Sabinene derivatives, synthesis, and uses thereof

Abstract

Derivatives of sabinene, and more particularly to sabinene carboxaldehyde and its derivatives described herein, as well as their synthesis and use in organoleptic applications is provided. The sabinene derivatives include a compound having a general Formula (1): wherein: • R 1 is selected from the group consisting of acetals, monothioacetals, (CH=CR 2) X(CHR) mOR 3, (CH=CR 2) X(CHR) nCHO, (CH = CR 2) X(CHR) pCN; and (CH = CR 2) X(CHR) qCO 2R 4; each R is independently selected from the group consisting of H or methyl;R is selected from the group consisting of H, methyl, and ethyl; • R 3 is selected from the group consisting of H, C1-C3 aliphatics, and C(O)R, where R 2 is H or ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, neohexyl, or cyclohexyl; • R 4 is selected from the group consisting of C1-C3 alkyls; x is an integer equal to 0 or 1; and m, n, p, and q are integers independently selected from 0 to 7, with a proviso that when R and R 3 are each H, then x and m are not both equal to 0.

Description

SABINENE DERIVATIVES, SYNTHESIS, AND USES THEREOFFIELD OF THE INVENTION

[0001] The present invention relates generally to novel derivatives of sabinene, and more particularly to derivatives of sabinene carboxaldehyde and their use in organoleptic applications.BACKGROUND OF THE INVENTION

[0002] To increase the range of notes available to perfumers and flavorists in their creations, the perfume and flavor industry is constantly looking for new organoleptic compounds to meet increasing regulatory requirements, such as replacing compounds identified by regulatory bodies as undesirable or even unacceptable. Additionally, cost constraints are increasingly important.

[0003] Amongst the organoleptic molecules, compounds with aldehyde, flowering, lily of the valley notes are known, but many are subject to regulatory restrictions. Among the most used compounds are Lilial™ (3-(4-te / t-butylphenyl)-2-methylpropanal), Sylvial™ (3-(4-isobutylphenyl)-2-methylpropanal), Bourgeonal™ (3-(4-tert- butylphenyl)propanal), Lyral™ (4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1 - carbaldehyde), and Hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal). The first three are suspected of being carcinogenic, mutagenic and reprotoxic (CMR). Lyral™ has been banned since 2017 in cosmetic products. Hydroxycitronellal content is limited in formulas because it sensitizes and irritates skin.

[0004] Accordingly, in order to meet the constant needs of the perfume and flavor industry, and to expand the palette of perfumers and flavorists, there is a need for new compounds having aldehyde, flowery, lily of the valley and I or green note.SUMMARY OF THE INVENTION

[0005] Certain aspects of the present disclosure are described in the appended claims. There are additional features and advantages of the subject matter described herein. They will become apparent as this specification proceeds. In this regard, it is to be understood that the claims serve as a brief summary of varying aspects of the subject matter described herein. The various features described in the claims and below for various embodiments may be used in combination or separately. For example, specified ranges may be inclusive of their recited endpoints, unless explicitlyexcluded. Any particular embodiment need not provide all features noted above, nor solve all problems or address all issues noted above.

[0006] According to an embodiment of the invention, a compound having a general Formula (I) is provided:Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals,each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C1 -C6 acyls;R4is selected from the group consisting of C1 -C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7, with a proviso that when R and R3are each H, then x and m are not both equal to 0.

[0007] In accordance with another embodiment of the invention, a fragrant composition is provided comprising a solvent; and at least one compound of generalFormula (I) is provided.

[0008] In accordance with yet another embodiment of the invention, a process for preparing a compound of general Formula (I) is provided, the process comprising: hydroformylating sabinene to form sabinene carboxaldehyde; and optionally, reacting sabinene carboxaldehyde with formaldehyde, a C1 -C3 primary alcohol, C2-C5 aliphatic diol, a thioalcohol, a phosphorus ylide, an enolate, a reducing agent, an oxidizing agent, or a combination thereof; or optionally condensing sabinene carboxaldehyde with a hydroxylamine, an O- alkoxyamine, or an O-acyloxyamine and dehydrating the oxime intermediate, alkyloxime intermediate, or acyloxime intermediate.

[0009] In accordance with yet another embodiment of the invention, a use of at least one compound of general Formula (I) is provided, said use is to confer, modify or enhance the organoleptic properties of a substance, composition, or article.BRIEF DESCRIPTION OF THE DRAWINGS

[0010] The accompanying drawing, which are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and, together with a general description of the invention given above, and the detailed description given below, serve to explain the invention. It will be appreciated that for purposes of clarity and where deemed appropriate, reference numerals have been repeated in the figures to indicate corresponding features.

[0011] FIG. 1 is a synthetic schematic showing conversion of sabinene to sabinene carboxaldehyde, which may then be further derivatized to form other compounds of general Formula (I); and

[0012] FIG. 2 is a synthetic schematic showing various generalized derivatization pathways for making one or more compounds of general Formula (I).DETAILED DESCRIPTION

[0013] Unless otherwise explained, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. In case of conflict, the present specification, including explanations of terms, will control. The singular terms "a," "an," "at least one," “one or more”, and "the" include plural referents unless context clearly indicates otherwise. Similarly, the word "or" is intended to include "and" unless the context clearly indicates otherwise. The term "comprising" means "including;" hence, "comprising A or B" means including A or B, as well as A and B together.

[0014] Embodiments of the invention relate to new compounds derived from sabinene carboxaldehyde, said compounds having aldehyde, flowery, lily of the valley and I or green notes, their preparation process, as well as their uses in the chemical industry, and in particular in perfumery, cosmetics, parapharmacy, in the detergent industry, as well as in food, said compounds having interesting organoleptic properties and a particular potency and persistence.

[0015] Thus, in accordance with an embodiment of the invention, compounds derived from sabinene have a general Formula (I):Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals, (CH=CR2)x(CHR)mOR3, (CH=CR2)x(CHR)nCHO, (CH=CR2)x(CHR)pCN; and (CH=CR2)x(CHR)gCO2R4; each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C1 -C6 acyls;R4is selected from the group consisting of C1 -C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7, with a proviso that when R and R3are each H, then x and m are not both equal to 0.

[0016] In accordance with embodiments of the invention, sabinene (4-methylene-1 - (1 -methylethyl)bicyclo[3.1 .0]hexane), which may be synthetic or obtained from natural sources, may be a single compound, a single enantiomer, an enriched enantiomer, or a racemic mixture. Non-limiting natural sources include essential oils of a variety of plants including, but not limited to, orange, nutmeg, holm oak, or Norway spruce. In an embodiment, sabinene may be a mixture containing other monoterpenes comprising an exocyclic methylene group, such as beta-pinene.

[0017] As used herein, the term "C1 -C3 alkyls" refers to any monovalent radical derived from a saturated carbon chain containing 1 to 3 carbon atoms, e.g., methyl, ethyl, n-propyl, or isopropyl.

[0018] As used herein, the term "C1 -C3 aliphatics" refers to any monovalent radical derived from an alkyl, alkenyl, or alkynyl carbon chain, containing 1 to 3 carbon atoms, e.g., methyl, ethyl, propyl, allyl, or propargyl groups.

[0019] As used herein, the term "C1 -C6 acyls" refers to any monovalent radical derived from a general formula — C(O)Ra, where Rais H or an alkyl group containing 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, neohexyl, or cyclohexyl.

