Uses of organic compounds and aromatic alcohols

Abstract

Compounds represented by formula (I), which are ethers or esters, as precursors for producing aromatic alcohols according to formula (II); their use as fragrance precursors, as well as fragrance compositions and consumer products containing the compounds.

Description

[Technical Field]

[0001] Technical field The present invention generally relates to fragrance precursors capable of releasing aromatic alcohols. The present invention also relates to fragrance preparations and consumer products containing the precursors. The present invention further relates to methods for producing the fragrance precursors, fragrance preparations and consumer products, and to the use of the fragrance precursors and fragrance preparations in consumer products, such as personal care products and household care products.

[0002] background Fragrance-containing consumer products, such as personal care products, cleaning products, or laundry products, are well known in the art. However, it is known that fragrances can change through decomposition caused by interaction with air or when incorporated into a given consumer product base (where alkalinity, acidity, the presence of oxidizing agents, such as hypochlorite, or other base components can lead to the chemical decomposition of the fragrance). In addition, volatile fragrances tend to dissipate over time. Furthermore, when used in the aforementioned fragrance-containing consumer products, the deposition of fragrance onto substrates treated by washing and / or rinsing procedures is reduced.

[0003] Nevertheless, consumers desire products that can be stored over time and still provide a consistent fragrance impression. In particular, the impact of volatile components should be preserved. Furthermore, such products are desired to create a long-lasting, pleasant fragrance that gradually evaporates from the treated base material over time.

[0004] To address these needs, fragrance precursors, which are essentially odorless but decompose and release aromatic molecules in certain situations, can be used.

[0005] There are several classes of known precursors that release aromatic molecules upon activation, such as hydrolysis, temperature changes, oxygen, light, or enzymes. For example, WO2012085287 reports a group of precursors that can release fragrance by spontaneous air oxidation. WO2007143873 describes another group of precursors that can be cleaved by hydrolysis.

[0006] All precursors exhibit different stabilities and release aromatic molecules under different conditions. There remains a need for precursors that can release aromatic alcohols over extended periods and can be easily incorporated into various consumer products. [Overview of the Initiative]

[0007] overview According to the first aspect of the present invention, formula (II): [ka] Formula (I): A precursor for producing aromatic alcohols represented by the formula (I): [ka] During the ceremony, [ka] This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryl having a maximum of 2 substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalen-1-yl or naphthalen-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; and Alkanoyl (C(O)-R 10 ), where R 10 is linear or branched C4-C 18 alkyl, linear or branched C4-C 18 alkenyl having 1 or 2 double bonds, linear or branched C4-C 18 ether and oxoalkyl, and hydroxyphenyl, a compound represented by, provided that the compound is not nona-2,6-dien-1-yl palmitate, said compound is provided.

[0008] According to a second aspect of the present invention, there is provided the use of a compound represented by formula (I) as a fragrance precursor capable of releasing an aromatic alcohol represented by formula (II) over a long period of time.

[0009] According to a third aspect of the present invention, there are provided a fragrance composition and a consumer product comprising the compound represented by formula (I).

[0010] According to a fourth aspect of the present invention, there is provided a method of releasing an aromatic alcohol represented by formula (II).

[0011] According to a fifth aspect of the present invention, there is provided a method of making the fragrance precursor, the fragrance preparation and the consumer product.

[0012] According to a sixth aspect of the present invention, the use of the fragrance precursor and fragrance preparation represented by formula (I) in consumer products, such as fabric care products, personal care products, and household care products, is provided.

[0013] A method for imparting, enhancing, improving, or modifying the hedonic properties of a fragrance composition or consumer product is provided in accordance with a seventh aspect of the present invention.

[0014] A particular aspect of any aspect of the present invention may provide one or more of the following advantages: ● Release of aromatic alcohol, ● Efficient delivery of the fragrance of aromatic alcohol in consumer products, and ● Stability of fragrance precursors in consumer products and their stability after deposition on substrates.

[0015] Details, examples, and preferences provided with respect to any specific one or more aspects of the described aspects of the Invention will be further described herein and will apply equally to all aspects of the Invention. Any combination of aspects, examples, and preferences in all possible variations described herein is covered by the Invention unless otherwise shown herein or unless clearly contradicted by the context.

[0016] Detailed description This invention is based on the surprising finding that ethers and esters of aromatic alcohols can function as fragrance precursors capable of releasing the aromatic alcohols. These fragrance precursors offer high persistence of the aromatic alcohols and are robust in a variety of consumer products.

[0017] Therefore, equation (II): [ka] Formula (I): A precursor for producing aromatic alcohols represented by the formula (I): [ka] During the ceremony, [ka] This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; and Alkanoyl(C(O)-R) 10 ), here R 10 C4~C are linear or branched. 18 Alkyl, linear or branched C4-C with 1 or 2 double bonds 18 Alkenyl, linear or branched C4-C 18 Ethers and oxoalkyls, and hydroxyphenyls, A compound represented by, However, the compound provided is not nona-2,6-diene-1-yl palmitate.

[0018] substituent R in the compound represented by formula (II) 1 -R 6 The bond with the dotted line is defined as in the compound represented by formula (I).

[0019] The term "alyl" means, for example, phenyl or naphthyl.

[0020] The term alkylalkenoate refers to, for example, methyl or ethyl acrylate.

[0021] Linear or branched C4~C 18 The term alkyl refers to all linear or branched alkyl chains having between 4 and 18 carbon atoms, such as C5, C6, C7, C8, C9,8, C9, C6, C8, C9, C6, C8 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 or C 17 This refers to alkyl groups, etc.

[0022] Linear or branched C4~C 18 The term alkenyl refers to all linear or branched alkenyl chains having one or more double bonds, e.g., C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 or C 17 This refers to alkenyls. In the case of double bonds, they can be isolated or conjugated.

[0023] Linear or branched C4~C 18 The terms ether and oxoalkyl, oxoalkenyl refer to all linear or branched alkyl or alkenyl chains having between 4 and 18 carbon atoms and containing an ether group or an oxo group in the chain, such as 3-oxobutyl.

[0024] The term benzyl having a substituent selected from the group consisting of hydroxymethyl, formyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzyl position means, for example, 2-phenylethanal, 2-phenylethanol, (2-oxopropyl)-1-phenyl, methyl 2-phenylethanoate, and 2-oxo-1,2-diphenyl-1-ethyl.

[0025] The terms phenyl, naphthalene-1-yl, or propane-2-yl with naphthalene-2-yl substituted at the 2-position mean, for example, 2-(naphthalene-2-yl)propane-2-yl or 2-phenylpropane-2-yl.

[0026] Unless otherwise specified, the CC double bond(s) in the compounds represented by formula (I) and formula (II) have either an E-configuration or a Z-configuration, or the compounds are a mixture of E and Z isomers. If further double bonds are present, each of them has either an E-configuration or a Z-configuration, and the compounds may exist as pure isomers or concentrated isomers, for example, as 2E,6Z-nonadienol, or as a mixture of double bond isomers.

[0027] The compounds represented by formula (I) and formula (II) may have one or more stereocenters, and as a result exist as different stereoisomers (e.g., diastereomers or enantiomers), all of which are covered by the present invention. The chiral compounds represented by formula (I) or formula (II) may be enantiomerically pure, concentrated, or racemic. If more than one stereocenter is present, the compound may be a distereomer mixture, a diastereomerally concentrated, or a pure distereomer.

[0028] In aromatic alcohols according to formula (II) and compounds represented by formula (I), their corresponding fragments are substituents R 1 ~R 6 It changes in R 1 , R3 , R 4 , R 5 and R 6 These are independently selected from the group consisting of H, Me, and Et, and R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3. [ka] This indicates a carbon-carbon single or double bond between C2 and C3.

[0029] For example, equation (II): [ka] Formula (I): A precursor for producing aromatic alcohols represented by the formula (I): [ka] During the ceremony, [ka] This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; and Alkanoyl(C(O)-R) 10 ), here R 10 C4~C are linear or branched. 18 Alkyl, linear or branched C4-C with 1 or 2 double bonds 18 Alkenyl, linear or branched C4-C 18 Ethers and oxoalkyls, and hydroxyphenyls, A compound represented by, However, the compound is not nona-2,6-diene-1-yl palmitate. Here, the aromatic alcohol represented by formula (II) released from the compound represented by formula (I) is selected from the group consisting of 3,7-dimethylnonano-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, 6-nonenol, 6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol, and the compound is provided.

[0030] The aromatic alcohol represented by formula (II) exhibits a good perceptual threshold when released slowly from the compound represented by formula (I). In contrast, other alcohols, such as citronellol (3,7-dimethylocta-6-en-1-ol) or geraniol (3,7-dimethylocta-2,6-dien-1-ol), have higher thresholds, which makes them less effective in slow release modes when released from the corresponding compound represented by formula (I).

[0031] For example, in the compounds represented by formula (I) and formula (II), the stereochemistry of the double bond between C6 and C7 is Z. Alternatively, the stereochemistry of the double bond may be E, or the compound may be an E / Z mixture.

