Patent Description:
The perfumery industry is constantly on the lookout for new ingredients in order to support the creativity of perfumer by diversifying the notes present in their palette. Furthermore, perfumers seek powerful and tenacious perfuming ingredients allowing bringing to any compositions a typical character perceived during several hours. However, only a few ingredients imparting incense note are available. So there is a need to develop alternatives.

<CIT> and <NPL> reports, as a compound imparting said olfactive properties, the compound of formula (I), wherein n is <NUM>. Most particularly the second prior art mentions that incense note is due to the two following diasteroiomers: cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid and trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic. However, it has been surprisingly now shown that the trans diastereoisomers have a negative impact on the organoleptic properties of compound of formula (I) and that cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid is also an important diastereoisomer.

<CIT> describes <NUM>-octylcyclopropyl-<NUM>-carboxylic acid, in particular in the form of one of the isomers thereof in isolated form or in the form of a mixture of at least two of said isomers.

So, the present invention provides a novel composition of matter as defined above comprising mainly cis-diastereoisomers leading to a very powerful and substantive incense note combined with citrus aspect never reported in the prior art. The prior art does not anticipate that the present composition of matter provides such increase in performance while delivering a citrus note.

The invention relates to a composition of matter as defined above never disclosed imparting, in addition to incense odor note, a citrus odor note and its use as a perfuming ingredient.

So a first object of the present invention is a composition of matter comprising a compound of formula (I)
<CHM>
wherein n is <NUM> or <NUM>; the weight ratio of the cis-diastereoisomers to the trans-diastereoisomers is comprised in the range between <NUM>:<NUM> and <NUM>:<NUM> and comprising at least <NUM>% w/w of cis-(<NUM>,2R) diastereoisomer, the percentage being relative to the total weight of the composition of matter.

A second object of the present invention is a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or of a surface, which method comprises adding to said composition or perfumed article an effective amount of a composition of matter as defined above.

Another object of the present invention is the use as perfuming ingredient of a composition of matter as defined above.

Another object of the present invention is a perfuming composition comprising.

A further object of the present invention is a perfumed consumer product comprising a composition of matter as defined above or a perfuming composition as defined above.

A surprising synergic effect has been discovered between the <NUM> diastereoisomers of the compound of formula (I) leading to the invention composition of matter possessing a powerful and substantive incense note and surprisingly also imparting citrus aspect.

So, a first object of the present invention is a composition of matter comprising a compound of formula (I)
<CHM>
wherein n is <NUM> or <NUM>; and the weight ratio of the cis-diastereoisomers to the trans-diastereoisomers is comprised in the range between <NUM>:<NUM> and <NUM>:<NUM> and comprising at least <NUM>% w/w of cis-(<NUM>,2R) diastereoisomer, the percentage being relative to the total weight of the composition of matter.

Said composition of matter can be used as perfuming ingredient, for instance to impart powerful and substantive odor notes of the incense type with citrus facet.

By the terms "cis-diastereoisomers" and "trans-diastereoisomers", it is meant the normal meaning understood by a person skilled in the art, i. e the cis-diastereoisomers correspond to cis-(<NUM>,2R)-<NUM>-nonylcyclopropanecarboxylic acid and cis-(1R,<NUM>)-<NUM>-nonylcyclopropanecarboxylic acid when n is <NUM> or cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid and cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid when n is <NUM> and trans-diastereoisomers correspond to trans-(<NUM>,<NUM>)-<NUM>-nonylcyclopropanecarboxylic acid and trans-(1R,2R)-<NUM>-nonylcyclopropanecarboxylic acid when n is <NUM> or trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid and trans-(1R,2R)-<NUM>-octylcyclopropanecarboxylic acid when n is <NUM>.

By the term "cis-(<NUM>,2R) diastereoisomer", it is meant the normal meaning understood by a person skilled in the art, i. e cis-(<NUM>,2R)-<NUM>-nonylcyclopropanecarboxylic acid when n is <NUM> and cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid when n is <NUM>.

According to any embodiments of the invention, the invention's composition of matter comprises at least <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w of cis-(<NUM>,2R) diastereoisomer, the percentage being relative to the total weight of the composition of matter. In particular, the invention's composition of matter comprises at least <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w, <NUM>% w/w of cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, the percentage being relative to the total weight of the composition of matter.

According to any embodiments of the invention, n is <NUM>. In other words, the invention's composition of matter comprises:.

the percentage being relative to the total weight of the composition of matter.

According to any embodiments of the invention, trans-<NUM>-octylcyclopropanecarboxylic acid may be in a form of a pure enantiomer or in the form of a mixture of two enantiomers. Trans-<NUM>-octylcyclopropanecarboxylic acid can be in a racemic form or scalemic form. Therefore, trans-<NUM>-octylcyclopropanecarboxylic acid may be trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, trans-(1R,2R)-<NUM>-octylcyclopropanecarboxylic acid or a mixture thereof. Particularly, trans-<NUM>-octylcyclopropanecarboxylic acid may be in a racemic form; i.e. a mixture of trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid and trans-(1R,2R)-<NUM>-octylcyclopropanecarboxylic acid in a weight ratio of <NUM> : <NUM>.

According to any embodiments of the invention, cis-<NUM>-octylcyclopropanecarboxylic acid may be in a form of a pure enantiomer or in the form of a mixture of two enantiomers. Cis-<NUM>-octylcyclopropanecarboxylic acid can be in a racemic form or scalemic form. Therefore, cis-<NUM>-octylcyclopropanecarboxylic acid may be cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid or a mixture thereof. Particularly, cis-<NUM>-octylcyclopropanecarboxylic acid may be in a racemic form; i.e. a mixture of cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid and cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid in a weight ratio of <NUM> : <NUM>.

According to any embodiments of the invention, the invention composition of matter may comprise at least <NUM>% w/w of cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, the percentage being relative to the total weight of the composition of matter.

According to any embodiments of the invention, in the present composition of matter the various constituents mentioned above are present in the following amounts:.

According to an embodiment of the invention, in the present composition of matter the various constituents mentioned above are present in the following amounts:.

According to any one of the above embodiments of the invention, the present composition of matter may comprise from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, particularly from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid, and more particularly from about <NUM> to <NUM>% w/w of (cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid.

According to a particular embodiment of the invention, the present composition of matter may comprise from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, even more particularly, from about <NUM> to <NUM>% w/w of cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid.

According to any one of the above embodiments of the invention, the present composition of matter may comprise from about <NUM> to <NUM>% w/w of trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid, and more particularly from about <NUM> to <NUM>% w/w of trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid.

According to any one of the above embodiments of the invention, the present composition of matter may comprise from about <NUM> to <NUM>% w/w of trans-(1R,2R)-<NUM>-octylcyclopropanecarboxylic acid, and more particularly from about <NUM> to <NUM>% w/w of trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid.