[0020] As used herein, the term "acetals" refers to compounds formed by a condensation of alcohol molecules with an aldehyde functional group. In an embodiment, simple primary alcohols, such as methanol, ethanol, propanol, etc. form acyclic acetals. In a preferred embodiment, the alcohol molecule is an aliphatic diol, such as 1 ,2-alkanediols, 1 ,3-alkanediols, 1 ,4-alkanediols, 1 ,4-alkenediols, which thus forms a cyclic acetal. Non-limiting examples of said aliphatic diols include, but are not limited to, ethylene glycol; 1 ,2-propanediol; 1 ,3-propanediol; 2-methyl-1 ,3- propanediol; 2, 2-dimethyl-1 ,3-propanediol; 1 ,2-butanediol, 1 ,3-butanediol; 2,3- butanediol; 1 ,4-butanediol; and cis-butene-1 ,4-dioL

[0021] As used herein the term "monothioacetals" refers to compounds formed by the condensation of a thioalcohol molecule with an aldehyde functional group, which thereby forms a cyclic monothioacetal. Non-limiting examples of said thiolalcohol molecule includes, but is not limited to, 2-mercaptoethanol, 1 -mercapto-2-propanol, and 3-mercapto-1 -propanol.

[0022] As used herein the expression “integer selected from 0 to 7” means that the integer may be equal to 0, 1 , 2, 3, 4, 5, 6 or 7.

[0023] In one embodiment, the compounds of the invention have a general Formula(I):Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals,each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C(O)Ra, where Rais H or ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, neohexyl, or cyclohexyl;R4is selected from the group consisting of C1-C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7,with a proviso that when R and R3are each H, then xand m are not both equal to 0.

[0024] In one embodiment, m and x cannot both be equal to zero (0).

[0025] In one embodiment, R1is selected from acetals and monothioacetals and the compounds have a general Formula (II) or (III):wherein Z is selected from O or S, wherein R5is selected from nil, CR8R9, or HC=CH; wherein R6, R7R8, and R9are independently selected from H or methyl; and wherein R10is selected from C1 -C3 aliphatics.

[0026] In one embodiment, the compounds of the invention are selected from the group consisting of:2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-oxathiolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,5-dimethyl-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,7-dihydro-1 ,3-dioxepine,6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hex-4-enenitrile,6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanenitrile,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl formate,4-(2-(allyloxy)ethyl)-1 -isopropylbicyclo[3.1 .0]hexane,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl acetate,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl propionate, ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enoate, ethyl 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylbut-2-enoate,ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)butanoate,4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-enal, 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbutanal, 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-en-1 -ol, 2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal, 2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol, 2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol, 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enal, 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enol, 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-octanol, ethyl 3-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylpropanoate,3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-propanol, ethyl 3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanol, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetonitrile, and 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanoL

[0027] The presence and / or creation of asymmetric centers in the structure of the compounds of Formula (I) according to the invention causes the existence, for each of them, of several enantiomeric and I or diastereomeric forms. The invention also covers the compounds represented by the general Formula (I) in the form of mixtures of enantiomers and I or diastereomers, in varying proportions, in particular racemic mixtures. The invention also comprises compounds of Formula (I) in the form of a single enantiomer and I or diastereomer. Enantiomer / diastereomer mixtures or pure forms may be obtained by synthesis from optically enriched or optically pure starting materials, or by crystallization or chromatographic separation methods.

[0028] A second object of the present invention relates to a fragrant composition is provided, which comprises a solvent, and at least one compound of general formula (I):Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals, (CH=CR2)x(CHR)mOR3, (CH=CR2)x(CHR)nCHO, (CH=CR2)x(CHR)pCN; and (CH=CR2)x(CHR)gCO2R4; each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C1 -C6 acyls;R4is selected from the group consisting of C1-C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7, with a proviso that when R and R3are each H, then x and m are not both equal to 0.

[0029] In one embodiment, the fragrant composition of the invention comprises a solvent, and at least one compound of general formula (I):Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals, (CH=CR2)x(CHR)mOR3, (CH=CR2)x(CHR)nCHO, (CH=CR2)x(CHR)pCN; and (CH=CR2)X(CHR)PCO2R4; each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C(O)Ra, where Rais H or ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, neohexyl, or cyclohexyl;R4is selected from the group consisting of C1-C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7,with a proviso that when R and R3are each H, then xand m are not both equal to 0.

[0030] In one embodiment, m and x cannot both be equal to zero (0).

[0031] In accordance with another embodiment of the invention, a fragrant composition is provided, which comprises a solvent and at least one compound selected from the group consisting of:2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-oxathiolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,5-dimethyl-1 ,3-dioxolane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxane,2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,7-dihydro-1 ,3-dioxepine,6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hex-4-enenitrile,6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanenitrile,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl formate,4-(2-(allyloxy)ethyl)-1 -isopropylbicyclo[3.1 .0]hexane,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl acetate,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl propionate, ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enoate, ethyl 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylbut-2-enoate, ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)butanoate,4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-enal,4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbutanal,4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-en-1 -ol,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enal,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enol,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-octanol,- io - ethyl 3-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylpropanoate, 3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-propanol, ethyl 3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanol, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetonitrile, and 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanoL

[0032] The effective amount of the compounds of the invention to be incorporated into these compositions depends on the nature of said compositions, the desired odorous or flavoring effect and the nature of other odorous or flavoring compounds possibly present. It is easily determined by those skilled in the art, and can vary in a very wide range, from 100 ppb to 50%. For example, in an embodiment, the compound(s) of general Formula (I) may be incorporated into composition in an amount from 100 ppb to 50%, or from 0.001 to 50%, in particular 0.01 to 30%. The preceding percentages are expressed in total weight of the composition.

[0033] In one embodiment of the invention, the composition is a perfume composition comprising at least one compound of general Formula (I) and at least one other odorous substance. Other odorous substances that can be used in combination with the compounds of the present invention may be natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic products such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, nitriles etc., including saturated or unsaturated, aliphatic, heterocyclic, or carbocyclic compounds. Such odorous substances are mentioned, for example, in S. Arctander, "Perfume and Flavor Chemicals" (Montclair, N.J., 1969), or in "Common Fragrance and Flavor Materials", Wiley-VCH, Weinheim, 2006. Finally, a plurality of compounds of general Formula (I) can also be used in combination in the same composition.

[0034] Because of the pleasant smell they emit, the compounds of general Formula (I) find many applications in perfumery. The term "perfumery" is used here in its general sense; it refers not only to traditional perfumery (alcoholic or not), but also to other areas in which the smell / fragrance of products is important. Reference may thus be made to perfumery compositions in the usual and traditional sense (such as perfume bases and concentrates, perfumes, colognes, eau de toilette, indoor airfresheners, home fragrances, scented candles and similar products), to topical compositions including cosmetic compositions (such as face and I or body creams, talcum powders, hair oils, shampoos, hair lotions, bath salts and oils, shower and / or bath gels, toilet soaps, antiperspirants and body deodorants, shaving lotions and creams, soaps, toothpastes, mouthwashes, ointments, and similar products), as well as cleaning products, in particular household cleaning products (such as detergents, detergents, fabric softeners, home air fresheners, home fragrances and similar products).

[0035] Thus, embodiments of the invention extend to a perfume composition comprising at least one compound of general Formula (I). It may, in particular, be a composition of the traditional perfumery, a cosmetic composition, cleaning product, or a so-called "intermediate composition", intended to be used for the preparation of compositions or finished products (including perfumes, cosmetics, cleaning products).

[0036] Such a perfume composition is generally prepared from a basic product, in which the compound or compounds of the invention are found to be incorporated. The basic product will be easily determined by those skilled in the art according to the composition envisaged and therefore the intended use. The composition of these basic products and the nature of their usual components, such as solvent (s) and I or adjuvant (s), are well known to those skilled in the art.

[0037] The compounds used in these perfume compositions, in particular the compounds of the invention, may be incorporated into or on an inert support material. The carrier materials that can be used are many and varied, for example polar solvents, oils, greases, finely divided solids, cyclodextrins, maltodextrins, gums, resins, and any other carrier material known for such compositions (for example, soaps, candles, ointments, textiles, wipes, scented gels, or the like).