[0032] For example, the aromatic alcohol represented by formula (II) may be selected from the group consisting of (Z)-3,7-dimethylnonona-6-en-1-ol, (S,Z)-3,7-dimethylnonona-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, (Z)-6-nonenol, (Z)-6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and (2E,6Z)-nonadienol.

[0033] In one embodiment of the present invention, a compound represented by formula (I) as defined above is provided, where R 1 ~R 6 The total number of carbon atoms provided by the compound must not exceed 8. In other words, an aromatic alcohol (a compound represented by formula (II)) that can be produced from a compound represented by formula (I) must have a total number of carbon atoms between 9 and 15.

[0034] In one embodiment of the present invention, a compound represented by formula (I) is provided as defined above, provided that R 2 If Me, then R 5 and R 6 At least one of the substituents is H or Et, while the other substituents are independently selected from the group consisting of H, Me, and Et.

[0035] In one embodiment of the present invention, formula (II): [ka] Formula (I): A precursor for producing aromatic alcohols represented by the formula (I): [ka] During the ceremony, [ka] This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; A compound represented by, Here, the aromatic alcohol represented by formula (II) released from the compound represented by formula (I) is selected from the group consisting of 3,7-dimethylnonano-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, 6-nonenol, 6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol, and the compound is provided.

[0036] The compound may be referred to as an ether-type compound represented by formula (I).

[0037] In one embodiment of the present invention, an ether-type compound represented by formula (I) is provided, where R 1 ~R 6 The total number of carbon atoms provided by the compound must not exceed 8. In other words, an aromatic alcohol (a compound represented by formula (II)) that can be produced from a compound represented by formula (I) must have a total number of carbon atoms between 9 and 15.

[0038] In one embodiment of the present invention, an ether-type compound represented by formula (I) is provided as defined above, provided that R 2 If Me, then R 5 and R 6 At least one of the substituents is H or Et, while the other substituents are independently selected from the group consisting of H, Me, and Et.

[0039] In one embodiment of the present invention, an ether-type compound represented by formula (I) is provided, where R 1 ~R 6 The total number of carbon atoms provided by R must not exceed 8, however R 2 If Me, then R 5 and R 6 At least one of the substituents is H or Et, while the other substituents are independently selected from the group consisting of H, Me, and Et.

[0040] For example, the compound represented by formula (I) is 1-((3,7-dimethylnona-6-en-1-yl)oxy)naphthalene, 2-((3,7-dimethylnona-6-en-1-yl)oxy)naphthalene, 4-((3,7-dimethylnona-6-en-1-yl)oxy)phenol, ethyl 3-(4-((3,7-dimethylnona-6-en-1-yl)oxy)phenyl)acrylate, 1-((3,7-dimethylnona-6-en-1-yl)oxy)-4-methoxybenzene, 2-(3,7-dimethylnona-6-en-1-yl)oxy)benzaldehyde, 1-((3,7-dimethylnona- 6-en-1-yl)oxy)-2-methoxybenzene, 2-((3,7-dimethylnona-6-en-1-yl)oxy)-2-phenylacetaldehyde, 2-((3,7-dimethylnona-6-en-1-yl)oxy)phenol, 3-((3,7-dimethylnona-6-en-1-yl)oxy)phenol, 1-((3,7-dimethylnona-6-en-1-yl)oxy)-3-methoxybenzene, 1-(nona-6-en-1-yloxy)naphthalene, 2-(nona-6-en-1-yloxy)naphthalene, 4-(nona-6 -en-1-yloxy)phenol, ethyl 3-(4-(nona-6-en-1-yl)oxy)phenyl)acrylate, 1-methoxy-4-(nona-6-en-1-yloxy)benzene, 2-(nona-6-en-1-yloxy)bensaldehyde, 1-methoxy-2-(nona-6-en-1-yloxy)benzene, 3-methoxy-4-(nona-6-en-1-yloxy)benzaldehyde, 2-(nona-6-en-1-yloxy)phenol, 3-(nona-6-en-1-yloxy)phenol, 1-methoxy-3 -(nona-6-en-1-yloxy)benzene, 3-ethoxy-4-(nona-6-en-1-yloxy)benzaldehyde, 4-((2,4,7-trimethylocta-6-en-1-yl)oxy)phenol, 4-((1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methoxy)phenol, 1-methoxy-2-((nona-2,6-dien-1-yl)oxy)benzene, 1-((6-ethyl-3-methylocta-6-en-1-yl)oxy)naphthalene, 3-ethoxy-4-((nona-2,It may be selected from the group consisting of (6 - diene - 1 - yl)oxy)benzaldehyde, 4-(4-((nona - 2,6 - diene - 1 - yl)oxy)phenyl)butan - 2 - one, 4 - allyl - 2 - methoxy - 1 - ((nona - 2,6 - diene - 1 - yl)oxy)benzene, methyl 2 - ((3,7 - dimethylnona - 6 - en - 1 - yl)oxy)-2 - phenylacetate, 2 - ((3,7 - dimethylnona - 6 - en - 1 - yl)oxy)-1,2 - diphenylethane - 1 - one, (2 - ((3,7 - dimethylnona - 6 - en - 1 - yl)oxy)propan - 2 - yl)benzene, and 2-(2-(3,7 - dimethylnona - 6 - en - 1 - yl)oxy)propan - 2 - yl)naphthalene.,

[0041] In a further aspect of the present invention, the following formula (II):

Chemical formula

Chemical formula

Chemical formula

[0042] The aromatic alcohol represented by formula (II) exhibits a good perceptual threshold when released slowly from the compound represented by formula (I). In contrast, other alcohols, such as citronellol (3,7-dimethylocta-6-en-1-ol) or geraniol (3,7-dimethylocta-2,6-dien-1-ol), have higher thresholds, which makes them less effective in slow release modes when released from the corresponding compound represented by formula (I).

[0043] The compound may be referred to as an ester-type compound represented by formula (I).

[0044] In one embodiment of the present invention, an ester compound represented by formula (I) is provided as defined above, where R 1 ~R 6 The total number of carbon atoms provided by the compound must not exceed 8. In other words, an aromatic alcohol (a compound represented by formula (II)) that can be produced from a compound represented by formula (I) must have a total number of carbon atoms between 9 and 15.

[0045] In one aspect of the present invention, there is provided an ester-type compound represented by formula (I) as defined above, provided that R 2 when is Me, at least one of R 5 and R 6 is H or Et, while the other substituents are independently selected from the group consisting of H, Me, and Et.

[0046] In one aspect of the present invention, there is provided an ester-type compound represented by formula (I), where the total number of carbon atoms provided by R 1 ~R 6 shall not exceed 8, provided that when R 2 is Me, at least one of R 5 and R 6 is H or Et, while the other substituents are independently selected from the group consisting of H, Me, and Et.

[0047] For example, the compound represented by formula (I) may be selected from the group consisting of 3,7-dimethyInon-6-en-1-yl palmitate, 3,7-dimethyInon-6-en-1-yl 4-oxopentanoate, 2,4,7-trimethyloct-6-en-1-yl palmitate, 2,4,7-trimethyloct-6-en-1-yl 4-oxopentanoate, (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methyl palmitate, (1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methyl 4-oxopentanoate, 6-ethyl-3-methyloct-6-en-1-yl palmitate, 6-ethyl-3-methyloct-6-en-1-yl 4-oxopentanoate, non-6-en-1-yl palmitate, non-6-en-1-yl 4-oxopentanoate, nona-2,6-dien-1-yl 4-oxopentanoate, non-6-en-1-yl 2-hydroxybenzoate, and nona-2,6-dien-1-yl 2-hydroxybenzoate.

[0048] Since esters are expected to be stable on dry fibers, the precursor effect of the compound represented by formula (I) is surprising. Therefore, it is surprising that aromatic alcohols are released from the ester represented by formula (I) at a sufficiently high rate, generating a perceptible odor signal. Furthermore, ethers are considered stable in consumer products and their applications. Therefore, it is surprising that a perceptible amount of fragrance alcohol is released from ethers under environmental conditions.

[0049] The compound represented by formula (I) is typically odorless or has little odor and can release the aromatic alcohol represented by formula (II), which is the main odor compound produced by the presented precursor. Typically, the residual portion of the compound represented by formula (I) contributes either nothing to the overall odor or only a relatively small amount, so the main odor characteristics of the aromatic alcohol represented by formula (II) are recognized, and only the odor aspect is altered.

[0050] However, in some embodiments of the present invention, the compound represented by formula (I) may have a characteristic odor.

[0051] In a further embodiment of the present invention, formula (II): [ka] Formula (I): A precursor for producing aromatic alcohols represented by the formula (I): [ka] During the ceremony, [ka] This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; and Alkanoyl(C(O)-R) 10 ), here R 10 C4~C are linear or branched. 18 Alkyl, linear or branched C4-C with 1 or 2 double bonds 18 Alkenyl, linear or branched C4-C 18 Ethers and oxoalkyls, and hydroxyphenyls, A compound represented by, However, the use of the compound is provided, but the compound is not nona-2,6-diene-1-yl palmitate.