According to another particular embodiment of the invention, in the present composition of matter the various constituents mentioned above are present in the following amounts:.

According to any one of the above embodiments of the invention, the weight ratio of the cis-diastereoisomers to the trans-diastereoisomers is comprised in the range between <NUM>:<NUM> and <NUM>:<NUM>, more particularly in the range between <NUM>:<NUM> and <NUM>:<NUM>; and more particularly in the range between <NUM>:<NUM> and <NUM>: <NUM>.

As mentioned above, the composition of matter of the invention possesses a very powerful natural incense organoleptic properties allied with a citrus character while possessing a long-lastingness. The overall odor profile is highly appreciated by perfumers since it opens up new directions in the perfumer's creativity when compared with the prior art ingredients.

Indeed, when the odor of the invention's composition of matter is compared with prior art composition of matter comprising more than <NUM>% w/w of trans isomers, then the invention's compositions of matter distinguish themselves by a clearly different odor profile having citrus facet never reported while maintaining an intense and natural incense and lacking the fatty and dusty characteristic of the prior art compounds. Moreover, the invention's compositions of matter impart a clearly stronger and more substantive note while bringing more radiance to perfuming compositions. The invention's compositions of matter distinguish themselves also by showing a nicer olfactive profile.

Said differences lend the invention's compositions of matter and the prior art compounds to be each suitable for different uses, i.e. to impart different organoleptic impressions.

As mentioned above, the invention concerns the use of the invention's compositions of matter as a perfuming ingredient. In other words, it concerns a method or a process to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or of a surface, which method comprises adding to said composition or article an effective amount of the invention's composition of matter, e.g. to impart its typical note. Understood that the final hedonic effect may depend on the precise dosage and on the organoleptic properties of the invention's composition of matter, but anyway the addition of the invention's compositions of matter will impart to the final product its typical touch in the form of a note, touch or aspect depending on the dosage. In addition, the invention's composition of matter may also be used to enhance the organoleptic properties of perfuming ingredient or to decrease the unpleasant olfactory impression such as metallic, dusty or chemical facet of some perfuming ingredients.

By "use of the invention's compositions of matter it has to be understood here also the use of any composition containing the invention's compositions of matter and which can be advantageously employed in the perfumery industry.

Said compositions, which in fact can be advantageously employed as perfuming ingredients, are also an object of the present invention.

Therefore, another object of the present invention is a perfuming composition comprising:.

By "perfumery carrier" it is meant here a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples, solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoether, <NUM>,<NUM>,<NUM>-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate <NUM>,<NUM>-diacetyloxypropan-<NUM>-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, <NUM>-(<NUM>-ethoxyethoxy)-<NUM>-ethano, tri-ethyl citrate or mixtures thereof, which are the most commonly used. For the compositions which comprise both a perfumery carrier and a perfumery base, other suitable perfumery carriers than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor® RH <NUM> (origin: BASF).

Solid carrier is meant to designate a material to which the perfuming composition or some element of the perfuming composition can be chemically or physically bound. In general such solid carriers are employed either to stabilize the composition, or to control the rate of evaporation of the compositions or of some ingredients. Solid carriers are of current use in the art and a person skilled in the art knows how to reach the desired effect. However by way of non-limiting examples of solid carriers, one may cite absorbing gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood based materials, organic or inorganic gels, clays, gypsum talc or zeolites.

As other non-limiting examples of solid carriers, one may cite encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band <NUM> der Schriftenreihe Lebensmittelchemie, Lebensmittelqualität, Behr's Verlag GmbH & Co. , Hamburg, <NUM>. The encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, by using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation techniques.

As non-limiting examples of solid carriers, one may cite in particular the core-shell capsules with resins of aminoplast, polyamide, polyester, polyurea or polyurethane type or a mixture threof (all of said resins are well known to a person skilled in the art) using techniques like phase separation process induced by polymerization, interfacial polymerization, coacervation or altogether (all of said techniques have been described in the prior art), optionally in the presence of a polymeric stabilizer or of a cationic copolymer.

Resins may be produced by the polycondensation of an aldehyde (e.g. formaldehyde, <NUM>,<NUM>-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof. Alternatively one may use preformed resins alkylolated polyamines such as those commercially available under the trademark Urac® (origin: Cytec Technology Corp. ), Cymel® (origin: Cytec Technology Corp. ), Urecoll® or Luracoll® (origin: BASF).

Other resins are the ones produced by the polycondensation of a polyol, like glycerol, and a polyisocyanate, like a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (known with the tradename of Takenate®, origin: Mitsui Chemicals), among which a trimer of xylylene diisocyanate with trimethylolpropane and a Biuret of hexamethylene diisocyanate are preferred.

Some of the seminal literature related to the encapsulation of perfumes by polycondensation of amino resins, namely melamine based resins with aldehydes includes articles such as those published by<NPL>, <NUM> and <NUM>, as well as <NUM>, vol. <NUM>, page <NUM>. Such articles already describe the various parameters affecting the preparation of such core-shell microcapsules following prior art methods that are also further detailed and exemplified in the patent literature. US <NUM>'<NUM>'<NUM>, to the Wiggins Teape Group Limited is a pertinent early example of the latter. Since then, many other authors have enriched the literature in this field and it would be impossible to cover all published developments here, but the general knowledge in encapsulation technology is very significant. More recent publications of pertinence, which disclose suitable uses of such microcapsules, are represented for example by the article of <NPL>.

By "perfumery base" what is meant here is a composition comprising at least one perfuming co-ingredient.

By "perfuming co-ingredient" it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. The perfuming co-ingredient may impart an additional benefit beyond that of modifying or imparting an odor, such as long-lasting, blooming, malodour counteraction, antimicrobial effect, antiviral effect, microbial stability, or pest control.

The nature and type of the perfuming co-ingredients present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.

In particular, one may cite perfuming co-ingredients which are commonly used in perfume formulations, such as:.

According to a particular embodiment, the invention's perfuming composition comprises, as a perfuming co-ingredient, at least one woody ingredient.