[0038] According to another embodiment of the invention, the composition is an aromatic composition comprising at least one compound of Formula (I) and at least one other aromatic substance. For example, in one aspect, the aromatic composition may be an ingestible product, which refers to a "food", an "edible composition" and / or a "food product". Said ingestible product preferentially relates, but is not limited to, products intended for human consumption, intended for animal feed (pets) or pharmaceutical compositions. Examples of food products may include, but are not limited to, snacks, confectionery, plant materials, and meals that may or may not provide essential nutrients. Plant materials include cocoa, cocoa beans, coffee, coffeebeans, and tea leaves or powder. Examples of food products include salad dressings, sauces, sauces, marinades, sticks, nutrition bars, pastries, breads, caramel, cooked cereals, meat products, poultry products, meat, poultry, poultry, fish, marine protein sources, beans, pasta, confectionery products, salty snacks, dairy products, cheeses, yogurt, butter, margarine, ready-to-eat cereals, condiments and sauces and beverages. In particular, the term "beverage" includes mixtures and concentrates, including, but not limited to, ready-to-drink alcoholic and non-alcoholic beverages and dry powdered beverages. Non-limiting examples of beverages include, but are not limited to, soft drinks, brewed beverages, dairy products, drinking yogurt, milk, coffee whitening agents, nutritional drinks, and the like. Non-limiting examples of animal feed may include, but are not limited to, pet food, such as dogs and cats; rodent food; livestock feed; cattle feed; horse feed; and the like. Other applications for the compounds of general Formula (i) may also include tobacco products or tobacco- related products.

[0039] In accordance with another embodiment of the invention, a process for preparing compounds of general Formula (I), as defined above, is provided.

[0040] In reference to FIG. 1 , compounds of general Formula (I) are obtained by a first hydroformylation reaction of sabinene (4-methylene-1 -(1 - methylethyl)bicyclo[3.1 .0]hexane) to form sabinene carboxaldehyde (2-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde). In a preferred embodiment, sabinene is hydroformylated in the presence of a ruthenium catalyst. In a more preferred embodiment, sabinene is hydroformylated in the presence of triphenylphosphine and (acetylacetonato)dicarbonylrhodium(l) in toluene solvent under an atmosphere of a 50:50 mixture of hydrogen and carbon monoxide. Via various chemical reactions and / or reaction sequences, numerous other general Formula (I) compounds may be realized, as further described below.

[0041] In reference to FIG. 2, additional derivative compounds within the scope of general Formula (I) can be prepared from sabinene carboxaldehyde (or 2-(5- isopropylbicyclo[3.1 .0]-hexan-2-yl)acetaldehyde). For example, some of these derivative compounds may be formed by initially performing an alpha-methylenation of sabinene carboxaldehyde with aqueous formaldehyde, followed by hydrogenation, as described by A. Erkkila and P. Pihko, J. Org. Chem. 2006, 71 , 6, 2538-2541 , to introduce a methyl group in the alpha position (relative to the aldehyde) and thereby form 2-(5-isopropylbicyclo[3.1 .0]-hexan-2-yl)propionaldehyde). Transformation of thealdehyde to a carboxylic acid, an ester, or a nitrile can be realized via known methods. For example, aldehydes can be transformed into carboxylic acids through a Pinnick oxidation with sodium chlorite, as decribed by B.O. Lindgren, T. Nilsson, S. Husebye, O. Mikalsen, K. Leander, C. Swahn, Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite", Acta Chem. Scand., 1973, 27, 888-890. Then carboxylic acids can be transformed into esters through esterification with an alcohol. Aldehydes can also be transformed into nitriles via the corresponding aldoximes (U. B. Patil, S. S. Shendage, J. M. Nagarkar, Synthesis, 2013, 45, 3295-3299).

[0042] Other approaches involve derivatizing sabinene carboxaldehyde by reacting sabinene carboxaldehyde with an aliphatic alcohol, an aliphatic diol, a thioalcohol, a phosphorus ylide, an enolate, and / or a reducing agent, as further described below. In an embodiment, the derivatizing reaction may be one or more of the following named or well-known reactions: acetalization, Wittig, Wittig-Horner, aldolization, reduction, and optionally followed by esterification or etherification, and / or reduction.

[0043] PATH A (acetalization): In an embodiment, an aliphatic alcohol (R10OH, where R10is a C1 -C3 aliphatic), a diol (where Z is oxygen), or a thioalcohol (where Z is sulfur), where R5is selected from nil, CR8R9, or HC=CH; and where R6, R7R8, and R9are independently selected from H or methyl is reacted with Sabinene carboxaldehyde in the presence of an acid, such as para-toluene sulfonic acid, as shown in Scheme 1 below. In an embodiment, sabinene carboxaldehyde is reacted with the aliphatic alcohol, the diol, or the thioalcohol in refluxing cyclohexane in the presence of an acid catalyst, where the liberated water is removed by azeotropic distillation to provide the acetal or the thioacetal derivative.

[0044] PATH B (reduction, optional esterification or etherification): In an embodiment, the aldehyde functional group of sabinene carboxaldehyde may be reduced to the corresponding alcohol (R3= H). The corresponding alcohol may be further derivatized by esterification (R3= C1 -C6 acyls), such as by reacting the corresponding alcohol with a C1 -C6 carboxylic acid, with or without an additional acid catalyst. Another complementary approach includes treatment of the alcohol by an acid chloride in the presence of a base (e.g., amine base). Alternatively, the corresponding alcohol may be derivatized by etherification (R3= C1 -C3 aliphatic), such as by the well-known method of Williamson (reacting an aliphatic halide and nucleophilic alkoxide). PATH B is generally exemplified in SCHEME 2.SCHEME 2

[0045] PATH C (Wittig, optional hydrogenation): In an embodiment, the aldehyde functional group of sabinene carboxaldehyde may be reacted with a phosphonium ylide to form an alkene derivative. For example, the carbanion of a previously deprotonated (cyanoalkyl)triphenylphosphonium halide may be reacted with sabinene carboxaldehyde to form the corresponding unsaturated nitrile, which optionally may be subsequently hydrogenated to form the corresponding saturated nitrile. In an embodiment, the alkyl chain between the nitrile and phosphonium groups may be from 1 to 7 carbons (C1 -C7 alkyl chain). In an example, (3- cyanopropyl)triphenylphosphonium chloride may be deprotonated with sodium tert- butoxide and its corresponding anion reacted with sabinene carboxaldehyde to provide 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hex-4-enenitrile, which may be optionally hydrogenated to form the saturated nitrile 6-(5-isopropylbicyclo[3.1 .0]hexan- 2-yl)hexanenitrile, in accordance with a general approach shown in SCHEME 3.[C] = alkyl [C] = alkyl

[0046] Path D (Wittig-Horner, optional hydrogenation): In an embodiment, the aldehyde functional group of sabinene carboxaldehyde may be reacted with a stabilized phosphonate carbanion to form an alkene derivative. For example, the anion of previously deprotonated trialkylphosphono-acetate (or -propionate) may be reacted with sabinene carboxaldehyde to form the corresponding unsaturated ester, which may be subsequently hydrogenated to form the corresponding saturated ester. In an example, triethyl phosphono-acetate (R2=H) or triethyl 2-phosphono-proprionate (R2=CHa) may be deprotonated with sodium ethoxide and its corresponding anion reacted with sabinene carboxaldehyde to provide the unsaturated ethyl ester, which may be optionally hydrogenated to form the saturated ethyl ester, as generally shown in SCHEME 4.SCHEME 4

[0047] PATH E (Aldolization, optional hydrogenation or reduction) : In an embodiment, the aldehyde functional group of sabinene carboxaldehyde may be reacted with another aldehyde, such as a saturated linear aldehyde, in the presence of a base to form an alpha, beta-unsaturated aldehyde, which optionally may be hydrogenated to its corresponding saturated derivative; optionally reduced to its corresponding allylic alcohol; or optionally hydrogenated and reduced to its corresponding saturated alcohol. For example, as shown in SCHEME 5, acetaldehyde (R2=H) or propionaldehyde (R2=CHa) may be reacted in the presence of a base (e.g., sodium hydroxide) with sabinene carboxaldehyde to provide the corresponding alpha, beta-unsaturated aldehyde, which optionally can be hydrogenated afterwards. Alternatively, the unsaturated aldehyde may also be reduced, for example with sodium borohydride, and optionally hydrogenated afterwards.SCHEME 5

[0048] In accordance with yet another embodiment of the invention, the use of at least one compound of general Formula (I), in a form of a stereoisomer or a mixture of stereoisomers, or a racemic mixture, to confer, modify, or enhance the organoleptic properties of a substance, a composition, or an article is provided.

