molten antiperspirant composition. Reference samples containing equimolar levels of the expected ketone and formates were prepared in the same manner. The molten samples were poured into deodorant stick molds and macerated at room temperature for one day. 0.25 g of each sample was evenly dispersed on a 4.5 cm x 12 cm paper scent paper. The scent paper was stored at ambient conditions for 6 hours and 24 hours. After 6 hours and 24 hours, the odor intensity of the samples was olfactory evaluated by a panel. Panelists were asked to rate the perceived odor intensity on a scale of 1 (hardly noticeable) to 7 (very strong). Table 4 summarizes the data obtained from the panel evaluation.

[0264] Table 4: Olfactory evaluation using antiperspirant / deodorant sticks

[0265]

[0266]

[0267] These data show that 6 hours after application of the antiperspirant stick, the compound of formula (I) produced a higher odor intensity on the scent paper than the corresponding reference sample. This indicates that the compounds of the present invention produce the desired sustained release effect.

[0268] 7. Olfactory evaluation in Eau de Toilette

[0269] A 1% solution of the enol ether in ethanol 40B and water (85:15 by weight) was prepared. Reference samples containing equimolar levels of the expected ketone and formate were prepared. If the mixture was not homogeneous, the enol ether and the corresponding reference sample were sonicated in a 25°C water bath for 10 to 20 minutes. 20 μl of each solution was applied to the center of a 4.5 cm × 12 cm paper sniffing sheet. The sniffing sheet was stored under ambient conditions for 3 hours and 6 hours. After 6 hours and 24 hours, a panel of 20 to 25 people olfactorily evaluated the odor intensity of the samples. Panelists were asked to rate the perceived odor intensity on a scale of 1 (hardly perceptible) to 7 (very strong). Table 5 summarizes the data obtained from the panel evaluations.

[0270] Table 5: Olfactory evaluation in Eau de Toilette

[0271]

[0272] These data show that the compound of formula (I) produces a higher odor intensity on the scent paper than the corresponding reference sample 3 hours and 6 hours after application of the ethanol solution. This shows that the compound of the present invention produces the desired sustained release effect.

[0273] 8. Preparation of liquid detergents containing the compounds of the present invention

[0274] Table 6: Composition of liquid detergent formulations

[0275]

[0276] 1) Hostapur SAS 60; Source: Clariant

[0277] 2) Edenor K 12-18; Source: Cognis

[0278] 3) Genapol LA 070; Source: Clariant

[0279] 4) Source: Genencor International

[0280] 5) Aculyn 88; Source: Dow Chemical

[0281] Liquid detergents are prepared by adding to the unperfumed liquid detergent formulation of Table 6, under gentle shaking, 0.01 to 0.5 wt. % of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the liquid detergent.

[0282] 9. Preparation of a transparent homogeneous shampoo comprising the composition of the present invention

[0283] Table 7: Composition of a transparent homogeneous shampoo formulation

[0284]

[0285] 1) Ucare Polymer JR-400, source: Noveon

[0286] 2) Source: Schweizerhall

[0287] 3) Glydant, source: Lonza

[0288] 4) Texapon NSO IS, source: Cognis

[0289] 5) Tego Betain F 50, source: Evonik

[0290] 6)Amphotensid GB 2009, source: Zschimmer&Schwarz

[0291] 7) Monomuls 90L-12, source: Gruenau

[0292] 8) Monosodium paraben, source: NIPA

[0293] The shampoo is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are added one by one while mixing thoroughly after each adjuvant is added. This premix is ​​then added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Then, premixed Phase B and premixed Phase C (Monomuls 90L-12 is heated to melt in Texapon NSO IS) are added while stirring. Phase D and Phase E are added while stirring. The pH is adjusted with citric acid solution until pH: 5.5-6.0 to obtain an unperfumed shampoo formulation.

[0294] Perfumed shampoos are prepared by adding to the unperfumed shampoo formulation of Table 7, under gentle shaking, 0.01 to 0.5% by weight of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the shampoo.

