Cyclic acetals and ketals for the photoinduced release of active aldehydes and ketones

Abstract

The present invention relates to a delivery system based on compounds of formula (I), i.e. photoresponsive cyclic acetal or ketal compounds, which can release active volatile carbonyl compounds to their surroundings in a controlled manner upon exposure to light.Furthermore, the present invention relates to the use of said compounds in perfumery, and to perfumed compositions or perfumed consumer products comprising the compounds of the present invention.

Description

[Technical field]

[0001] The present invention relates to a delivery system based on compounds of formula (I), i.e. photoresponsive cyclic acetal or ketal compounds, which can release active volatile carbonyl compounds to their surroundings in a controlled manner upon exposure to light.Furthermore, the present invention relates to the use of said compounds in perfumery, and to perfumed compositions or perfumed consumer products comprising the compounds of the present invention.

[0002] Background technology In the perfume industry, compositions and additives that are able to extend or enhance the perfuming effect of a mixture of multiple fragrances mixed together over a period of time are of particular interest. It is particularly desirable to obtain persistence for standard perfume raw materials that are themselves too volatile, have poor retention properties, or deposit only small amounts on the surfaces of the final application. Furthermore, some perfume ingredients, especially aldehydes, are unstable and need to be protected from slow decomposition before use. Persistent perfumes are desirable for various applications, for example in fine perfumery, functional perfumery and cosmetic preparations. Textile washing and softening are particularly areas in which there is a constant demand for the effect of active substances, especially perfumes, to be able to remain effective for a certain period of time after washing, softening and drying. Indeed, many substances with odors that are particularly suitable for this type of application are known to have poor adhesion to laundry or do not remain on the laundry even after rinsing, so that their perfuming effect is only obtained for a short time and is not very strong. Given the importance of this type of application in the perfumery industry, research in this field has been continued, in particular with the aim of finding new and more effective solutions to the aforementioned problems.

[0003] It has now surprisingly been found that the photosensitive cyclic acetals or ketals according to the present invention overcome the above problems and are capable of efficiently unencapsulating some active volatile carbonyl compounds upon exposure to light in many practical applications. To the best of the inventors' knowledge, there is no prior art document that suggests or gives the expectation that the photosensitive acetal and ketal compounds of formula (I) may in fact be suitable as delivery systems for the controlled release of volatile compounds. [Brief description of the drawings]

[0004] [Figure 1] Photoinduced release of phenylketone derivatives of formula (III) and carbonyl compounds (aldehydes or ketones) of formula (II) from cyclic acetals or ketals according to formula (I) upon irradiation with a xenon lamp and 1H-NMR spectroscopy. Compound 1 (top) releases acetophenone and benzaldehyde, and compound 2 (bottom) releases acetophenone and undecanal. [Diagram 2] Photoinduced release of phenylketone derivatives of formula (III) and carbonyl compounds (aldehydes or ketones) of formula (II) from cyclic acetals or ketals according to formula (I) upon irradiation with a xenon lamp and 1H-NMR spectroscopy. Compound 13 (top) releases two molecules of acetophenone (the recorded 1H-NMR integrals of the released acetophenone were adjusted to correspond to two molar equivalents). Compound 16 (bottom) releases acetophenone and benzaldehyde.

[0005] Description of the invention It has now been discovered that compounds of formula (I) can be advantageously used as delivery systems that release an active volatile aldehyde or ketone along with an active volatile phenylketone derivative from a given surface into the surrounding environment upon exposure to light.

[0006] A first subject of the invention is therefore a compound of formula [ka] [In the formula, n is 0 or 1; X is an oxygen atom or NR 9 is a group, R 9 is a hydrogen atom or a methyl group; R 1 is C 1-18 represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom; R 2 is a hydrogen atom or R 1 represents a group; or R 1 and R 2 If they are combined, C 5-16 Cycloalkyl groups, C 5-16 Cycloalkenyl group, C 4-14 Heterocycloalkyl group or C 4-14 heterocycloalkenyl groups, each of which is optionally 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 6-10 Aryl groups and / or C 6-10 aryloxy groups, each of which is optionally substituted with one or more of 1-8 Alkyl group, C 1-8 Alkoxy groups, carboxylic acid groups and / or C 1-4 substituted with one or more of a carboxylic acid ester group, wherein the heteroatom represents one or more oxygen atoms; R 3 and R 4 are each independently a hydrogen atom, C 1-6 Alkoxy group or C 1-12 an alkyl group, optionally including a hydroxy group, C 1-6 It represents a group substituted with an alkoxy group or an oxo group, or two adjacent R 3 The groups, when taken together, are C 3-8 A linear alkanediyl group, optionally containing a hydroxy group, C 1-3Alkyl group and / or C 1-3 substituted with one or more alkoxy groups; R 5 is a hydrogen atom or C 1-6 represents a hydrocarbon group or R 4 and R 5 If they are combined, C 1-4 represents a linear, branched or cyclic alkanediyl group, optionally containing one oxygen atom; R 6 represents a hydrogen atom or a methyl group; R 7 and R 8 are each independently a hydrogen atom or C 1-6 represents an alkyl group; and base R 1 and R 2 has a total of at least 4 carbon atoms] or a mixture thereof.

[0007] For the sake of clarity, expressions such as "any one stereoisomer of the compound or a mixture thereof" have the usual meaning understood by the skilled artisan, i.e., that the compound of formula (I) may be a pure enantiomer (if optically active) or a diastereomer. In other words, the compound of formula (I) may have several stereocenters, each of which may have two different configurations (e.g. R or S). The compound of formula (I) may be in the form of a pure enantiomer or in the form of a mixture of enantiomers or diastereomers. The compound of formula (I) may be in racemic or scalene form. Thus, the compound of formula (I) may be in the form of one stereoisomer or in the form of a composition of matter that comprises or consists of various stereoisomers.

[0008] "...hydrocarbon group..." is understood to mean that said group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), saturated cyclic hydrocarbon (e.g. cycloalkyl) or unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl group), aromatic hydrocarbon, i.e. aryl group, or mixtures of said types of groups, e.g. a particular group may contain linear alkyl, branched alkenyl (e.g. having one or more carbon-carbon double bonds), (poly)cycloalkyl and aryl moieties, unless a specific limitation to only one type is mentioned. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of more than one type of topology (e.g., linear, cyclic or branched) and / or being saturated or unsaturated (e.g., alkyl, aromatic or alkenyl), it also means the group can have any one of said topologies or contain moieties that are saturated or unsaturated, as explained above. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of one type of saturated or unsaturated (e.g., alkyl), it means that the group can be in any type of topology (e.g., linear, cyclic or branched) or have several moieties with various topologies.

[0009] The term "hydrocarbon radical, optionally including ..." is understood to mean that said hydrocarbon radical optionally includes an alcohol, ketone, aldehyde, ether, thioether, ester, carboxylic acid, amine, amide, carbamate, nitrile or thiol group, which may be attached laterally to said hydrocarbon radical by replacing a hydrogen atom of said hydrocarbon radical or may be incorporated into the hydrocarbon chain by replacing a carbon atom of the hydrocarbon radical (if chemically possible). For example, the -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group containing an alcohol group (substitution of a hydrogen atom), i.e. a C4 hydrocarbon containing an oxygen atom, the -CH2-CH2-COO-CH2-CH2-CH2-CH2-CH2- group represents a C6 hydrocarbon group containing one ester group (substitution of a carbon atom / incorporation into the hydrocarbon chain), i.e. a C7 hydrocarbon containing two oxygen atoms, and similarly, the -CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a C6 hydrocarbon group containing two ether groups, i.e. a C6 hydrocarbon containing two oxygen atoms.

[0010] The term "optionally" is understood to mean that an optionally substituted or optionally included group may or may not be substituted with a functional group or may or may not contain a certain atom. The term "one or more" is understood to mean that it is substituted with 1 to 7, preferably 1 to 5, more preferably 1 to 3, functional groups.

[0011] The terms "alkyl" and "alkenyl" are understood to include branched and straight chain alkyl and alkenyl groups. The terms "alkenyl", "cycloalkenyl" and "heterocycloalkenyl" are understood to include one, two or three olefinic double bonds, preferably one or two olefinic double bonds. The terms "cycloalkyl", "cycloalkenyl", "heterocycloalkyl", "heterocycloalkenyl" and "heterocyclic" are understood to include monocyclic or fused, spiro and / or bridged bicyclic or tricyclic cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl groups, as well as heterocyclic groups, preferably monocyclic cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl groups.

[0012] The term "aryl" is understood to include any group containing at least one aromatic group, such as a phenyl, indenyl, indanyl, benzodioxolyl, dihydrobenzodioxinyl, tetrahydronaphthalenyl or naphthalenyl group.

[0013] The term "oxo group" is understood to include any group of formula =O, i.e., ketones or aldehydes, etc. In other words, C optionally substituted with an oxo group. 1-6 An alkyl group is an alkyl group having from 1 to 6 carbon atoms, one of which may be a terminal carbon or may be substituted with one =O group in place of two hydrogen atoms.

[0014] "Basic R 1 and R 2 has a total of at least 4 carbon atoms" is intended to 1 Carbon atoms of the group and R 2 It is understood that the total number of carbon atoms in the group is 4 or more, i.e., R 2 When the group is a hydrogen atom, R 1 The group is a C group such as a butyl group. 4-18 is a hydrocarbon group; or R 1When the group is a methyl group, R 2 The group is a C group such as a propyl group. 3-18 It is a hydrocarbon group.

[0015] According to an optional embodiment of the present invention, R 7 is a hydrogen atom or C 1-4 In particular, R 7 is a hydrogen atom or C 1-3 In particular, R 7 may be a hydrogen atom or a methyl or ethyl group. In particular, R 7 may be a hydrogen atom or a methyl group. Even more particularly, R 7 may be a hydrogen atom.

[0016] According to an optional embodiment of the present invention, R 8 is a hydrogen atom or C 1-4 In particular, R 8 is a hydrogen atom or C 1-3 In particular, R 8 may be a hydrogen atom or a methyl or ethyl group. In particular, R 8 may be a hydrogen atom or a methyl group. Even more particularly, R 8 may be a hydrogen atom.

[0017] According to an optional embodiment of the present invention, R 6 may be a hydrogen atom.

[0018] According to an optional embodiment of the present invention, R 5 is a hydrogen atom or C 1-6 Linear or branched alkyl group, or C 2-6 It may be a linear or branched alkenyl group. In particular, R 5 is a hydrogen atom or C 1-4 Linear or branched alkyl group, or C 2-4 It may be a linear or branched alkenyl group. In particular, R 5 is a hydrogen atom or C 1-3 Linear or branched alkyl group, or C2-3 In particular, R 5 may be a hydrogen atom or a methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl or allyl group. 5 may be a hydrogen atom or a methyl group. Even more particularly, R 5 may be a hydrogen atom.

[0019] According to an optional embodiment of the present invention, R 9 may be a hydrogen atom.

[0020] According to any embodiment of the present invention, X may be an oxygen atom or an NH group. In particular, X may be an oxygen atom.

[0021] According to any embodiment of the present invention, n may be 0.

[0022] According to any embodiment of the present invention, the compound of the present invention has the formula [ka] [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 has the same meaning as defined above] in the form of any one of the stereoisomers or mixtures thereof.

[0023] According to any embodiment of the present invention, the compound of the present invention has the formula [ka] [In the formula, R 1 , R 2 , R 3 , R 4 and R 5has the same meaning as defined above] in the form of any one of the stereoisomers or mixtures thereof.

[0024] According to an optional embodiment of the present invention, each R 3 are each independently a hydrogen atom, C 1-5 Alkoxy group or C 1-10 an alkyl group, optionally including a hydroxy group, C 1-3 In particular, each R 3 are each independently a hydrogen atom, C 1-4 Alkoxy group or C 1-8 an alkyl group, optionally including a hydroxy group, C 1-3 In particular, each R 3 are each independently a hydrogen atom, C 1-3 Alkoxy group or C 1-6 an alkyl group, optionally including a hydroxy group, C 1-3 In particular, each R 3 are each independently a hydrogen atom, a methoxy group or C 1-4 In particular, one or two R 3 are each independently a hydrogen atom, a methoxy group or C 1-4 In particular, one or two R 3 are each independently a hydrogen atom, a methoxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group or a sec-butyl group, and the others are a hydrogen atom. In particular, one or two R 3 may each independently be a hydrogen atom, a methoxy group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and the others are hydrogen atoms. 3 may each independently be a hydrogen atom, a methoxy group or a methyl group, and other R 3 is a hydrogen atom. Even more particularly, R 4 R in meta position 3may be a hydrogen atom, a methoxy group or a methyl group, and other R 3 is a hydrogen atom.

[0025] According to an optional embodiment of the present invention, two adjacent R 3 The groups, when taken together, are C 3-6 A linear alkanediyl group, optionally containing a hydroxy group, C 1-3 Alkyl group and / or C 1-3 In particular, two adjacent R 3 The groups, when taken together, are C 3-4 A linear alkanediyl group, optionally containing hydroxy groups and / or C 1-3 In particular, two adjacent R 3 The groups, when taken together, are C 3-4 A linear alkanediyl group, optionally 1-3 In particular, two adjacent R 3 The groups, when taken together, are C 3-4 It is a straight-chain alkanediyl group, which may be optionally substituted with one, two, three, four or five of the following groups: methyl, ethyl or isopropyl.

[0026] According to an optional embodiment of the present invention, R 4 is a hydrogen atom, C 1-4 Alkoxy group or C 1-8 an alkyl group, optionally including a hydroxy group, C 1-3 It may be substituted with an alkoxy group or an oxo group. In particular, R 4 is a hydrogen atom, C 1-3 Alkoxy group or C 1-6 an alkyl group, optionally including a hydroxy group, C 1-3 It may be substituted with an alkoxy group or an oxo group. In particular, R 4 is a hydrogen atom, a methoxy group or C 1-4 In particular, R 4 is a hydrogen atom, a methoxy group or C1-3 In particular, R 4 may be a hydrogen atom, a methoxy group or a methyl group. Even more particularly, R 4 may be a hydrogen atom.

[0027] According to an optional embodiment of the present invention, R 4 and R 5 may together represent a C1-C3 linear or branched alkanediyl group. In particular, R 4 and R 5 together can represent a methanediyl group or a propane-2,2-diyl group.

[0028] According to an optional embodiment of the present invention, R 1 and R 2 is the formula R 1 CHO (i.e., R 2 is a hydrogen atom) or an active aldehyde of the formula (R 1 )(R 2 ) C=O ketone; said aldehyde or ketone has a molecular weight of 80 to 230 g / mol and is C5 to C 18 It is a compound.

[0029] According to an optional embodiment of the present invention, R 1 is C 1-15 It is a hydrocarbon group, which may optionally contain 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom. In particular, R 1 is C 1-12 It is a hydrocarbon group, which may optionally contain 1 to 3 oxygen atoms. In particular, R 1 is C1~C 10 It is a hydrocarbon group, which may optionally contain 1 to 3 oxygen atoms. In particular, R 1 is a C1 to C9 hydrocarbon group, optionally containing 1 to 3 oxygen atoms. Even more particularly, R 1 is a C1 to C8 hydrocarbon group, which may optionally contain 1 to 3 oxygen atoms.