[0052] For example, formula (I) as a precursor for producing the aromatic alcohol represented by formula (II) as described above: [ka] A compound represented by, Herein, the use of the compound is provided, wherein the aromatic alcohol (II) released from the compound represented by formula (I) is selected from the group consisting of 3,7-dimethylnonano-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, 6-nonenol, 6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol.

[0053] By using the compound represented by formula (I) as an alternative to aromatic alcohols, it is possible to provide the scent of aromatic alcohols for extended periods. Furthermore, the precursor can be incorporated into various consumer products.

[0054] In addition, the compound represented by formula (I) gradually releases the strong odor of the aromatic alcohol represented by formula (II) at low concentrations. Some of the compounds represented by formula (II) have a high odor impact and can therefore only be used in fragrance compositions in very small amounts, for example, less than 0.5%. Thus, it is not possible to administer such aromatic alcohols in amounts sufficient to affect the scent after drying in rinse-off applications, such as laundry detergent applications. The compound represented by formula (I) solves this technical problem.

[0055] The compound represented by formula (I) above releases aromatic alcohols upon prolonged exposure (e.g., several days such as 2–7 days or even longer) to ambient air and / or humidity (by oxidation and / or hydrolysis).

[0056] Exposure of the precursor compound to the ambient air means exposure to molecular oxygen, which causes cleavage of the compound represented by formula (I) and release of the compound represented by formula (II). Since the concentration of oxygen in the atmosphere is sufficient to cleave the compound represented by formula (I), the cleavage product can be detected in the ambient air, for example, by olfactory detection or GC-MS analysis of headspace samples.

[0057] Exposure of the precursor compound to humidity means exposure to water, which can lead to the cleavage of the compound represented by formula (I) and the release of the compound represented by formula (II). Even a small amount of water is already sufficient to enable the cleavage of the compound represented by formula (I).

[0058] The compound represented by formula (I) is finely dispersed in fibers, such as cotton fabric fibers, synthetic fibers, hair, or hard surfaces, such as ceramics or plastics, thereby maximizing surface coverage and enabling exposure to air and moisture.

[0059] The compound represented by formula (I) is extremely stable when not exposed to ambient air and / or humidity. Therefore, the compound represented by formula (I) can find use in a wide range of consumer products where long-term and defined release of aromatic compounds is desired.

[0060] The compound represented by formula (I) may be used alone or in combination with one or more conventionally used components or excipients, such as carrier materials and other auxiliary agents commonly used in the art, in combination with known odor molecule molecules selected from a wide range of natural products, currently available synthetic molecules, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocyclic and heterocyclic compounds, and / or in combination with odor molecules in fragrance compositions.

[0061] For example, the compound represented by formula (I) can be used in combination with the free aromatic alcohol represented by formula (II). Such a combination ensures the continuous perception of the aromatic alcohol over time.

[0062] In a further aspect, the compound represented by formula (I) may be used in combination with other fragrance precursors, either with further compounds represented by formula (I) or precursors having different chemical structures. The combination of precursors allows for the release of fragrance composition.

[0063] In a further aspect, a fragrance composition is provided comprising at least one compound represented by formula (I). For example, the fragrance composition comprises one or more known odor molecules or fragrance precursors and / or one or more components or excipients conventionally used in combination with odor substances in the fragrance composition.

[0064] As used herein, “carrier material” means a material that is practically neutral in terms of odor, i.e., a material that does not significantly alter the sensory properties of odor substances.

[0065] The term "adjuvant" refers to an ingredient that may be used for reasons not specifically related to the olfactory performance of a fragrance composition. For example, an adjuvant may be an ingredient that acts as an aid in processing one or more fragrance ingredients, or a composition containing such ingredients, or an ingredient that can improve the handling or storage of fragrance ingredients or compositions containing them. It may also be an ingredient that provides additional benefits, such as imparting color or texture. It may also be an ingredient that imparts light resistance and chemical stability to one or more ingredients contained in a fragrance composition. A detailed description of the properties and types of adjuvants commonly used in fragrance compositions containing adjuvants may not be comprehensive, but it should be noted that such ingredients are well known to those skilled in the art.

[0066] As used herein, “fragrance composition” means any composition comprising a compound represented by formula (I) and a base material, for example, diluents conventionally used in combination with odorants, such as diethylphthalate (DEP), dipropylene glycol (DPG), isopropyl myristart (IPM), pentane 1,2-diol, triethyl citrate (TEC), and alcohol (e.g., ethanol). Optionally, the composition may include an antioxidant adjuvant. The antioxidant may be selected from Tinogard® TT (BASF), Tinogard® Q (BASF), tocopherol (including its isomers, CAS 59-02-9; 364-49-8; 18920-62-2; 121854-78-2), 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT, CAS 128-37-0) and related phenols, hydroquinone (CAS 121-31-9).

[0067] The following unrestricted list includes examples of known odor molecules that may be combined with the compound represented by (I) in a fragrance composition: ● Essential oils and extracts, for example, castorium, costus root oil, oakmoss absolute, geranium oil, treemoss absolute, basil oil, fruit oils, for example, bergamot oil and mandarin oil, myrtle oil, palmarose oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil, or ylang-ylang oil;

[0068] ● Alcohols, for example, cinnamic alcohol ((E)-3-phenylpropane-2-en-1-ol); cis-3-hexenol ((Z)-hexa-3-en-1-ol); Citronellol (3,7-dimethylocta-6-en-1-ol); dihydro myrcenol (2,6-dimethylocta-7-en-2-ol); Ebanol (trademark) ((E)-3-methyl-5-(2,2,3-trimethylcyclopenta-3-en-1-yl)penta-4-en-2-ol); eugenol (4-allyl-2-methoxyphenol); ethyl linalool((E)-3,7-dimethylnonano-1,6-dien-3-ol);farnesol((2)E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol);geraniol((E)-3,7-dimethylocta-2,6-dien-1-ol);Super Muguet(trademark)((E)-6-ethyl-3-methylocta-6-en-1-ol);linalool(3,7-dimethylocta-1,6-dien-3-ol);menthol(2-isopropyl-5-methylcyclohexanol);Nerol(3,7-dimethyl-2,6-octadien-1-ol);phenyl ethyl alcohol (2-phenylethanol); Rhodinol (trademark) (3,7-dimethylocta-6-en-1-ol); Sandalore (trademark) (3-methyl-5-(2,2,3-trimethylcyclopenta-3-en-1-yl)pentan-2-ol); terpineol (2-(4-methylcyclohexa-3-en-1-yl)propan-2-ol); or Timberol (trademark) (1-(2,2,6-trimethylcyclohexyl)hexane-3-ol); 2,4,7-trimethylocta-2,6-dien-1-ol and / or [1-methyl-2(5-methylhexa-4-en-2-yl)cyclopropyl]methanol;

[0069] ● Aldehydes and ketones, for example, anisaldehyde (4-methoxybenzaldehyde); alpha amyl cinnamic aldehyde (2-benzylidene heptanal); Georgywood (trademark) (1-(1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone); Hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal); Iso E Super(1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone); Isoraldeine((E)-3-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-1); Hedione(methyl 3-oxo-2-pentylcyclopentane acetate); Nympheal(3-(4-isobutyl-2-methylphenyl)propanal); Mahonial(5,9-dimethyl-9-hydroxydecene-4-al); maltol; methyl cedryl ketone; methylionone; verbenone; and / or vanillin;

[0070] ● Ethers and acetals, for example, Ambrox® (3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran); geranyl methyl ether ((2E)-1-methoxy-3,7-dimethylocta-2,6-diene); rose oxide (4-methyl-2-(2-methylpropa-1-en-1-yl)tetrahydro-2H-pyran); or Spirambrene® (2',2',3,7,7-pentamethylspiro[bicyclo[4.1.0]heptane-2,5'-[1,3]dioxane]);

[0071] ● Esters and lactones, for example, benzyl acetate; cedryl acetate ((1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methaneazulene-6-yl acetate); γ-decalactone (6-pentyltetrahydro-2)H-pyran-2-one); Helvetolide® (2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylpropionate); γ-undecalactone (5-heptyloxolan-2-one); and / or vetiveryl acetate ((4,8-dimethyl-2-propane-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulene-6-yl) acetate);

[0072] ● Large rings, for example, Ambrettolide ((Z)-oxacycloheptadeca-10-en-2-one); ethylene brassylate (1,4-dioxacycloheptadecan-5,17-dione); and / or Exaltolide® (16-oxacyclohexadecan-1-one); and

[0073] ● Heterocyclic rings, for example, isobutylquinoline (2-isobutylquinoline).

[0074] In general, the compounds represented by formula (I) can be used alone, in mixtures thereof, or in combination with other fragrance components and / or their precursors. Such other fragrance components also include, for example, fragrance compounds and essential oils of natural or synthetic origin, as described in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 2003.