[0049] The present invention also relates to a process for modifying the organoleptic properties of a substance, a composition or an article comprising at least one of the following steps: adding a compound of formula (I) to said substance, composition or article, or applying a compound of formula (I) to the surface of said article.

[0050] As used herein, "organoleptic properties" means any property likely to modify, improve or enhance the organoleptic perception of a substance, composition or article by a user (e.g. olfactory or gustatory perception)

[0051] In a first embodiment, at least one compound of formula (I) is used as a fragrant agent, alone or in combination with at least one other odorant substance, and I or at least one solvent, and I or at least one adjuvant. The additional odorant agent(s), solvents and adjuvants are known to those skilled in the art who will be able to choose the most appropriate or the most appropriate according to the desired effect.

[0052] As used herein, the term "fragrant" is used here to refer to any organoleptic compound that pleasantly stimulates the sense of smell. The terms “fragrant” or “perfume” are used interchangeably in the present disclosure. Thus the expressions “fragrant composition” and “perfume composition” refer to the same objects.

[0053] The compounds according to the invention may particularly be used as a masking agent or as an odor neutralizing agent. As used herein, the term "masking agent" or "odor neutralizing agent" is meant to identify a characteristic of the compounds within the scope of the invention to reduce or eliminate the perception ofa bad odor generated by one or more other molecules present in a composition or a product.

[0054] In a second embodiment, at least one compound of general formula (I) is used as an aromatic compound, alone or in combination with at least one other aromatic substance and I or at least one solvent, and I or at least one adjuvant.

[0055] The additional flavoring agent(s), solvents and adjuvants are known to those skilled in the art who will be able to choose the most appropriate or the most appropriate according to the desired effect. The solvents used not only allow an exact dosage of the compound according to the invention for food and beverages, but also facilitates a uniform distribution of the compound according to the invention in food and beverages. Suitable solvents may be hydrophilic solvents such as water, propylene glycol, glycerol, ethanol and triacetin or hydrophobic solvents such as vegetable oils, e.g. palm oil, soybean oil, rapeseed oil, sunflower oil, peanut oil, medium-chain triglycerides (MCTs). Medium-chain triglycerides are triglycerides based on aliphatic fatty acids comprising 6 to 12 carbon atoms.

[0056] By aromatic is meant any use of the compounds of the invention for the flavoring of any liquid or solid foodstuff, human or animal including beverages, dairy products, ice cream. The compounds of general Formula (I) may further find use in tobacco products or tobacco-related products.

[0057] In particular, the compounds according to the invention can be used alone or in combination with taste-modulating compounds that is to say which modify taste and sensory perceptions. In any case, the specificity of such taste-modulating compounds is that they do not exhibit noticeable taste and aromatic properties (without taste and aroma). Such aroma-altering compounds can be of synthetic or natural origin.

[0058] EXAMPLES

[0059] The following examples illustrate a particular way of preparing the compounds of the invention, as well as the olfactory I aromatic profile of each of the exemplified compounds. These examples are for illustrative purposes only and should not be understood as limiting the general scope of the invention.

[0060] Example 1 : 2-(5-isopropylbicyclo[3.1.0]hexan-2-yl)acetaldehyde

[0061] In an autoclave reactor, 80 g of Sabinene, 15.40 g of triphenylphosphine and 0.45 g of (acetylacetonato)dicarbonylrhodium(l) are introduced into 225 ml of toluene. After the reactor is closed, 3 nitrogen purges and one purge with a 50:50 mixture of hydrogen and carbon monoxide are carried out. The reaction medium is heated to 130°C and placed under a continuous pressure of 20 bar of 50:50 mixture of hydrogen and carbon monoxide. After 24 hours, the reaction medium is cooled, the autoclave is purged with nitrogen 3 times, then the reaction medium is concentrated under vacuum and finally distilled under 6.6 Torr at 85-87 °C. 43 g of 2-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde is obtained as a mixture of isomers. Olfactory description: aldehyde, green, citrus, slightly lemony, watery, powerful. The resulting 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 9.81-9.64 (m, 1 H), 2.66-2.14 (m, 3H), 1 .99- 1.12 (m, 5H), 1.16-0.82 (m, 5H), 0.83 (t, J= 1.0 Hz, 1 H), 0.40-0.10 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 204.80, 203.24, 203.00, 202.91 , 202.67,54.75, 54.65, 51.99, 51.01 , 50.58, 49.87, 48.26, 46.22, 45.57, 41.01 , 40.45, 39.49,38.64, 36.48, 36.31 , 36.25, 34.97, 34.61 , 34.34, 34.21 , 34.15, 33.37, 32.47, 32.42,32.26, 29.90, 29.58, 28.61 , 27.89, 27.69, 27.49, 27.44, 26.74, 26.62, 26.32, 26.10,24.76, 24.29, 23.19, 23.15, 21.97, 21.92, 20.26, 20.03, 19.92, 19.85, 19.81 , 19.75,17.93, 17.72, 16.99, 16.50, 12.65, 10.07, 8.81.MS [El+] (m / z) (%) major isomer: 200 (M+, 9), 127(100), 109(55), 83(25), 69(34), 56(10), 55(35), 46(12), 43(26), 41 (25), 39(10).

[0062] Example 2: 2-((5-isopropylbicyclo[3.1.0]hexan-2-yl)methyl)-1 ,3- dioxolane

[0063] In a 3-necked flask fitted with a thermometer, and an azeotropic distillation apparatus, 8 g of Sabinene carboxaldehyde prepared as in example 1 , 100 ml of cyclohexane, 5.97 g of ethylene glycol, then 0.46 g of para-toluene sulfonic acid are placed. The reaction medium is heated at reflux for 2 hours. Gas chromatography analysis indicates that the conversion of Sabinene carboxaldehyde is complete. The heat is turned off, the medium is poured over an aqueous solution saturated with sodium bicarbonate, the organic phase is washed with water, dried, and then concentrated under vacuum. The result is 9.9 g of crude product as a mixture of isomers, which is distilled under reduced pressure: its boiling point is 77 °C under 0.77 Torr. Olfactory description: green, fruity, woody, aromatic. The resulting 2-((5- isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxolane has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 6 (ppm) 4.91 -4.88 (m, 1 H), 4.00-3.77 (m, 4H), 2.28- 2.02 (m, 1 H), 1 .78-1 .05 (m, 8H), 0.95-0.80 (m, 7H), 0.33-0.31 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 104.44, 104.13, 103.77, 65.07, 64.72, 64.65, 64.30, 53.82, 45.19, 41.06, 39.65, 37.90, 36.58, 36.03, 35.98, 35.59, 33.90, 33.86, 32.65, 32.60, 32.50, 31.70, 28.14, 27.99, 27.43, 26.85, 26.70, 24.76, 24.50, 20.35, 20.00, 19.81 , 18.08, 17.71 , 16.63, 12.69, 8.72.

