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The present invention relates to novel compounds having a cooling effect on the skin or human mucous membranes, including the oral mucosa and pituitary. Indeed it is described by the patent DEwhich discloses the cleavage of said compound menfhe order to release chromatogrwphie.

This document contains however no mention nor suggestion of any organoleptic properties taste and smell of the compound. Furthermore, the prior art discloses a number of compounds, natural or synthetic origin, including a cooling effect was observed on the skin or human mucous membranes, the best known compound being – – menthol which found in nature in mint oil, including mentha arvensis L and mentha viridis L.

Among the large number of publications in the field of synthetic cooling agents, in particular those derived from menthol, mention should be made to DE-OS describes certain esters of menthol with hydroxylated carboxylic acids, e. EP-A discloses cooling agents which are acetals of certain ketones, especially glycerol ketal of 1-menthone.

To be suitable as an agent refreshing, a compound must meet certain requirements. For the reasons stated above, the use of menthol is limited, and the same for other compounds that are unsuitable for use in certain products.

Moreover, for crhomatographie applications, it is desirable that the cooling effect be of prolonged duration, so that this effect can be seen even a few minutes after the active agent is no longer in contact with the skin or mucous membranes.

Menthol is highly volatile, it does not fulfill this condition, despite its pronounced cooling effect. In most applications, it is more desirable to have cooling agents that do not have a strong odor, as is the case for menthol has the typical smell and pronounced peppermint.

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Finally, a cooling agent must not have an unpleasant taste to an application in the field of flavors possible. Once again, menthol has a bitter taste when fhromatographie in high concentrations. In summary, we can say that the particular menthol, but also other compounds having a cooling effect and above, fill, certainly, some of the conditions outlined above, sought in fresheners “cooling agents”but we always search for new compounds with properties that allow to obtain original effects, and preferably advantageous in that area.

Indeed, the stereoisomerism of the compounds I is dictated by that of the starting menthol and one can thus obtain all stereoisomers sieop the compounds I corresponding to those of menthol. Of these stereoisomers, the compounds I derived from the – – menthol are particularly popular and preferred according to the invention for their pronounced cooling effect when used in the applications described below.

As is apparent from the formula Ithe compounds according to the invention may include an alcohol or methoxy group in the terminal position of mennthe chain. In the context of the present invention, it is preferred to use compounds having chrimatographie methoxy group at the terminal position.


Methoxyacetate – – menthyl has a fruity flavor note head reminiscent menthyl acetate, while the 3. These two compounds are highly appreciated in the field of flavors and, depending on the application, one can use either of these compounds, or both.

For example, in applications where a bitter taste is undesirable, methoxyacetate – – menthyl will preferably be used, then we will use the 3. According to another embodiment of the invention, a methoxyacetate mixture of – – menthyl 3,6-dioxaheptanoate – – menthyl. In these mixtures, the two components may be present in a variety of relative proportions which depend on the effect that is desired.


Indeed, the use of these mixtures to delete certain taste characteristics of either of these two compounds, when they are less preferred in some applications, while enhancing cooling effect. Furthermore, these compounds are also suitable for applications other than in the field of flavors, for example in product tangible or cosmetic treatments.

Thus compounds of the invention can be used in all areas in which a cooling effect is desired to give the products in which they are incorporated. For example, mention should be made drinks such as fruit juices, soft drinks or cold tea, ice cream and sorbets, sweets, confectionery, chewing gum, chewing tobacco, cigarettes, pharmaceuticals, dental products, such as gels and toothpaste, toothpaste water gargles, body and hair care products such as shampoos, shower gels or bath, body deodorants and antiperspirants, aftershave lotions and balms, shaving foams, perfumes, etc.

The proportions in which the compounds of the invention may be incorporated in the different products mentioned above vary in a broad range of values.

For example, one can cite typical concentrations of the order of 0. It should be noted that the concentrations of compounds of the invention used in these applications depend on both the product to be flavored and on the desired effect.

Ainsi par exemple, dans des applications telles que boissons et bonbons, on utilisera typiquement des concentrations de l’ordre de 0.

For example, in applications such as beverages and sweets, concentrations typically used in the range of 0. The syntheses that are suitable for the products of formula I all use menthol as the starting material. The reaction proceeds under catalysis of an acid, such as p-toluenesulfonic acid, phosphoric acid or any acid known for this type of esterification.

Preferably, the reaction is carried out in a solvent which allows separation of the water formed by azeotropic distillation, such as toluene, benzene or xylene.

This esterification is performed under conditions similar to those described in the previous paragraph. As qu’alcoolate, one can use the alcoholate of an alkali metal, preferably sodium.

For the Williamson reaction, preferably using an aprotic polar solvent such as, for example, dimethylformamide.

After the reaction, the compounds of formula I are isolated and purified by standard techniques, such as for example distillation or chromatography.

The invention will now be described in more detail in the following examples in which the temperature is indicated in surr Celsius and the abbreviations have the usual meaning in the art.