A perfumery base according to the invention may not be limited to the above mentioned perfuming co-ingredients, and many other of these co-ingredients are in any case listed in reference texts such as the book by<NPL>, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance. Non-limiting examples of suitable properfume may include <NUM>-(dodecylthio)-<NUM>-(<NUM>,<NUM>,<NUM>-trimethyl-<NUM>-cyclohexen-<NUM>-yl)-<NUM>-butanone, <NUM>-(dodecylthio)-<NUM>-(<NUM>,<NUM>,<NUM>-trimethyl-<NUM>-cyclohexen-<NUM>-yl)-<NUM>-butanone, trans-<NUM>-(dodecylthio)-<NUM>-(<NUM>,<NUM>,<NUM>-trimethyl-<NUM>-cyclohexen-<NUM>-yl)-<NUM>-butanone, <NUM>-(dodecyl sulfonyl)-<NUM> -(<NUM>,<NUM>,<NUM>-trimethylcyclohex-<NUM> -en-<NUM> - yl)butan-<NUM>-one, a linear polysiloxane co-polymer of (<NUM>-mercaptopropyl)(methyl)dimethoxysilane, <NUM>-(dodecylthio)octan-<NUM>-one, <NUM>-(dodecylsulfonyl)octan-<NUM>-one, <NUM>-oxooctan-<NUM>-yl dodecanoate, <NUM>-phenylethyl oxo(phenyl)acetate, <NUM>,<NUM>-dimethylocta-<NUM>,<NUM>-dien-<NUM>-yl oxo(phenyl)acetate, (Z)-hex-<NUM>-en-<NUM>-yl oxo(phenyl)acetate, <NUM>,<NUM>-dimethyl-<NUM>,<NUM>-octadien-<NUM>-yl hexadecanoate, bis(<NUM>,<NUM>-dimethylocta-<NUM>,<NUM>-dien-<NUM>-yl) succinate, (2E,6Z)-<NUM>,<NUM>-nonadienyl hexadecanoate, (2E,6Z)-<NUM>,<NUM>-nonadien-<NUM>-yl tetradecanoate, (2E,6Z)-<NUM>,<NUM>-nonadien-<NUM>-yl dodecanoate, (<NUM>-((<NUM>-methylundec-<NUM>-en-<NUM>-yl)oxy)ethyl)benzene, <NUM>-methoxy-<NUM>-(<NUM>-methyl-<NUM>-phenethoxybut-<NUM>-en-<NUM>-yl)benzene, (<NUM>-methyl-<NUM>-phenethoxybut-<NUM>-en-<NUM>-yl)benzene, <NUM> -(((Z)-hex-<NUM> -en-<NUM> -yl)oxy)-<NUM>-methylundec-<NUM>-ene, (<NUM>-((<NUM>-methylundec-<NUM>-en-<NUM>-yl)oxy)ethoxy)benzene, <NUM>-methyl-<NUM>-(octan-<NUM>-yloxy)undec-<NUM>-ene, <NUM>-methoxy-<NUM>-(<NUM>-phenethoxyprop-<NUM>-en-<NUM>-yl)benzene, <NUM>-methyl-<NUM>-(<NUM>-phenethoxyprop-<NUM>-en-<NUM>-yl)benzene, <NUM>-(<NUM>-phenethoxyprop-<NUM>-en-<NUM>-yl)naphthalene, (<NUM>-phenethoxyvinyl)benzene, <NUM>-(<NUM>-((<NUM>,<NUM>-dimethyloct-<NUM>-en-<NUM>-yl)oxy)prop-<NUM>-en-<NUM>-yl)naphthalene, (<NUM>-((<NUM>-pentylcyclopentylidene)methoxy)ethyl)benzene, <NUM>-allyl-<NUM>-methoxy-<NUM>-((<NUM>-methoxy-<NUM>-phenylvinyl)oxy)benzene, (<NUM>-((<NUM>-heptylcyclopentylidene)methoxy)ethyl)benzene, <NUM>-methoxy-<NUM>-(<NUM>-phenethoxyprop-<NUM>-en-<NUM>-yl)benzene, (<NUM>-((<NUM>-methyl-<NUM>-(<NUM>,<NUM>,<NUM>-trimethylcyclohex-<NUM>-en-<NUM>-yl)but-<NUM>-en-<NUM>-yl)oxy)ethyl)benzene, <NUM>-methoxy-<NUM>-(<NUM>-methyl-<NUM>-phenethoxyallyl)benzene, (<NUM>-((<NUM>-isopropyl-<NUM>-methylcyclohexylidene)methoxy)ethyl)benzene, <NUM>-isopropyl-<NUM>-methyl-<NUM>-((<NUM>-pentylcyclopentylidene)methoxy)benzene, <NUM>-methoxy-<NUM>-((<NUM>-pentylcyclopentylidene)methoxy)-<NUM>-propylbenzene, <NUM>-ethoxy-<NUM>-((<NUM>-methoxy-<NUM>-phenylvinyl)oxy)-<NUM>-methylbenzene, <NUM>-methoxy-<NUM>-((<NUM>-methoxy-<NUM>-phenylvinyl)oxy)benzaldehyde, <NUM>-isopropyl-<NUM>-((<NUM>-methoxy-<NUM>-phenylvinyl)oxy)-<NUM>-methylbenzene, <NUM>-((<NUM>-(hexyloxy)-<NUM>-phenylvinyl)oxy)-<NUM>-methoxybenzaldehyde or a mixture thereof.

By "perfumery adjuvant", it is meant here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming composition cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art. One may cite as specific non-limiting examples the following: viscosity agents (e.g. surfactants, thickeners, gelling and/or rheology modifiers), stabilizing agents (e.g. preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT), coloring agents (e.g. dyes and/or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti irritant agents), abrasives, skin cooling agents, fixatives, insect repellants, ointments, vitamins and mixtures thereof.

It is understood that a person skilled in the art is perfectly able to design optimal formulations for the desired effect by admixing the above mentioned components of a perfuming composition, simply by applying the standard knowledge of the art as well as by trial and error methodologies.

An invention's composition consisting of at least one composition of matter as defined above and at least one perfumery carrier consists of a particular embodiment of the invention as well as a perfuming composition comprising at least one composition of matter as defined above, at least one perfumery carrier, at least one perfumery base, and optionally at least one perfumery adjuvant.

For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the composition of matter of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive composition of matter in a suitable form for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.

The invention's composition of matter can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said composition of matter is added. Consequently, another object of the present invention consists of a perfumed consumer product comprising, as a perfuming ingredient, at least one composition of matter, as defined above.

The invention's composition of matter can be added as such or as part of an invention's perfuming composition.

For the sake of clarity, "perfumed consumer product" is meant to designate a consumer product which delivers at least a pleasant perfuming effect to the surface or space to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product which comprises a functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, and an olfactive effective amount of at least one invention's composition of matter. For the sake of clarity, said perfumed consumer product is a non-edible product.

The nature and type of the constituents of the perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product.

Non-limiting examples of suitable perfumed consumer products include a perfume, such as a fine perfume, a splash or eau de parfum, a cologne or a shave or after-shave lotion; a fabric care product, such as a liquid, a pod or solid detergent or tablet, a fabric softener, a liquid or solid scent booster, a dryer sheet, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product; a body-care product, such as a hair care product (e.g. a shampoo, , a leave-on or rinse-off hair conditioner, a coloring preparation or a hair spray, a color-care product, a hair shaping product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g. a skin cream or lotion, a vanishing cream or a deodorant or antiperspirant (e.g. a spray or roll on), a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup); or a skin-care product (e.g. a soap, a shower or bath mousse, oil or gel, or a hygiene product or a foot/hand care products); an air care product, such as an air freshener or a "ready to use" powdered air freshener which can be used in the home space (rooms, refrigerators, cupboards, shoes or car) and/or in a public space (halls, hotels, malls, etc.. ); or a home care product, such as a mold remover, a furnisher care product, a wipe, a dish detergent or a hard-surface (e.g. a floor, bath, sanitary or a window-cleaning) detergent; a leather care product; a car care product, such as a polish, a wax or a plastic cleaner.