[0064] Example 3: 2-((5-isopropylbicyclo[3.1.0]hexan-2-yl)methyl)-1 ,3- oxathiolane

[0065] 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-oxathiolane is prepared according to the protocol described in Example 2 using 2-mercaptoethanol instead of ethylene glycol. The crude product, obtained as a mixture of isomers, is distilled under reduced pressure: its boiling temperature is 100 °C under 0.7 mbar. Olfactory description: green, tomato leaves, onion, garlic. The resulting 2-((5- isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-oxathiolane has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 5.10-5.07 (m, 1 H), 4.32-4.28 (m, 1 H), 3.75- 3.72 (m, 1 H), 3.02-2.98 (m, 2H), 1 .87-1 .30 (m, 12H), 1 .15-0.79 (m, 4H), 0.29-0.27 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 86.73, 86.45, 86.21 , 86.09, 85.84, 85.78, 85.05, 71.07, 71.04, 71.00, 70.93, 70.66, 70.52, 54.83, 46.37, 46.30, 45.70, 44.35, 44.28, 42.26, 42.17, 41.25, 40.67, 40.54, 39.15, 38.77, 38.63, 38.15, 38.09, 38.01 ,37.88, 36.81 , 36.47, 36.30, 34.02, 33.92, 33.90, 33.81 , 33.41 , 32.87, 32.62, 32.60,32.56, 32.53, 32.45, 31.86, 31.61 , 28.07, 27.86, 27.84, 27.50, 27.41 , 26.86, 26.59,26.43, 26.34, 24.85, 24.83, 24.42, 23.21 , 23.18, 22.23, 22.20, 20.33, 20.09, 19.99,19.86, 19.84, 18.15, 18.10, 17.78, 16.70, 16.65, 12.69, 12.66, 8.86, 8.75.

[0066] Example 4: Preparation of 2-(5-isopropylbicyclo[3.1.0]hexan-2-yl)ethan- 1-ol

[0067] In a 3-necked flask fitted with a thermometer and a condenser, 15 g of Sabinene carboxaldehyde prepared as in example 1 , and 100 ml of ethanol are placed. The reaction medium is cooled at 15 °C. Then, 1.7 g of sodium borohydride are added portionwise. The mixture is stirred at room temperature. After 1 hour, gas chromatography analysis indicates that the conversion of Sabinene carboxaldehyde is complete. The medium is poured over a 50:50 mixture of a 1 % aqueous solution of HCI and tert-butyl methyl ether, the organic phase is washed with water, dried, andthen concentrated in vacuum. The result is 17.6 g of crude product obtained as a mixture of isomers, which is distilled under reduced pressure: its boiling point is 73 °C under 0.15 Torr. Olfactory description: floral, rosy, lily of the valley, powerful. The resulting 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 3.71 -3.62 (m, 2H), 1.71 -1.30 (m, 11 H), 1.01 - 0.80 (m, 6H), 0.32-0.25 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 139.74, 130.78, 62.53, 61.58, 61.07, 60.70,54.61 , 45.79, 44.58, 40.89, 40.28, 39.47, 38.60, 36.92, 36.84, 36.82, 36.44, 35.88,33.91 , 33.82, 32.76, 32.69, 32.61 , 31.66, 31.1 1 , 29.08, 27.97, 27.83, 27.47, 26.79,26.69, 26.42, 24.89, 24.50, 23.39, 22.28, 20.36, 20.13, 20.00, 19.85, 19.83, 18.08,17.75, 17.40, 16.60, 12.75, 9.84, 8.69.

[0068] Example 5: Preparation of 2-(5-isopropylbicyclo[3.1.0]hexan-2-yl)ethyl acetate

[0069] In a 3-necked flask fitted with a thermometer and a condenser, 10 g of 2-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol prepared as in example 4, 7.2 ml of triethylamine, 0.1 g of dimethylaminopyridine and 150 ml of tert-butyl methyl ether are placed and the mixture is cooled at 10 °C. Then, 5.1 ml of acetyl chloride are added dropwise. After 2 hours, gas chromatography analysis indicates that the conversion of 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol is complete. The medium is poured over water, the organic phase is washed with water, dried, and then concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 67 °C under 0.87 Torr. Olfactory description: fruity, soapy, musky. The resulting 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl acetate has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 4.12-4.03 (m, 2H), 2.04-1.17 (m, 10H), 2.01 (s, 3H), 0.99-0.79 (m, 6H), 0.30-0.24 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 171 .21 , 171.12, 64.21 , 63.50, 63.38, 63.03, 62.67, 62.45, 61.53, 54.38, 46.37, 46,15, 45,61 , 41 ,30, 40,83, 39,33, 38,65, 38,62, 37,77,36,95, 36,81 , 36,74, 36,68, 36,44, 36,27, 35,82, 35,59, 35,05, 34,27, 33,87, 33,80,33,47, 32,94, 32,68, 32,61 , 32,54, 32,49, 31 ,63, 31 ,47, 28,09, 27.97, 27.81 , 27.76,27.70, 27.55, 27.47, 26.94, 26.73, 26.68, 26.57, 26.42, 26.33, 26.28, 24.88, 24.80,24.40, 23.30, 23.20, 22.32, 22.12, 21.08, 21.03, 21.01 , 20.93, 20.34, 20.31 , 20.05,19.97, 19.94, 19.83, 19.79, 18.04, 17.73, 17.68, 17.20, 16.54, 12.74, 12.72, 9.72, 8.67, 8.63.

[0070] Example 6: Preparation of Ethyl 4-(5-isopropylbicyclo[3.1.0]hexan-2- yl)but-2-enoate

[0071] In a 3-necked flask fitted with a thermometer and a condenser, 46 g of triethyl phosphono-acetate and 17 g of sodium ethoxide in 150 ml of tetrahydrofuran are placed. The mixture is heated at reflux temperature for 1 hour. Then, 30 g of Sabinene carboxaldehyde prepared as in example 1 are added dropwise. After 1 night stirring at reflux, gas chromatography analysis indicates that the conversion of Sabinene carboxaldehyde is complete. The medium is cooled at room temperature and poured over water, the organic phase is washed with water, dried, and then concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 89 °C under 0.6 Torr. Olfactory description: green, aldehyde, citrus, lemongrass. The resulting 4-(5-isopropylbicyclo[3.1 .0]hexan-2- yl)but-2-enoate ethyl has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 7.07-6.84 (m, 1 H), 5.83-5.73 (m, 1 H), 4.17- 4.10 (m, 2H), 2.45-1.93 (m, 2H), 1.67-1.46 (m, 2H), 1.36-1.22 (m, 9H), 0.94-0.82 (m, 6H), 0.35-0.21 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 166.68, 165.84, 165.76, 148.96, 148.35, 122.04, 121.43, 63.56, 62.69, 62.60, 61.54, 61.26, 60.12, 49.89, 48.35, 39.57, 39.23, 38.43, 36.71 , 35.25, 34.36, 34.08, 33.47, 32.58, 32.52, 27.68, 27.61 , 27.55, 26.76, 26.51 , 26.34, 24.89, 24.78, 20.67, 20.32, 19.93, 19.85, 19.82, 16.35, 16.27, 16.16, 16.07, 14.26, 14.15, 14.07, 12.80, 8.78.

[0072] Example 7: Preparation of 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2- methylbutanal

[0073] Step 1 : Preparation of 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2- enal - In a 3-necked flask fitted with a thermometer, a dropping funnel and a condenser, 2.4 g of sodium hydroxide and 300 ml of methanol are placed. The mixture is heated at reflux temperature. Then, 100.7 g of Sabinene carboxaldehyde prepared as in example 1 in 218 ml of propanaldehyde are added dropwise. After 2 hours stirring at reflux, gas chromatography analysis indicates that the conversion of Sabinene carboxaldehyde is complete. The medium is cooled at room temperature and poured over water and tert-butyl methyl ether, the organic phase is washed with water, dried,and then concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 91 °C under 0.6 Torr.