[0295] 10. Preparation of structured shower gel containing the composition of the present invention

[0296] Table 8: Composition of shower gel formula

[0297] Element Amount (% by weight) Deionized water 49.350 <![CDATA[Sodium EDTA 1) > 0.050 <![CDATA[Acrylate copolymer 2) > 6.000 <![CDATA[Sodium C12 - C15 alcohol polyether sulfate 3) > 35.000 Sodium hydroxide 20% aqueous solution 1.000 <![CDATA[Cocamidopropyl betaine 4) > 8.000 <![CDATA[Methylchloroisothiazolinone and methylisothiazolinone 5) > 0.100 Citric acid (40%) 0.500

[0298] 1) EDETA B powder; Trademark and source: BASF

[0299] 2) CARBOPOL AQUA SF-1 polymer; Trademark and source: NOVEON

[0300] 3) ZETESOL AO 328U; Trademark and source: ZSCHIMMER&SCHWARZ

[0301] 4)TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0302] 5) KATHON CG; Trademark and source: ROHM & HASS

[0303] Prepare a body wash by adding 0.01 to 0.5 wt % of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the body wash, to the unperfumed body wash formulation of Table 8 with gentle shaking.

[0304] 11. Preparation of a transparent shower gel comprising the composition of the present invention

[0305] Table 9: Composition of the transparent shower gel formula

[0306] Element Concentration (% by weight) Deionized water 52.40 <![CDATA[Sodium EDTA 1) > 0.10 Sodium Benzoate 0.50 Propylene glycol 2.00 <![CDATA[Sodium C12 - C15 alcohol polyether sulfate 2) > 35.00 <![CDATA[Cocamidopropyl betaine 3) > 8.00 <![CDATA[Polyquaternium-7 4) > 0.20 Citric acid (40%) 1.00 Sodium chloride 0.80

[0307] 1) EDETA B powder; Trademark and source: BASF

[0308] 2) ZETESOL AO 328U; Trademark and source: ZSCHIMMER&SCHWARZ

[0309] 3)TEGO-BETAIN F 50; Trademark and source: GOLDSCHMIDT

[0310] 4) MERQUAT 550; Trademark and source: LUBRIZOL

[0311] Prepare a clear body wash by adding 0.01 to 0.5 wt % of a compound of the invention of Example 20, 28 or 33 to the unperfumed body wash formulation of Table 9 with gentle shaking, relative to the total weight of the body wash.

[0312] 12. Preparation of a milky shower gel comprising the composition of the present invention

[0313] Table 10: Composition of the emulsion shower gel formula

[0314] Element Concentration (% by weight) Deionized water 50.950 <![CDATA[Sodium EDTA 1) > 0.050 Sodium Benzoate 0.500 Glycerin 86% 3.500 <![CDATA[Sodium dodecyl polyoxyethylene sulfate 2) > 27.000 <![CDATA[Polyquaternium-7 3) > 1.000 <![CDATA[Coco - Betaine 4) > 6.000 <![CDATA[Methyl Gluceth-120 Trioleate 5) > 1.000 Citric acid (40%) 1.000 <![CDATA[Ethylene glycol distearate & Laureth-4 & Cocamidopropyl betaine 6) > 3.000 Sodium chloride 20% 5.000 <![CDATA[PEG-40 Hydrogenated Castor Oil 7) > 1.000

[0315] 1) EDETA B powder; Trademark and source: BASF

[0316] 2)Texapon NSO IS; Trademark and source: COGNIS

[0317] 3) MERQUAT 550; Trademark and source: LUBRIZOL

[0318] 4)DEHYTON AB-30; Trademark and source: COGNIS

[0319] 5) GLUCAMATE LT; Trademark and source: LUBRIZOL

[0320] 6)EUPERLAN PK 3000AM; Trademark and source: COGNIS

[0321] 7) CREMOPHOR RH 40; Trademark and source: BASF

[0322] Prepare a clear body wash by adding 0.01 to 0.5 wt % of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the body wash, to the unperfumed body wash formulation of Table 10 with gentle shaking.

[0323] 13. Preparation of a hand dishwashing detergent comprising the composition of the present invention

[0324] Table 11: Composition of hand dishwashing detergent formulations

[0325] Element Amount (% by weight) <![CDATA[Linear alkylbenzene sulfonic acid (1) > 20 <![CDATA[Diethanolamide (2) > 3.5 <![CDATA[Sodium hydroxide (50%) (3) > 3.4 <![CDATA[Secondary alcohol ethoxolate (4) > 2.5 Sodium xylene sulfonate 6.3 water 64.3

[0326] 1) Biosoft Trademark and source: Stepan Company

[0327] 2) Ninol Trademark and source: Stepan Company

[0328] 3) Stepanate Trademark and source: Stepan Company

[0329] 4) Tergitol Trademark and source: Dow Chemical Company

[0330] Mix water with sodium hydroxide and diethanolamide. Add LAS. After neutralizing the LAS, add the remaining ingredients. Check the pH (=7-8) and adjust if necessary.