[0030] According to an optional embodiment of the present invention, R 1 and R 2 If they are combined, C 5-16 Cycloalkyl group or C 5-16 cycloalkenyl groups, each of which is optionally 1-8 Alkyl group, C 2-8 Alkenyl group, C 1-8 Alkoxy group, C 3-8 Cycloalkyl groups, C 5-8 cycloalkenyl, C6 aryl and / or C6 aryloxy groups, each of which is optionally substituted with one or more of: 1-6 Alkyl group, C 1-6 Alkoxy groups, carboxylic acid groups and / or C 1-4 In particular, R 1 and R 2 If they are combined, C 5-16 Cycloalkyl group or C 5-16 cycloalkenyl groups, each of which is optionally 1-6 Alkyl group, C 2-6 Alkenyl group, C 1-6 Alkoxy group, C 3-6 Cycloalkyl groups, C 5-6 cycloalkenyl, C6 aryl and / or C6 aryloxy groups, each of which is optionally substituted with one or more of: 1-4 Alkyl group, C 1-4 Alkoxy groups, carboxylic acid groups and / or C 1-3 carboxylic acid ester groups. Even more particularly, R 1 and R 2 If they are combined, C 5-16 Cycloalkyl group or C 5-16 cycloalkenyl groups, each of which is optionally 1-4 Alkyl group, C 2-4 Alkenyl group, C 1-4 Alkoxy group, C 3-6 Cycloalkyl groups, C 5-6cycloalkenyl, C6 aryl and / or C6 aryloxy groups, each of which is optionally substituted with one or more of: 1-3 Alkyl group, C 1-3 Alkoxy groups, carboxylic acid groups and / or C 1-2 It is substituted with one or more carboxylic acid ester groups.

[0031] According to any one of the above embodiments, the compound of formula (I) is 1-phenyl-3-(2-phenyl-1,3-dioxan-4-yl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-(2-phenylpropyl)-1,3-dioxolan-4-yl)propan-1-one, 1-phenyl-3-(2-(undecan-2-yl)-1,3-dioxolan-4-yl)propan-1-one, 1-phenyl-3-(2-(undec-3-en-1-yl)ethyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-(2,4-dimethylcyclohex-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-(2-(4,4-dimethylcyclohex-1-en-1-yl)ethyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-(undec-3-en-1-yl)ethyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one 3-(2-(2-(4-methylcyclohex-3-en-1-yl)propyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-(6-methylhept-5-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, (E / Z)-3-(2-(4,8-dimethylnon-3-en-1-yl)-1,3-dioxolan-4-yl)- 1-Phenylpropan-1-one, (E / Z)-3-(2-(5-cyclohexyl-4-methylpent-4-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-methyl-2-phenyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(6-pentyl-1,4-dioxaspiro[4.4]nonan-2-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-phenyl-1,3-dioxolan-4-yl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-(p-tolyl)propan-1-one, 3-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-(4-ethylphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one, The stereoisomeric form of any one of the following isomers: 2-methyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 2,2-dimethyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-phenethyl-1,3-dioxolan-4-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one, 3-(5-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, or 3-(5,5-dimethyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one.

[0032] In certain embodiments of the present invention, the following compounds are excluded from formula (I): methyl 3-methoxy-2-(2-methyl-5-(4-(3-oxo-3-phenylpropyl)-1,3-dioxolan-2-yl)benzyl)acrylate, methyl 3-methoxy-2-(methyl(3-(4-(3-oxo-3-phenylpropyl)-1,3-dioxolan-2-yl)phenyl)amino)acrylate, methyl 2-(methoxyimino)-3-(2-methyl-5 ... 2-(methoxyimino)-N-methyl-3-(2-methyl-5-(4-(3-oxo-3-phenylpropyl)-1,3-dioxolan-2-yl)phenyl)propanoate, 2-(methoxyimino)-N-methyl-3-(2-methyl-5-(4-(3-oxo-3-phenylpropyl)-1,3-dioxolan-2-yl)phenyl)propenamide and 3-(2-(3-(2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-(methoxyimino)ethyl)-4-methylphenyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one.

[0033] According to an optional embodiment, the compounds of formula (I) are non-volatile and substantially odorless, while at the same time they are relatively stable in perfumed compositions or perfumed consumer products.

[0034] The non-volatile and substantially odorless compound is advantageously characterized by a vapor pressure of less than 2.0 Pa, calculated using the software EPIwin v.3.10 (2000, available from the United States Environmental Protection Agency). Preferably, said vapor pressure is less than 0.2 Pa, even more preferably less than 0.02 Pa.

[0035] The compound according to formula (I) can be decomposed to give the compound of formula [ka] [In the formula, R 1 , R 2 has the same meaning as above], [ka] [In the formula, R 3 ~R 6 has the same meaning as above] can be released together with a phenyl ketone derivative of

[0036] The term "carbonyl" means R 2 Depending on the meaning of the group, it represents an aldehyde or a ketone, i.e. the carbonyl compound of formula (II) 2 When R represents a hydrogen atom, the carbonyl compound of formula (II) is an aldehyde. 2 is not a hydrogen atom, it is a ketone.

[0037] The decomposition reaction leading to the release of the compounds of formula (II) and formula (III) is believed to be induced by light, particularly light of wavelengths greater than 300 nm, preferably greater than 330 nm, and even more preferably greater than 350 nm. The compounds of formula (I) decompose upon exposure to light to give phenylketone derivatives of formula (III) and 4-methylene-1,3-dioxolane derivatives (n=0 and X=O), 4-methyleneoxazolidine derivatives (n=0 and X=NR 9 ), 4-methylene-1,3-dioxane derivatives (n=1 and X=O) or 4-methylene-1,3-oxazinane derivatives (n=1 and X=NR 9 ) is believed to form. Each dioxolane, oxazolidine, dioxane or oxazinane derivative is hydrolytically unstable and hydrolyzes to form the carbonyl compound of formula (II). Cleavage of the hydrolytically stable cyclic acetals or ketals or oxazolidines or 1,3-oxazinanes of the present invention is thus induced by light, thereby forming a hydrolytically unstable intermediate which releases the desired compound in a two-step sequence. Depending on the structure, three (n=0 and R 7 and R 8 is a hydrogen atom) or 4 (n=1 and R 7 and R 8Since all carbon atoms except for (wherein is a hydrogen atom) are converted into active compounds, the delivery system according to the present invention is very atom economical.

[0038] [ka]

[0039] According to any embodiment, the compounds of formula (II) and (III) are advantageously characterized by a vapour pressure calculated with the software EPIwin v.3.10 (2000, available from the United States Environmental Protection Agency) of greater than 1.0 Pa. According to another embodiment, said vapour pressure is greater than 5.0 Pa or even greater than 7.0 Pa.

[0040] In certain embodiments, R 2 is a hydrogen atom; i.e., the compound of formula (II) R 1 The aldehyde of CHO is Benzaldehyde , 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 3-butoxybenzaldehyde, 5-Cyclohexyl-2,4-dimethylpent-4-enal , Decalogue , 2,4-decadienal, 2-decenal, 4-decenal, 8-decenal, 9-decenal, 3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)propanal, 2,4-Dimethyl-3-cyclohexene-1-carbaldehyde (Triplal®, Supplier: International Flavors & Fragrances, New York, USA), 3,5-dimethyl-3-cyclohexene-1-carbaldehyde, 1-(3,3-dimethyl-1-cyclohexyl)-1-ethanone, 3-(4,4-Dimethylcyclohex-1-enyl)propanal , 5,9-dimethyl-4,8-decadienal, 4,8-dimethyl-4,9-decadienal, 5,9-Dimethyldec-4-enal , 2,6-Dimethyl-5-heptenal (Melonal), (E / Z)- 3,7-Dimethyl-2,6-octadienal (citral, neral), 3,7-dimethyloctanal, 3,7-Dimethyl-6-octenal (Citronellal), (3,7-dimethyl-6-octenyl)acetaldehyde, dodecanal, 2-dodecenal, 3-dodecenal, 4-Dodecenal , 3-ethoxy-4-hydroxybenzaldehyde (ethyl vanillin), 4-Ethylbenzaldehyde , 3-(2- and 4-ethylphenyl)-2,2-dimethylpropanal, 2-furancarbaldehyde (furfural), 2,4-heptadienal, 4-heptenal, 2-hexenal, 3-hexenal, 2-hydroxybenzaldehyde, 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal), 4-hydroxy-3-methoxybenzaldehyde (vanillin), 4- and 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde (Lyral®, Supplier: International Flavors and Fragrances, New York, USA), 3-(4-isobutyl-2-methylphenyl)propanal, 3-(4-isobutylphenyl)propanal, 4-isopropylbenzaldehyde (cuminaldehyde), 3-(4-isopropylcyclohex-1-en-1-yl)propanal, 3-(3-isopropylphenyl)butanal, 3-(4-isopropylphenyl)-2-methylpropanal, 2-(4-isopropylphenyl)propanal, 4-Methoxybenzaldehyde (anisaldehyde) , 6-methoxy-2,6-dimethylheptanal (methoxymelonal), 8(9)-methoxytricyclo[5.2.1.0.(2,6)]decane-3(4)-carbaldehyde (Scentenal®, supplied by Firmenich SA, Geneva, Switzerland), 4-methylbenzaldehyde, 3-(4-methylcyclohex-3-en-1-yl)butanal, 2-methyldecanal, 2-(4-methylenecyclohexyl)propanal, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde (Precyclemone® B, supplied by International Flavors and Fragrances, New York, USA), 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde (Empetal, supplied by Givaudan-Roure SA, Vernier, Switzerland), (4-methylphenoxy)acetaldehyde, (4-methylphenyl)acetaldehyde, 3-methyl-5-phenylpentanal (Phenexal®, supplied by Firmenich SA, Geneva, Switzerland), 3-methyl-3-phenylpropanal, 2-Methylundecanal , 2,4-nonadienal, 2,6-nonadienal, 2-nonenal, 3-nonenal, 6-nonenal, 8-nonenal, 4-(octahydro-5H-4,7-methanoinden-5-ylidene)butanal, octanal, 2-octenal, phenoxyacetaldehyde, phenylacetaldehyde, 3-Phenylbutanal (Trifernal®, Supplier: Firmenich SA, Geneva, Switzerland), 2-phenylpropanal (hydratropaldehyde), 3-Phenylpropanal, 3-(4-tert-butylphenyl)-2-methylpropanal (Lilial®, supplied by Givaudan-Roure SA, Vernier, Switzerland), 3-(4-tert-butylphenyl)propanal (Bourgeonal®, supplied by Quest International, Naarden, The Netherlands), tricyclo[5.2.1.0(2,6)]decane-4-carbaldehyde, exotricyclo[5.2.1.0(2,6)]decane-8-exocarbaldehyde (Vertral®, supplied by Symrise, Holzminden, Germany), 2,6,6-trimethylbicyclo[3.1.1]heptane-3-carbaldehyde (formylpinane), 2,6,6-trimethylcyclohexa-1,3 -diene-1-carbaldehyde (safranal), 2,4,6- and 3,5,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,2,3-trimethyl-3-cyclopentene-1-acetaldehyde (camholenaldehyde), 2,6,10-trimethyl-2,6,9,11-dodecatetraenal, 2,5,6-trimethyl-4-heptenal, 3,5,5-trimethylhexanal, 2,6,10-trimethyl-9-undecenal, Undecanal , 2-undecenal, 10-Undecenaline or 9-Undecenaal and mixtures thereof, such as Intreleven aldehyde (supplied by International Flavors and Fragrances, New York, USA), and Aldehyde Supra (supplied by Firmenich SA, Geneva, Switzerland), and 4-vinylcyclohex-1-ene-1-carbaldehyde; where the underlined compounds represent aldehydes that are particularly useful in preferred embodiments of the present invention.

[0041] In certain embodiments, R 2 is not a hydrogen atom; i.e., a compound of formula (II) 1 )(R 2Ketones with C=O are 4-(1,3-benzodioxol-5-yl)-2-butanone, 2-butanone, (4E / Z,8E / Z)-cyclododeca-4,8-dien-1-one, 2-cyclohexyl-4-methyl-2-pentanone, cyclopentadecanone, (Z)-cyclopentadec-4-en-1-one, (Z)-cycloheptadec-9-en-1-one, 1-(3,5-diisopropylphenyl)ethan-1-one, 1-(3,3-dimethylcyclohexyl)ethan-1-one, 1-[2,6-dimethyl-4-(2-methyl-2-propanyl)phenyl]ethanone, 2,5-dimethyl 2-octen-6-one, 4,7-dimethyl-6-octen-3-one, 2,6-dimethyl-7-octen-4-one (dihydrotagetone), 4-(1,1-dimethylpropyl)cyclohexan-1-one, (5-E / Z)-6,10-dimethylundeca-5,9-dien-2-one, 2-ethyl-4,4-dimethylcyclohexan-1-one, 4-ethyl-8-methyloctahydronaphthalen-1(2H)-one, 1-(4-ethylphenyl)ethan-1-one, 1-(3-ethyl-1.1,3,6-tetramethyl-2,3-dihydro-1H-inden-5-yl)ethanone, 2-Heptanone , 3-heptanone, 2-heptylcyclopentan-1-one, 4,4a,6,7,8,8a-hexahydro-1,4-methanonaphthalen-5(1H)-one, 1-(1,1,2,3,3,6-hexamethyl-2,3-dihydro-1H-inden-5-yl)ethanone (Phantolid®, supplied by PFW Aroma Chemicals, Barneveld, The Netherlands), 1-(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethan-1-one (Fixolide®, supplied by Givaudan SA, Vernier, Switzerland), 2-hexanone, 2-(5-Hexen-1-yl)cyclopentan-1-one , 4-(4-hydroxyphenyl)-2-butanone , 1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one, 5-isopropyl-2-methylcyclohexan-1-one, 2-Isopropyl-5-methylcyclohexan-1-one (Menthone) , 1-(5-isopropyl-2-methylcyclohex-2-en-1-yl)propan-1-one, 1-(3-isopropyl-1,1,2,6-tetramethyl-5-indanyl)ethan-1-one, 4-(4-methoxyphenyl)-2-butanone, 1-(4-Methoxyphenyl)ethan-1-one(Acetanisole, Supplier: Givaudan SA, Vernier, Switzerland), 1-(2-methoxyphenyl)propan-1-one, 7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, 2-(2-(4-methylcyclohex-3-en-1-yl)propyl)cyclopentan-1-one, 3-methylcyclopentadecan-1-one, 3-methylcyclopentadec-4-en-1-one, 3-methylcyclopentadec-5-en-1-one, 5-methyl-3-methylcyclopentadecan-1-one, 5-methyl-3-methylcyclopentadecan-4-en-1-one, 5-methyl-3-methylcyclopentadecan-5 ... -heptanone, 6-methyl-5-hepten-2-one, 7-methyloctahydro-1,4-methanonaphthalen-6(2H)-one, methyl (Z)-2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetate (methyl jasmonate), methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1-(4-methyl-1-phenoxy)-2-propanone, 3-methyl-1-phenylbutan-1-one, 1-(4-methylphenyl)ethan-1-one , 2-methyl-1-phenylpropan-1-one, 1-(4-methylphenyl)propan-1-one, 1-[4-(2-methyl-2-propanyl)phenyl]ethan-1-one, 2-(1-methylpropyl)cyclohexan-1-one, 2-nonanone, 4-nonanone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone (mixture of isomers, Iso E Super®, supplied by International Flavors & Fragrances, New York, USA), 2-octanone, 3-octanone, oct-2-en-4-one, 2-pentadecanone, 2-pentanone, 2-Pentylcyclopentan-1-one (Delphone, supplied by Firmenich SA, Geneva, Switzerland), 1-phenylbutan-1-one, 4-Phenyl-2-butanone , 1-Phenylethane-1-one (acetophenone), 1-phenylhexan-1-one, 1-phenylpentan-1-one, 1-phenyl-4-penten-1-one (Lavonax, supplied by International Flavors & Fragrances, New York, USA), 1-Phenylpropan-1-one(propiophenone), 7-propyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, 1-(5-propylbenzo[d][1,3]dioxol-2-yl)ethan-1-one, 2-(tert-butyl)cyclohexan-1-one, 4-(tert-butyl)cyclohexan-1-one, 1-(6-tert-butyl-1,1-dimethyl-4-indanyl)-1-ethanone (Crysolide, Givaudan SA, Vernier, Switzerland), 1-(5,6,7,8-tetrahydro-2-naphthalenyl)ethan-1-one (Florantone®, supplied by Takasago International Corporation, Tokyo, Japan), 3,6,8,8-tetramethylhexahydro-1H-3a,7-methanoazulen-5(4H)-one, 1,1,5,5-tetramethylhexahydro-2H-2,4a-methanonaphthalen-8(5H)-one (isolongifolanon), 2,4a,8,8-tetramethyloctahydrocyclopropa[d]naphthalen-3(1H)-one (thujopsan-4-one), 2,2,7,9-tetramethylspiro[5. 5] Undec-7-en-1-one, 2-tridecanone, 1,3,3-trimethylbicyclo[2.2.1]heptan-2-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 2,2,4-trimethylbicyclo[3.1.1]heptan-3-one, 2,6,6-trimethylcycloheptan-1-one, 2,2,6-trimethylcyclohexan-1-one, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-one (dihydro-α-ionone), 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one (dihydro-β-ionone), 2,3,3-trimethyl-2,3-dihydro-1H-inden-1-one, 2,2,5-trimethyl-5-pentylcyclopentan-1-one, 2-undecanone and 5-undecanone; wherein the underlined compounds represent ketones that are particularly useful in preferred embodiments of the present invention.