[0074] Step 2: Hydrogenation of 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut- 2-enal - In an autoclave reactor, 68 g of 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2- methylbut-2-enal and 3.5 g of Palladium on charcoal are introduced into 300 ml of toluene. After the reactor is closed, 3 nitrogen purges and one purge with hydrogen are carried out. The reaction medium is heated to 50 °C and placed under a continuous pressure of 10 bar of hydrogen. After 18 hours, the reaction medium is cooled, the autoclave is purged with nitrogen 3 times, then the reaction medium is filtered over a pad of Celite and the filtrate is concentrated under vacuum and finally distilled under 0.4 Torr at 75-77 °C. 52 g of 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbutanal are obtained as a mixture of isomers. Olfactory Description: Floral, Aldehyde, Marine, Watery, Green. The resulting 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbutanal has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 9,62 (s, 1 H), 2.48-2.29 (m, 2H), 1 .87-1 .06 (m, 14H), 0.92-0.79 (m, 6H), 0.27-0.24 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 205.60, 205.45, 205.43, 55.59, 55.50, 46.97, 46.56, 46.43, 42.83, 41.46, 40.94, 40.33, 40.29, 40.21 , 40.19, 40.07, 39.65, 39.56,39.46, 39.33, 36.85, 35.47, 35.18, 34.84, 34.72, 34.66, 34.28, 33.75, 33.70, 33.67,33.08, 32.98, 32.85, 32.81 , 32.78, 32.69, 32.64, 32.61 , 31.83, 31.72, 31.48, 31.41 ,31.29, 31.19, 29.73, 28.80, 28.73, 28.62, 28.18, 27.91 , 27.86, 27.83, 27.79, 27.76,27.58, 26.80, 26.77, 26.64, 26.47, 26.42, 26.34, 25.62, 24.87, 24.84, 24.48, 23.39,22.47, 22.40, 20.33, 20.08, 19.96, 19.84, 19.80, 19.78, 19.73, 18.16, 17.99, 17.70,16.98, 16.91 , 16.75, 16.58, 13.41 , 13.35, 13.32, 12.83, 8.60, 8.58.

[0075] Example 8: Preparation of 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2- methylbut-2-en-1 -ol

[0076] In a 3-necked flask fitted with a thermometer and a condenser, 15 g of 4-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-enal prepared as in example 7 step 1 , and 100 ml of ethanol are placed. The reaction medium is cooled at 15 °C. Then, 1 .4 g of sodium borohydride are added portionwise. The mixture is stirred at room temperature. After 1 hour, gas chromatography analysis indicates that the conversion of 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylbut-2-enal is complete. The medium is poured over a 50:50 mixture of a 1% aqueous solution of HCI and tert-butyl methyl ether, the organic phase is washed with water, dried, and then concentrated invacuum. The result is 17.2 g of crude product as a mixture of isomers, which is distilled under reduced pressure: its boiling point is 82 °C under 0.15 Torr. Olfactory description: woody, green, camphor, aromatic. The resulting 4-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-in-1 -ol has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 5.49-5.35 (m, 1 H), 3.98-4.13 (m, 2H), 2.14- 1.18 (m, 14H), 0.98-0.77 (m, 6H), 0.32-0.21 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 139.19, 135.43, 135.1 1 , 134.65, 134.56, 130.86, 127.73, 125.94, 125.56, 125.32, 124.1 1 , 69.38, 69.12, 69.07, 61.65, 56.22,45.18, 40.90, 40.61 , 39.34, 36.75, 35.66, 35.16, 34.55, 34.14, 33.94, 33.89, 33.62,33.54, 32.69, 32.61 , 32.58, 31.87, 31.62, 27.95, 27.83, 27.67, 27.59, 26.79, 26.55,26.43, 26.34, 25.09, 23.31 , 22.35, 21.30, 20.33, 20.08, 19.98, 19.84, 18.30, 17.91 ,16.62, 13.92, 13.86, 13.74, 12.64, 8.78.Example 9: Preparation of 2-(5-isopropylbicyclo[3.1.0]hexan-2-yl)propanal

[0077] Step 1 : Preparation of 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acrylaldehyde - In a 3-necked flask fitted with a thermometer, a dropping funnel and a condenser, 140 ml of 37%wt. aqueous formaldehyde solution are placed. 13.3 g of pyrrolidine are added dropwise over 30 minutes, then 14 g of propionic acid are added dropwise over 30 minutes. The mixture is heated at 50 °C. Finally, 312 g of Sabinene carboxaldehyde prepared as in example 1 are added dropwise over 2 hours. The mixture is heated at 50 °C overnight. The medium is cooled at room temperature and poured over water and tert-butyl methyl ether, the organic phase is washed with water, dried, and then concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 55-58 °C under 1 mbar.

[0078] Step 2: Preparation of 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal - In an autoclave reactor, 50 g of 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acrylaldehyde and 25 g of Palladium on charcoal are introduced into 200 ml of toluene. After the reactor is closed, 3 nitrogen purges and one purge with hydrogen are carried out. The reaction medium is heated to 50 °C and placed under a continuous pressure of 10 bar of hydrogen. After 18 hours, the reaction medium is cooled, the autoclave is purged with nitrogen 3 times, then the reaction medium is filtered over a pad of Celite and the filtrate is concentrated under vacuum and finally distilled under 0.4 Torr at 52-53 °C. 39 g of 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal are obtained as a mixture of isomers. Olfactory Description: Floral, Aldehyde, Marine, Watery, Green. The resulting2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 9.63 (s, 1 H), 2.26-2.10 (m, 2H), 1 .93-1 .39 (m, 7H), 1.22-0.77 (m, 9H), 0.39-0.15 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 207.46, 207.00, 205.73, 205.54, 205.41 ,58.32, 58.13, 52.51 , 52.25, 51.89, 51.00, 50.85, 50.56, 42.61 , 41.93, 41.82, 41.59,41.33, 41.04, 40.24, 37.04, 36.91 , 36.23, 35.06, 34.93, 34.24, 33.85, 33.22, 32.68,32.53, 32.26, 32.18, 29.33, 28.50, 27.66, 26.83, 26.77, 26.72, 26.27, 25.94, 25.78,25.75, 24.85, 24.74, 24.71 , 24.47, 20.14, 20.09, 20.03, 19.98, 19.93, 19.89, 19.79,18.04, 17.52, 17.45, 17.1 1 , 16.46, 16.43, 13.13, 12.79, 12.37, 1 1.76, 1 1.59, 1 1.25,9.81 , 9.48, 9.16, 9.10.Example 10: Preparation of 6-(5-isopropylbicyclo[3.1.0]hexan-2-yl)hex-4- enenitrile

[0079] In a 3-necked flask fitted with a thermometer, a dropping funnel and a condenser, 47 g of (3-cyanopropyl)triphenylphosphonium chloride and 300 ml of toluene are placed. 15 g of potassium tert-butoxide are added. The mixture is stirred and heated at 70 °C for 1 hour. Then, 15 g of Sabinene carboxaldehyde prepared as in example 1 are added dropwise over 1 hour. The mixture is heated at 70 °C overnight. The medium is cooled at room temperature and poured over a 10% HCI aqueous solution, the organic phase is washed with water, dried, and then concentrated under vacuum. The crude product is diluted in 300 ml of tert-butyl methyl ether. This solution is cooled at 4 °C overnight to precipitate triphenylphosphine oxide formed during the reaction. The solid is filtered and the filtrate is concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 102 °C under 0.4 mbar. Olfactory Description: Green, celery, nutmeg, spicy. The resulting 6-(5-isopropylbicyclo[3.1 .0]hexan-2- yl)hex-4-enenitrile has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 5.58-5.52 (m, 1 H), 5.42-5.35 (m, 1 H), 2.41 -2.33 (m, 4H), 2.16-1.85 (m, 3H), 1.74-1.25 (m, 6H), 0.99-0.74 (m, 7H), 0.31 -0.22 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 139.58, 137.22, 137.08, 136.86, 133.81 , 133.56, 133.08, 132.90, 132.53, 132.36, 132.14, 132.00, 130.90, 130.48, 128.69, 128.60, 128.51 , 128.42, 126.58, 126.01 , 125.79, 125.65, 125.56, 125.27, 125.01 , 124.90, 1 19.48, 1 19.38, 1 15.35, 62.80, 56.01 , 45.59, 45.12, 41.50, 41.46, 41.40,40.85, 40.67, 40.47, 40.45, 40.24, 39.99, 39.33, 38.97, 38.67, 38.61 , 36.88, 36.73,36.45, 35.81 , 35.16, 35.04, 34.93, 34.70, 33.94, 33.90, 33.87, 33.77, 33.25, 32.81 ,32.65, 32.60, 32.53, 31.56, 31.45, 29.57, 28.56, 28.45, 28.17, 27.92, 27.80, 27.69,27.60, 27.48, 27.34, 26.75, 26.39, 26.36, 26.23, 25.71 , 25.46, 25.31 , 25.05, 24.86,24.45, 23.51 , 23.43, 23.39, 23.30, 23.26, 23.23, 22.24, 22.18, 20.37, 20.31 , 20.06,19.96, 19.89, 19.86, 19.84, 18.26, 17.88, 17.73, 17.55, 17.52, 17.49, 17.46, 16.59,16.47, 12.82, 12.65, 9.70, 8.73.