[0075] In a further aspect, a consumer product is provided comprising a compound represented by at least one chemical formula (I) and a consumer product base.

[0076] Consumer products are selected from, for example, fine fragrances, personal care products (body care products, hair care products, cosmetic products), fabric care products, household care products, and air care products. As used herein, “consumer product base” means a composition for a consumer product that performs a specific task, such as cleaning, softening, and caring or similar.

[0077] Personal care products to which the compound represented by formula (I) may be added include, for example, all kinds of body care products. Products of particular interest are hair care products, such as shampoos, conditioners, and hairsprays, as well as skin care products, such as lotions or creams. Furthermore, the compound represented by formula (I) may be added to soaps, bath and shower gels, and deodorants. The compound represented by formula (I) may be added to cosmetic products.

[0078] Household care products to which the compound represented by formula (I) may be added include all kinds of detergents, window cleaners, hard surface cleaners, all-purpose cleaners, and furniture polishes. Preferably, the product is a liquid, for example, a fabric detergent or conditioner composition.

[0079] For example, the compound represented by formula (I) can act as a fragrance precursor in consumer products that further contain enzymes.

[0080] Compositions according to formula (I) can be used in a wide range of fragrance consumer products, for example, in any area of ​​high-quality and functional fragrances, such as fragrances, air care products, household products, laundry products, body care products, and cosmetics. The compound can be used in a wide variety of amounts, depending on the specific consumer product and the properties and amounts of other odor substance components. The proportion of formula (I) is typically 0.0001% to 5% by weight in a consumer product. In one embodiment, the compound represented by formula (I) can be used in fabric softeners in amounts of 0.001% to 0.3% by weight (for example, 0.01% to 0.1% by weight, including 0.05% by weight). In another embodiment, the compound represented by formula (I) can be used not only in high-quality fragrances but also in consumer products such as shampoos, fabric softeners, and fabric detergents in amounts of 0.001% to 30% by weight (for example, up to about 10% or up to 20%), more preferably between 0.01% and 5% by weight. However, these values ​​are given only as examples, as experienced perfumers may be able to achieve the same effect at lower or higher concentrations, or even create entirely new fragrances.

[0081] In one embodiment, a consumer product is provided that contains an acceptable amount of a compound represented by formula (I). For example, a fragranced consumer product may contain, based on the total amount of the consumer product, a compound represented by formula (I) in amounts ranging from 0.000001% by weight to 90% by weight (including 0.00001% by weight, 0.001% by weight, 0.01% by weight, 0.05% by weight, 0.1% by weight, 0.5% by weight, 1% by weight, 5% by weight, 8% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 50% by weight, 60% by weight, and 65% by weight).

[0082] The compound represented by formula (I) may be incorporated into a consumer product base by simply directly mixing the compound of the present invention or a fragrance composition containing the compound represented by formula (I) with the consumer product base, or by being encapsulated in an earlier step with an encapsulating material, such as polymers, capsules, microcapsules, and nanocapsules, liposomes, membrane-forming agents, absorbents, such as carbon or zeolites, cyclic oligosaccharides, and mixtures thereof, and then mixed with the consumer product base. The consumer base may further contain an encapsulating material that can release other aromatic compounds.

[0083] Accordingly, the present invention also provides a method for producing a consumer product, comprising incorporating the compound represented by formula (I) by either directly mixing the compound represented by formula (I) into a consumer product base, or by mixing a fragrance composition containing the compound represented by formula (I) and then mixing it into the consumer product base using prior art or methods. Through the addition of an acceptable amount of the compound of the present invention as described herein, the scent note of the applied consumer product will be improved, imparted, enhanced, or modified.

[0084] As used herein, “consumer product base” means a composition for a consumer product that performs a specific task, such as cleaning, softening, and caring or similar.

[0085] In a further aspect of the present invention, a method is provided for releasing an aromatic alcohol represented by formula (II), wherein a compound represented by formula (I) according to claim 1 is exposed to ambient air and / or humidity.

[0086] The compounds of the present invention can be prepared by methods known to those skilled in the art of organic synthesis. For illustrative purposes, a general description of such methods is provided below. In all cases, isolation and purification of the product are achieved according to preferred workup and purification methods known to those skilled in the art.

[0087] For example, a compound represented by the ether form of formula (I) (where X is selected from the group consisting of aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate) can be prepared by reacting phenol or hydroxynaphthalene (Aryl-OH) with a substituted alkyl "R-CH2-B" (where B is chloride, bromide, iodide, tosylate, or mesylate) in a solvent (e.g., dimethylformamide (DMF)) in the presence of a base (e.g., calcium carbonate) at a temperature between 25°C and 150°C for a time between 1 hour and 24 hours. [ka]

[0088] For example, a compound represented by the ester formula (I) (where X is alkanoyl(C(O)-R) 10 ), R 10 Linear or branched C4~C 18 Alkyl, linear or branched C4-C with 1 or 2 double bonds 18 Alkenyl, linear or branched C4-C 18 Ethers and oxoalkyls, as well as hydroxyphenyls, can be prepared by reacting a carboxylate chloride "R'-C(O)-Cl" with an alcohol "R-CH2-OH" in a solvent (e.g., dichloromethane, toluene, or heptane) at a temperature between 0°C and 100°C for a period of 1 to 48 hours, optionally in the presence of 1 mol% to 10 mol% of a catalyst (e.g., 4-(N,N-dimethylamino)pyridine) in the presence of a base (e.g., pyridine, triethylamine, potassium carbonate, or sodium hydroxide). [ka]

[0089] Alternatively, the esterified compound (R'-C(O)-O-CH2-R) represented by formula (I) can be prepared by a transesterification reaction between a carboxylic acid ester "R'-C(O)-O(Me,Et)" and an alcohol "R-CH2-OH" at a temperature between 50°C and 200°C under low pressure and distillation of a MeOH or EtOH alcohol (preferably without a solvent) in the presence of 1 mol% to 20 mol% of a catalyst (e.g., titanium tetraisopropoxide). [ka]

[0090] In another aspect, the present invention also provides a method for imparting, enhancing, improving or modifying the hedonic properties of a fragrance composition or consumer product, the method comprising adding at least one compound represented by formula (I) to the composition or consumer product.

[0091] The present invention is further described with reference to the following non-limiting examples. These examples are for illustrative purposes only and can be modified and altered by those skilled in the art.

[0092] example General: All reagents and reaction solvents were analytical grade, purchased from commercial suppliers, and used without additional purification. Reactions were monitored by GC-FID (Zebron ZB-5 GC capillary column, 12 m x 0.32 mm x 0.25 μm, or Zebron ZB-wax, 15 m x 0.32 mm x 0.25 μm). Flash column chromatography was performed on a pre-packed Biotage silica gel column (particle size 20 μm) with the indicated eluent and a flow rate of 50 mL / min. Unless otherwise specified, all reported yields refer to spectroscopically and chromatographically pure isolated compounds; isomer ratios are indicated where appropriate. Typical NMR spectra were recorded with Bruker Avance III HD (500 MHz) and AW 400 MHz Bruker, and 2D NMR spectra were recorded with a Bruker Avance-III 600 MHz using a 1.7 mm TCI microcryoprobe. The chemical shift of protons was reported in ppm(δ) against tetramethylsilane (TMS), with solvent resonance used as the internal standard (CDCl3δ 7.27 ppm). Data are reported as follows: chemical shift, multiplicity (s=singlet, d=doublet, t=triplet, q=quadruplet, p=quintlet, sextet, h=septuplet, m=multitlet, br=broad), coupling constant (Hz), and integral. The chemical shift of 13C is reported in ppm from tetramethylsilane (TMS) with solvent resonance as the internal standard (CDCl3δ 77.0 ppm).

[0093] Example 1: 3,7-dimethylnonano-6-en-1-yl-4-oxopentanoate A mixture of 3,7-dimethylnonona-6-en-1-ol (E / Z mixture, 6.39 g, 37.5 mmol, 1.5 equiv.), methyl 4-oxopentanoate (3.25 g, 25.0 mmol, 1 equiv.), and titanium(IV) isopropoxide (355 mg, 1.25 mmol, 5 mol%) was placed in a two-necked 25 mL glass flask and mounted in a distillation apparatus with a 6 cm Vigloo column. The mixture was heated under reduced pressure (500 mbar) to 110 °C with stirring for 40 minutes, then heated at 350 mbar at 130 °C for 2.5 hours. After cooling to RT, the crude product was purified by FC (heptane / Â, gradient 0%~100% Â). The resulting product was subjected to valve-to-valve distillation (100 °C / 0.11 mbar) to remove excess 3,7-dimethylnonona-6-en-1-ol. The residue consisted of 3,7-dimethylnona-6-en-1-yl-4-oxopentanoate (colorless liquid, 4.79 g, 69%, E / Z 69:31, purity >97%).