[0042] In certain embodiments, the compound of formula (III) is 1-[2,6-dimethyl-4-(2-methyl-2-propanyl)phenyl]ethanone, 1-(3,5-diisopropylphenyl)ethan-1-one, 1-(4-ethylphenyl)ethan-1-one, 1-(3-ethyl-1,1,3,6-tetramethyl-2,3-dihydro-1H-inden-5-yl)ethanone, 1-(1,1,2,3,3,6-hexamethyl-2,3-dihydro-1H-inden-5-yl)ethanone (Phantolid®, supplied by PFW Aroma Chemicals, Barneveld, The Netherlands), 1-(3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethan-1-one (Fixolide®, supplied by Givaudan SA, Vernier, Switzerland), 1-(3-isopropyl-1,1,2,6-tetramethyl-5-indanyl)ethan-1-one, 1-(4-Methoxyphenyl)ethan-1-one (acetanisole, supplied by Givaudan SA, Vernier, Switzerland), 1-(2-methoxyphenyl)propan-1-one, 3-methyl-1-phenylbutan-1-one, 1-(4-methylphenyl)ethan-1-one , 2-Methyl-1-phenylpropan-1-one , 1-(4-methylphenyl)propan-1-one, 1-[4-(2-methyl-2-propanyl)phenyl]ethan-1-one, 1-Phenylbutan-1-one , 1-phenylhexan-1-one, 1-phenylpentan-1-one, 1-phenyl-4-penten-1-one (Lavonax, supplied by International Flavors & Fragrances, New York, USA), 1-Phenylethane-1-one (Acetophenone), 1-Phenylpropan-1-one (propiophenone), 1-(6-tert-butyl-1,1-dimethyl-4-indanyl)-1-ethanone (Crysolide, Givaudan SA, Vernier, Switzerland), 1-(5,6,7,8-tetrahydro-2-naphthalenyl)ethan-1-one (Florantone®, supplied by Takasago International Corporation, Tokyo, Japan), 1-(5,6,7,8-tetrahydronaphthalene-2-yl)ethan-1-oneand 2,3,3-trimethyl-2,3-dihydro-1H-inden-1-one; where the underlined compounds represent phenyl ketone derivatives that are particularly useful in preferred embodiments of the present invention, with 1-phenylethan-1-one (acetophenone) being the most preferred phenyl ketone derivative.

[0043] The present invention also relates to a microcapsule comprising at least one compound of formula (I). In one embodiment, at least one compound of formula (I) is encapsulated in a core-shell microcapsule, in which at least one compound of formula (I) is housed in a core surrounded by a shell. In one embodiment, the shell of the microcapsule protects the compound of formula (I) from the environment. The shell is made of a material capable of releasing at least one compound of formula (I) and / or compounds of formula (II) and / or (III). In one embodiment, the shell is made of a material capable of releasing the compound of formula (I) and / or compounds of formula (II) and / or (III) upon destruction of the shell and / or by diffusion through the shell. The skilled person is familiar with the methods of producing said microcapsules. Thus, a microcapsule comprising at least one compound of formula (I) is one subject of the present invention.

[0044] In a preferred embodiment, the encapsulation of the compound of formula (I) can provide an environment within the capsule in which all or a portion of the compound of formula (I) can degrade, thereby releasing the individual carbonyl compounds of formula (II) and the phenyl ketones (III) within the capsule. In a preferred embodiment, the shell of the microcapsule can act as a permeability barrier, thereby preventing leakage of the individual carbonyl compounds of formula (II) and the phenyl ketones (III) from the capsule.

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

[0046] According to certain embodiments, the core-shell microcapsules are also obtained by using different or more than one encapsulation method.

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

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

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

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

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

[0052] In certain embodiments, the microcapsules have a polymer shell obtained by complex coacervation, which may be crosslinked.

[0053] In a particular embodiment of the core-shell microcapsule, the core-shell microcapsule comprises an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), and a composite shell comprising a first material and a second material, the first material and the second material being different, the first material being a coacervate and the second material being a polymeric material.

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

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

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

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

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

[0059] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules are an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), - optionally an inner shell made of polymerized multifunctional monomers; - a biopolymer shell comprising proteins, wherein at least one of the proteins is crosslinked; Includes.

[0060] According to a particular embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium caseinate, calcium caseinate, casein, whey protein, hydrolyzed proteins, gelatin, gluten, pea protein, soy protein, silk protein, and mixtures thereof, preferably sodium caseinate.

[0061] According to a particular embodiment, the proteins include sodium caseinate and globular proteins, preferably selected from the group consisting of whey proteins, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins, and mixtures thereof.

[0062] The protein is preferably a mixture of sodium caseinate and whey protein.

[0063] According to certain embodiments, the biopolymer shell comprises cross-linked proteins selected from the group consisting of sodium caseinate and / or whey protein.

[0064] According to a particular embodiment, the microcapsule slurry comprises at least one microcapsule, the microcapsule comprising: an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), - an inner shell made of polymerized multifunctional monomers; preferably polyisocyanates having at least two isocyanate functional groups; - a biopolymer shell comprising proteins, at least one protein being crosslinked; said proteins preferably comprising a mixture comprising sodium caseinate and globular proteins, preferably whey proteins; - optionally with at least an outer inorganic layer It is made of.

[0065] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0066] The weight ratio of sodium caseinate to whey protein is preferably 0.01-100, preferably 0.1-10, and more preferably 0.2-5.

[0067] In certain embodiments, the microcapsules comprise: 1) mixing a perfume oil with a polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) dispersing or dissolving an aminoplast resin and, optionally, a stabilizer in water to form an aqueous phase; 3) mixing the oil phase and the water phase to produce an oil-in-water dispersion having an average droplet size of 1 to 100 microns; 4) carrying out a curing step to form the walls of the microcapsules; 5) Optionally, drying the final dispersion to obtain dry core-shell microcapsules. and (b) preparing a one-shell aminoplast core-shell microcapsule comprising:

[0068] In certain embodiments, the core-shell microcapsules are formaldehyde-free capsules. A typical method for making a formaldehyde-free aminoplast microcapsule slurry includes: 1) The following: a. a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound containing two NH2 functional groups; b. Glyoxal and C 4-6 An aldehyde component in the form of a mixture of 2,2-dialkoxyethanal and, optionally, glyoxalate, said mixture being glyoxal / C 4-6 an aldehyde component, the molar ratio of which is 1 / 1 to 10 / 1 of 2,2-dialkoxyethanal; and c. Protonic acid catalyst; preparing an oligomeric composition comprising or obtainable by the reaction product of 2) The droplet diameter is 1 to 600 microns and is as follows: a. Oil; b.Aqueous medium: c. at least one oligomeric composition obtained in step 1; d. Below: i.C4~C 12Aromatic or aliphatic di- or tri-isocyanates and their biuret, triuret, trimer, trimethylolpropane adducts and mixtures thereof; and / or ii.Formula: Q-(Oxirane-2-ylmethyl) m di- or tri-oxirane compounds of the formula: [wherein m is 2 or 3 and Q is a C2-C6 group optionally containing 2-6 nitrogen and / or oxygen atoms]; at least one crosslinker selected from; e. Optionally, a C1-C4 compound containing two NH2 functional groups; preparing an oil-in-water dispersion comprising: 3) heating the dispersion; 4) cooling the dispersion; Includes.

[0069] The above method is described in detail in WO 2013 / 068255.

[0070] In certain embodiments of the core-shell microcapsules, the core-shell microcapsules are an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), - below: Acyl chlorides, a first amino compound, ·Second Amino Compound and a polyamide shell comprising or obtainable therefrom. The polyamide core-shell polyamide microcapsules are

[0071] According to a particular embodiment, the polyamide core-shell microcapsules are an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), below: acyl chlorides, preferably in an amount of 5-98%, preferably 20-98%, more preferably 30-85% w / w, a first amino compound, preferably in an amount between 1% and 50% w / w, preferably between 7 and 40% w / w; a second amino compound, preferably in an amount between 1% and 50% w / w, preferably between 2 and 25% w / w, A stabilizer, preferably a biopolymer, preferably in an amount of 0-90%, preferably 0.1-75%, more preferably 1-70%. and a polyamide shell comprising or obtainable therefrom. Includes.

[0072] According to a particular embodiment, the polyamide core-shell microcapsules are an oily core comprising a hydrophobic active agent, preferably at least one compound of formula (I), - below: Acyl chlorides, a first amino compound which is an amino acid, preferably selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof, a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof, A biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and / or mixtures thereof and a polyamide shell comprising or obtainable therefrom. Includes.

[0073] The first amino compound can be different from the second amino compound.

[0074] Typically, a method for producing polyamide-based microcapsules includes the steps of: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) in an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) carrying out a curing step to form a slurry of polyamide microcapsules; Including, A stabilizer is added to the oil phase and / or to the water phase, and at least one second amino compound is added to the water phase prior to the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0075] In certain embodiments, the shell of the microcapsule is polyurea- or polyurethane-based. Examples of methods for producing polyurea- and polyurethane-based microcapsule slurries are described, for example, in WO 2007 / 004166, EP 2300146 and EP 2579976. Typically, the method for producing a polyurea- or polyurethane-based microcapsule slurry includes: a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding an oil phase to an aqueous phase to form an oil-in-water dispersion having an average droplet size of 1-500 μm, preferably 5-50 μm; d) applying conditions sufficient to induce interfacial polymerization to form microcapsules in a slurry; Includes.

[0076] In a particular embodiment, the microcapsules can be in powder form, which can be obtained in particular by subjecting the microcapsule slurry to a drying process, such as spray drying, to provide the microcapsules in such form, i.e., in powder form. It is understood that any standard method known to those skilled in the art for carrying out such drying can be applied. In particular, the slurry can be spray dried, preferably in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, gum arabic, vegetable gum, pectin, xanthan, alginate, carrageenan or cellulose derivatives, to provide the microcapsules in powder form.

[0077] However, other drying methods may be mentioned, such as extrusion, plating, spray granulation, fluidized bed processes, or even drying at room temperature using materials (carriers, desiccants) that meet certain criteria, as disclosed in WO 2017 / 134179.

[0078] Compounds of formula (I) can be prepared from phenyl ketone derivatives of formula (III) in a two-step sequence. In the first step, phenyl ketones are α-alkylated with (2,2-dimethyl-1,3-dioxolan-4-yl)methanol (solketal) (n=0) or 4-(hydroxymethyl)-2-phenyl-1,3-dioxane (n=1) in the presence of [Ir(cod)Cl]2, as described in M. Rueping, VB Phapale, Green Chemistry, 2012, Vol. 14, pages 55-57. [Ir(cod)Cl]2 acts as a hydrogen transfer catalyst and first dehydrogenates the primary alcohol function to form an aldehyde, which undergoes aldol condensation with the phenyl ketone. The resulting α,β-unsaturated ketone is then hydrogenated with the Ir catalyst. This results in a phenyl ketone having a 3,4- or 3,5-diol function protected as a cyclic acetal. In the second step of the process, the carbonyl compound protecting the diol function is converted to a phenyl ketone of formula R by an acid-catalyzed transacetalization reaction. 1 The desired active aldehyde of CHO or formula (R 1 )(R 2)C=O with a ketone to form the compound of formula (I). Another synthetic strategy to obtain the compound of formula (I) (n=0) is to introduce an allyl group on the alkyl carbon α to the carbonyl group of the compound of formula (III). 1,2-dihydroxylation of the alkene group followed by acetalization with the carbonyl compound of formula (II) gives the compound of formula (I). Allylation can be achieved by Claisen rearrangement of the allyl enol ether formed in situ of the carbonyl compound of formula (I). This was achieved by heating a mixture of the dimethyl acetal of the phenyl ketone and allyl alcohol in the presence of an acid catalyst. The carbonyl group was masked in the subsequent reaction by reducing it to an alcohol with NaBH4 and then converting it to an acetate ester. The alkene was epoxidized using metachloroperbenzoic acid. The resulting epoxide was converted to the corresponding acetonide by treatment with acetone in the presence of FeCl3 (S. Saha, SK Mandal, SC Roy, Tetrahedron Letters, 2008, Vol. 49, pages 5928-5930). Acid-catalyzed hydrolysis of the acetonide afforded 1,2-diols that could be used to prepare cyclic acetals of carbonyl compounds of formula (II). This was also achieved in one step by acid-catalyzed transacetalization reaction of the acetonide with activated carbonyl compounds of formula (II). Removal of the acetate group by methanolysis under basic conditions modified the alcohol functionality, and oxidation of the alcohol to a ketone afforded compounds of formula (I) (n=0).

[0079] The compounds of formula (I) of the present invention are delivery systems capable of releasing active compounds under specific conditions.

[0080] The term "active compound", "active volatile compound", "active volatile aldehyde, ketone or phenylketone" or similar terms herein means that the aldehyde, ketone or phenylketone to which it refers can provide a benefit or effect to its surrounding environment. In particular, the active compound is selected from the group consisting of perfumery ingredients, flavoring ingredients, medicinal ingredients, cosmetic ingredients, agricultural chemical ingredients, malodor neutralizing ingredients, antimicrobial ingredients and insect repellent or attractant ingredients. Thus, to be considered as an "active compound", the compound must have at least one property that is useful as a perfumery ingredient, flavoring ingredient, medicinal ingredient, cosmetic ingredient, agricultural chemical ingredient, malodor neutralizing ingredient, antimicrobial ingredient and insect repellent or attractant ingredient. It is also clear to those skilled in the art that the active aldehyde or ketone is essentially a volatile compound.

[0081] The term "perfuming ingredient" is understood to be a compound that is used primarily as an active ingredient in a perfume preparation or composition to impart a hedonic effect. In other words, a compound that is considered to be a perfuming ingredient must be recognized by those skilled in the art of perfumery as one that is capable of imparting or modifying the odor of a composition in a positive or pleasant way, rather than simply having an odor. Perfuming ingredients can impart additional benefits other than modifying or imparting an odor, such as persistence, blooming, malodor neutralization, cosmetic effects, antimicrobial effects, antiviral effects, microbial stability, or pest control. The term "flavoring ingredient" is understood to be one that is capable of imparting a taste sensation to the taster's palette. The term "malodor neutralizing ingredient" is understood to be one that is capable of reducing the perception of malodor, i.e., odors that are unpleasant or unpleasant to the human nose. The term "beauty ingredient" is understood to be one that is capable of providing a beauty effect, such as, for example, a moisturizing effect or a skin care effect. The term "antimicrobial component" is understood to be capable of killing or reducing or preventing the growth and / or accumulation of microorganisms, and includes antibacterial, antibiotic, antifungal, antiviral and antiparasitic components. The term "insect attractant or repellent" is understood to be a compound that has a positive or negative effect on insects. Examples of insect attractant or repellent components are given in the literature and other works of a similar nature, for example AM ​​El-Sayed, The Pherobase 2005, http: / / www.pherobase.net.