Some of the above-mentioned perfumed consumer products may represent an aggressive medium for the invention's composition of matter, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically binding it to another chemical which is suitable to release the invention's ingredient upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.

The proportions in which the composition of matter according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base when the composition of matter according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

For example, in the case of perfuming compositions, typical concentrations are in the order of <NUM> % to <NUM> % by weight, or even more, of the composition of matter of the invention based on the weight of the composition into which they are incorporated. In the case of perfumed consumer product, typical concentrations are in the order of <NUM> % to <NUM> % by weight, or even more, of the composition of matter of the invention based on the weight of the consumer product into which they are incorporated.

The invention will now be described in further detail by way of the following examples, wherein the abbreviations have the usual meaning in the art, the temperatures are indicated in degrees centigrade (°C). NMR spectra were acquired using either a Bruker Avance II Ultrashield <NUM> plus operating at <NUM>, (<NUM>H) and <NUM> (<NUM>C) or a Bruker Avance III <NUM> operating at <NUM> (<NUM>H) and <NUM> (<NUM>C) or a Bruker Avance III <NUM> cryoprobe operating at <NUM> (<NUM>H) and <NUM> (<NUM>C). Spectra were internally referenced relative to tetramethyl silane <NUM> ppm. <NUM>H NMR signal shifts are expressed in δ ppm, coupling constants (J) are expressed in Hz with the following multiplicities: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; b, broad (indicating unresolved couplings) and were interpreted using Bruker Topspin software. <NUM>C NMR data are expressed in chemical shift δ ppm and hybridization from DEPT <NUM> and DEPT <NUM> experiments, C, quaternary (s); CH, methine (d); CH<NUM>, methylene (t); CH<NUM>, methyl (q). GC method GC-<NUM> (<NUM>, <NUM>, <NUM>, H<NUM>, <NUM> at <NUM>/min).

of ethyl diazoacetate (<NUM>%/w in CH<NUM>Cl<NUM>, <NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>) was added via a syringe pump in <NUM> to a mixture of <NUM>-decyne (<NUM>, <NUM> mmol) and Rh<NUM>(OAc)<NUM> (<NUM>, <NUM> mmol). The solvent was removed in vacuo, and the residue was purified by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>) to afford ethyl <NUM>-octylcycloprop-<NUM>-ene-<NUM>-carboxylate in <NUM>% yield (based on the ethyl diazoacetate; <NUM>% yield based on used/recuperated <NUM>-decyne).

<NUM>H-NMR: <NUM> (s, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>). <NUM>C-NMR: <NUM> (s); <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (q); <NUM> (q).

LiOH (<NUM>, <NUM> mmol) was added to a soln. of ethyl <NUM>-octylcycloprop-<NUM>-ene-<NUM>-carboxylate (<NUM>, <NUM> mmol) in THF/H<NUM>O <NUM>:<NUM> (<NUM>), then the reaction mixture was heated to reflux for <NUM>. The cold reaction mixture was concentrated in vacuo, diluted with H<NUM>O (<NUM>) and extracted with Et<NUM>O (<NUM> x <NUM>). phase was acidified to pH <NUM> with <NUM>% aq. HCl, then re-extracted with Et<NUM>O (<NUM> x <NUM>). phase was dried (Na<NUM>SO<NUM>), concentrated to afford quantitatively pure acid <NUM>-octylcycloprop-<NUM>-ene-<NUM>-carboxylic acid. This latter was used crude, without distillation, for the next hydrogenation step.

<NUM>H-NMR: <NUM> (brs, <NUM> OH); <NUM> (s, <NUM>); <NUM> (tt, J = <NUM>, <NUM>, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM> (dquint, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (t) ; <NUM> (t); <NUM> (d); <NUM> (q).

of <NUM>-octylcycloprop-<NUM>-ene-<NUM>-carboxylic acid (<NUM>, <NUM> mmol) in AcOEt (<NUM>) was hydrogenated over Lindlar cat (<NUM>, <NUM>% Pd/CaCO<NUM>) for <NUM> (theor. <NUM> H<NUM>). After full conversion, the reaction mixture was filtered through a short path of Celite®, then concentrated in vacuo and bulb-to-bulb distilled to afford quantitatively a mixture comprising <NUM>% of cis-(1SR,2RS)-<NUM>-octylcyclopropanecarboxylic acid and <NUM>% of trans-(1SR,2SR)-<NUM>-octylcyclopropanecarboxylic acid.

Analyses in accord with those obtained for the optically active version, as described in Example <NUM>.

of ethyl <NUM>-octylcycloprop-<NUM>-ene-<NUM>-carboxylate ester (<NUM>, <NUM> mmol) in AcOEt (<NUM>) was hydrogenated over Lindlar cat (<NUM>, <NUM>% Pd/CaCO<NUM>) for <NUM> (theor. <NUM> H<NUM>). After full conversion, the reaction mixture was filtered through a short path of Celite®, then concentrated in vacuo and bulb-to-bulb distilled to afford quantitatively ethyl <NUM>-octylcyclopropane-<NUM>-carboxylate with a cis : trans ratio of <NUM> : <NUM>.

<NUM>H-NMR: <NUM> (q, J = <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM>,<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t) ; <NUM> (t) ; <NUM> (t) ; <NUM> (t) ; <NUM> (d) ; <NUM> (d); <NUM> (q); <NUM> (q); <NUM> (t).

A <NUM>% aq. LiOH (<NUM>) was added to a soln. of ethyl cis-<NUM>-octylcyclopropane-<NUM>-carboxylate (<NUM>, <NUM> mmol) in MeOH (<NUM>) at <NUM>. The reaction mixture was stirred at this temperature for <NUM>, then acidified with 2N aq. HCl, and extracted with Et<NUM>O. The organic layer was dried (Na<NUM>SO<NUM>), concentrated to afford a mixture comprising <NUM>% of cis-(1SR,2RS)-<NUM>-octylcyclopropanecarboxylic acid and <NUM>% of trans-(1SR,2SR)-<NUM>-octylcyclopropanecarboxylic acid in <NUM>% yield. Analyses in accord with those obtained for the optically active version, as described in Example <NUM>.