[0094] 1 H-NMR (500 MHz, CDCl3) 5.04 - 5.12 (m, 1 H), 4.07 - 4.15 (m, 2 H), 2.73 - 2.77 (m, 2 H), 2.56 - 2.59 (m, 2 H), 2.20 (s, 3 H), 1.91 - 2.07 (m, 3 H), 1.68 (q, J = 1.2 Hz, 0.5 H), 1.62 - 1.73 (m, 1 H), 1.60 (br. s, 2.5 H), 1.50 - 1.59 (m, 1 H), 1.31 - 1.48 (m, 3 H), 1.14 - 1.23 (m, 1 H), 0.98 (q, J = 7.6 Hz, 3H), 0.91 (dd, J = 6.7, 2.1 Hz, 3H). 13C-NMR (126 MHz, CDCl3) 206.6 (s), 172.8 (s), 137.1,136.8 (s), 124.2,122.9 (d), 63.3, 63.2 (d), 38.0 (t), 37.3, 37.0 (t), 35.4 (t), 32.3 (t), 29.9, 29.5 (d), 28.0 (t), 25.2, 24.7 (t), 22.9 (q), 19.4, 19.4 (q), 15.9 (q), 12.8, 12.8 (q).

[0095] Example 2: (E / Z)-3,7-dimethylnonano-6-en-1-ylpalmitate The procedure described in Example 1 was repeated with 3,7-dimethylnona-6-en-1-ol (E / Z mixture, 3.8 g, 23 mmol, 1.5 equiv.), methyl palmitate (4.1 g, 15.0 mmol, 1 equiv.), and titanium(IV) isopropoxide (210 mg, 0.75 mmol, 5 mol%), resulting in a colorless liquid product after chromatographic purification (4.2 g, 66%, E / Z 62:35).

[0096] 1 H-NMR (500 MHz, CDCl3) 5.07 - 5.12 (m, 1 H), 4.09 - 4.15 (m, 2 H), 2.30 (t, J=7.6 Hz, 2 H), 1.96 - 2.06 (m, 4 H), 1.55 - 1.71 (m, 5 H), 1.62 (br. s, 3H), 1.43 - 1.48 (m, 1 H), 1.19 - 1.41 (m, 25 H), 0.99 (q, J=7.6 Hz, 3 H), 0.92 - 0.95 (m, 3 H), 0.90 (t, J=7.3 Hz, 3 H). 13C-NMR (126 MHz, CDCl3) 174.0 (s), 137.1, 136.8 (s), 124.2, 123.0 (d), 62.8 (t), 37.3 (t), 37.0 (t), 35.5 (t), 34.5 (t), 32.4 (t), 31.9 (t), 29.7 (4t), 29.6 (t), 29.5 (d), 29.5 (t), 29.4 (t), 29.3 (t), 29.2 (t), 25.3, 25.0 (t), 25.0, 24.8 (t), 22.7 (t), 19.5, 19.4 (q), 15.9 (q), 14.1 (q), 12.9, 12.8 (q).

[0097] Example 3: 2,4,7-trimethylocta-6-en-1-yl-4-oxopentanoate The procedure described in Example 1 was repeated with 2,4,7-trimethylocta-6-en-1-ol (5.1 g, 30 mmol, 1.5 equiv.), 4-oxopentanoate (2.6 g, 20.0 mmol, 1 equiv.), and titanium(IV) isopropoxide (284 mg, 1.0 mmol, 5 mol%), and after chromatographic purification, the product was produced as a colorless liquid (3.6 g, 67%, 2 diastereomers, dr56:43).

[0098] 1H-NMR (500 MHz, CDCl3) 5.10 - 5.15 (m, 1 H), 3.91 - 4.00 (m, 1 H), 3.81 - 3.87 (m, 1 H), 2.75 - 2.78 (m, 2 H), 2.58 - 2.62 (m, 2 H), 2.21 (s, 3 H), 1.83 - 2.00 (m, 2 H), 1.71 (br. s, 3 H), 1.60 (br. s, 3 H), 1.55 (dq, J = 13.4, 6.7 Hz, 1 H), 1.33 (dt, J = 13.7, 6.9 Hz, 1 H), 1.12 - 1.16 (m, 1 H), 0.95 - 1.02 (m, 1 H), 0.93 (d, J = 6.7 Hz, 1 H), 0.89 (dd,J = 8.9, 6.7 Hz, 3 H), 0.85 (d, J = 6.4 Hz, 2 H). 13 C-NMR (126 MHz, CDCl3) 206.6 (2s), 172.8 (2s), 132.2 (s), 123.1, 122.9 (d), 70.2, 69.6 (t), 40.8, 40.4 (t), 38.0 (t), 36.1, 35.0 (t), 30.9, 30.8 (d), 30.1 (2d), 29.9 (q), 28.0 (t), 25.8, 25.8 (q), 20.1, 19.2 (q), 17.9, 17.7 (q), 16.6 (q).

[0099] Example 4: (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methyl-4-oxopentanoate The procedure described in Example 1 was repeated with (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol (4.1 g, 22.5 mmol, 1.5 equiv.), 4-oxopentanoate (2.0 g, 15.0 mmol, 1 equiv.), and titanium(IV) isopropoxide (213 mg, 0.75 mmol, 5 mol%), and after chromatographic purification, the product was produced as a colorless liquid (2.3 g, 54%, 2 distereomers, dr, 61:32).

[0100] 1H-NMR (500 MHz, CDCl3) 5.10 - 5.19 (m, 1 H), 3.78 - 3.88 (m, 2 H), 2.73 - 2.78 (m, 2 H), 2.57 - 2.65 (m, 2 H), 2.19 (s, 3 H), 2.01 - 2.14 (m, 1 H), 1.90 - 1.99 (m, 1 H), 1.69 - 1.72 (m, 3 H), 1.61 (s, 3 H), 1.13 - 1.15 (m, 1 H), 1.12 (s, 2 H), 0.99 - 1.10 (m, 2 H), 0.92 - 0.98 (m, 2 H), 0.47 - 0.62 (m, 2 H), -0.01 - 0.12 (m, 1 H). 13 C-NMR (126 MHz, CDCl3) 206.6 (2s), 172.9 (2s), 132.0, 131.8 (s), 123.0, 122.9 (d), 74.0, 73.9 (t), 38.0 (2t), 35.7, 35.5 (t), 34.6, 34.1 (d), 29.9 (q), 29.5, 29.4 (d), 28.0 (2t), 25.9, 25.8 (q), 20.1, 19.9 (q), 19.9, 19.1 (s), 17.8 (q), 16.8, 16.1 (t), 15.7 (q).

[0101] Example 5: (Z)-nona-6-en-1-il4-oxopentanoart The procedure described in Example 1 was repeated with (Z)-nona-6-en-1-ol (4.3 g, 30.0 mmol, 1.5 equiv.), 4-oxopentanoate (2.6 g, 20.0 mmol, 1 equiv.), and titanium(IV) isopropoxide (284 mg, 1.0 mmol, 5 mol%), resulting in a colorless liquid product after chromatographic purification (3.4 g, 70%).

[0102] 1H-NMR (500 MHz, CDCl3) 5.27 - 5.39 (m, 2 H), 4.06 (t, J=6.7 Hz, 2 H), 2.74 (t, J=6.4 Hz, 2 H), 2.57 (t, J=6.7 Hz, 2 H), 2.19 (s, 3 H), 1.97 - 2.06 (m, 4 H), 1.59 - 1.66 (m, 2 H), 1.31 - 1.40 (m, 4 H), 0.95 (t, J=7.6 Hz, 3 H). 13 C-NMR (126 MHz, CDCl3) 206.6 (s), 172.8 (s), 131.8 (d), 128.8 (d), 64.8 (t), 37.9 (t), 29.9 (q), 29.3 (t), 28.5 (t), 28.0 (t), 26.9 (t), 25.5 (t), 20.5 (t), 14.4 (q).

[0103] Example 6: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)naphthalene a) 9-bromo-3,7-dimethylnonano-3-ene Tribromophosphan (55.6 g, 0.21 mol, 0.35 equiv.) was added dropwise at 5°C to a stirred mixture of 3,7-dimethylnona-6-en-1-ol (E / Z mixture, 100 g, 0.59 mol, 1.5 equiv.) and pyridine (9.3 g, 0.12 mol, 0.2 equiv.). Stirring was continued at 2-10°C for 1 hour, after which the mixture was poured into water (300 mL). The organic layer was washed with water and brine and dried over MgSO4. A colorless oil (78.8 g, 58%) was produced by distillation of the crude product (126 g of slightly turbid liquid) using a 10 cm Vigloo column (160°C in the tank, 100°C at the top).

[0104] b) 2-((3,7-dimethylnonano-6-en-1-yl)oxy)naphthalene To a solution of naphthalene-2-ol (2.0 g, 14 mmol, 1 equiv.) in N,N-dimethylformamide (DMF, 50 mL), potassium carbonate (3.8 g, 28 mmol, 2 equiv.) was added, and the mixture was stirred at RT for 20 minutes. The above-prepared 9-bromo-3,7-dimethylnona-3-ene (3.9 g, 17 mmol, 1.2 equiv.) was added, and the resulting mixture was stirred at 95°C for 6 hours. Workup was achieved as described in Part A above. The crude product was purified by FC (heptane / MTBE 60:1) in SiO2, yielding a colorless oil (0.8 g, 20%, triisomers 50:36:12).