[0082] According to all the above and below embodiments of the present invention, the compound of formula (I) of the present invention, which is a delivery system, is particularly useful when the active volatile aldehyde, ketone or phenylketone released is a perfuming ingredient, i.e., a perfuming aldehyde, ketone or phenylketone. "Perfuming aldehyde, ketone or phenylketone" refers to a compound currently used in the perfume industry, i.e., a compound used as an active ingredient in a perfuming preparation or composition to impart a hedonic effect. In other words, such an aldehyde, ketone or phenylketone that is considered to be perfuming must be recognized by those skilled in the art of perfumery as not only having an odor, but also being able to impart or modify the odor of a composition in a positive or pleasant way. The perfuming aldehyde, ketone or phenylketone may be of natural or synthetic origin. Many of these auxiliary ingredients are in any case listed in reference works such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its latest editions, other works of a similar nature, and in the numerous patent literature in the field of perfumery.

[0083] In the following, the inventors will also call said "perfuming aldehyde, ketone or phenyl ketone" "perfuming compound".

[0084] In fact, the present invention is carried out in exactly the same way regardless of the exact characteristics of the active ketone or phenyl ketone.Thus, even if the present invention is further described herein below with specific reference to "perfuming compound", it is understood that the following embodiment is also applicable to other active aldehydes or ketones (i.e., the expression "perfuming" can be replaced with, for example, "flavoring", "pharmaceutical", "pesticidal", "malodor neutralizing", "cosmetic", "antibacterial", "antimicrobial", "insect attractant" or "insect repellent").According to a particular embodiment of the present invention, preferably active aldehydes are used.

[0085] Therefore, another subject of the present invention is the use of the compound of formula (I) above as a delivery system for releasing perfume compounds; that is, the use of the compound of formula (I) defined above as a perfume ingredient for providing a long-lasting odor / effect.In other words, it is a method for imparting, enhancing, improving or modifying the odor characteristics of a perfume composition, the air surrounding said perfume composition, a surface or a perfumed article, said method comprising adding an effective amount of at least one compound of formula (I) defined above to said composition or article, or contacting an effective amount of at least one compound of formula (I) defined above with a surface, or treating a surface with an effective amount of at least one compound of formula (I) defined above.By "use of the compound of the present invention" in this specification, it should also be understood to be the use of any composition that contains said compound and can be advantageously used in the perfume industry as an active ingredient.

[0086] The term "surface" as used herein may refer to the skin, hair, textiles or hard surfaces of a user to which a perfume composition comprising or containing at least one compound of formula (I) is applied.

[0087] For ease of understanding, a sustained effect is typically achieved when a given compound releases a greater amount of odor into the environment after a period of time, e.g., hours or days, than a reference compound.

[0088] Said compositions, which in fact can be advantageously used as perfuming ingredients, are also the subject of the present invention.

[0089] Another subject of the invention is therefore i) at least one compound of formula (I) according to the invention as defined above as a perfuming ingredient, ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; iii) optionally at least one flavor adjuvant; The fragrance composition comprises:

[0090] By "perfume carrier" is meant herein a material that is substantially neutral from the perfume point of view, i.e. does not significantly alter the organoleptic properties of the perfuming ingredients. Said carrier may be liquid or solid.

[0091] The liquid carrier may be, as a non-limiting example, an emulsifying system, i.e., a solvent and surfactant system, or a solvent commonly used in perfumery. The nature and type of solvents commonly used in perfumery cannot be described in full detail. However, as a non-limiting example, it may be the most commonly used solvents such as butylene glycol or propylene glycol, glycerin, dipropylene glycol and its monoethers, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, Abalyn® (rosin resin, available from Eastman), benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethano, triethyl citrate or mixtures thereof, or naturally occurring solvents such as glycerin, or various vegetable oils such as palm oil, sunflower oil, linseed oil. For compositions containing both a fragrance carrier and a fragrance base, suitable fragrance carriers other than those defined above may include ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (supplied by Exxon Chemical), or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (supplied by Dow Chemical Company), or hydrogenated castor oil such as those known under the trademark Cremophor RH 40 (supplied by BASF).

[0092] Solid carrier means a material that can be chemically or physically bound to perfume composition or some of the components of perfume composition.Generally, such solid carrier is used to stabilize composition or control the evaporation rate of composition or some of the components.Solid carrier is currently used in the art, and the skilled person knows how to obtain the desired effect.However, non-limiting examples of solid carrier can include absorbent gum or polymer or inorganic material, such as porous polymer, cyclodextrin, dextrin, maltodextrin, wood-based material, organic or inorganic gel, clay, gypsum, talc or zeolite.

[0093] Other non-limiting examples of solid carriers can include encapsulating materials. Examples of such materials include wall-forming and plasticizing materials, such as glucose syrup, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, vegetable gums, such as gum acacia (gum arabic), urea, sodium chloride, sodium sulfate, sodium carbonate, sodium bicarbonate, calcium carbonate, magnesium sulfate, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, sugars, such as sucrose, monosaccharides, disaccharides, trisaccharides and polysaccharides, and derivatives, such as chitosan, starch, cellulose, carboxymethyl methylcellulose, ... These may include, for example, cellulose, hydroxyethylcellulose, ethylcellulose, propylcellulose, polyols / sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, polyethylene glycol (PEG), polyvinylpyrrolidine (PVP), polyvinyl alcohol, acrylamide, acrylates, polyacrylic acid and related structures, maleic anhydride copolymers, amine functional polymers, vinyl ethers, styrene, polystyrene sulfonate, vinyl acid, ethylene glycol-propylene glycol block copolymers, pectin, xanthan, alginates, carrageenan, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof, or even materials listed in references such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996.Encapsulation is a process well known to those skilled in the art and can be carried out using techniques such as spray drying, agglomeration or even extrusion; or it can consist of coating encapsulation, including coacervation and complex coacervation techniques.

[0094] Non-limiting examples of solid carriers include core-shell capsules comprising aminoplast, polyamide, polyester, polyurea or polyurethane type resins or mixtures thereof (all of which are well known to those skilled in the art) using techniques such as phase separation processes induced by polymerization, interfacial polymerization, coacervation, or all of which are described in the prior art, optionally in the presence of polymeric stabilizers or cationic copolymers.

[0095] The resins can be prepared by polycondensation of aldehydes (e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with amines such as urea, benzoguanamine, glycouril, melamine, methylolmelamine, methylated methylolmelamine, guanazole and mixtures thereof. Alternatively, preformed resins, alkylolated polyamines, such as those commercially available under the trademarks Urac® (supplied by Cytec Technology Corp.), Cymel® (supplied by Cytec Technology Corp.), Urecoll® or Luracoll® (supplied by BASF) can be used.

[0096] Other resins are produced by polycondensation of polyols such as glycerin with polyisocyanates such as the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate or xylylene diisocyanate, the biuret of hexamethylene diisocyanate or the trimethylolpropane adduct of the trimer of xylylene diisocyanate (known under the trade name Takenate®, supplier: Mitsui Chemicals, Inc.), of which the trimethylolpropane adduct of the trimer of xylylene diisocyanate and the biuret of hexamethylene diisocyanate are preferred.

[0097] Some of the seminal publications related to the encapsulation of perfumes by polycondensation of amino resins, i.e. melamine-based resins with aldehydes, include 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., which already described the various parameters that affect the production of such core-shell microcapsules according to prior art methods, which are further detailed and illustrated in the patent literature. U.S. Patent No. 4,396,670 by Wiggins Teape Group Limited is a good early example of the latter. Since then, many other authors have enriched the literature in this field, and although it is impossible to cover all the published developments here, a general knowledge in encapsulation technology is very important. A more recent relevant publication disclosing suitable uses of such microcapsules is, for example, the article by K. Bruyninckx and M. Dusselier in ACS Sustainable Chemistry & Engineering, 2019, Vol. 7, pages 8041-8054.

[0098] As meant herein, a "perfume base" is a composition that includes at least one perfuming co-ingredient.

[0099] A perfuming co-ingredient is not a compound according to the invention.Furthermore, the term "perfuming co-ingredient" means a perfuming ingredient as defined above.

[0100] The nature and type of perfuming co-ingredients present in the base are not warranted to be described in greater detail here, but in any case are not exhaustive, and the skilled person can select them according to the intended use or application and the desired sensory effect, based on his / her common knowledge.In general terms, these perfuming co-ingredients belong to various chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpene hydrocarbons, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and they can be of natural or synthetic origin.In particular, the following perfuming co-ingredients that are commonly used in perfume formulations can be mentioned: - aldehyde-like components: decanal, dodecanal, 2-methylundecanal, 10-undecenal, octanal, nonanal and / or nonenal; - Aromatic Herbal Ingredients: Eucalyptus Oil, Camphor, Eucalyptol, 5-Methyltricyclo[6.2.1.0 2,7 ]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene; - Balsamic ingredients: ethyl vanillin and / or vanillin; - Citrus Ingredients: Dihydromyrcenol, Citral, Orange Oil, Linalyl Acetate, Citronellyl Nitrile, Orange Terpenes, Limonene, 1-p-Menthen-8-yl Acetate and / or 1,4(8)-p-Menthadiene; - Floral ingredients: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3- , (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, sa Hexyl licylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl cis-dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, vergyl proprionate , geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; - fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate and / or diethyl 1,4-cyclohexanedicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, 3-methyl-5-cyclohexyl lopentadecen-1-one, 4,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl]ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2,7 ]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, Clearwood®, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopentene- 1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; - other ingredients (e.g. amber, powdery-spicy or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal.

[0101] The composition according to the invention is not limited to the above-mentioned perfuming co-ingredients, and many others of these co-ingredients are in any case listed in references such as the book Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, by S. Arctander, or its newer versions, or other works of a similar nature and in the abundant patent literature in the perfumery field.It is also understood that said co-ingredients may be compounds known to release in a controlled manner various types of perfuming compounds, also known as pro-perfumes or pro-fragrances. Non-limiting examples of suitable propurfumes include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 3-(dodecylsulfonyl)-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one, linear polysiloxane copolymers of (3-mercaptopropyl)(methyl)dimethoxysilane, 3-(dodecylthio)-1-(6-ethyl-2,6-dimethylcyclohex-3-en-1-yl)butan-1-one, 2 ... thio)octan-4-one, 2-(dodecylsulfonyl)octan-4-one, 4-oxooctane-2-yl dodecanoate, 2-phenylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7-dimethyl-2 ,6-Octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2E,6Z)-2,6-nonadienyl hexadecanoate, (2E,6Z)-2,6-nonadien-1-yl tetradecanoate, (2E,6Z)-nona-2,6-dien-1-yl dodecanoate, (2E,6Z)-nona-2,6-dien-1-yl hexadecanoate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methyl 1-Methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenethoxyprop-1-en-2-yl)benzene, (2-phenethoxyvinyl)benzene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, (2-((2-methyl-4 -(2,6,6-trimethylcyclohex-1-en-1-yl)but-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(2-methyl-3-phenethoxyallyl)benzene, (2-((2-isopropyl-5-methylcyclohexylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)phenyl 1-isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 1-isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde 3-methyl-5-phenylpentyl palmitate, 3-(dodecylthio)-2-methyl-1-(2,6,6-trimethylcyclohex-3-en-1-yl)butan-1-one, 3,5-bis(1-(4-isopropylphenyl)propan-2-yl)dihydro-1H,3H,5H-oxazolo[3,4-c]oxazole, 3,5-Di(undecan-2-yl)dihydro-1H,3H,5H-oxazolo[3,4-c]oxazole, 3,5-bis(2,4-dimethylcyclohex-3-en-1-yl)dihydro-1H,3H,5H-oxazolo[3,4-c]oxazole, ethyl 2-acetyl-4-methyltridec-2-enoate, dec-9-en-1-yl(E)-3-(2-hydroxyphenyl)acrylate, 4-(dodecylthio)-4-methylpentan-2-one, methyl or Examples of the esters include ethyl N,S-bis(4-oxo-4-(2,6,6-trimethylcyclohexyl-3-en-1-yl)butan-2-yl)-L-cysteinate, 1-butoxy-3-((1E,4Z)-hepta-1,4-dien-1-yl)benzene, 2-methoxy-4-((1E,4Z)-hepta-1,4-dien-1-yl)phenol, 2-ethoxy-4-((1E,4Z)-hepta-1,4-dien-1-yl)phenol, or mixtures thereof.

[0102] In a particular embodiment, the perfuming composition according to the invention comprises a perfume adjuvant.

[0103] The term "perfume adjuvants" refers to ingredients that may impart further additional benefits such as color, specific light resistance, chemical stability, etc. The nature and type of adjuvants commonly used in perfume bases cannot be described in exhaustive detail, but it must be mentioned that such ingredients are well known to those skilled in the art. However, specific non-limiting examples include: viscosity agents (e.g. surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light and / or buffers or chelating agents, e.g. BHT), colorants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or antiirritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof. A "fixative", also called a "modulator", is understood herein to be an agent capable of influencing the manner in which the odor of a composition incorporating said modulator, in particular the evaporation rate and intensity, can be perceived over time by the observer or user, compared to the same perception in the absence of said modulator. In particular, a modulator makes it possible to extend the time for which the fragrance is perceived.Non-limiting examples of suitable modulators include methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol diethylhexanoate; sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether. Examples of the modulators include: polyglycerol-4 ether; isocetyl-5; isocetyl-7, isocetyl-10; isocetyl-12; isocetyl-15; isocetyl-20; isocetyl-25; isocetyl-30; disodium lauroamphodipropionate; hexaethylene glycol monododecyl ether; and mixtures thereof; neopentyl glycol diisononanoate; cetearyl ethylhexanoate; panthenol ethyl ether, DL-panthenol, n-hexadecyl n-nonanoate, noctadecyl n-nonanoate, cyclodextrin, and combinations thereof. Up to 20% by weight of the modulator, based on the total weight of the perfume composition, can be incorporated into the perfumed consumer product.

[0104] It is understood that a person skilled in the art is entirely capable of designing the optimal formulation for obtaining the desired effect by mixing the above-mentioned components of the perfuming composition not only by applying standard knowledge in the art but also by trial and error method.

[0105] The composition of the present invention, which comprises at least one compound of formula (I) and at least one perfume carrier, constitutes a particular embodiment of the present invention, and also comprises a perfume composition 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.

[0106] According to a particular embodiment, the above-mentioned compositions comprise one or more compounds of formula (I) and allow the perfumer to prepare accords or fragrances having the olfactory properties of the various compounds of the invention, thus creating new building blocks for creative purposes.

[0107] For the sake of clarity, it is also understood that mixtures resulting directly from a chemical synthesis, which may contain the compounds of the invention as starting materials, intermediates or final products, such as reaction media without appropriate purification, cannot be considered as perfuming compositions according to the invention, unless said mixtures provide the compounds of the invention in a form suitable for perfumery.Unless otherwise stated, unpurified reaction mixtures are generally excluded from the present invention.

[0108] The compounds of the invention can also be advantageously used in the field of modern perfumery, i.e. in all fields of fine perfumery or functional perfumery, to positively impart or modify the odor of consumer products to which the compounds of formula (I) are added. Another subject of the invention therefore also relates to perfumed consumer products comprising, as perfuming ingredient, at least one compound of formula (I) as defined above.

[0109] The compounds of the present invention can be added as such or as part of the perfuming composition of the present invention.

[0110] For the sake of clarity, it must be mentioned that the term "perfumed consumer product" means a consumer product that is expected to provide at least a pleasant fragrance effect to the surface to which the consumer product is applied (e.g., skin, hair, textile or hard surface). In other words, the perfumed consumer product according to the present invention is a perfumed consumer product that comprises the compound or perfume composition of the present invention, and optionally additional benefit agents depending on the desired consumer product, for example, conditioner, detergent or air freshener, and an olfactory effective amount of the perfume composition according to the present invention. For the sake of clarity, the perfumed consumer product is a non-edible product.