Obtained from the known undec-<NUM>-yn-<NUM>-ol [<NPL>] according to the procedure published in <NPL>. Then purification by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>/<NUM> to <NUM>/<NUM>) to reach a stereochemical purity of <NUM>% (+)-cis-(<NUM>,2R)-<NUM>-octylcyclopropanecarboxylic acid and <NUM>% (-)-trans-(1R,2R)-<NUM>-octylcyclopropanecarboxylic acid. Rf = <NUM> (c-hexane/AcOEt <NUM>:<NUM>). [α]D<NUM> = +<NUM> (c = <NUM>, CHCl<NUM>). <NUM>H-NMR: <NUM> (brs, <NUM> OH); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (hept, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>). <NUM>C-NMR: <NUM> (s); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (q).

of ethyl diazoacetate (<NUM>%/w in CH<NUM>Cl<NUM>, <NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>) was added via a syringe pump in <NUM> to a mixture of <NUM>-undecyne (<NUM>, <NUM> mmol) and Rh<NUM>(OAc)<NUM> (<NUM>, <NUM> mmol). After <NUM> at <NUM>, the solvent was removed in vacuo, and the residue was purified by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>) to afford the desired (+-)-ethyl <NUM>-nonyl-<NUM>-cyclopropene-<NUM>-carboxylate in <NUM>% yield (based on the ethyl diazoacetate; <NUM>% yield based on used/recuperated <NUM>-undecyne).

<NUM>H-NMR: <NUM> (brq, J = <NUM>, <NUM>); <NUM> (dq, J = <NUM>, <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM> (quint, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (q); <NUM> (q).

of (+-)-ethyl <NUM>-nonyl-<NUM>-cyclopropene-<NUM>-carboxylate (<NUM>, <NUM> mmol) in AcOEt (<NUM>) was hydrogenated over Lindlar cat (<NUM>, <NUM>% Pd/CaCO<NUM>) for <NUM> (theor. <NUM> H<NUM>). After full conversion, the reaction mixture was filtered through a short path of Celite®, then concentrated in vacuo and bulb-to-bulb distilled to afford quantitatively the saturated ethyl <NUM>-nonylcyclopropanecarboxylate with a cis : trans ratio of <NUM> : <NUM>. Bp: <NUM>/<NUM> mbar.

<NUM>H-NMR: <NUM> (q, J = <NUM>, <NUM>); <NUM>,<NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (d); <NUM> (q); <NUM> (q) ; <NUM> (t).

LiOH (<NUM>, <NUM> mmol) was added to a soln. of (+-)-ethyl <NUM>-nonyl-<NUM>-cyclopropene-<NUM>-carboxylate (<NUM>, <NUM> mmol) in THF/H<NUM>O <NUM>:<NUM> (<NUM>), then the reaction mixture was heated to reflux for <NUM>. The cold reaction mixture was concentrated in vacuo, diluted with H<NUM>O (<NUM>) and extracted with Et<NUM>O (<NUM> x <NUM>). Phase was acidified to pH <NUM> with <NUM>% aq. HCl, then re-extracted with Et<NUM>O (<NUM> x <NUM>). phase was dried (Na<NUM>SO<NUM>), concentrated to afford quantitatively pure (+-)-<NUM>-nonyl-<NUM>-cyclopropene-<NUM>-carboxylic acid. This latter was used crude, without distillation, for the next hydrogenation step.

<NUM>H-NMR: <NUM> (brs, <NUM>) ; <NUM> (brq, J = <NUM>, <NUM>); <NUM> (brt, J = <NUM>, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM> (brquint, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (q).

A <NUM>% aq. LiOH (<NUM>) was added to a soln. of (1RS,2SR)-<NUM>-nonylcyclopropanecarboxylate (<NUM>, <NUM> mmol) in MeOH (<NUM>) at <NUM>. The reaction mixture was stirred at this temperature for <NUM>, then acidified with 2N aq. HCl, and extracted with Et<NUM>O. The org layer was dried (Na<NUM>SO<NUM>), concentrated to afford a mixture comprising <NUM>% of cis-(1RS,2SR)-<NUM>-nonylcyclopropane-<NUM>-carboxylic acid and <NUM>% of trans-(1RS,2RS)-<NUM>-nonylcyclopropanecarboxylic acid in <NUM>% yield.

Also obtained quantitatively by Lindlar hydrogenation of (+-)-<NUM>-nonyl-<NUM>-cyclopropene-<NUM>-carboxylic acid, according to the conditions described above. Bp <NUM>/<NUM> mbar.

<NUM>H-NMR: <NUM> (brs, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (brquint, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s), <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (<NUM>t); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (q).

A E/Z mixture of commercially available <NUM>-undec-<NUM>-enal (<NUM>, <NUM> mmol), AcOK (<NUM>, <NUM> mmol) in Ac<NUM>O (<NUM>, <NUM>, <NUM> mmol) was refluxed for <NUM>. The cold reaction mixture was poured onto ice/H<NUM>O ( (<NUM>). Et<NUM>O (<NUM>) was added and the partitioned org. phase was washed with satd. NaHCO<NUM> until neutrality (solid NaHCO<NUM> was also added), then brine. phase was dried (Na<NUM>SO<NUM>), concentrated, and the resulting oil was purified by bulb-to-bulb distillation to afford undeca-<NUM>,<NUM>-dien-<NUM>-yl acetate in <NUM>% yield as a ca. <NUM>:<NUM>:<NUM>:<NUM> mixture of stereoisomers.

<NUM>H-NMR of the mixture: <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (s, <NUM>); <NUM> (s, <NUM>); <NUM> (s, <NUM>); <NUM> (s, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR (tentatively deduced from the mixture): major <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (<NUM>t); <NUM> (<NUM>t); <NUM> (t); <NUM> (q); <NUM> (q); main medium <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (<NUM>t); <NUM> (<NUM>t); <NUM> (t); <NUM> (q); <NUM> (q); minor medium <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (<NUM>t); <NUM> (<NUM>t); <NUM> (t); <NUM> (q); <NUM> (q); minor <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (<NUM>t); <NUM> (<NUM>t); <NUM> (t); <NUM> (q); <NUM> (q).

Undeca-<NUM>,<NUM>-dien-<NUM>-yl acetate (<NUM>, <NUM> mmol), maleic acid (<NUM>, <NUM> mmol), [(Cp*)Ru(<NUM>,<NUM>-COD)][BF<NUM>] (<NUM>, <NUM> mmol), and acetone (<NUM>) were charged in an autoclave under N<NUM>. The autoclave was purged and then pressurized with H<NUM>. After <NUM> at <NUM>/<NUM> bar, the autoclave was cooled down, depressurized and the reaction mixture was diluted with AcOEt (<NUM>). Filtration over SiO<NUM> (<NUM>) and concentration afforded an oil which was purified by CC/SiO<NUM> (<NUM>, cyclohexane/AcOEt <NUM>:<NUM>) to afford (Z)-undec-<NUM>-en-<NUM>-yl acetate in <NUM>% yield as a <NUM>:<NUM> mixture of Z/E stereoisomer.