[0331] Perfumed hand dishwashing detergents are prepared by adding 0.01 to 0.5 wt % of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the hand dishwashing detergent, to the unperfumed hand dishwashing detergent formulation of Table 11 with gentle shaking.

[0332] 14. Preparation of a universal cleaner comprising the composition of the present invention

[0333] Table 12: Composition of general purpose cleaner formulation

[0334] Element Amount (% by weight) <![CDATA[Ethoxylated alcohol (C9 - C11, 8EO) (1) > 20 <![CDATA[Sodium dodecylbenzenesulfonate (2) > 16 <![CDATA[Sodium cumenesulfonate (3) > 8 <![CDATA[Methylchloroisothiazolinone Methylisothiazolinone 3.3:1 (4) > 0.8％ water 55.9

[0335] 1) Neodol Trademark and source: Shell Chemical

[0336] 2) Biosoft Trademark and source: Stepan Company

[0337] 3) Stepanate Trademark and source: Stepan Company

[0338] 4) Kathon Trademark and source: Dow Chemical Company

[0339] Mix all ingredients together and then dilute the mixture to 100% with water.

[0340] An all-purpose cleaner was prepared by adding 0.01 to 0.5 wt % of a compound of the invention of Example 20, 28 or 33, relative to the total weight of the all-purpose cleaner, to the unperfumed all-purpose cleaner formulation of Table 12 with gentle shaking.

[0341] 15. Microencapsulation of the compound of formula (I)

[0342] Synthesis of Microcapsules Containing Compounds of the Invention: In this example, the technique used to synthesize microcapsules with a fragrance oil core is the interfacial polymerization of a biopolymer-stabilized oil-in-water emulsion with an oil-soluble polyisocyanate monomer that self-polymerizes at the oil-water interface.

[0343] SuperStab AA Senegalese gum arabic was purchased from Nexira, Somerville, NJ. D-110N was purchased from Mitsui Chemicals, Tokyo, Japan. Desmodur N100 was obtained from Covestro (formerly Bayer Material Science), Pittsburgh, Pennsylvania. Guanidine carbonate (≥99%, 120222500) was purchased from Acros Organics, New Jersey, USA.

[0344] Microcapsules containing fragrance precursors or individual fragrance material components were prepared by first preparing an oil phase and an aqueous phase and a guanidine carbonate crosslinker solution. The oil phase was prepared by mixing 10 g of the fragrance precursor molecule (or fragrance raw material) described in Example 2 with 2.24 g of Desmodur N100 in a scintillation vial and mixing by a magnetic stir bar at room temperature until the isocyanate was completely dissolved. The aqueous phase was prepared by dissolving 0.50 g of Superstab AA powder in 33.6 g of 18.2 MΩ·cm water by a magnetic stir bar at room temperature. The guanidine carbonate crosslinker solution was prepared by dissolving 0.56 g of guanidine carbonate in 3.10 g of 18.2 MΩ·cm water. The oil phase was added dropwise to the aqueous phase by pipette while emulsifying the aqueous phase at 18000 rpm for 3 minutes using an IKA UltraTurrax homogenizing rod. The emulsion was poured into a jacketed reactor and stirred at 500 rpm by an overhead stirrer. The crosslinker solution was automatically injected slowly into the reactor at a rate of 125 μL / min by a syringe pump until it was completely incorporated into the emulsion. The reactor temperature was raised to 50°C in 30 minutes and then to 70°C in another 30 minutes. The reactor was then kept at 70°C for 4 hours and then cooled to room temperature. The resulting slurry was discharged into a wide-mouth bottle.

[0345] The particle size of each slurry was characterized using a Mastersizer 3000 (Malvern Instruments Ltd., UK). The average particle size or D[4,3] of the microcapsules containing the fragrance precursor was 31.1 μm. The morphology of the particles was characterized using a JEOL JSM-6010PLUS scanning electron microscope (JEOL Ltd, Tokyo, Japan).

[0346] The measurement of oil loading was performed to deduce the solid content of the microcapsule slurry, which was characterized by thermogravimetric analysis using a TA Q50 TGA (TA Instruments, Delaware, USA). The slurry was exposed to high temperature (50°C) to evaporate as much water as possible to determine the amount of encapsulated oil and shell material remaining, or solid content. The solid content was calculated as the percentage of the original mass remaining after maintaining the high temperature for 250 minutes.