[0111] A more detailed description herein of the nature and type of ingredients of the perfumed consumer product is not warranted, but in any case is not exhaustive, and the skilled person can select them on the basis of his common knowledge and depending on the nature of the product and the desired effect.

[0112] In certain embodiments, the perfumed consumer product is a perfume, a fabric care product, a body care product, a cosmetic, a skin care product, an air care product, or a home care product.

[0113] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, splash perfumes or eau de parfums, colognes, shave or aftershave lotions; fabric care products, such as liquid or solid detergents, optionally in pod or tablet form, fabric softeners, liquid or solid scent boosters, dryer sheets, fabric refreshers, ironing waters, paper, bleach, carpet cleaners, curtain care products; body care products, such as hair care products (e.g., shampoos, leave-on or rinse-off hair conditioners, coloring preparations or hairsprays, color care products, hair styling products, dental care products), disinfectants, intimate care products; cosmetics (e.g., skin creams or lotions, vanishing creams or deodorants or antiperspirants, e.g., sprays or roll-ons), depilatories, tanning or after-sun products, nail products, skin cleansers, cosmetics; or skin care products (e.g. soaps, shower mousses, shower oils or gels or bath mousses, bath oils or gels, or hygiene or foot / hand care products); air care products, e.g. air fresheners or "ready to use" powdered air fresheners that can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or in public spaces (hall, hotel, mall, etc.); or home care products, e.g. mould removers, furniture care products, wipes, dishwashing detergents or hard surface (e.g. floor, bathroom, hygiene or window cleaner) cleaners; leather care products; car care products, e.g. car air fresheners, polishes, waxes or plastic cleaners. In particular, the perfumed consumer product may be a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, paper, a bleach, a carpet cleaner, a curtain care product, a disinfectant, a hygiene product, an air freshener, a "ready to use" powder air freshener, a mold remover, a furniture care product, a wipe, a dishwashing detergent or hard surface cleaner, a leather care product, or a car care product.

[0114] According to a particular embodiment, the perfumed consumer product of the present invention is in the form of a personal care, home care or fabric care consumer product, in particular a personal care, home care or fabric care consumer product comprising ingredients common in shower gels, shampoos, soaps, fabric detergents or softeners and all-purpose cleaners. The main functional ingredients of the perfumed consumer product are surfactants and / or softener ingredients capable of cleaning and / or softening fabrics and / or textiles of various natures, such as clothing, curtain fabrics, carpets, furniture fabrics, or other household surfaces, skin or hair, and are usually used in a large amount of water or aqueous solvent. Thus, these are formulations in which the amount of water generally accounts for 50-99% by weight of the perfumed consumer product, except for soaps or solid detergents, where the amount of water is at most 20%.

[0115] Although a more detailed description of such fabric cleaning and / or softener formulations is not warranted herein, many descriptions of current liquid formulations can be found in the cleaner / fabric softener patents and other related literature, such as the textbook "Detergents et Produits de Soins Corporels" by Louis Ho Tan Tai, especially chapters 1-7, Dunod, Paris, 1999, or other similar and / or more recent textbooks related to the technology of liquid fabric softener and all-purpose cleaner formulations. WO 2010 / 105873 is also cited as an example insofar as it describes typical current ingredients other than perfumes of such liquid products, especially on pages 9 to 21. Of course, many other examples of liquid cleaner and / or fabric softener formulations are described in the literature. Any such liquid formulation, i.e., liquid fabric cleaner or conditioner and / or all-purpose cleaner, can be used in the compositions described herein. Other examples of fabric detergent or softener compositions that can incorporate the compounds of the present invention are described in WO 97 / 34986 or US Pat. Nos. 4,137,180 and 5,236,615 or EP 799885.Other exemplary detergent and softening compositions that can be used are described in such works as 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, 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.

[0116] According to a particular embodiment of the present invention, the perfumed consumer product of the present invention may be a liquid fabric softener comprising at least one compound of formula (I) and a fabric softener active base in an amount of 85-100% by weight based on the total weight of the perfumed consumer product. The main component of the fabric softener active base is water or an aqueous solvent. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg ester quats, triethanolamine quats, silicones and mixtures thereof. Optionally, component a) of the composition may further comprise a viscosity modifier in an amount of 0.05-1% by weight based on the total weight of the liquid base; this is preferably selected from the group consisting of calcium chloride.

[0117] According to a particular embodiment of the present invention, the consumer product of the present invention is an all-purpose cleaner comprising at least one compound of formula (I) and an all-purpose cleaner active base in an amount of 85-100% by weight based on the total weight of the consumer product. The main component of the all-purpose cleaner active base is water or an aqueous solvent. The all-purpose active base may comprise a linear alkylbenzene sulfonate (LAS) in an amount of 0-4%, preferably 1-2%, a nonionic surfactant in an amount of 0-8%, preferably 2-4%, and an acid such as citric acid in an amount of 0.1-0.5%.

[0118] According to a particular embodiment of the present invention, the consumer product of the present invention is a liquid detergent comprising at least one compound of formula (I) and a liquid detergent active base in an amount of 85-100% by weight based on the total weight of the consumer product. The main component of the liquid detergent active base is water or an aqueous solvent. The liquid detergent active base may comprise anionic surfactants such as alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), sodium lauryl ether sulfate (SLES), methyl ester sulfonates (MES); nonionic surfactants such as alkyl amines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucosamides, or mixtures thereof.

[0119] According to a particular embodiment of the present invention, the consumer product of the present invention is a solid detergent comprising at least one compound of formula (I) and a solid detergent active base in an amount of 85-100% by weight based on the total weight of the consumer product. The solid detergent active base may comprise at least one surfactant selected from the group consisting of anionic surfactants, nonionic surfactants, cationic surfactants, zwitterionic surfactants and mixtures thereof. The surfactant in the solid detergent active base is preferably selected from the group consisting of linear alkene benzene sulfonates (LABS), sodium laureth sulfate, sodium lauryl ether sulfate, sodium lauryl sulfate (SLS), alpha-olefin sulfonates (AOS), sulfonic acid methyl esters, alkyl polyglucosides (APG), primary alcohol ethoxylates, in particular lauryl alcohol ethoxylates (LAE), primary alcohol sulfonates, soaps and mixtures thereof. The solid detergent active base may contain further ingredients commonly used in powder detergent consumer products selected from the group consisting of bleaching agents such as TAED (tetraacetylethylenediamine); buffers; builders such as zeolites, sodium carbonate or mixtures thereof; soil releasing polymers or soil suspending polymers; granular enzyme particles such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitors; antifoam agents; foam suppressors; dyes; fillers such as sodium silicate, sodium sulfate or mixtures thereof; hydrogen peroxide sources such as sodium percarbonate or sodium perborate; and mixtures thereof.

[0120] The proportions in which the perfuming compositions according to the invention can be incorporated into the various articles or compositions mentioned above vary within wide ranges of values, depending on the nature of the article or composition to be perfumed and the desired olfactory effect, and, in the case of mixing the compounds according to the invention with perfuming co-ingredients, solvents or additives commonly used in the art, also on the nature of the co-ingredients in a given composition.

[0121] For example, in the case of perfumed compositions, typical concentrations of the compounds of the invention are on the order of 0.001 to 10% by weight or more, based on the weight of the composition in which they are incorporated, and in the case of perfumed consumer products, typical concentrations of the compounds of the invention are on the order of 0.0001 to 1% by weight or more, based on the weight of the consumer product in which they are incorporated.

[0122] Another aspect of the present invention relates to the use of a perfuming composition according to the present invention for improving, enhancing, imparting and / or modifying the fragrance impression and / or fragrance intensity of a consumer product.

[0123] Another aspect of the present invention relates to a method for improving, enhancing, imparting and / or modifying the fragrance impression and / or fragrance intensity of a consumer product, comprising the step of adding to the consumer product a perfuming composition according to the present invention.

[0124] Another aspect of the present invention is to prepare a medicament for use in a method for the preparation of a medicament for use in a pharmaceutical preparation comprising the steps of: a) Formula [ka] [In the formula, R 1 is C 1-18 represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom; R 2 is a hydrogen atom or R 1 represents a group; or R 1 and R 2 If they are combined, C 5-16 Cycloalkyl groups, C 5-16 Cycloalkenyl group, C 4-14 Heterocycloalkyl group or C 4-14 heterocycloalkenyl groups, each of which is optionally 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 6-10Aryl groups and / or C 6-10 aryloxy groups, each of which is optionally substituted with one or more of 1-8 Alkyl group, C 1-8 Alkoxy groups, carboxylic acid groups and / or C 1-4 and in the form of any one of the stereoisomers or mixtures thereof of carbonyl compounds of the formula: b) Formula [ka] [In the formula, R 3 and R 4 are each independently a hydrogen atom, C 1-6 Alkoxy group or C 1-12 an alkyl group, optionally including a hydroxy group, C 1-6 It represents a group substituted with an alkoxy group or an oxo group, or two adjacent R 3 The groups, when taken together, are C 3-8 A linear alkanediyl group, optionally containing a hydroxy group, C 1-3 Alkyl group and / or C 1-3 substituted with one or more alkoxy groups; R 5 is a hydrogen atom or C 1-6 represents a hydrocarbon group or R 4 and R 5 If they are combined, C 1-4 R represents a linear, branched or cyclic alkanediyl group, optionally containing one oxygen atom; 6 represents a hydrogen atom or a methyl group], and to an environment where the compound is hydrolyzed, comprising: The precursor compound is represented by the formula (I) [ka] [In the formula, R 1 , R2 , R 3 , R 4 , R 5 and R 6 has the same meaning as defined above; n is 0 or 1 and X is an oxygen atom or NR 9 R 9 is a hydrogen atom or a methyl group, and R 7 and R 8 are each independently a hydrogen atom or a C1-C6 alkyl group, This release is achieved by exposure of the precursor compound of formula (I) to light.

[0125] In a further aspect, the present invention also provides a method for the preparation of a method for treating a pulmonary arthritis comprising the steps of: a) Formula [ka] [In the formula, R 1 is C 1-18 represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom; R 2 is a hydrogen atom or R 1 represents a group; or R 1 and R 2 If they are combined, C 5-16 Cycloalkyl groups, C 5-16 Cycloalkenyl group, C 4-14 Heterocycloalkyl group or C 4-14 heterocycloalkenyl groups, each of which is optionally 1-15 Alkyl group, C 2-15 Alkenyl group, C 1-15 Alkoxy group, C 3-15 Cycloalkyl groups, C 5-15 Cycloalkenyl group, C 6-10 Aryl groups and / or C 6-10 aryloxy groups, each of which is optionally substituted with one or more of 1-8 Alkyl group, C 1-8Alkoxy groups, carboxylic acid groups and / or C 1-4 substituted with one or more of a carboxylic acid ester group, wherein the heteroatom represents one or more oxygen atoms; b) Formula [ka] [In the formula, R 3 and R 4 are each independently a hydrogen atom, C 1-6 Alkoxy group or C 1-12 an alkyl group, optionally including a hydroxy group, C 1-6 It represents a group substituted with an alkoxy group or an oxo group, or two adjacent R 3 The groups, when taken together, are C 3-8 A linear alkanediyl group, optionally containing a hydroxy group, C 1-3 Alkyl group and / or C 1-3 substituted with one or more alkoxy groups; R 5 is a hydrogen atom or C 1-6 represents a hydrocarbon group or R 4 and R 5 If they are combined, C 1-4 R represents a linear, branched or cyclic alkanediyl group, optionally containing one oxygen atom; 6 represents a hydrogen atom or a methyl group] and 2. Use of a precursor compound for releasing a compound selected from the group consisting of: The precursor compound is represented by the formula (I) [ka] [In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 has the same meaning as defined above; n is 0 or 1 and X is an oxygen atom or NR 9 is a group, R9 is a hydrogen atom or a methyl group, and R 7 and R 8 are each independently a hydrogen atom or a C1-C6 alkyl group, This release is achieved by exposure of the precursor compound of formula (I) to light.

[0126] Another aspect of the present invention is a method for enhancing or prolonging the diffusion effect of the characteristic fragrance of at least one carbonyl compound of formula (II) and at least one ketone of formula (III) as defined above on a surface or in the air surrounding a perfuming composition, which comprises treating the surface or the air with at least one compound (I) as defined above or with a composition or article comprising at least one compound (I) under conditions that may allow the release over time of at least one ketone or aldehyde of formula (II) and at least one ketone of formula (III).

[0127] In a further aspect, the present invention relates to the use of at least one compound of formula (I) as defined above for enhancing or prolonging the diffusion effect and / or perception of the characteristic fragrance of at least one carbonyl compound of formula (II) and / or at least one phenyl ketone of formula (III) as defined above on a surface, wherein the surface is treated with at least one compound of formula (I) as defined above or with a composition or article comprising at least one compound of formula (I) under conditions that may allow the release over time of at least one carbonyl compound of formula (II) and / or at least one phenyl ketone of formula (III).

[0128] In a further aspect, the present invention relates to the use of at least one compound of formula (I) as defined above for imparting, enhancing, improving or modifying the odour properties of a perfuming composition, the air surrounding said perfuming composition, a surface or a perfumed article, comprising adding an effective amount of at least one compound of formula (I) as defined above to the composition or article, or contacting a surface with an effective amount of at least one compound of formula (I) as defined above, or treating the surface with an effective amount of at least one compound of formula (I) as defined above.

[0129] Working Example The present invention will now be described in further detail by the following examples. Abbreviations have their usual meaning in the art and temperatures are given in degrees Celsius (°C). NMR spectral data were obtained in CDCl3 on a BRUKER AMX 500 spectrometer unless otherwise noted. 1 H is 500MHz, 13 C was recorded at 125.8 MHz, chemical shifts δ are given in ppm relative to Si(CH3)4 as standard, coupling constants J are given in Hz (br. = broad peak). Reactions were carried out under N2 in standard glassware. Commercially available reagents and solvents were used without further purification unless otherwise stated.

[0130] Although specific conformations or configurations are shown for some compounds, this is not meant to limit the use of these compounds to the isomers depicted, and all possible conformational or configurational isomers are expected to have similar effectiveness according to the present invention.

[0131] Typical modes for preparing the compounds of this invention and for carrying out the methods of this invention are reported herein below in the Examples.

[0132] Example 1 Preparation of cyclic acetals or ketals according to formula (I) (a) Synthesis of (±)-cis-1-phenyl-3-(2-phenyl-1,3-dioxan-4-yl)propan-1-one (Compound 1) Toluene (2.5 mL), (±)-cis-4-(hydroxymethyl)-2-phenyl-1,3-dioxane (2.5 g, 12.9 mmol, B. Herradon, S. Valverde, Tetrahedron Asymmetry, 1994, Vol. 5, pages 1479-1500), acetophenone (3.1 g, 25.8 mmol), [Ir(cod)Cl]2 (0.173 g, 0.26 mmol), triphenylphosphine (0.20 g, 0.77 mmol), and lithium hydroxide monohydrate (0.22 g, 5.2 mmol) were added to a 25 mL round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C (oil bath) for 23 h. The mixture was diluted with diethyl ether (200 mL) and washed with water (3 × 150 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The residue was heated (100-120 °C) under vacuum (4.7 Pa) to remove excess acetophenone, then subjected to flash chromatography (SiO2, hexane / ethyl acetate (EtOAc), 100:0-80:20) to give the title compound (0.87 g, 23% yield) as an amber solid.

[0133] [ka]

[0134] (b) Synthesis of (±)-3-(2-decyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (compound 2) Part 1 Synthesis of (±)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (compound 2a). Toluene (30 mL), (±)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (solketal, 20.00 g, 151 mmol), acetophenone (27.3, 227 mmol), [Ir(cod)Cl]2 (2.0 g, 3.02 mmol), triphenylphosphine (2.37 g, 9.07 mmol), and lithium hydroxide monohydrate (2.55 g, 60.7 mmol) were added to a 100 mL round-bottom flask equipped with a reflux condenser and nitrogen bubbler. The dark red solution was heated at 110 °C for 21 h. The mixture was diluted with diethyl ether (200 mL) and washed with water (3 x 150 mL). The organic phase was dried over Na2SO4, filtered, and concentrated. Compound 2a (25.1 g, 71% yield) was isolated as a pale yellow oil by Kugelrohr distillation (170°C oven, 3.3 Pa).