<NUM>H-NMR: (Z)-isomer <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM> (q, J = <NUM>, <NUM>); <NUM> (s, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>). (E)-isomer tentatively deduced from the mixture <NUM>-<NUM> (m, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (s, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: (Z)-isomer <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t) ; <NUM> (t) ; <NUM> (<NUM>t) ; <NUM> (t) ; <NUM> (t); <NUM> (t); <NUM> (q); <NUM> (q). (E)-isomer tentatively deduced from the mixture <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (q); <NUM> (q).

(Z)-undec-<NUM>-en-<NUM>-yl acetate (<NUM>, <NUM> mmol) in MeOH (<NUM>) was saponified with KOH (<NUM>, <NUM> mmol) at <NUM> for <NUM>. The cold reaction mixture was concentrated under vacuo, and the residue was partitioned between Et<NUM>O (<NUM>) and H<NUM>O (<NUM>). phase was washed with brine, dried (Na<NUM>SO<NUM>), then concentrated. Purification by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>) afforded quantitatively (Z)-undec-<NUM>-en-<NUM>-ol as a <NUM>:<NUM> mixture of Z/E stereoisomer.

<NUM>H-NMR: (Z)-isomer <NUM>-<NUM> (m, <NUM>); <NUM> (brt, J = <NUM>, <NUM>); <NUM> (q, J = <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>). (E)-isomer <NUM>-<NUM> (m, <NUM>); <NUM> (d, J = <NUM>, <NUM>); <NUM> (q, J = <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: (Z)-isomer <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (q). (E)-isomer <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (q).

Et<NUM>Zn (<NUM>/hexane, <NUM>, <NUM> mmol) was added to a soln. of <NUM>:<NUM> (Z/E)-undec-<NUM>-en-<NUM>-ol (<NUM>, <NUM> mmol) in hexane (<NUM>) at -<NUM>, followed by CH<NUM>I<NUM> (<NUM>, <NUM> mmol). The reaction mixture was slowly equilibrated at <NUM> and after <NUM> is cooled down again at -<NUM>. NH<NUM>Cl (<NUM>) is added dropwise and the reaction mixture is equilibrated to <NUM>. After partition, the aq. phase is washed with Et<NUM>O (<NUM> x <NUM>). The combined org. phases are washed with brine, dried (Na<NUM>SO<NUM>), concentrated, and the resulting orange oil is purified by CC/SiO<NUM> (cyclohexane/Et<NUM>O <NUM>:<NUM> to <NUM>:<NUM>) to afford cis-<NUM>-octylcyclopropyl-<NUM>-methanol (<NUM>% yield) as a colorless <NUM>:<NUM> cis/trans mixture.

Eventually, further purification by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>/<NUM> to <NUM>/<NUM>) then bulb-to-bulb distillation afforded pure <NUM>-octylcyclopropyl-<NUM>-methanol with a cis : trans ratio of <NUM> : <NUM> in <NUM>% yield.

Rf = <NUM> (<NUM>:<NUM>). Bp: <NUM>/<NUM> mbar.

<NUM>H-NMR: cis-isomer3. <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); -<NUM> (q, J = <NUM>, <NUM>). trans-isomer <NUM> (dq, J = <NUM>, <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM> (q, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>). <NUM>C-NMR: cis-isomer <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (d); <NUM> (q); <NUM> (t). trans-isomer <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (d); <NUM> (q); <NUM> (t).

Jones reagent (CrO<NUM>, <NUM> in <NUM>% H<NUM>SO<NUM>, <NUM>, <NUM> mmol) was added dropwise to a soln. of <NUM>-octylcyclopropyl-<NUM>-methanol alcohol (<NUM>, <NUM> mmol <NUM>:<NUM> cis/trans) in acetone (<NUM>) at <NUM>. After <NUM> at <NUM>, cold H<NUM>O (<NUM>) was added and the mixture was extracted with pentane (<NUM> x <NUM>). phase was extracted with <NUM>% NaOH (<NUM>). This basic aq. phase was acidified with <NUM>% aq. HCl, and partitioned with pentane (<NUM> x <NUM>). phase was washed with brine (<NUM> x <NUM>), dried (Na<NUM>SO<NUM>), filtered, concentrated to afford the acid mixture in <NUM>% yield (<NUM>:<NUM> cis-(1SR,2RS)-<NUM>-octylcyclopropanecarboxylic acid / trans-(1RS,2RS)-<NUM>-octylcyclopropanecarboxylic acid). Analyses in accord with those obtained for the optically active version, as described in Example <NUM>.

Et<NUM>N (<NUM>, <NUM> mmol) was added at <NUM> to a soln. of ethyl <NUM>-(triphenylphosphoranylidene)acetate (<NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>). After <NUM>. at <NUM>, a soln. of nonanoyl chloride (<NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>) was added dropwise at <NUM>. After <NUM> at <NUM>, the solvent was concentrated under vacuum. The residue was diluted with Et<NUM>O (<NUM>), then filtered. This process was repeated four times to precipitate Ph<NUM>PO. A further purification over SiO<NUM> (<NUM>, cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>) afforded pure ethyl undeca-<NUM>,<NUM>-dienoate in <NUM>% yield.

<NUM>H-NMR: <NUM> (q, J = <NUM>, <NUM>); <NUM> (hex, J = <NUM>, <NUM>); <NUM> (dq, J = <NUM>, <NUM>, <NUM>); <NUM> (dq, J = <NUM>, <NUM>, <NUM>); <NUM> (quint, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (q); <NUM> (q).

of ethyl undeca-<NUM>,<NUM>-dienoate ester (<NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>) was added dropwise in <NUM>. of DIBAH (<NUM> in toluene, <NUM>, <NUM> mmol) in CH<NUM>Cl<NUM> (<NUM>) at <NUM>. After <NUM>, MeOH (<NUM>) was added carefully, followed by 3N HCl. phase was extracted with Et<NUM>O. phase was washed with <NUM>% NaOH, dried (Na<NUM>SO<NUM>), filtered, and concentrated under vacuum to afford in <NUM>% yield pure undeca-<NUM>,<NUM>-dien-<NUM>-ol (<NUM>% yield when used without further purification in the next step).

<NUM>H-NMR: <NUM>-<NUM> (m, <NUM>); <NUM> (brs, <NUM>); <NUM> (dq, J = <NUM>, <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM> (quint, J = <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: <NUM> (s); <NUM> (d); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (t); <NUM> (q).