[0105] 1 H-NMR (500 MHz, CDCl3) 7.75 - 7.82 (m, 3 H), 7.47 (ddd, J=8.1, 6.9, 1.3 Hz, 1 H), 7.34 - 7.39 (m, 1 H), 7.18 (s, 1 H), 7.19 (d, J=8.6 Hz, 1 H), 5.13 - 5.29 (m, 1 H), 4.10 - 4.20 (m, 2 H), 1.89 - 2.14 (m, 4 H), 1.60 - 1.84 (m, 7 H), 1.38 - 1.55 (m, 2 H), 1.22 - 1.36 (m, 1 H), 0.95 - 1.08 (m, 4 H).

[0106] Example 7: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)phenol A mixture of 1,2-didooxybenzene (2.0 g, 18 mmol, 1 equiv.), potassium carbonate (5.0 g, 36 mmol, 2 equiv.), and 9-bromo-3,7-dimethylnonano-3-ene (5.1 g, 22 mmol, 1.2 equiv., as prepared in Example 6a) in DMF (50 mL) was heated to 80°C for 20 hours with stirring. The mixture was poured into water (100 mL), acidified with 2 Maq. HCl solution, and extracted with heptane. After drying with MgSO4 and evaporation of the solvent, a clear brown liquid (3.7 g) was obtained, which was purified by FC (heptane / MTBE 30:1) in SiO2 to produce a colorless oil product (1.8 g, 36%, mixture of E / Z isomers).

[0107] 1 H-NMR (500 MHz, CDCl3) 6.96 - 6.99 (m, 1 H), 6.85 - 6.94 (m, 3 H), 5.70 (s, 1 H), 5.02 - 5.42 (m, 1 H), 4.07 - 4.15 (m, 2 H), 1.99 - 2.11 (m, 2 H), 1.87 - 1.94 (m, 1 H), 1.60 - 1.76 (m, 6 H), 1.21 - 1.51 (m, 3 H), 0.98 - 1.06 (m, 6 H).

[0108] Example 8: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)benzaldehyde The procedure described in Example 7 was repeated with salicylaldehyde (2.0 g, 16 mmol, 1 equiv.), potassium carbonate (4.5 g, 32 mmol, 2 equiv.), and 9-bromo-3,7-dimethylnona-3-ene (4.6 g, 20 mmol, 1.2 equiv., as prepared in Example 6a) in DMF (50 mL). After purification of the crude product by FC (heptane / MTBE 30:1) in SiO2, the product was isolated as a colorless oil (4.0 g, 88%, mixture of E / Z isomers).

[0109] 1H-NMR (500 MHz, CDCl3) 10.52 (s, 1 H), 7.84 (dd, J=7.7, 1.8 Hz, 1 H), 7.54 (ddd, J=8.3, 7.5, 1.8 Hz, 1 H), 6.98 - 7.04 (m, 2 H), 5.03 - 5.30 (m, 1 H), 4.10 - 4.16 (m, 2 H), 1.88 - 2.08 (m, 4 H), 1.56 - 1.77 (m, 6 H), 1.19 - 1.48 (m, 2 H), 0.96 - 1.02 (m, 6 H).

[0110] Example 9: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)-2-phenylethane-1-ol A mixture of styrene oxide (10.0 g, 83 mmol, 1 equiv., added in two portions at 0 and 24 hours) and (E,Z)-3,7-dimethylnonano-6-en-1-ol (14.2 g, 83 mmol, 1 equiv.) was mixed with FeCl3 (0.63 g, 4.1 mmol, 5 mol%, added in two portions at 0 and 24 hours). The mixture was stirred at 60°C for 48 hours, then poured into a sat.aq.NaHCO3 solution (100 mL) and extracted with MTBE. The organic layer was washed with water and brine and dried over MgSO4. After removal of the solvent, a clear dark brown liquid (13.1 g) was obtained, which was then distilled by valve-to-valve distillation (180°C, 0.05 mbar) and purified by FC (heptane / MTBE 3:1) with SiO2, yielding the product as a slightly yellow liquid (2.98 g, 27%, mixture of E and Z isomers).

[0111] 1H-NMR (400 MHz, CDCl3) 7.27 - 7.43 (m, 5 H), 5.05 - 5.14 (m, 1 H), 4.42 (dd, J=8.4, 4.0 Hz, 1 H), 3.57 - 3.75 (m, 2 H), 3.35 - 3.56 (m, 2 H), 2.36 (dd, J=9.4, 3.1 Hz, 1 H), 1.93 - 2.08 (m, 3 H), 1.54 - 1.73 (m, 5 H), 1.26 - 1.49 (m, 3 H), 1.10 - 1.24 (m, 1 H), 0.84 - 1.05 (m, 6 H).

[0112] Example 10: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)-2-phenylacetaldehyde The product of Example 9 (1.0 g, 3.4 mmol) was oxidized with desmartin periodinane (1.1 equiv.) in dichloromethane (50 mL), followed by FC (heptane / MTBE 9:1) in SiO2, after which the product was produced as a colorless liquid (0.27 g, 27%, mixture of E and Z isomers).

[0113] 1 H-NMR (400 MHz, CDCl3) 9.62 (d, J=2.2 Hz, 1 H), 7.28 - 7.68 (m, 5 H), 5.01 - 5.14 (m, 1 H), 4.71 - 4.75 (m, 1 H), 3.45 - 3.75 (m, 2 H), 1.83 - 2.07 (m, 3 H), 1.79 (br. s, 3 H), 1.63 - 1.81 (m, 2 H), 1.45 - 1.60 (m, 1 H), 1.13 - 1.43 (m, 3 H), 0.80 - 1.04 (m, 6 H).

[0114] Example 11: (2E,6Z)-nona-2,6-dien-1-yl2-hydroxybenzoate A mixture of methyl salicylate (4.0 g, 26.3 mmol, 1 equiv.), 2E,6Z-nona-2,6-dien-1-ol (18.4 g, 131 mmol, 5 equiv.), and sodium methoxide (0.14 g, 2.6 mmol, 0.1 equiv.) was stirred at 85°C for 3 hours. The mixture was poured into a 2Naq.HCl solution (100 mL) and then extracted with MTBE. The organic layer was washed with water and brine and dried over MgSO4. After solvent removal, the resulting residue was subjected to valve-to-valve distillation (100°C / 0.08 mbar) to produce the product as a clear, colorless liquid (3.81 g, 56%).

[0115] 1 H-NMR (400 MHz, CDCl3) 10.83 (s, 1 H), 7.89 (dd, J=8.2, 1.6 Hz, 1 H), 7.47 (ddd, J=8.5, 7.2, 1.7 Hz, 1 H), 7.00 (dd, J=8.3, 1.0 Hz, 1 H), 6.90 (t, J=7.6 Hz, 1 H), 5.87 - 5.95 (m, 1 H), 5.67 - 5.77 (m, 1 H), 5.31 - 5.54 (m, 2 H), 4.82 (dd, J=6.5, 0.9 Hz, 2 H), 1.99 - 2.26 (m, 6 H), 0.98 (t, J=7.5 Hz, 3 H). 13 C-NMR (100 MHz, CDCl3) 170.0 (s), 161.7 (s), 136.7 (d), 135.6 (d), 132.4 (d), 130.0 (d), 127.8 (d), 123.5 (d), 119.1 (d), 117.5 (d), 112.6 (s), 66.0 (t), 32.4 (t), 26.5 (t), 20.6 (t), 14.3 (q).

[0116] Example 12: 4-Allyl-2-methoxy-1-((((2E,6Z)-non-2,6-dien-1-yl)oxy)benzene a) (2E,6Z)-1-bromonona-2,6-diene Tetrabromomethane (92.2 g, 0.28 mol, 1.3 equiv.) was added dropwise at 5°C to a stirred solution of (2E,6Z)-nona-2,6-dien-1-ol (30 g, 0.21 mol, 1 equiv.) and triphenylphosphan (72.9 g, 0.28 mol, 1.3 equiv.) in dichloromethane (400 mL). Stirring was continued at room temperature for 1 hour, then the solvent was evaporated and pentane (250 mL) was added. The mixture was left in a refrigerator overnight, and the resulting precipitate was filtered. By concentrating the filtrate, (2E,6Z)-1-bromona-2,6-diene was produced as a yellow liquid (45.1 g, >99%).

[0117] b) 4-Allyl-2-methoxy-1-(((2E,6Z)-non-2,6-dien-1-yl)oxybenzene A mixture of eugenol (5.0 g, 28 mmol, 1 equiv.), (2E,6Z)-1-bromonona-2,6-diene (as prepared above, 6.3 g, 31 mmol, 1.1 equiv.), potassium carbonate (9.7 g, 70 mmol, 2.5 equiv.), and DMF (70 mL) was stirred at 80°C for 7 hours. By normal workup and chromatography (heptane / MTBE 30:1), the product was produced as a yellow liquid (1.75 g, 39%).