[0135] [ka]

[0136] Part 2. A solution of compound 2a (1.21 g, 5.16 mmol), undecanal (2.64 g, 15.5 mmol, 3 equiv.) and para-toluenesulfonic acid monohydrate (pTSA, 0.06 g, 0.32 mmol, 0.06 equiv.) in toluene (20 mL) was stirred at room temperature (rt) for 3 h. The mixture was diluted with diethyl ether (100 mL) and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. Excess undecanal was removed by Kugelrohr distillation (40 °C oven, 6.7 Pa). Flash chromatography (SiO2, hexane / EtOAc, 100:0 to 93:7) afforded 1.2 g (68% yield) of the title compound as a pale yellow viscous oil (diastereomeric ratio (dr) = 67:33).

[0137] [ka]

[0138] (c) Synthesis of (±)-1-phenyl-3-(2-(2-phenylpropyl)-1,3-dioxolan-4-yl)propan-1-one (compound 3) The title compound (1.22 g, 73% yield, colorless liquid) was prepared from compound 2a (1.21 g, 5.16 mmol) and 3-phenylbutanal (2.3 g, 15.5 mmol) following the procedure described for compound 2 and was isolated as a mixture of diastereomers.

[0139] [ka]

[0140] (d) Synthesis of (±)-1-phenyl-3-(2-(undecane-2-yl)-1,3-dioxolan-4-yl)propan-1-one (compound 4) The title compound (4.68 g, 38% yield, colorless liquid) was prepared from compound 2a (8.0 g, 34.1 mmol) and 2-methylundecanal (12.6 g, 68.4 mmol) following the procedure described for compound 2 and was isolated as a mixture of diastereomers.

[0141] [ka]

[0142] (e) Synthesis of (±)-3-(2-(dec-9-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (compound 5) The title compound (3.75 g, 98% yield, colorless liquid) was prepared from compound 2a (2.5 g, 10.7 mmol) and 10-undecenal (3.6 g, 21.3 mmol) according to the procedure described for compound 2 and was isolated as a mixture of two diastereomers (dr=63:37).

[0143] [ka]

[0144] (f) Synthesis of (±)-3-(2-(2,4-dimethylcyclohex-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 6) The title compound (2.41 g, 72% yield, colorless viscous liquid) was prepared from compound 2a (2.5 g, 10.7 mmol) and 2,4-dimethylcyclohex-3-ene-1-carbaldehyde (2.95 g, 21.3 mmol) following the procedure described for compound 2 and was isolated as a mixture of diastereomers.

[0145] [ka]

[0146] (g) Synthesis of (±)-3-(2-(4,4-dimethylcyclohex-1-en-1-yl)ethyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 7) The title compound (1.64 g, 64% yield, amber oil) was prepared from compound 2a (1.75 g, 7.5 mmol) and 3-(4,4-dimethylcyclohex-1-en-1-yl)propanal (4.2 g, 31.4 mmol) following the procedure described for compound 2 and was isolated as a mixture of two diastereomers (dr=60:40).

[0147] [ka]

[0148] (h) Synthesis of (±)-(Z)-1-phenyl-3-(2-(undec-3-en-1-yl)-1,3-dioxolan-4-yl)propan-1-one (Compound 8) The title compound (2.11 g, 79% yield, colorless liquid) was prepared from compound 2a (1.75 g, 7.5 mmol) and (Z)-4-dodecenal (5.7 g, 31.4 mmol) following the procedure described for compound 2 and was isolated as a mixture of two diastereomers (dr=76:24).

[0149] [ka]

[0150] (i) Synthesis of (±)-3-(2-(2-(4-methylcyclohex-3-en-1-yl)propyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 9) The title compound (2.53 g, 69% yield, colorless viscous liquid) was prepared from compound 2a (2.5 g, 10.7 mmol) and 3-(4-methylcyclohex-3-en-1-yl)butyraldehyde (3.55 g, 21.4 mmol) following the procedure described for compound 2 and was isolated as a mixture of diastereomers.

[0151] [ka]

[0152] (j) Synthesis of (±)-3-(2-(6-methylhept-5-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 10) The title compound (1.84 g, 55% yield, pale yellow liquid) was prepared from compound 2a (2.5 g, 10.7 mmol) and 2,6-dimethyl-5-hepten-1-al (6.0 g, 42.8 mmol) following the procedure described for compound 2 and was isolated as a mixture of diastereomers.

[0153] [ka]

[0154] (k) Synthesis of (E / Z)-3-(2-(4,8-dimethylnon-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 11) A solution of compound 2a (1.00 g, 4.3 mmol), (E / Z)-5,9-dimethyldec-4-enal (2.33 g, 12.8 mmol) and pTSA (0.04 g) in toluene (20 mL) was stirred at rt for 15 h. The reaction mixture was washed with saturated aqueous Na2CO3 (15 mL), extracted with EtOAc (15 mL), neutralized with demineralized water (15 mL), dried (Na2SO4) and concentrated. Excess (E / Z)-5,9-dimethyldec-4-enal was removed by Kugelrohr distillation (120 °C oven, 0.1 mbar). Flash chromatography (SiO2, heptane / EtOAc 9:1) afforded 1.11 g (73% yield) of the title compound isolated as a mixture of diastereomers (dr = 66:34) as a colorless oil.

[0155] [ka]

[0156] (l) Synthesis of (E / Z)-3-(2-(5-cyclohexyl-4-methylpent-4-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 12) The title compound (1.26 g, 80% yield, colorless viscous oil) was prepared from (E / Z)-5-cyclohexyl-2,4-dimethylpent-4-enal (2.49 g, 12.8 mmol) following the procedure described for compound 11 and isolated as a mixture of diastereomers (dr ca. 30:30:20:20) after Kugelrohr distillation (140° C. oven, 0.1 mbar) and column chromatography.

[0157] [ka]

[0158] (m) Synthesis of (±)-3-(2-methyl-2-phenyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 13) A solution of compound 2a (5 g, 21.3 mmol), acetophenone (7.7 g, 64 mmol) and pTSA (0.22 g, 1.3 mmol) in toluene (50 mL) was stirred at room temperature under a vacuum of 12 mbar for 3 h. The mixture was diluted with diethyl ether (200 mL) and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over MgSO4, filtered and concentrated. Flash chromatography of the remaining residue (SiO2, hexane / EtOAc, 100:0 to 95:5) afforded 1.4 g (22% yield) of the title compound as a white solid (dr=67:33).

[0159] [ka]

[0160] (n) Synthesis of (±)-3-(2-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (compound 14) The title compound (2.2 g, 40% yield, colorless oil) was prepared from compound 2a (4.0 g, mmol) and 4-phenyl-2-butanone (7.6 g, 51.2 mmol) following the procedure described for compound 13 and was isolated as a mixture of two diastereomers (dr=57:43).

[0161] [ka]

[0162] (o) Synthesis of (±)-3-(6-pentyl-1,4-dioxaspiro[4.4]nonan-2-yl)-1-phenylpropan-1-one (Compound 15) The title compound (1.4 g, 20% yield, white solid) was prepared from compound 2a (5.0 g, 21.3 mmol) and 2-pentylcyclopentanone (9.9 g, 64 mmol) following the procedure described for compound 13 and was isolated as a mixture of four diastereomers.

[0163] [ka]

[0164] (p) Synthesis of (±)-1-phenyl-3-(2-phenyl-1,3-dioxolan-4-yl)propan-1-one (Compound 16) Toluene (70 mL), glycerol acetal of benzaldehyde (15.0 g, 83.2 mmol, mixture of 5- and 6-membered cyclic acetals), acetophenone (20.0, 166 mmol), [Ir(cod)Cl]2 (1.12 g, 1.66 mmol), triphenylphosphine (1.31 g, 5.0 mmol), and lithium hydroxide (1.4 g, 58.3 mmol) were added to a round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C for 22 h. The mixture was diluted with diethyl ether and water and stirred vigorously for 1 h. The phases were separated and the aqueous phase was extracted with diethyl ether (2 × 150 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated. The residue was heated (170 °C) under vacuum (2.7 Pa) to remove excess residual reagent. The residue was subjected to shot-path distillation (bp 130 °C, 2.4 Pa) followed by flash chromatography (SiO2, hexane / EtOAc, 100:0 to 50:50) to give the title compound (7.2 g, 31% yield) as a colorless oil (dr = 50:50).

[0165] [ka]

[0166] (q) Synthesis of (±)-3-(2-decyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)propan-1-one (compound 17) Part 1 Synthesis of (±)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)propan-1-one (compound 17a). Toluene (25 mL), solketal (5.0 g, 37.8 mmol), paramethoxyacetophenone (8.52 g, 56.7 mmol), [Ir(cod)Cl]2 (0.51 g, 0.75 mmol), triphenylphosphine (0.59 g, 2.25 mmol), and lithium hydroxide monohydrate (0.64 g, 26.0 mmol) were added to a 100 mL round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C (oil bath) for 20 h. The mixture was diluted with diethyl ether (200 mL) and washed with water (3 × 150 mL). The organic phase was dried over Na2SO4, filtered, and concentrated. The title compound (2.65 g, 26.5% yield) was isolated as a colorless liquid by Kugelrohr distillation (170-180 °C oven, 3.3 Pa).

[0167] [ka]

[0168] Part 2 A solution of compound 17a (1.5 g, 5.67 mmol), undecanal (2.9 g, 17.0 mmol) and pTSA (0.29 g, 1.7 mmol) in toluene (50 mL) was stirred at rt for 1 day. The mixture was diluted with diethyl ether and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, hexane / EtOAc, 100:0 to 88:12) afforded 1.3 g (61% yield) of the title compound (dr=59:41).

[0169] [ka]

[0170] (r) Synthesis of (±)-3-(2-decyl-1,3-dioxolan-4-yl)-1-(p-tolyl)propan-1-one (compound 18) Part 1 Synthesis of (±)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-1-(p-tolyl)propan-1-one (compound 18a). Toluene (25 mL), solketal (5.0 g, 37.8 mmol), paramethylacetophenone (7.6 g, 56.7 mmol), [Ir(cod)Cl]2 (0.51 g, 0.75 mmol), triphenylphosphine (0.60 g, 2.27 mmol), and lithium hydroxide monohydrate (0.63 g, 15 mmol) were added to a 100 mL round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C (oil bath) for 20 h. The mixture was filtered through a layer of Celite®, diluted with ethyl acetate (200 mL), and washed with water (3 x 150 mL). Flash chromatography (SiO2, hexanes / EtOAc, 95:5) afforded 4.72 g (50% yield) of the title compound as a light amber solid.

[0171] [ka]

[0172] Part 2 A solution of compound 18a (1.5 g, 6.0 mmol), undecanal (3.1 g, 18.1 mmol) and pTSA (0.32 g, 1.84 mmol) in toluene (20 mL) was stirred at rt for 2 days. The mixture was diluted with diethyl ether and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, hexane / EtOAc, 100:0 to 90:10) afforded 1.5 g (69% yield) of the title compound as a white solid (dr=61:39).

[0173] [ka]

[0174] Synthesis of (s)(±)-cis-3-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one (Compound 19) Toluene (10 mL), (±)-cis-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)methanol (6.0 g, 26.8 mmol, B. Herradon, S. Valverde, Tetrahedron Asymmetry, 1994, Vol. 5, pages 1479-1500), acetophenone (4.82 g, 40.1 mmol), [Ir(cod)Cl]2 (0.37 g, 0.54 mmol), triphenylphosphine (0.42 g, 1.60 mmol), and lithium hydroxide monohydrate (0.45 g, 10.7 mmol) were added to a round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C (oil bath) for 24 h. The mixture was diluted with diethyl ether and washed with water. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was subjected to flash chromatography (SiO2, hexane / EtOAc, 100:0 to 70:30) to give the title compound (3.1 g, 35% yield) as a white solid.

[0175] [ka]

[0176] (t) Synthesis of (±)-cis-3-(2-(4-ethylphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one (Compound 20) Part 1 Synthesis of (±)-cis-(2-(4-ethylphenyl)-1,3-dioxan-4-yl)methanol (compound 20a). A solution of 1,2,4-butanetriol (14.6 g, 137 mmol), dimethyl acetal of paraethylbenzaldehyde (16.5, 92 mmol) and Amberlyst® 15 resin in dichloromethane (120 ml) was stirred at rt for 7 h. The solution was filtered and concentrated. The remaining residue was dissolved in diethyl ether and washed with saturated NaHCO3. The organic phase was dried over Na2SO4, filtered and concentrated. Kugelrohr distillation afforded 16.5 g (81% yield) of the title compound as a colorless oil containing about 8% dioxolane by-product.

[0177] [ka]

[0178] Part 2 Toluene (15 mL), compound 20a (4.0 g, 18 mmol), acetophenone (3.24 g, 27 mmol), [Ir(cod)Cl]2 (0.25 g, 0.36 mmol), triphenylphosphine (0.28 g, 1.1 mmol), and lithium hydroxide monohydrate (0.30 g, 7.2 mmol) were added to a round-bottom flask equipped with a reflux condenser and a nitrogen bubbler. The dark red solution was heated at 110 °C for 24 h. The mixture was diluted with diethyl ether and washed with water. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was heated (120 °C) under vacuum (2.7 Pa) to remove excess acetophenone, and then subjected to flash chromatography (SiO2, hexane / EtOAc, 100:0 to 80:20) to give the title compound (2.7 g, 46% yield) as a white solid.

[0179] [ka]

[0180] (u) Synthesis of (±)-cis-3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one (Compound 21) A solution of compound 1 (8 g, 26.9 mmol), undecanal (18.4 g, 108 mmol) and pTSA (1.4 g, 8.2 mmol) in toluene (200 mL) was stirred at room temperature for 1 day. The mixture was diluted with diethyl ether (200 mL) and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over MgSO4, filtered and concentrated. Excess undecanal was removed by Kugelrohr distillation (95 °C oven, 2.7 Pa). Flash chromatography of the remaining residue (SiO2, hexane / EtOAc, 100:0 to 92:8) afforded 3.9 g (40% yield) of the title compound as a white solid.

[0181] [ka]

[0182] (v) Synthesis of (±)-cis-3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one (Compound 22) A solution of compound 1 (6 g, 20.2 mmol), 2-methylundecanal (11.2 g, 60.7 mmol) and paratoluenesulfonic acid monohydrate (1.1 g, 6.2 mmol) in toluene (150 mL) was stirred at room temperature for 5 days. The mixture was diluted with diethyl ether (200 mL) and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography (SiO2, hexane / EtOAc, 100:0 to 95:5) followed by Kugelrohr distillation (230 °C oven, 2.4 Pa) to give 3.87 g (51% yield) of the title compound as a colorless oil (dr=56:44).

[0183] [ka]

[0184] (w) Synthesis of (±)-2-methyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 23) A mixture of allyl alcohol (25.8 g, 444 mmol), dimethyl acetal of propiophenone (20 g, 111 mmol, T. Rossolini, B. Ferko, D. Dixon, Organic Letters, 2019, Vol. 21, pages 6668-6673) and citric acid (0.43 g, 2.22 mmol) was added to an autoclave reactor, which was placed in an oil bath heated to 165 °C. The mixture was stirred and heated for 1 day. Excess allyl alcohol was removed by distillation under vacuum (2.7 Pa). The remaining residue was dissolved in diethyl ether and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over MgSO4, filtered and concentrated. Kugelrohr distillation of the crude product (120° C. oven, 3.3 Pa) gave 2-methyl-1-phenylpent-4-en-1-one (14.3 g) as a colorless liquid.