[0080] Example 11 : Preparation of 6-(5-isopropylbicyclo[3.1.0]hexan-2- yl)hexanenitrile

[0081] In an autoclave reactor, 5 g of 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hex-4- enenitrile prepared as in example 10 and 0.25 g of Palladium on charcoal are introduced into 100 ml of toluene. After the reactor is closed, 3 nitrogen purges and one purge with hydrogen are carried out. The reaction medium is heated to 50 °C and placed under a continuous pressure of 10 bar of hydrogen. After 18 hours, the reaction medium is cooled, the autoclave is purged with nitrogen 3 times, then the reaction medium is filtered over a pad of Celite and the filtrate is concentrated under vacuum and finally distilled under 1 Torr at 100 °C. 2.9 g of 6-(5-isopropylbicyclo[3.1 .0]hexan- 2-yl)hexanenitrile are obtained as a mixture of isomers. Olfactory Description: Green, celery, coriander, citrus. The resulting 6-(5-isopropylbicyclo[3.1 .0]hexan-2- yl)hexanenitrile has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 2.35-2.28 (m, 2H), 1.85-1.78 (m, 1 H), 1.69- 1 .54 (m, 6H), 1 .47-1 .1 1 (m, 9H), 0.97-0.76 (m, 6H), 0.28-0.20 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 1 19.84, 1 19.80, 62.91 , 55.59, 51.66, 46.37, 45.79, 45.27, 41.53, 41.39, 40.99, 40.81 , 40.12, 40.03, 39.32, 38.68, 37.70, 37.36,37.08, 36.84, 36.55, 36.10, 35.29, 34.73, 34.69, 34.56, 34.16, 33.70, 33.66, 33.56,32.77, 32.70, 32.63, 32.22, 31.60, 30.73, 29.82, 29.64, 29.00, 28.95, 28.89, 28.35,28.23, 28.01 , 27.95, 27.84, 27.79, 27.61 , 27.22, 27.00, 26.84, 26.69, 26.53, 26.35,25.67, 25.43, 25.39, 25.24, 24.91 , 24.53, 23.79, 23.49, 23.39, 23.29, 22.69, 22.51 ,22.47, 21.39, 20.34, 20.09, 19.97, 19.85, 19.81 , 19.52, 18.37, 18.20, 18.16, 17.74,17.70, 17.10, 17.07, 16.57, 14.24, 12.83, 8.56.Example 12: Preparation of 8-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-oct-6-enol

[0082] In a 3-necked flask fitted with a thermometer, a dropping funnel and a condenser, 160 g of (6-hydroxyhexyl)triphenylphosphonium bromide and 400 ml of toluene are placed. 40.5 g of potassium tert-butoxide are added. The mixture is stirred and heated at 70 °C for 1 hour. Then, 50 g of Sabinene carboxaldehyde prepared as in example 1 are added dropwise over 1 hour. The mixture is heated at 70 °C overnight. The medium is cooled at room temperature and poured over a 10% HCI aqueous solution, the organic phase is washed with water, dried, and then concentrated under vacuum. The crude product is diluted in 400 ml of tert-butyl methylether. This solution is cooled at 4 °C overnight to precipitate triphenylphosphine oxide formed during the reaction. The solid is filtered and the filtrate is concentrated under vacuum. The crude product obtained as a mixture of isomers, is distilled under reduced pressure: its boiling point is 130 °C under 0.4 mbar. Olfactory Description: Aldehyde, weak. The resulting 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enol has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 5.46-5.30 (m, 2H), 3.63-3.59 (m, 2H), 2.18- 1 .87 (m, 6H), 1 .66-1 .46 (m, 13H), 0.97-0.77 (m, 6H), 0.32-0.19 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 139.04, 131.09, 130.89, 130.57, 130.22, 130.14, 129.85, 129.55, 129.41 , 128.99, 128.83, 127.24, 62.83, 56.04, 45.56, 45.18, 41.71 , 41.50, 40.91 , 40.74, 40.68, 40.33, 39.30, 38.83, 38.68, 38.18, 36.75, 35.15,34.87, 34.60, 33.83, 33.80, 33.73, 33.23, 32.66, 32.59, 31.51 , 31.47, 29.84, 29.56,29.52, 29.49, 29.41 , 28.20, 27.93, 27.75, 27.66, 27.63, 27.38, 27.33, 27.22, 27.20,27.08, 26.78, 26.56, 26.49, 26.34, 26.25, 25.45, 25.42, 25.34, 25.25, 25.10, 24.93,24.54, 23.30, 23.24, 22.27, 20.32, 20.07, 19.96, 19.84, 18.29, 17.90, 16.60, 12.78,12.62, 8.72.

[0083] Example 13: Preparation of 8-(5-isopropylbicyclo[3.1.0]hexan-2-yl)- octanol

[0084] In an autoclave reactor, 10 g of 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6- enol prepared as in example 12 and 0.5 g of Palladium on charcoal are introduced into 150 ml of toluene. After the reactor is closed, 3 nitrogen purges and one purge with hydrogen are carried out. The reaction medium is heated to 50 °C and placed under a continuous pressure of 10 bar of hydrogen. After 18 hours, the reaction medium is cooled, the autoclave is purged with nitrogen 3 times, then the reaction medium is filtered over a pad of Celite and the filtrate is concentrated under vacuum and finally distilled under 1 Torr at 120 °C. 4.8 g of 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-octanol are obtained as a mixture of isomers. Olfactory Description: Aldehyde, weak. The resulting 8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-octanol has the following spectral characteristics:1H-NMR (300 MHz, CDCh): 5 (ppm) 3.64 (t, J = 6.6 Hz, 2H), 1.91 -1.65 (m, 3H), 1.65- 1 .56 (m, 2H), 1 .56-1 .23 (m, 18H), 0.94-0.65 (m, 6H), 0.33-0.17 (m, 1 H).13C-NMR (75 MHz, CDCh): 5 (ppm) 63.03, 55.66, 46.48, 45.90, 41.60, 41.05,40.29, 40.19, 39.34, 38.19, 37.78, 36.86, 36.62, 36.53, 35.69, 34.81 , 34.68, 34.57,34.25, 33.95, 33.81 , 33.68, 33.57, 32.78, 32.74, 32.70, 31.75, 30.64, 29.94, 29.83,29.69, 29.66, 29.64, 29.57, 29.49, 29.44, 29.40, 28.86, 28.28, 28.12, 28.08, 27.88,27.83, 27.66, 27.22, 26.76, 26.70, 26.58, 25.75, 24.95, 24.62, 24.53, 23.52, 23.43, 23.30, 22.60, 20.37, 20.12, 19.99, 19.87, 19.81 , 18.23, 17.78, 16.60, 12.82, 8.55.