[0347] The total oil content in the whole slurry was determined by diluting 1 mL of the slurry in 4 mL of acetonitrile and filtering out the residual solid matter with a 17 mm, 0.45 μm regenerated cellulose (RC) filter, followed by a 4 mm, 0.2 μm RC filter. The solution was analyzed by GCMS, and the content of the individual substances was determined by comparison with an external calibration curve. The oil content in the aqueous phase of the slurry was determined by separating the aqueous phase by centrifuging 1 mL of the slurry at 10,000 rpm for 5 minutes. The separated aqueous phase was filtered through a 17 mm, 0.45 μm RC filter and a 4 mm, 0.2 μm RC filter, and the filtrate was diluted in 4 mL of acetonitrile. The solution was analyzed by GCMS, and the content of the individual substances was determined by comparison with an external calibration curve.

[0348] The amount of oil inside the microcapsules was defined as the difference between the two measurements (bulk slurry oil content minus water phase oil content). The encapsulation efficiency is the ratio between the amount of oil inside the microcapsules and the amount of oil loaded into the slurry during the microencapsulation process and is expressed as a percentage.

[0349]

[0350] When analyzed by this method, the amounts of the individual raw materials acetophenone, 3-hexen-1-yl formate, and 3-hexen-1-ol were less than what was initially loaded into the slurry, accounting for only 78.5% of acetophenone, 77.78% of 3-hexen-1-yl formate, and 69.0% of 3-hexen-1-ol, with encapsulation efficiencies of 74.78%, 70.97%, and 57.41% of the original loadings of these compounds, respectively. This poor encapsulation efficiency is not unexpected due to the low log P of each compound, resulting in these materials partitioning into the aqueous phase, and the high volatility of each material, which may have resulted in evaporation and mass loss due to the increased temperature during the encapsulation reaction. The 93.04% encapsulation efficiency of the fragrance precursor shows higher encapsulation efficiencies than the individual control materials.

[0351] Publications cited in their entirety are hereby incorporated by reference in their entirety. Although various aspects of the present invention have been described above with reference to examples and preferred embodiments, it should be understood that the scope of the present invention is not limited by the foregoing description, but by the appended claims appropriately interpreted under the principles of patent law.

Claims

1. A method of releasing a compound selected from the group consisting of: a) a ketone or aldehyde of formula (II), Wherein n represents an integer from 0 to 5; R 1 Simultaneously or independently represent at least one substituent of an aromatic ring and are hydroxyl, C 1-6 Alkyl, C 1-6 Alkoxy or RCOO, ROCO groups, where R is a hydrogen atom or C 1-4 Alkyl; or two adjacent R 1 When combined together they represent -O-(CH2) m O-, where m is 1 or 2, or forms C 5-10 A saturated or unsaturated ring, optionally substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 Alkoxy; R 2 represents hydrogen atom, C 1-6 Alkyl or C 6-10 Aryl, optionally substituted with hydroxyl, C 1-3 Alkyl, C 1-3 Alkoxy, RCOO or ROCO group, in which R is independently a hydrogen atom or a C 1-4 alkyl; b) a formic acid ester of the formula (III), Where R 3 , R 4 and R 5 represents simultaneously or independently a hydrogen atom or a C optionally containing 1 to 3 oxygen atoms 1-18 Hydrocarbyl; or R 3 and R 4 When combined together, it represents a C optionally containing 1 to 3 oxygen atoms. 3-18 a hydrocarbon group; and c) an alcohol of formula (IV), Where R 3 , R 4 and R 5 has the same meaning as defined above; wherein the precursor compound comprises a compound of formula (I), Where n, R 1 , R 2 , R 3 , R 4 and R 5 has the same meaning as defined above; The method is carried out by exposing a precursor compound of formula (I) to ambient conditions, in, The precursor compound of formula (I) is oxidized in the absence of any catalyst, and the ambient conditions are those at room temperature in the air, sunlight and atmospheric pressure.

2. The method according to claim 1, wherein: n is 0, 1 or 2.

3. The method according to claim 1, wherein R 1 Simultaneously or independently represent a hydroxyl group, C 1-4 Alkyl or C 1-3 Alkoxy; or two adjacent R 1 When combined together, they represent -O-CH2-O- group, -(CH2)4- group, -(CH)4- group.

4. The method according to claim 1, wherein R 2 represents hydrogen atom, C 1-3 Alkyl, or phenyl.

5. The method according to claim 1, wherein R 3 represents a C optionally containing 1 to 3 oxygen atoms 2-18 Hydrocarbon.