[0185] The ketone (13.8 g, 79.2 mmol) was dissolved in methanol (100 ml) and the solution was cooled in an ice bath. NaBH4 (6.0 g, 158.4 mmol) was added in small portions. The mixture was removed from the cold bath and stirred at rt for 1 h. Water (30 ml) was added to the mixture and the methanol was removed on a rotary evaporator. The remaining aqueous residue was extracted with diethyl ether. The combined organic phases were dried over MgSO4, filtered and concentrated to give 2-methyl-1-phenylpent-4-en-1-ol (12.97 g) as a colorless oil, which was used in the next step without further purification.

[0186] 2-Methyl-1-phenylpent-4-en-1-ol was added in portions to an ice-bath cooled solution of acetyl chloride (7.0 g), pyridine (7.0 g) and 4-dimethylaminopyridine (0.27 g) in dichloromethane (100 ml). The solution was stirred at rt overnight. The reaction mixture was washed with 1N HCl (25 ml) and the separated dichloromethane layer was concentrated under vacuum. The residue was dissolved in diethyl ether and washed successively with 1N HCl, water, saturated aqueous NaHCO3, and saturated aqueous ammonium chloride. The organic phase was dried over MgSO4, filtered and concentrated. Kugelrohr distillation (100°C oven, 3.3 Pa) gave 2-methyl-1-phenylpent-4-en-1-yl acetate (12.5 g) as a colorless oil.

[0187] The resulting acetate (11.5 g) was dissolved in dichloromethane (150 ml) and the solution was cooled in an ice bath. Metachloroperbenzoic acid (16.8) was added and the resulting slurry was stirred at rt for 1 day. After addition of 20% aqueous sodium thiosulfate (25 ml), the mixture was stirred for 30 min and then the dichloromethane was removed on a rotary evaporator. Diethyl ether (500 ml) was added and the solution was washed successively with saturated aqueous Na2CO3 (3 x 30 ml) and water (2 x 25 ml). The ether phase was dried over MgSO4, filtered and concentrated to give 11.7 g of the epoxide 2-methyl-3-(oxiran-2-yl)-1-phenylpropyl acetate as a pale yellow slightly viscous oil.

[0188] The epoxide (11.2 g) and anhydrous FeCl3 (0.4 g) were dissolved in reagent grade acetone (210 ml) and the solution was stirred at rt for 3 h. The acetone was then removed on a rotary evaporator and the remaining brown residue was diluted with diethyl ether. The solution was washed with saturated aqueous Na2CO3 and water. The organic phase was dried over MgSO4, filtered and concentrated to give 12.7 g of the corresponding acetonide 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methyl-1-phenylpropyl acetate as a yellowish oil.

[0189] The acetonide was then converted to the corresponding cyclic 3-phenylpropanal acetal by a transacetalization reaction. A solution of the acetonide (12.42 g), 3-phenylpropanal (22.8 g) and pTSA (0.4 g) in toluene (100 ml) was stirred at rt for 3 h. The mixture was diluted with diethyl ether and washed with saturated aqueous Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and concentrated. The excess 3-phenylpropanal was removed by Kugelrohr distillation (120-140 °C oven, 6.7 Pa) to give 3-phenylpropanal acetal, 2-methyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropyl acetate (15.2 g) as a pale yellow oil.

[0190] The above acetal (15 g) was treated with methanol (500 ml) and K2CO3 (0.57 g) to remove the acetate group. The solution was stirred at rt for 1 day. Then the methanol was removed on a rotary evaporator. The remaining residue was diluted with diethyl ether and the solution was washed with brine. The organic phase was dried over MgSO4, filtered and concentrated to give 2-methyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-ol (11.1 g) as a light amber viscous oil.

[0191] Pyridinium chlorochromate (11.1 g, 50.5 mmol) was added to a stirred solution of the above alcohol (11 g) in dichloromethane (125 ml) at rt. After stirring for 2 h, the reaction mixture was filtered through a pad of silica covered with a layer of Celite®. The filtrate was concentrated and the remaining residue was subjected to flash chromatography (SiO2, hexane / EtOAc, 100:0 to 80:20) to give 10.3 g (36% overall yield from the dimethyl acetal of propriophenone) of the title compound, isolated as a mixture of diastereomers (dr ca. 45:35:10:10) as a colorless oil.

[0192] [ka]

[0193] (x) Synthesis of (±)-2,2-dimethyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 24) The title compound was prepared starting from the dimethyl acetal of isobutyrophenone and allyl alcohol following the multi-step procedure described for compound 23. Flash chromatography (SiO, hexane / EtOAc, 100:0 to 80:20) afforded the title compound as a colorless viscous oil isolated as a mixture of diastereomers (dr=80:20).

[0194] [ka]

[0195] (y) Synthesis of (±)-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one (Compound 25) The title compound was prepared starting from the dimethyl acetal of 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one (Florantone®, supplied by Takasago International Corporation, Tokyo, Japan) and allyl alcohol following the multi-step procedure described for compound 23. Flash chromatography (SiO2, hexane / EtOAc, 100:0 to 80:20) afforded the title compound as a white solid isolated as a mixture of diastereomers (dr=65:35).

[0196] [ka]

[0197] (z) Synthesis of (±)-3-(5-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 26) The title compound was prepared starting from the dimethyl acetal of acetophenone and 3-buten-2-ol following the multi-step procedure described for compound 23. Flash chromatography (SiO, hexane / EtOAc, 100:0 to 80:20) afforded the title compound as a colorless oil isolated as a single diastereomer.

[0198] [ka]

[0199] (aa) Synthesis of (±)-3-(5,5-dimethyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one (Compound 27) The title compound was prepared starting from the dimethyl acetal of acetophenone and 2-methyl-3-buten-2-ol following the multi-step procedure described for compound 23. Flash chromatography (SiO, hexane / EtOAc, 100:0 to 90:10) afforded the title compound as a colorless oil (dr=80:20).

[0200] [ka]

[0201] Example 2 Kinetics of the light-induced decomposition of compounds according to formula (I) The compound according to formula (I) (approximately 50 mg) and DMSO (acting as an internal standard, approximately 5 mg) were weighed into a volumetric flask and filled to 5 mL with CD3CN. The solution was poured into a homemade Pyrex glass cell and thermostated at 25°C. The sample was then illuminated with a xenon lamp at 7.0 mW cm -2 The samples were irradiated at approximately 90,000 lux. Aliquots (750 μL) of sample were taken with a pipette before irradiation (first data point) and every 30 min after the lamp was turned on for 150 min (data points 2–6). Samples were quantified. 1The decomposition of compounds 1, 2, 13 and 16 according to formula (I) was analyzed by H-NMR spectroscopy. 2 The formation of aldehyde, ketone and phenylketone derivatives was also followed relative to the DMSO signal. The data in Figures 1 and 2 demonstrate the rapid reaction of the compounds according to formula (I) after exposure to a light source. The photosensitive cyclic acetals or ketals according to the present invention decompose almost completely after 2 hours of irradiation with a xenon lamp, whereupon the corresponding phenylketone derivatives of formula (III) are decomposed to give the corresponding phenylketone derivatives of formula R 1 CHO aldehyde or formula (R 1 )(R 2 ) C=O ketone (according to formula (II)) is formed.

[0202] Example 3 Dynamic Headspace Analysis of Perfume Release from Compounds of Formula (I) of the Invention Incorporated into Consumer Products (Fabric Softeners) A fabric softener base was prepared with the following final composition: Stepantex® VL90 A (supplied by Stepan) 16.5% by weight Calcium chloride (10% aqueous solution) 0.6% by weight Water 82.9% by weight.

[0203] In a beaker, a solution of the photosensitive cyclic acetal or ketal derivative of formula (I) described in Example 1 (0.078 mmol) in acetone (0.6 mL) was added to the fabric softener (5.4 g). After homogenization, a portion of the sample (1.8 g) was dispersed in cold demineralized tap water (600 mL). One cotton sheet (EMPA cotton test fabric No. 221, supplier: Eidgenoessische Materialpruefanstalt, prewashed with unscented detergent powder and cut into sheets of approximately 12 x 12 cm, approximately 3.2 g) was added, stirred by hand for 3 minutes, allowed to stand for 2 minutes, squeezed by hand and weighed to obtain a constant amount of residual water (approximately 7.0 g). A reference sample consisting of an equimolar amount (0.078 mmol) of the corresponding aldehyde or ketone to be released in acetone (0.6 mL) was added to the fabric softener (5.4 g) and analyzed in the same way. The cotton sheets (with the addition of the photosensitive cyclic acetal or ketal derivatives and the corresponding fragrance to be released) were hung to dry in the dark for 24 hours. The cotton sheets were then analyzed. For the measurements, the sheets containing the photosensitive cyclic acetal or ketal derivatives were placed in a headspace sampling cell (internal volume approximately 160 mL) and illuminated with a xenon lamp (Solarbox 1500, CO.FO.ME.GRA Srl, approximately 7–8 mW / cm). 2The sheets were irradiated with a constant 1000 lux (approximately 90,000 lux). Meanwhile, the sheets containing the unencapsulated fragrance were placed in a headspace sampling cell exposed to natural indoor daylight. The headspace sampling cell was thermostated at 25° C. and exposed to a constant airflow of approximately 200 mL / min. The air was filtered through activated charcoal and drawn through a saturated solution of NaCl (to keep the air humidity at approximately 75%). The system was equilibrated for 15 min while volatiles were adsorbed onto a waste poly(2,6-diphenyl-p-phenylene oxide) (Tenax® TA, 100 mg) cartridge. The volatiles were then adsorbed onto a clean Tenax® cartridge for 10 min and a waste Tenax® cartridge for 20 min, six consecutive times. A total of six data points were collected over a period of 175 min. The spent cartridge was discarded and the other cartridge was desorbed in a Perkin Elmer TurboMatrix ATD desorber connected to an Agilent Technologies 7890A gas chromatograph equipped with a HP-1 capillary column (30 m, 0.32 mm internal diameter, 0.25 μm film) and an FID detector. Volatiles were eluted with helium (1 mL / min) with a temperature gradient of 15° C. / min starting from 80° C. to 260° C. Headspace concentrations (ng / L in air) were obtained by external standard calibration with five different concentrations of released fragrance in ethanol. Each calibration solution (0.1 μL) was injected into a clean Tenax® cartridge and desorbed and analyzed under the same conditions. The results obtained for the release of the different fragrances after 175 min are summarized in Table 1. All values ​​are the average of at least two measurements.

[0204] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6]

[0205] This data clearly shows that the persistence of light-induced fragrance release from the compound of formula (I) of the present invention is significantly improved over the unencapsulated reference fragrance. The data in Table 1 focus on the release of the active carbonyl compound of formula (II) resulting from the second step of the light-induced two-step mechanism outlined above. Overall, a very large increase in headspace concentration was observed for the release of acetophenone (the compound of formula (III) released from the compound of formula (I) of the present invention in the first step of the light-induced two-step sequence) over the corresponding unencapsulated acetophenone (reference).

[0206] Example 4 Dynamic Headspace Analysis of Perfume Release from Compounds of Formula (I) of the Invention Incorporated into a Consumer Product (All-Purpose Cleaner) An all-purpose cleaner (APC) formulation was prepared with the following final composition: Neodol® 91-8 (supplied by Shell Chemicals) 5.0% by weight Marlon® A 375 (supplied by Huels AG) 4.0% by weight Sodium cumene sulfonate 2.0% by weight Kathon(R) CG (Supplier: Rohm and Haas) 0.2% by weight Water 88.8% by weight.

[0207] In a flask, one compound of formula (I) of the present invention (0.0369 mmol) was dissolved in ethanol (0.1 mL). Then, APC formulation (3.0 g) was added and the sample was gently shaken. Aliquots (1 mL) of these samples were taken with a pipette and diluted with demineralized tap water (9 mL). A film (0.75 mL) of this solution was pipetted onto a porous ceramic plate (approximately 5×10 cm) and left at room temperature in the dark. Similarly, a reference sample consisting of unmodified aldehyde or ketone (0.0369 mmol) instead of one compound of formula (I) of the present invention in ethanol (0.1 mL) was prepared and treated in the same manner.

[0208] After 1 day, each ceramic plate was placed in a headspace sampling cell (approximately 625 mL) and exposed to a constant airflow of approximately 200 mL / min. The air was filtered through activated charcoal and drawn through a saturated solution of NaCl (to keep air humidity at approximately 75%). The headspace sampling cell was then exposed to a UVA lamp (center wavelength 370 nm) at approximately 2.2 mW / cm. 2 The headspace system was equilibrated by adsorbing the volatiles onto a used Tenax® cartridge for 15 minutes. The volatiles were then alternately adsorbed onto a clean Tenax® cartridge for 10 minutes and onto a used Tenax® cartridge for 20 minutes (6x). The used cartridge was discarded and the clean cartridge was desorbed and analyzed as described in Example 3. All measurements were performed at least twice. The average headspace concentrations of aldehydes and / or ketones released from the compound of formula (I) or the reference sample prepared in Example 1 after 115 minutes of sampling above the porous ceramic plate are listed in Table 2. Table 2 also shows the ratio of the aldehydes or ketones released from the compound of formula (I) of the present invention to the reference sample.

[0209] [Table 2]

[0210] The data clearly demonstrate that the persistence of light-induced fragrance release from compounds of formula (I) of the present invention is significantly improved over the unencapsulated reference fragrance.

[0211] Example 5 Manufacture of perfume oils Non-limiting examples of typical perfume oils are prepared by mixing the following perfuming co-ingredients: component weight% Ethyl 2-methylbutanoate 0.16 Hexyl acetate 0.37 Limonene 1.67 2,6-Dimethyl-7-octen-2-ol 0.94 2-Phenylethanol 2.15 Linalool 0.73 (2RS,4SR / 4RS)-4-Methyl-2-(2-methyl-1-propen-1-yl)tetrahydro-2H-pyran 0.30 2-Methyl-1,3-dioxolane-2-ethyl acetate 0.32 Benzyl acetate 2.46 Allyl heptanoate 0.38 α-Terpineol 0.88 3,7-Dimethyl-6-octen-1-ol 0.55 4-Methoxybenzaldehyde 1.00 (E)-4-Methyl-3-decen-5-ol 0.37 [cis / trans-4-(2-propanyl)cyclohexyl]methanol 0.47 1-Methoxy-4-[(1E)-1-propen-1-yl]benzene 0.15 (1RS,2RS / 2SR)-2-(2-methyl-2-propanyl)cyclohexyl acetate 1.95 1,1-Dimethyl-2-phenylethyl acetate 0.95 Tricyclo[5.2.1.0 2,~ ]Deca-3 / 4-en-8-yl acetate 3.34 Allyl 3-cyclohexylpropanoate 0.26 3-(4-isopropylphenyl)-2-methylpropanal 8.18 (3E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one and (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 1.13 2-Phenoxyethyl 2-methylpropanoate 5.38 Tricyclo[5.2.1.0(2,6)]dec-3 / 4-en-8-ylpropanoate 2.32 5-Heptyldihydro-2(3H)-furanone 2.30 2 / 3-Methylbutyl salicylate 1.42 Salicylic acid (3Z)-3-hexen-1-yl 0.31 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone 16.03 Hexyl 2-hydroxybenzoate 5.04 (2E)-2-benzylidene octanal 21.22 (-)-(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan 0.27 Habanolide® 4.78 Exaltolide® 3.82 Benzyl 2-hydroxybenzoate 3.01 Dipropylene glycol 5.39 Total:100.

[0212] Example 6 Preparation of Liquid Detergent Formulations Containing Compounds of Formula (I) of the Present Invention A typical unscented liquid detergent formulation is listed in Table 3. A perfumed liquid detergent is prepared by adding the perfume oil of Example 5 (0.3-0.8% by weight based on the total weight of the liquid detergent) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight based on the total weight of the liquid detergent) with gentle shaking to the unscented liquid detergent formulation of Table 3.