[0085] Perfume Compositions Examples A-C

[0086] Exemplary comparative and inventive perfume compositions were prepared in accordance with the materials listed in Table 1 . The comparative examples (Comp Ex A - Comp Ex C) were evaluated by trained perfumers in comparison to the inventive examples (Ex A, B1 , B2, and C), where a portion of the solvent (dipropylene glycol) was replaced with an equivalent amount of a compound of general Formula (I).Table 1 : Perfume CompositionsComp Ex A Comp Ex Ex Comp Ex C Ex A Ex B B1 B2 Ex. CMaterial Qty Qty Qty Qty Qty Qty QtyCompound of Example 1a3 1 5 1DIPROPYLENE GLYCOL 130 127 154 153 149 100 99MUSK T™ 224 224HEDIONE™ 280 280 165 165BENZYL SALICYLATE 160 16050%DPGVERDOX™ 50%DPG 65 65PHENYLETHYL ALCOOL 58 58 450 450 450 50 50LEMON EQ 40 40HEXYL ACETATE 30 30BENZOIN / WOODY 30 30SpecialtyGAMMA 25 25UNDECALACTONEHEXYL SALICYLATE 25 25CYCLAMEN ALDEHYDE 14 14 14 20 20ALPHA ISOMETHYL 15 15IONONEMUGANE™ 15 15ALLYL CAPROATE 15 15BENZYL ACETATE 7 7TONKA / PATCHOULI 5 5Specialty NAPHTHYL ETHYL 4 4ETHER 10%DPG UNDECAVERTOL 3 3OXANE™ 10%D PG 2 2CITRONELLOL 222 222 222GERANIOL 110 110 110PHENYLETHYL 25 25 25PHENYLACETATE PHENOXANOL™ 20 20 14 14 14HEXENYL CIS 3 6 6 6ACETATEDIPHENYL OXIDE 3 3 3BETAHYDRANE™ 2 2 2FLOROL™ 140 140HEXYLCINNAMIC 80 80ALDEHYDEORANGE EO 55 55LEMON EO 45 45PATCHOULI EO 40 40DMBC ACETATE 36 36HABANOLIDE™ 28 28HELIONAL™ 25 25MADERAL™ 20 20ALPHA ISOMETHYL 16 16IONONECEDARWOOD EO 10 10AMBRETTOLIDE 10 10DAMASCENONE 10% 4 4DPGCALONE™ 2 2MELONAL™ 10%DPG 1 11000 1000 1000 1000 1000 1000 1000a2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde

[0087] Addition of the inventive compound of Example 1 (2-(5- isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde) at 3 parts per thousand (ppt) to the perfume formulation of Comparative Example A provides a natural effect, which is more zesty, with crunchy effects, to Example A. Addition of the inventive compound of Example 1 at 1 ppt to the perfume formulation of Comparative Example B boosts the note in Example B1 , but the effect is more interesting and gives more nuances by adding 5 ppt (Example B2). Addition of the inventive compound of Example 1 at 1 ppt to the perfume formulation of Comparative Example C gives more impact to the accord and brings more fruitiness.

[0088] While the invention has been illustrated by the description of one or more embodiments thereof, and while the embodiments have been described in considerable detail, they are not intended to restrict or in any way limit the scope of the appended claims to such detail. Additional advantages and modifications will readily appear to those skilled in the art. The invention in its broader aspects is therefore not limited to the specific details, representative product and / or method and examples shown and described. The various features of exemplary embodimentsdescribed herein may be used in any combination. Accordingly, departures may be made from such details without departing from the scope of the general inventive concept.

Claims

Claims1 . A compound having a general Formula (I):Formula (I), wherein:R1is selected from the group consisting of acetals, monothioacetals, (CH=CR2)x(CHR)mOR3, (CH=CR2)x(CHR)nCHO, (CH=CR2)x(CHR)pCN; and (CH=CR2)x(CHR)pCO2R4; each R is independently selected from the group consisting of H or methyl;R2is selected from the group consisting of H, methyl, and ethyl;R3is selected from the group consisting of H, C1 -C3 aliphatics, and C(O)Ra, where Rais H or ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, isohexyl, neohexyl, or cyclohexyl;R4is selected from the group consisting of C1 -C3 alkyls; x is an integer equal to 0 or 1 ; and m, n, p, and q are integers independently selected from 0 to 7, with a proviso that when R and R3are each H, then x and m are not both equal to 0.

2. The compound according to claim 1 , wherein R1is selected from acetals and monothioacetals.

3. The compound according to claim 2, wherein the compounds have a general Formula (II) or (III):wherein Z is selected from O or S, wherein R5is selected from nil, CR8R9, or HC=CH; wherein R6, R7R8, and R9are independently selected from H or methyl; andwherein R10is selected from C1 -C3 aliphatics.

4. The compound according to claim 1 , wherein R1is (CH=CR2)x(CHR)mOR3.

5. The compound according to claim 1 , wherein R1is (CH=CR2)x(CHR)nCHO.

6. The compound according to claim 1 , wherein R1is (CH=CR2)x(CHR)pCN.

7. The compound according to claim 1 , wherein R1is (CH=CR2)x(CHR)pCO2R4.

8. The compound according to claim 1 , selected from the group consisting of:2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetaldehyde, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxolane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxolane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-oxathiolane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,5-dimethyl-1 ,3-dioxolane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-1 ,3-dioxane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4-methyl-1 ,3-dioxane, 2-((5-isopropylbicyclo[3.1 .0]hexan-2-yl)methyl)-4,7-dihydro-1 ,3-dioxepine, 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hex-4-enenitrile, 6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanenitrile, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethan-1 -ol, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl formate, 4-(2-(allyloxy)ethyl)-1 -isopropylbicyclo[3.1 .0]hexane, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl acetate, 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethyl propionate, ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enoate, ethyl 4-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylbut-2-enoate, ethyl 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)butanoate, 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-enal, 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbutanal, 4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-methylbut-2-en-1 -ol, 2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-enal,2-ethyl-4-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)but-2-en-1 -ol,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enal,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-oct-6-enol,8-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-octanol, ethyl 3-(5-isopropylbicyclo[3.1.0]hexan-2-yl)-2-methylpropanoate,3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)-2-propanol, ethyl 3-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)ethanoate, ethyl 2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanoate,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanal,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)propanol,2-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)acetonitrile,6-(5-isopropylbicyclo[3.1 .0]hexan-2-yl)hexanol, and combinations thereof.

9. A fragrant composition comprising a solvent, and the compound according to any one of claims 1 to 8.

10. A method of synthesizing the compound according to any one of claims 1 to 8, comprising: hydroformylating sabinene to form sabinene carboxaldehyde; and optionally, reacting sabinene carboxaldehyde with formaldehyde, a C1 -C3 aliphatic alcohol, in particular a primary alcohol, a diol, in particular a C2-C5 aliphatic diol, a thioalcohol, a phosphorus ylide, an enolate, a reducing agent, an oxidizing agent, or a combination thereof; or optionally condensing sabinene carboxaldehyde with a hydroxylamine, an O- alkoxyamine, or an O-acyloxyamine and dehydrating the oxime intermediate, alkyloxime intermediate, or acyloxime intermediate.11 . The method according to claim 10, wherein sabinene carboxaldehyde is reacted with a reducing agent to obtain an alcohol and the alcohol is further derivatized by esterification or etherification.

12. The method according to claim 10, wherein sabinene carboxaldehyde is reacted with a phosphonium ylide, such as the carbanion of a previously deprotonated (cyanoalkyl)triphenylphosphonium halide, to form an alkene derivative and wherein the alkene derivative is optionally hydrogenated.

13. The method according to claim 10, wherein sabinene carboxaldehyde is reacted with a stabilized phosphonate carbanion, such as the anion of previously deprotonated trialkylphosphono-acetate (or -propionate), to form an alkene derivative and wherein the alkene derivative is optionally hydrogenated.

14. The method according to claim 10, wherein sabinene carboxaldehyde is reacted with another aldehyde, such as a saturated linear aldehyde, in the presence of a base to form an alpha, beta-unsaturated aldehyde and wherein the alpha, beta-unsaturated aldehyde is optionally hydrogenated and / or reduced.

15. Use of the compound according to any one of claims 1 to 8 to confer, modify or enhance the organoleptic properties of a substance, composition, or article.