6. The method according to claim 1, wherein R 3 Represents C 4-10 Straight-chain, branched or cyclic alkyl, alkenyl or diene group, phenyl, benzyl, C 7-16 Arylalkyl or styryl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3 Alkoxy, phenoxymethyl or C 8-15 a saturated or unsaturated alicyclic group, which optionally contains an ether function; R 4 and R 5 represents hydrogen or C 1-6 Alkyl or C 2-6 alkenyl; or R 3 and R 4 Together they represent C 5-12 A straight-chain or branched alkanediyl or alkenediyl, or C 5-12 Alicyclic group.

7. The method of claim 1, wherein at least one of the compounds of formula (II), formula (III) or formula (IV) is a perfuming ingredient.

8. The method according to claim 1, wherein at least two of the compounds of formula (II), formula (III) or formula (IV) are perfuming ingredients.

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

10. A method for enhancing or prolonging the diffusion of the characteristic aroma of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive alcohol of formula (IV) as defined in claims 1 to 8 on a surface or in the air surrounding a perfuming composition, wherein the surface or the air is treated with at least one compound (I) as defined in claims 1 to 8, or with a composition or an article comprising at least one compound (I), under conditions suitable to allow the release of at least one reactive aldehyde or ketone of formula (II), at least one reactive formate of formula (III) and / or at least one reactive alcohol of formula (IV) over time.

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

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

13. The perfumed consumer product according to claim 12, characterized in that The fragrance consumer product is a perfume, a fabric care product, a body care product, a cosmetic preparation, a skin care product, an air care product or a home care product.

14. A perfumed consumer product according to claim 13, characterised in that The fragrance consumer product is a fine perfume, a perfume to be spread or an eau de parfum, a cologne, a shaving lotion or aftershave, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, paper, a bleaching agent, a carpet cleaner, a curtain care product, a shampoo, a coloring preparation, a color care product, a hair styling product, a dental care product, a disinfectant, a private care product, a hair spray, a vanishing cream, a deodorant or an antiperspirant, a depilatory, a tanning or sun protection product, a nail product, a skin cleanser, a make-up product, a soap, a bath mousse, a bath oil or a shower gel, or a foot / hand care product, a hygiene product, an air freshener, a "ready-to-use" powder air freshener, a mildew remover, a furniture care agent, a wipe, a dishwashing detergent or a hard surface detergent, a leather care product, a car care product.

15. A compound of formula (I), Wherein n represents an integer from 0 to 5; R 1 Simultaneously or independently represent at least one substituent of an aromatic ring and are hydroxyl, C 1-6 Alkyl, C 1-6 Alkoxy or RCOO, ROCO groups, where R is a hydrogen atom or C 1-4 Alkyl; or two adjacent R 1 When combined together they represent -O-(CH2) m O-, where m is 1 or 2, or forms C 5-10 A saturated or unsaturated ring, optionally substituted with one or more hydroxyl groups, one or more C 1-3 Alkyl and / or one or more C 1-3 Alkoxy; R 2 represents hydrogen atom, C 1-6 alkyl; R 3 Represents C 4-10 Straight-chain, branched or cyclic alkyl, alkenyl or diene group, benzyl or C 7-16 Arylalkyl, optionally substituted with hydroxyl, C 1-3 Alkyl or C 1-3 Alkoxy, phenoxymethyl or C 8-15 a saturated or unsaturated alicyclic group, which optionally contains an ether function; R 4 and R 5 represents hydrogen or C 1-6 Alkyl or C 2-6 alkenyl; or R 3 and R 4 Together they represent C 5-12 A straight-chain or branched alkanediyl or alkenediyl, or C 5-12 alicyclic groups, The proviso is that (2-((3-methylbut-2-en-1-yl)oxy)vinyl)benzene, (1-(isopentyloxy)prop-1-en-2-yl)benzene, (2-(pentyloxy)vinyl)benzene, (1-(dodecyloxy)prop-1-en-2-yl)benzene, (2-(hexyloxy)vinyl)benzene, (2-(heptyloxy)vinyl)benzene, (2-(octyloxy)vinyl)benzene, (1-(2-cyclohexylethoxy)prop-1-en-2-yl)benzene benzene, (1-(2-(cyclohexylethoxy)prop-1-en-2-yl)benzene and 1-methyl-4-(1-((2-phenylcyclohexyl)oxy)prop-1-en-2-yl)benzene.

Images