[0213] [Table 3]

[0214] Example 7 Preparation of a solid detergent containing a compound of formula (I) of the present invention The framework of the model powder detergent base is composed of sodium sulfate, sodium carbonate, sodium dodecylbenzenesulfonate, sodium silicate, zeolite, C 12-15 It is composed of Pareth-7, bentonite, perborate, TAED, citric acid, sodium acrylate / MA copolymer, sodium percarbonate, tetrasodium etidronate, sodium chloride, sodium bicarbonate, cellulose gum, disodium anilinomorpholinotriazinylaminostilbene sulfonate, phenylpropyl dimethicone, enzymes, and dyes.

[0215] A typical unscented model powder detergent base is formulated as listed in Table 4. A perfumed solid detergent is prepared by adding the perfume oil of Example 5 (0.3-0.6 wt. % based on the total weight of the solid detergent) and at least one compound of formula (I) of the present invention (0.15 wt. % based on the total weight of the solid detergent) with gentle shaking.

[0216] [Table 4]

[0217] Example 8 Preparation of bleach-free detergent solids containing the compounds of formula (I) of the present invention A typical bleach-free powder detergent formulation contains sodium sulfate, sodium carbonate, sodium dodecylbenzenesulfonate, sodium silicate, zeolite, C 12-15 It is composed of Pareth-7, bentonite, citric acid, sodium acrylate / MA copolymer, sodium percarbonate, tetrasodium etidronate, sodium chloride, sodium bicarbonate, cellulose gum, disodium anilinomorpholinotriazinylaminostilbene sulfonate, phenylpropyl dimethicone, enzymes, and dyes.

[0218] A typical unscented model powder detergent base is formulated as listed in Table 5. A non-bleach perfumed solid is prepared by adding the perfume oil of Example 5 (0.3-0.6 wt. % based on the total weight of the non-bleach solid) and at least one compound of formula (I) of the present invention (0.15 wt. % based on the total weight of the non-bleach solid) with gentle shaking.

[0219] [Table 5]

[0220] Example 9 Preparation of hand dishwashing detergent formulations containing compounds of formula (I) of the present invention A typical manual dishwashing detergent formulation is listed in Table 6. Mix water, sodium hydroxide and diethanolamide. Then add linear alkylbenzene sulfonic acid. After neutralization, add remaining ingredients. Check pH (7-8) and adjust if necessary. A scented manual dishwashing detergent is prepared by adding perfume oil of Example 5 (0.4-0.8% by weight based on the total weight of the manual dishwashing detergent formulation) and at least one compound of formula (I) of the present invention (0.02-0.5% by weight based on the total weight of the unscented formulation) to the unscented manual dishwashing detergent formulation of Table 6 with gentle shaking.

[0221] [Table 6]

[0222] Example 10 Preparation of a clear isotropic shampoo formulation containing a compound of formula (I) of the present invention A typical unscented clear isotropic shampoo formulation is listed in Table 7. The unscented shampoo formulation is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are mixed separately by adding them in sequence with good mixing after each addition. This premix is ​​added to the Polyquaternium-10 dispersion and mixed for an additional 5 minutes. Premix Phase B and Premix Phase C are then added with stirring (Monomuls® 90L-12 is heated in Texapon® NSO IS to melt). Phase D and Phase E are added with stirring. The pH is adjusted to 5.5-6.0 with citric acid solution to obtain the unscented shampoo formulation listed in Table 7. A perfumed shampoo formulation is obtained by adding the perfume oil of Example 5 (0.1-0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) (0.05-0.5% by weight, based on the total weight of the unscented shampoo formulation) to the unscented shampoo formulation listed in Table 7 with gentle shaking.

[0223] [Table 7]

[0224] Example 11 Preparation of pearlescent shampoo formulations containing compounds of formula (I) of the present invention A typical fragrance-free pearlescent shampoo formulation is listed in Table 8. The fragrance-free shampoo formulation is prepared by dispersing tetrasodium EDTA, guar hydroxypropyltrimonium chloride, and polyquaternium-10 in water. Once Phase A is homogenous, add NaOH (10% in water, Phase B). Next, add premixed Phase C and heat the mixture to 75°C. Add Phase D ingredients and mix until the mixture is homogenous. Allow the mixture to cool. At 45°C, add Phase E ingredients with mixing. Adjust final viscosity with NaCl (25% in water) and adjust pH to 5.5-6.0 with NaOH (10% in water). A fragranced pearlescent shampoo formulation is obtained by adding the perfume oil of Example 5 (0.1-0.8% by weight, based on the total weight of the unscented shampoo formulation) and at least one compound of formula (I) (0.05-0.5% by weight, based on the total weight of the unscented shampoo formulation) with gentle shaking to an unscented pearlescent shampoo formulation listed in Table 8.

[0225] [Table 8-1] [Table 8-2]

[0226] Example 12 Preparation of Rinse-Off Hair Conditioner Formulations Containing Compounds of Formula (I) of the Invention A typical unscented rinse-off hair conditioner formulation is listed in Table 9. The unscented rinse-off hair conditioner formulation is prepared by mixing the ingredients in Phase A until a homogenous mixture is obtained. The Tylose® is completely dissolved. The mixture is then heated to 70-75°C. The ingredients in Phase B are combined and melted at 70-75°C. The ingredients in Phase B are then added to Phase A with good agitation and mixing is continued until the mixture is at a temperature of 60°C. The ingredients in Phase C are then added with agitation and mixing is continued until the mixture cools to 40°C. The pH is adjusted to 3.5-4.0 with citric acid solution. A fragranced rinse-off hair conditioner formulation is obtained by adding the perfume oil of Example 5 (0.2-1.0 wt. %, based on the total weight of the unscented conditioner formulation) and at least one compound of formula (I) (0.05-0.5 wt. %, based on the total weight of the unscented conditioner formulation) to an unscented rinse-off hair conditioner formulation listed in Table 9 with gentle shaking.

[0227] [Table 9]

[0228] Example 13 Preparation of structured shower gel formulations containing compounds of formula (I) according to the invention Exemplary unscented structured shower gel formulations are listed in Table 10. A scented structured shower gel is prepared by adding the perfume oil of Example 5 (0.1-1.5 wt. % based on the total weight of the structured shower gel) and at least one compound of formula (I) of the present invention (0.05-0.5 wt. % based on the total weight of the structured shower gel) to the unscented structured shower gel formulation of Table 10 with gentle shaking.

[0229] [Table 10]

[0230] Example 14 Preparation of transparent shower gel formulations containing compounds of formula (I) according to the invention A typical unscented clear shower gel formulation is listed in Table 11. A clear, perfumed shower gel is prepared by adding the perfume oil of Example 5 (0.5-1.5 wt. % based on the total weight of the clear shower gel) and at least one compound of formula (I) of the present invention (0.05-0.5 wt. % based on the total weight of the clear shower gel) to the unscented clear shower gel formulation of Table 11 with gentle shaking.

[0231] [Table 11]

[0232] Example 15 Preparation of a milky white shower gel formulation containing a compound of formula (I) according to the present invention A typical unscented milky shower gel formulation is listed in Table 12. A scented milky shower gel is prepared by adding the perfume oil of Example 5 (0.1-1.5% by weight, based on the total weight of the milky shower gel) and at least one compound of formula (I) of the present invention (0.05-0.5% by weight, based on the total weight of the milky shower gel) to the unscented milky shower gel formulation of Table 12 with gentle shaking.

[0233] [Table 12]

Claims

1. formula 【Chemistry 1】 [In the formula, n is 0 or 1; X is an oxygen atom or NR ９ is a group, and R ９ is a hydrogen atom or a methyl group; R １ is C １－１８ represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom; R ２ is a hydrogen atom or R １ represents a group; or R １ and R ２ When combined, C ５－１６ Cycloalkyl group, C ５－１６ Cycloalkenyl group, C ４－１４ Heterocycloalkyl group or C ４－１４ heterocycloalkenyl groups, each of which optionally includes C １－１５ Alkyl group, C ２－１５ Alkenyl group, C １－１５ Alkoxy group, C ３－１５ Cycloalkyl group, C ５－１５ Cycloalkenyl group, C ６－１０ aryl group and / or C ６－１０ aryloxy groups, each of which is optionally substituted with one or more of １－８ Alkyl group, C １－８ Alkoxy groups, carboxylic acid groups and / or C １－４ substituted with one or more carboxylic acid ester groups, wherein the heteroatom represents one or more oxygen atoms; R ３ and R ４ are each independently a hydrogen atom, C １－６ Alkoxy group or C １－１２ alkyl groups, optionally hydroxy groups, C １－６ substituted with an alkoxy group or an oxo group, or two adjacent R ３ The groups, when taken together, are C ３－８ A linear alkanediyl group, optionally containing a hydroxy group, C １－３ Alkyl group and / or C １－３ substituted with one or more alkoxy groups; R ５ is a hydrogen atom or C １－６ represents a hydrocarbon group, or R ４ and R ５ When combined, C １－４ represents a linear, branched or cyclic alkanediyl group, optionally containing one oxygen atom; R ６ represents a hydrogen atom or a methyl group; R ７ and R ８ are each independently a hydrogen atom or C １－６ represents an alkyl group; and group R １ and R ２ has a total of at least 4 carbon atoms, in the form of any one of said compound's stereoisomers or mixtures thereof.

2. R ７ and R ８ 2. The compound according to claim 1, wherein, independently of one another, represent a hydrogen atom or a methyl group, preferably a hydrogen atom.

3. R ６ The compound according to claim 1, wherein represents a hydrogen atom.

4. R ５ is a hydrogen atom, or C １－４ a linear or branched alkyl group, or C ２－４ represents a linear or branched alkenyl group, and preferably represents a ５ The compound according to claim 1, wherein represents a hydrogen atom.

5. 2. The compound according to claim 1, wherein X is an oxygen atom and n is 0.

6. R ３ and R ４ are independently a hydrogen atom, C １－３ Alkoxy group or C １－６ alkyl groups, optionally hydroxy groups, C １－３ substituted with an alkoxy group or an oxo group, or two adjacent R ３ The groups, when taken together, are C ３－４ A linear alkanediyl group, optionally containing hydroxy groups and / or C １－３ The compound of claim 1 , which is substituted with one or more alkyl groups.

7. R １ But C １－１２ represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms, or R １ and R ２ But when they are combined, C ５－１６ Cycloalkyl group or C ５－１６ cycloalkenyl groups, each of which optionally comprises C １－８ Alkyl group, C ２－８ Alkenyl group, C １－８ Alkoxy group, C ３－８ Cycloalkyl group, C ５－８ Cycloalkenyl group, C ６ aryl group and / or C ６ aryloxy groups, each of which is optionally substituted with one or more of １－６ Alkyl group, C １－６ Alkoxy groups, carboxylic acid groups and / or C １－４ The compound of claim 1 , substituted with one or more carboxylic acid ester groups.

8. The compound of formula (I) is 1-phenyl-3-(2-phenyl-1,3-dioxan-4-yl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-(2-phenylpropyl)-1,3-dioxolan-4-yl)propan-1-one, 1-phenyl-3-(2-(undecan-2-yl)-1,3-dioxolan-4-yl)propan-1-one, 3-(2-(dec-9-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropyl propan-1-one, 3-(2-(2,4-dimethylcyclohex-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-(2-(4,4-dimethylcyclohex-1-en-1-yl)ethyl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-(undec-3-en-1-yl)-1,3-dioxolan-4-yl)propan-1-one, 3-(2-(2-(4-methylcyclohex-3-en-1-yl)propyl)-1,3- (E / Z)-3-(2-(4,8-dimethylnon-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, (E / Z)-3-(2-(5-cyclohexyl-4-methylpent-4-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-(6-methylhept-5-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, (E / Z)-3-(2-(4,8-dimethylnon-3-en-1-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, (E / Z)-3-(2-(5-cyclohexyl-4-methylpent-4-en-2-yl)-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-methyl-2-furan-2-yl)- 1-phenyl-3-(2-phenyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(6-pentyl-1,4-dioxaspiro[4.4]nonan-2-yl)-1-phenylpropan-1-one, 1-phenyl-3-(2-phenyl-1,3-dioxolan-4-yl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-(4-methoxyphenyl)propan-1-one, 3-(2-decyl-1,3-dioxolan-4-yl)-1-(p-tolyl)propan-1-one, 3-(2-(4-methoxyphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-(4-ethylphenyl)-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 3-(2-decyl-1,3-dioxan-4-yl)-1-phenylpropan-1-one, 2-methyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one 2,2-dimethyl-3-(2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, 3-(2-phenethyl-1,3-dioxolan-4-yl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one, 3-(5-methyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one, and 3-(5,5-dimethyl-2-phenethyl-1,3-dioxolan-4-yl)-1-phenylpropan-1-one.

9. 10. Use of a compound of formula (I) as defined in claim 1 as a perfuming ingredient to provide a long-lasting odor.

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

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

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

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

14. The perfumed consumer product may be a fine perfume, splash perfume or eau de parfum, cologne, shave or aftershave lotion, liquid or solid detergent, optionally in pod or tablet form, fabric softener, liquid or solid scent booster, dryer sheet, fabric refresher, ironing water, paper, bleach, carpet cleaner, curtain care product, shampoo, leave-on or rinse-off hair conditioner, color preparation, color care product, hair styling product, dental care product, disinfectant, 14. The perfumed consumer product of claim 13, which is an intimate care product, hair spray, skin cream or lotion, vanishing cream, deodorant or antiperspirant, depilatory, tanning or sun product, nail product, skin cleanser, cosmetic, soap, shower or bath mousse, oil or gel, foot / hand care product, hygiene product, air freshener, "ready to use" powder air freshener, mold remover, furniture care product, wipe, dish detergent or hard surface cleaner, leather care product, car air freshener, polish, wax or plastic cleaner.

15. From the precursor compounds: a) Formula 【Chemistry 2】 [In the formula, R １ is C １－１８ represents a hydrocarbon group, optionally containing 1 to 3 oxygen atoms and / or 1 to 2 nitrogen atoms and / or 1 sulfur atom; R ２ is a hydrogen atom or R １ represents a group; or R １ and R ２ When combined, C ５－１６ Cycloalkyl group, C ５－１６ Cycloalkenyl group, C ４－１４ Heterocycloalkyl group or C ４－１４ heterocycloalkenyl groups, each of which optionally includes C １－１５ Alkyl group, C ２－１５ Alkenyl group, C １－１５ Alkoxy group, C ３－１５ Cycloalkyl group, C ５－１５ Cycloalkenyl group, C ６－１０ aryl group and / or C ６－１０ aryloxy groups, each of which is optionally substituted with one or more of １－８ Alkyl group, C １－８ Alkoxy groups, carboxylic acid groups and / or C １－４ carboxylic acid ester groups, wherein the heteroatoms represent one or more oxygen atoms, in the form of any one stereoisomer or mixtures thereof, b) Formula 【Transformation 3】 [In the formula, R ３ and R ４ are each independently a hydrogen atom, C １－６ Alkoxy group or C １－１２ alkyl groups, optionally hydroxy groups, C １－６ substituted with an alkoxy group or an oxo group, or two adjacent R ３ The groups, when taken together, are C ３－８ A linear alkanediyl group, optionally containing a hydroxy group, C １－３ Alkyl group and / or C １－３ substituted with one or more alkoxy groups; R ５ is a hydrogen atom or C １－６ represents a hydrocarbon group, or R ４ and R ５ When combined, C １－４ represents a linear, branched or cyclic alkanediyl group, optionally containing one oxygen atom; R ６ represents a hydrogen atom or a methyl group] or a mixture thereof.

1. A method for releasing a compound selected from the group consisting of: The precursor compound has the formula (I) 【Chemistry 4】 [In the formula, R １ , R ２ , R ３ , R ４ , R ５ and R ６ has the same meaning as defined above; n is 0 or 1; X is an oxygen atom or NR ９ is a group, and R ９ is a hydrogen atom or a methyl group; R ７ and R ８ are each independently a hydrogen atom or C １－６ represents an alkyl group; The method wherein said releasing is effected by exposure of said precursor compound of formula (I) to light.

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