Et<NUM>Zn (<NUM> in hexane, <NUM>, <NUM> mmol) was added to ClCH<NUM>CH<NUM>Cl (<NUM>) and this soln. was cooled down to -<NUM>. CH<NUM>I<NUM> (<NUM>, <NUM> mmol) in ClCH<NUM>CH<NUM>Cl (<NUM>) was added dropwise in <NUM> via a syringe pump, while a white precipitate was formed. After an additional <NUM> at - <NUM>, a soln. of undeca-<NUM>,<NUM>-dien-<NUM>-ol (<NUM>, <NUM> mmol) in ClCH<NUM>CH<NUM>Cl (<NUM>) was added dropwise in <NUM>. After an additional period of <NUM> at - <NUM>, the temp was equilibrated to -<NUM>, then slowly to <NUM>. The white soln. was poured carefully into sat. NH<NUM>Cl, then partitioned with Et<NUM>O. phase was washed with <NUM>% HCl, then aq. NaHCO<NUM>, then H<NUM>O, and dried (Na<NUM>SO<NUM>). Concentration afforded a <NUM>:<NUM> mixture of stereoisomers. Further purification over SiO<NUM>/AgNO<NUM> with cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>) afforded each of the diastereoisomers in <NUM>% yield, respectively.

<NUM>H-NMR: Major (Z) isomer Rf <NUM> (cyclohexane/AcOEt <NUM>:<NUM>) <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>). Minor (E) isomer Rf = <NUM> (cyclohexane/AcOEt <NUM> :<NUM>) <NUM> (qq, J = <NUM>, <NUM>, <NUM>); <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM> (dd, J = <NUM>, <NUM>, <NUM>); <NUM> (q, J = <NUM>, <NUM>); <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (t, J = <NUM>, <NUM>).

<NUM>C-NMR: Major (Z) isomer Rf <NUM> (cyclohexane/AcOEt <NUM>:<NUM>) <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (d); <NUM> (q); <NUM> (t). Minor (E) isomer Rf = <NUM> (cyclohexane/AcOEt <NUM>:<NUM>) <NUM> (s); <NUM> (d); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (d); <NUM> (q); <NUM> (t).

Usual hydrogenation of crude (<NUM>-octylidenecyclopropyl)methanol (as a <NUM>:<NUM> (Z)/(E) mixture) over Lindlar catalyst afforded quantitatively a <NUM>:<NUM> cis/trans mixture of <NUM>-octylcyclopropyl-<NUM>-methanol.

Analyses corresponding to those reported in Example <NUM>, Step <NUM> for <NUM>-octylcyclopropyl-<NUM>-methanol.

Usual Jones oxidation of a <NUM>:<NUM> cis/trans mixture of <NUM>-octylcyclopropyl-<NUM>-methanol as above, followed by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>:<NUM>) purification and bulb-to-bulb distillation afforded a <NUM>:<NUM> mixture of cis-(1SR,2RS)-<NUM>-octylcyclopropanecarboxylic acid / trans-(1RS,2RS)-<NUM>-octylcyclopropanecarboxylic acid.

Analyses in accord with those of the optically active stereoisomers, as described in Example <NUM> and <NUM>.

of ethyldiazoacetate (<NUM>%/CH<NUM>Cl<NUM>, <NUM>, <NUM> mmol) in <NUM>-decene (<NUM>, <NUM> mmol) was added dropwise in <NUM> to a suspension of anh. CuSO<NUM> (<NUM>, <NUM> mmol) in <NUM>-decene (<NUM>, <NUM> mmol) at <NUM>. The addition is accompanied by N<NUM> evolution. After completion, the temperature was maintained until evolution stopped. CuSO<NUM> was filtered, and the reaction mixture was purified by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>:<NUM> to <NUM>:<NUM>). Unreacted <NUM>-decene was recuperated, as well as ester ethyl cis-<NUM>-octylcyclopropane-<NUM>-carboxylate in <NUM>% yield, (<NUM>% yield based on used/recuperated) as a <NUM>:<NUM> cis/trans mixture of stereoisomer.

Analyses of the cis-diastereoisomer are reported in Example <NUM>. <NUM>C-NMR: trans isomer tentatively deduced from the mixture: <NUM> (s); <NUM> (t); <NUM> (t) <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (q); <NUM> (q); <NUM> (t).

A <NUM>:<NUM> cis/trans mixture of ethyl cis-<NUM>-octylcyclopropane-<NUM>-carboxylate (<NUM>, <NUM> mmol), and LiOH (<NUM>, <NUM> mmol) in THF (<NUM>) and H<NUM>O (<NUM>) was heated at reflux for <NUM>. The cold reaction mixture was partitioned between Et<NUM>O (<NUM> x <NUM>) and H<NUM>O (<NUM> x <NUM>). Phase was acidified to pH <NUM> with <NUM>% HCl, then re-extracted with Et<NUM>O (<NUM> x <NUM>), and washed with H<NUM>O (<NUM> x <NUM>), dried (Na<NUM>SO<NUM>), then concentrated to afford a <NUM>% pure <NUM>:<NUM> mixture of cis-(1SR,2RS)-<NUM>-octylcyclopropanecarboxylic acid / trans-(1SR,2SR)-<NUM>-octylcyclopropanecarboxylic acid in <NUM>% yield. Analyses in accord with those of the optically active stereoisomers, as described in Example <NUM> and in Example <NUM>.

Obtained from the known undec-<NUM>-yn-<NUM>-ol [<NPL>] according to the procedure published in <NPL>. Then purification by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>/<NUM> to <NUM>/<NUM>) to reach a chemical purity of <NUM>%. Rf = <NUM> (c-hexane/AcOEt <NUM>:<NUM>). [α]D<NUM> = +<NUM> (c = <NUM>, CHCl<NUM>). <NUM>H-NMR: <NUM> (brs, <NUM> OH); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>); <NUM> (t, J = <NUM>, <NUM>); <NUM> (dt, J = <NUM>, <NUM>, <NUM>). <NUM>C-NMR: <NUM> (s); <NUM> (t); <NUM> (t); <NUM> (t); <NUM> (<NUM>t); <NUM> (t); <NUM> (d); <NUM> (t); <NUM> (d); <NUM> (t) ; <NUM> (q).

Obtained from the known undec-<NUM>-yn-<NUM>-ol [<NPL>] according to the procedure published in <NPL>. Then purification by CC/SiO<NUM> (cyclohexane/AcOEt <NUM>/<NUM> to <NUM>/<NUM>) to reach a stereochemical purity of <NUM>% (-)-cis-(1R,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid and <NUM>% (+)-trans-(<NUM>,<NUM>)-<NUM>-octylcyclopropanecarboxylic acid. Bp: <NUM>/<NUM> mbar. [α]D<NUM> = -<NUM> (c = <NUM>, CHCl<NUM>). For analyses, see Example <NUM>.

A perfuming composition for fine fragrance was prepared by admixing the following ingredients:.