[0118] 1H-NMR (400 MHz, CDCl3) 6.81 (d, J=7.9 Hz, 1 H), 6.67 - 6.72 (m, 2 H), 5.96 (ddt, J=16.9, 10.1, 6.7, 6.7 Hz, 1 H), 5.69 - 5.87 (m, 2 H), 5.24 - 5.44 (m, 2 H), 5.03 - 5.13 (m, 2 H), 4.51 (d, J=5.4 Hz, 2 H), 3.85 (s, 3 H), 3.33 (d, J=6.6 Hz, 2 H), 1.98 - 2.20 (m, 6 H), 0.95 (t, J=7.5 Hz, 3 H).13C-NMR (101 MHz, CDCl3) 149.4 (s), 146.5 (s), 137.7 (d), 135.0 (d), 132.9 (s), 132.2 (d), 128.1 (d), 125.4 (d), 120.3 (d), 115.6 (t), 113.5 (d), 112.1 (d), 69.9 (t), 55.8 (d), 39.8 (t), 32.4 (t), 26.6 (t), 20.6 (t), 14.3 (q).

[0119] Example 13: 4-(4-((((2E,6Z)-non-2,6-dien-1-yl)oxy)phenyl)butan-2-one The procedure described in Example 12 was repeated with 4-(4-hydroxyphenyl)butan-2-one (5.0 g, 28 mmol, 1 equiv.), (2E,6Z)-1-bromonona-2,6-diene (6.3 g, 31 mmol, 1.1 equiv.), potassium carbonate (9.7 g, 70 mmol, 2.5 equiv.), and DMF (70 mL) to produce the product as a clear yellow liquid (2.15 g, 43%).

[0120] 1H-NMR (400 MHz, CDCl3) 6.99 - 7.10 (m, 2 H), 6.77 - 6.88 (m, 2 H), 5.78 - 5.93 (m, 1 H), 5.67 - 5.76 (m, 1 H), 5.26 - 5.44 (m, 2 H), 4.42 - 4.46 (m, 2 H), 2.80 - 2.86 (m, 2 H), 2.69 - 2.74 (m, 2 H), 1.94 - 2.22 (m, 9 H), 0.96 (t, J=7.5 Hz, 3 H). 13 C-NMR (101 MHz, CDCl3) 208.2 (s), 157.1 (s), 134.9 (d), 133.1 (s), 132.3 (d), 129.2 (2d), 128.0 (d), 125.3 (d), 114.8 (2d), 68.8 (t), 45.5 (t), 32.4 (t), 30.1 (q), 28.9 (t), 26.6 (t), 20.6 (t), 14.32 (q).

[0121] Example 14: (Z)-3-ethoxy-4-(nona-6-en-1-yloxy)benzaldehyde (Z)-9-bromonona-3-ene was prepared from (Z)-nona-6-en-1-ol according to the procedure described in Example 12a. The title compound was prepared from ethyl vanillin and (Z)-9-bromonona-3-ene according to the procedure described in Example 12b. Purification with FC (heptane / MTBE 6:1) yielded a clear, slightly yellowish liquid (4.44 g).

[0122] 1H-NMR (400 MHz, CDCl3) 9.84 (s, 1 H), 7.43 (d, J=8.1 Hz, 1 H), 7.41 (s, 1 H), 6.97 (d, J=8.3 Hz, 1 H), 5.32 - 5.45 (m, 2 H), 4.08 - 4.18 (m, 4 H), 1.99 - 2.11 (m, 4 H), 1.85 - 1.93 (m, 2 H), 1.48 (t, J=7.1 Hz, 5 H), 1.41-1.55 (m, 1 H), 1.27 - 1.32 (m, 1 H), 0.92 - 0.99 (m, 3 H). 13 C-NMR (101 MHz, CDCl3) 190.9 (d), 154.5 (s), 149.2 (s), 131.9 (d), 129.9 (s), 128.8 (d), 126.6 (d), 111.8 (d), 110.9 (d), 69.1 (t), 64.6 (t), 29.4 (t), 28.8 (t), 27.0 (t), 25.5 (t), 20.5 (t), 14.7 (q), 14.4 (q).

[0123] Example 15: (Z)-2-(nona-6-en-1-yloxy)naphthalene The procedure described in Example 14 was repeated with (Z)-9-bromononona-3-ene (17 mmol) and naphthalene-2-ol (14 mmol). After purification by column chromatography (heptane / MTBE 60:1), the product was obtained as a clear, colorless liquid (3.1 g, 77%).

[0124] 1H-NMR (400 MHz, CDCl3) 7.80 - 7.86 (m, 3 H), 7.52 (ddd, J=8.3, 6.9, 1.2 Hz, 1 H), 7.39 - 7.44 (m, 1 H), 7.24 - 7.28 (m, 1 H), 7.21 (d, J=2.4 Hz, 1 H), 5.43 - 5.54 (m, 2 H), 4.14 (t, J=6.6 Hz, 2 H), 2.12 - 2.22 (m, 4 H), 1.91 - 1.98 (m, 2 H), 1.51 - 1.66 (m, 4 H), 1.08 (t, J=7.6 Hz, 3H). 13 C-NMR (101 MHz, CDCl3) 157.2 (s), 134.7 (s), 131.9 (d), 129.4 (d), 129.0 (d), 129.0 (s), 127.7 (d), 126.8 (d), 126.3 (d), 123.5 (d), 119.1 (d), 106.6 (d), 68.0 (t), 29.6 (t), 29.3 (t), 27.1 (t), 25.9 (t), 20.7 (t), 14.5 (q).

[0125] Example 16: Methyl 2-((3,7-dimethylnonano-6-en-1-yl)oxy)-2-phenylacetate Sodium hydride (0.45 g, 60% wt, 11 mmol, 1.3 equiv) was added at 0°C to a solution of methyl 2-hydroxy-2-phenyl acetate (1.8 g, 11 mmol, 1.3 equiv.) in DMF (50 mL), and the mixture was stirred at rt for 1 hour. Then, 9-bromo-3,7-dimethylnona-3-ene (2.0 g, 8.6 mmol, 1.0 equiv.) was added to DMF (10 mL), and the mixture was stirred at rt for 16 hours. The mixture was poured into saturated ammonium chloride (100 mL) and extracted with ethyl acetate. After drying with MgSO4 and evaporation of the solvent, a clear brown liquid (3.7 g) was obtained, which was purified by FC (heptane / MTBE 10:1) with SiO2 to produce a colorless oil product (0.20 g, 7%, mixture of E / Z isomers).

[0126] 1H-NMR (400 MHz, CDCl3) δ 7.48 - 7.42 (m, 2H), 7.40 - 7.29 (m, 3H), 5.22 - 5.00 (m, 1H), 4.87 (s, 1H), 3.71 (s, 3H), 3.63 - 3.38 (m, 2H), 2.06 - 1.88 (m, 4H), 1.79 - 1.07 (m, 8H), 1.01 - 0.82 (m, 6H) ppm. 13 C-NMR (101 MHz, CDCl3) δ 171.5, 171.5, 136.9, 136.8, 136.7, 128.6, 127.1, 127.1, 124.4, 123.2, 81.1, 68.4, 52.2, 37.5, 37.4, 37.2, 37.1, 36.5, 36.5, 32.3, 29.5, 29.5, 25.3, 25.3, 25.0, 25.0, 24.7, 22.9, 19.5, 19.5, 19.5, 15.9, 12.9, 12.8 ppm.

[0127] Example 17: 2-((3,7-dimethylnonano-6-en-1-yl)oxy)-1,2-diphenylethane-1-one The procedure described in Example 16 was repeated with 2-hydroxy-1,2-diphenylethane-1-one (2.4 g, 11 mmol, 1.3 equiv.), sodium hydride (0.45 g, 60% wt, 11 mmol, 1.3 equiv.), and 9-bromo-3,7-dimethylnonano-3-ene (2.0 g, 8.6 mmol, 1 equiv.) in DMF (50 mL). After purification of the crude product by FC (heptane / MTBE 20:1) in SiO2, the product was isolated as a colorless oil (0.85 g, 27%, mixture of E / Z isomers).

[0128] 1H-NMR (400 MHz, CDCl3) δ 8.10 - 7.92 (m, 2H), 7.65 - 7.18 (m, 8H), 5.52 (s, 1H), 5.24 - 4.98 (m, 1H), 3.70 - 3.51 (m, 2H), 2.12 - 1.86 (m, 4H), 1.82 - 1.05 (m, 8H), 1.03 - 0.90 (m, 3H), 0.89 - 0.78 (m, 3H) ppm. 13 C-NMR (101 MHz, CDCl3) δ 198.1, 198.0, 136.9, 136.8, 136.7, 136.7, 135.0, 133.1, 129.3, 128.7, 128.6, 128.4, 128.2, 128.1, 127.1, 127.1, 127.1, 124.4, 123.2, 85.8, 68.5, 68.5, 37.4, 37.1, 36.7, 32.4, 29.5, 29.5, 25.3, 25.0, 24.7, 22.9, 19.6, 19.5, 19.5, 15.9, 12.9, 12.8 ppm.