The water evolved during the reaction is separated by azeotropic chrlmatographie. Refluxed for 3 hours a solution of – – menthol 5 g, 32 mmolacid 2-methoxyethoxy acetic acid 4. Is then distilled in vacuo to obtain 6.

Refluxed for 3 hours a solution of – – menthol 5 g, 32 mmol[2- 2-methoxyethoxy ethoxy] acetic acid 5. This product was synthesized in two steps: This product was synthesized in three steps: The products were then tested and evaluated blindly by flavourists.

After use and rinsing the menthw, it was found for each of these products, a freshness which developed after rinsing and lasted about 15 to 20 minutes.

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Zirop compared with menthol, it was found that the products of the invention mentioned above brought a freshness which had a relative delay effect to that of menthol and, in addition, we did not notice the typical taste thereof. By applying a mixture of the two compounds mentioned above in a dosage of 0. These candies without any additives, were then compared blind, by flavourists candy of the same composition to which had been added some inventive compounds. In the opinion of the tasters, addition of 0.

The addition of the same amount of 3,6-dioxaheptanoate 1R, 3R, 4S menthyl brought a similar freshness and, in addition, a bitterness which reinforced the natural bitterness of grapefruit oil. Was prepared in manner known per se confectionery grapefruit flavor from 30 g of gelatin, g of water, g sugar and g of glucose. This basic confectionery, with no additives, was then compared blind, by flavourists to the candy of the same composition to which had been added some compounds of the invention.


The addition of 0. This sorbet, without any chromatpgraphie, was then compared chromatograpnie, by flavourists sorbets of the same composition to which had been added some inventive compounds. Was then added to this mixture 0. This base of chewing gum, chhromatographie no additives, was then compared blind, by flavourists the chewing gum of the same composition siropp which had been added some inventive compounds.

Thus, the addition of 0. This basic drink with no additives, was then compared blind, by flavourists beverages of the same composition to which had been added some inventive compounds. We prepared two aftershaves for conventional manner from the following ingredients: Both lotions thus obtained were poured into an aerosol vial.

They were then applied in an amount of mg on the forearm and the cheek of each of the two forming the panel and compared on a blind. In the opinion of the panel, the lotion containing the compound according to the invention has shown a refreshing effect than the lotion containing the cooling agent of the prior art in 3 of 4 tests chromatogaphie.

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A compound according to claim 1, characterised in that it is in the form of the isomer of configuration 1R,3R,4S. Use, as a cooling agent, of a compound of formula. Use according to claim 6, characterised in that the compounds are in the form of the d of configuration 1R,3R,4S. Use of a mixture of 1R,3R,4S menthyl methoxyacetate and 1R,3R,4S menthyl 3,6-dioxaheptanoate as a cooling agent. A flavouring composition or flavoured product, containing as an ingredient a compound or a mixture according to one of claims 6 to A flavoured product according to claim 11, in the form of a drink, in particular a fruit juice, a soft drink or a cold tea, an ice cream or sorbet, a sweet, a preserve, a chewing gum, a cigarette, chewing tobacco, a pharmaceutical preparation, a dental-care or body-care product, in particular a dentifrice gel or paste, a mouth wash or a gargle.

A perfumed article, containing as an ingredient a compound or a chromatograpnie according to one of claims 6 to A perfumed article according to claim 13, in the form of a shampoo, a shower chromtaographie bath gel, a body deodorant or antiperspirant, an after-shave lotion or balm, a shaving foam or another cosmetic product, or a perfume.

A process for preparing a compound of formula I as specified in claim 1, characterised in that zur menthol is esterified with a derivative of acetic acid of formula. A process for preparing a compound of formula I as specified in claim 1, characterised in that: Sel sodique de folonne sodium salt of lauryl sulfate. Sel sodique de monofluorophosphate Sodium salt monofluorophosphate. Sel sodique de saccharine sodium salt of saccharin.

Colorant bleu blue chromatogrqphie.

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TiO 2 TiO 2. Parties en poids Parts by weight. Essence de pamplemousse Grapefruit Essence. Sirop de glucose Glucose syrup. Essence d’orange orange oil. Topical pain relief compositions of n,2,3-trimethylisopropylbutamide and chromahographie for using the same.

Disposable absorbent article having side panels with structurally, functionally and visually different regions. Compound having alicyclic structure, meth acrylic acid ester, and process for production of the meth acrylic acid ester. Process for perfuming ingestion of at least two edible fragrance substances having chrojatographie maximum diffusion times; perfuming agent multi components. Nylon prepared by mixing one chromwtographie of dibasic acid mono acid l- menthyl method.

Lambda-menthyl 3-hydroxybutyrate, production thereof, and chilling agent containing said compound as active component. Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same.

Means with physiological kuehleffekt and only to those medium suitable effective connections. Means having a physiological cooling effect, and suitable for these agents active compounds.