The addition of <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol to the above-described fine fragrance composition imparted to the latter an intense and natural incense effect which brings a lot of strength and diffusion to the fragrance. The invention's composition of matter blends particularly well with citrus elements such as <NUM>,<NUM>-dimethoxy-<NUM>,<NUM>,<NUM>-trimethyl-<NUM>-hexene, (E)-<NUM>-dodecenaL, (Z)-<NUM>-dodecenal and dodecanal, woody-powdery elements such as <NUM>-(<NUM>,<NUM>,C-<NUM>,T-<NUM>-tetramethyl-R-<NUM>-cyclohexyl)-<NUM>-buten-<NUM>-one and mixture of <NUM>-(<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>,<NUM>-octahydro-<NUM>,<NUM>,<NUM>,<NUM>-tetramethyl-<NUM>-naphtyl)ethan-<NUM>-one and isomers and amber elements, in particular (-)-(3aR,5aS,9aS,9bR)-3a,<NUM>,<NUM>,9a-tetramethyldodecahydronaphtho[<NUM>,<NUM>-b]furan.

The addition of the same amount of <NUM> parts by weight of the comparative composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol imparted an incense and citrus character but allied with fatty and dusty notes. The fine fragrance composition obtained by this addition is devoid of clean effect.

The addition of the same amount of <NUM> parts by weight of the comparative composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol imparted a similar effect than with the addition of comparative composition of matter described in Example <NUM> with stronger undesired fatty and dusty notes. Said composition was also less powerful than the invention's composition.

The addition of the same amount of <NUM> parts by weight of the comparative composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol imparted mainly an unpleasant fatty and dusty characters. Said composition was also less powerful than the invention's composition.

The addition of the same amount of <NUM> parts by weight of the comparative composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol imparted mainly an unpleasant fatty character. Said composition was also less powerful than the invention's composition.

The eau de toilette was prepared by adding <NUM>% by weight, relative to the total weight of the eau de toilette, of the invention's composition of example <NUM> into ethanol.

The liquid detergent is prepared by adding <NUM> to <NUM> % by weight, relative to the total weight of the liquid detergent, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol into the unperfumed liquid detergent formulation of Table <NUM> under gentle shaking.

The softener is prepared by weighting Methyl bis[ethyl (tallowate)]-<NUM>- hydroxyethyl ammonium methyl sulfate which was heated at <NUM>. Then Water and <NUM>,<NUM>-benzisothiazolin-<NUM>-one are placed in the reactor and are heated at <NUM> under stirring. To the above mixture is added Methyl bis[ethyl (tallowate)]-<NUM>- hydroxyethyl ammonium methyl sulfate. The mixture is stirred <NUM> minutes and CaCl<NUM> is added. Then <NUM> to <NUM>% by weight, relative to the total weight of the softener, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol is added. The mixture is stirred <NUM> minutes and is cooled down to room temperature under stirring (viscosity measure : result <NUM> +/- <NUM> mPas. (shear rate <NUM> sec-<NUM>)).

The shampoo is prepared by dispersed in water Polyquaternium-<NUM>. The remaining ingredients of phase A are mixed separately by addition of one after the other while mixing well after each adjunction. This pre-mix is added to the Polyquaternium-<NUM> dispersion and mixed for another <NUM>. Then, the premixed phase B and the premixed Phase C are added (Monomuls <NUM>-<NUM> is heated to melt in Texapon NSO IS) while agitating. Phase D and Phase E are added while agitating. PH is adjusted with citric acid solution till pH: <NUM> - <NUM> leading to an unperfumed shampoo formula.

The perfumed shampoo is prepared by adding <NUM> to <NUM>% by weight, relative to the total weight of the shampoo, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol into the unperfumed shampoo formulation of Table <NUM> under gentle shaking.

The shower gel is prepared by adding <NUM> to <NUM>% by weight, relative to the total weight of the shower gel, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol into the unperfumed shower gel formulation of Table <NUM> under gentle shaking.

The transparent shower gel is prepared by adding <NUM> to <NUM>% by weight, relative to the total weight of the shower gel, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol into the unperfumed shower gel formulation of Table <NUM> under gentle shaking.

The shampoo is prepared by dispersed in water and Tetrasodium EDTA, Guar Hydroxypropyltrimonium Chloride and Polyquaternium-<NUM>. NaOH <NUM>% solution (Phase B) is added once Phase A is homogeneous. Then, the premixed Phase C is added. and mixture is heated to <NUM>. Phase D ingredients are added and mixed till homogeneous. The mixture is cooled down. At <NUM>, Phase E ingredients are added while mixing. Final viscosity is adjusted with <NUM>% NaCl solution and pH of <NUM>-<NUM> is adjusted with <NUM>% NaOH solution.

The perfumed pearly shampoo is prepared by adding <NUM> to <NUM>% by weight, relative to the total weight of the shampoo, of the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol into the unperfumed shampoo formulation of Table <NUM> under gentle shaking.

Anhydrous antiperspirant spray formulation is prepared by using a high speed stirrer. Silica and Quaternium-<NUM>-hectorite are added to the mixture of isopropyl myristate and cyclomethicone. Once completely swollen, aluminium chlorohydrate is added portion-wise under stirring until the mixture becomes homogeneous and without lumps. Then a perfume oil being the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol is added.

Deodorant spray emulsion formulation is prepared by mixing and dissolving all the ingredients according to the sequence of Table <NUM>. Aerosol cans are filled, and the propellant is crimped and added. Aerosol filling: <NUM>% active solution <NUM>% propane / butane (<NUM> bar).

Deodorant stick formulation is btained by weighing all the components of Part A and heating to <NUM>-<NUM>. Ceteareth-<NUM> is added once the other Part A ingredients are mixed and heated. When the Ceteareth-<NUM> is dissolved, stearic acid is added. Part B is prepared by dissolving Triclosan in <NUM>,<NUM>-propylene glycol. Evaporated water is compensated. Then, slowly, under mixing, Part B is poured into Part A. A perfume oil being the invention's composition of Example <NUM> comprising <NUM> parts by weight of the invention's composition of matter described in Example <NUM> diluted at <NUM>% in dipropyleneglycol (Phase C) is added under gentle shaking. To stock, a plastic bag is put into the bucket to be sealed after cooling. Moulds were filled at about <NUM>.

Part A is prepared by sprinkling little-by-little the hydroxyethylcellulose into the water, whilst rapidly stirring with a turbine until the hydroxyethylcellulose is entirely swollen giving a limpid gel. Part B is slowly poured into Part A, whilst continuing stirring until the entire mixture is homogeneous. Then Parts C and D are added under gentle shaking.

Claim 1:
A composition of matter comprising a compound of formula (I)
<CHM>
wherein n is <NUM> or <NUM>; the weight ratio of the cis-diastereoisomers to the trans-diastereoisomers is comprised in the range between <NUM>:<NUM> and <NUM>:<NUM> and comprising at least <NUM>% w/w of cis-(<NUM>,2R) diastereoisomer, the percentage being relative to the total weight of the composition of matter.