[0129] Example 18: (2-((3,7-dimethylnonano-6-en-1-yl)oxy)propan-2-yl)benzene 2-phenylpropan-2-ol (1.1 g, 8.1 mmol, 1 equiv.), 3,7-dimethylnona-6-en-1-1-ol (2.75 g, 16 mmol, 2 equiv.), (hexafluoro-17-stibanail)silver (0.28 g, 0.80 mmol, 0.1 equiv.), and platinum(II) chloride (0.086 g, 0.32 mmol, 0.04 equiv.) were stirred at rt for 4 hours in dichloromethane (100 mL). The mixture was poured into water (100 mL) and extracted with ethyl acetate. After drying with MgSO4 and evaporation of the solvent, the crude oil was purified by FC (heptane / MTBE 50:1) with SiO2, yielding a colorless oil product (1.8 g, 76%, mixture of E / Z isomers).

[0130] 1H-NMR (400 MHz, CDCl3) δ 7.48 - 7.38 (m, 2H), 7.37 - 7.30 (m, 2H), 7.27 - 7.18 (m, 1H), 5.32 - 4.96 (m, 1H), 3.30 - 3.06 (m, 2H), 2.08 - 1.84 (m, 3H), 1.73 - 0.91 (m, 18H), 0.88 - 0.70 (m, 3H) ppm. 13 C-NMR (101 MHz, CDCl3) δ 146.8, 137.8, 136.8, 136.6, 136.3, 136.1, 128.1, 126.7, 125.7, 124.5, 123.3, 118.7, 118.0, 76.3, 61.0, 39.9, 37.6, 37.5, 37.2, 37.0, 36.7, 32.4, 31.6, 29.8, 29.6, 29.6, 28.5, 25.3, 25.3, 25.1, 24.7, 23.4, 22.9, 19.8, 19.7, 19.7, 19.7, 15.9, 15.6, 13.3, 13.2, 12.9, 12.8 ppm.

[0131] Example 19: 2-(2-((3,7-dimethylnonano-6-en-1-yl)oxy)propan-2-yl)naphthalene 2-(naphthalen-2-yl)propan-2-ol (2.0 g, 10.7 mmol, 1 equiv.), 3,7-dimethylnona-6-en-1-ol (3.66 g, 21.5 mmol, 2 equiv.), (hexafluoro-17-stibanail)silver (0.37 g, 1.1 mmol, 0.1 equiv.), and platinum(II) chloride (0.114 g, 0.43 mmol, 0.04 equiv.) were stirred in dichloromethane (100 mL). The mixture was poured into water (100 mL) and extracted with ethyl acetate. After drying with MgSO4 and evaporation of the solvent, the crude oil was purified by FC (heptane / MTBE 50:1) with SiO2, yielding a colorless oil product (2.9 g, 80%, mixture of E / Z isomers).

[0132] 1H-NMR (400 MHz, CDCl3) δ 7.74 - 7.66 (m, 4H), 7.56 - 7.48 (m, 1H), 7.38 - 7.31 (m, 2H), 5.01 - 4.91 (m, 1H), 3.15 - 3.04 (m, 2H), 1.95-1.13 (m, 17H), 1.05 - 0.82 (m, 4H), 0.77 - 0.66 (m, 3H) ppm. 13 C-NMR (101 MHz, CDCl3) δ 143.2, 135.7, 135.5, 132.1, 131.4, 127.0, 126.8, 126.4, 124.9, 124.6, 123.5, 123.1, 122.2, 75.3, 60.1, 36.5, 36.2, 31.3, 28.5, 28.5, 27.3, 27.3, 24.3, 24.0, 23.7, 21.8, 18.6, 18.6, 14.8, 11.8, 11.8 ppm.

[0133] Example 20: Application in liquid detergents A washing cycle at 40°C was performed using 55 g of unscented liquid detergent prepared with 0.2% wt / wt a) 2-((3,7-dimethylnonona-6-en-1-yl)oxy)naphthalene (compound of Example 6) and b) (E / Z)-3,7-dimethylnonona-6-en-1-yl palmitate (compound of Example 2), as well as a cotton / elastane blend fabric T-shirt with neutralized odor. Wet and line-dried fabrics (after 1 and 3 days) were evaluated by a panel of nine experts for odor intensity and quality. Odor intensity was recorded on an intensity scale from 0 (odorless) to 5 (very strong). As can be seen from the table below, the odor of the dried fabrics increased from day 1 to day 3. The scent of the dried fabrics was floral, fresh, and clean. [Table 1]

[0134] This explains that the precursor to the invention emits a fragrance that consumers can recognize.

[0135] Example 21: Biodegradability evaluation Representative results of biodegradability evaluation of the compounds of the present invention using the manometric respiration method (OECD 10 Guidelines for Materials Testing No. 301F, Paris 1992) are summarized below. [Table 2]

[0136] The results indicate that the compounds of the present invention, which have a changing phenol moiety and side chain, are biodegradable. A compound can be classified as biodegradable if it reaches 60% of the theoretical oxygen consumption required for complete mineralization. If a sample reaches a passing level within 10 days of the 28-day testing period, it is considered easily biodegradable. The 10-day window begins when the degree of biodegradation reaches 10%. If a pass level is achieved after a 28-day testing period, the compound can be classified as inherently biodegradable.

Claims

1. Formula (II): 【Chemistry 1】 As a precursor for producing aromatic alcohols represented by Equation (I): 【Chemistry 2】 During the ceremony, 【Transformation 3】 This indicates a carbon-carbon single or double bond between C2 and C3; R 1 , R 3 , R 4 , R 5 and R 6 This is independently selected from the group consisting of H, Me, and Et; R 2 It is selected from the group consisting of H, Me, and Et, or forms a three-membered ring together with carbon atoms C2 and C3; and, X is selected from the following group: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having a substituent selected from the group consisting of hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzylic position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; and Alkanoyl (C(O)-R 10 ), where R 10 is linear or branched C 4 -C 18 alkyl, linear or branched C 4 -C 18 alkenyl having 1 or 2 double bonds, linear or branched C 4 -C 18 ether and oxoalkyl, and hydroxyphenyl, A compound represented by, However, the compound is not nona-2,6-diene-1-yl palmitate.

2. The compound represented by formula (I) according to claim 1, wherein the aromatic alcohol represented by formula (II) released from the compound represented by formula (I) is selected from the group consisting of 3,7-dimethylnonano-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, 6-nonenol, 6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol.

3. X is a compound represented by formula (I) according to claim 1 or 2, selected from the group consisting of the following: Aryls having up to two substituents selected from the group consisting of hydroxy, methoxy, ethoxy, formyl, allyl, oxoalkyl, oxoalkenyl, and alkylalkenoate; Benzyl having hydroxymethyl, formyl, vinyl, (C=O)Me, (C=O)Et, (C=O)OMe, (C=O)OEt, and (C=O)Ph at the benzyl position; Propan-2-yl substituted at the 2-position with phenyl, naphthalene-1-yl, or naphthalene-2-yl; Dimethyl 2-malonate and diethyl 2-malonate; And here, the aromatic alcohol represented by formula (II) released from the compound represented by formula (I) is selected from the group consisting of 3,7-dimethylnonano-6-en-1-ol, 2,4,7-trimethylocta-6-en-1-ol, 6-nonenol, 6-ethyl-3-methylocta-6-en-1-ol, (1-methyl-2-(5-methylhexa-4-en-2-yl)cyclopropyl)methanol, and 2,6-nonadienol.

4. Use of a compound represented by formula (I) according to any one of claims 1 to 3 as a precursor for producing an aromatic alcohol represented by formula (II) according to claim 1.

5. A fragrance composition comprising at least one compound represented by formula (I) as described in any one of claims 1 to 3.

6. A consumer product comprising a consumer product base and at least one compound represented by formula (I) as described in any one of claims 1 to 3.

7. A method for releasing an aromatic alcohol represented by formula (II) as defined in any one of claims 1 to 3, wherein a compound represented by formula (I) as defined in any one of claims 1 to 3 is exposed to ambient air and / or humidity.

8. A method for manufacturing consumer products, comprising the following steps: a) Providing a compound represented by formula (I) according to any one of claims 1 to 3, or a fragrance composition according to claim 5; and b) Blending into a consumer product base The method, including the method described above.

9. Use in consumer products of a compound represented by formula (I) according to any one of claims 1 to 3 or a fragrance composition according to claim 5.

10. A method for imparting, enhancing, improving or modifying the hedonic properties of a fragrance composition or consumer product, the method comprising adding to the composition or consumer product at least one compound represented by formula (I) as described in any one of claims 1 to 3.

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