Patent number 8754259 is assigned to
The following quote was obtained by the news editors from the background information supplied by the inventors: "Coolants or compounds that have a physiological cooling effect particularly on oral and other mucosal surfaces and skin are common ingredients in a wide variety of consumer products including edible compositions and personal and health care compositions and in flavor or perfume compositions for use in such products. Examples of edible compositions include confectionery, candies, chocolate, chewing gum, beverages and oral medicines. Personal care compositions for application to the skin, hair and mucosal surfaces include lotions or creams, skin cleansers, shampoos and conditioners, wipes and towelettes and cosmetic products such as lipsticks and foundations. A particular class of personal and health care compositions to which the present invention relates is for oral and throat care, which include products in powder, paste or liquid forms and which on being used are retained for a time sufficient to contact the surface and the internal mucous membrane of the oral or nasal cavities or the pharynx. Such products include for example, mouthwashes, dental and throat lozenges, gargles, chewing gum, dentifrice or toothpastes, toothpicks, dental tablets and powders and topical solutions for application in dental treatment, as well as cough-syrups, chewable antacids and digestion promoting preparations.
"The pleasant cooling sensation provided by coolants contributes to the appeal and acceptability of the products. In particular, oral care products such as dentifrices and mouthwashes are formulated with coolants because they provide breath freshening effects and a clean, cool, fresh feeling in the mouth.
"A large number of coolant compounds of natural or synthetic origin have been described. The most well-known compound is menthol, particularly l-menthol, which is found naturally in peppermint oil, notably of Mentha arvensis L and Mentha viridis L. Of the isomers of menthol, the l-isomer occurs most widely in nature and is typically what is referred by the name menthol having coolant properties. L-menthol has the characteristic peppermint odor, has a clean fresh taste and exerts a cooling sensation when applied to the skin and mucosal surfaces. Other isomers of menthol (neomenthol, isomenthol and neoisomenthol) have somewhat similar, but not identical odor and taste, i.e., having disagreeable notes described as earthy, camphor, musty. The biggest difference among the isomers is in their cooling potency. L-menthol provides the most potent cooling, i.e., having the lowest cooling threshold of about 800 ppb, i.e., the concentration where the cooling effect could be clearly recognized. At this level, there is no cooling effect for the other isomers. For example, d-neomenthol is reported to have a cooling threshold of about 25,000 ppb and l-neomenthol about 3,000 ppb. [
"Among synthetic coolants, many are derivatives of or are structurally related to menthol, i.e., containing the cyclohexane moiety, and derivatized with functional groups including carboxamide, ketal, ester, ether and alcohol. Examples include the .rho.-menthanecarboxamide compounds such as N-ethyl-.rho.-menthan-3-carboxamide, known commercially as 'WS-3', and others in the series such as WS-5 (N-ethoxycarbonylmethyl-.rho.-menthan-3-carboxamide), WS-12 [N-(4-methoxyphenyl)-.rho.-menthan-3-carboxamide] and WS-14 (N-tert-butyl-.rho.-menthan-3-carboxamide). Examples of menthane carboxy esters include WS-4 and WS-30. An example of a synthetic carboxamide coolant that is structurally unrelated to menthol is N,2,3-trimethyl-2-isopropylbutanamide, known as 'WS-23'. Additional examples of synthetic coolants include alcohol derivatives such as 3-(l-menthoxy)-propane-1,2-diol known as TK-10, isopulegol (under the tradename Coolact P) and .rho.-menthane-3,8-diol (under the tradename Coolact 38D) all available from
"Many of the compounds above including menthol have relatively low potency and the duration of the cooling effect is typically short-lived. Thus, it is necessary to include fairly high levels of such compounds when formulating products, which increases cost. In addition, many of these compounds are relatively high cost ingredients since they are expensive to manufacture on an industrial scale. Therefore, compounds with high cooling potency and long lasting sensory effect are highly sought that will require only small amounts for incorporation in a variety of consumer products to provide high impact and long-lasting effect. Such potent and long lasting coolant compounds have recently been described for example in WO 2005/049553A1 to
"Similar to other commercially available synthetic coolants, the new Givaudan Evercool (G-180) coolant is a relatively expensive ingredient. It is believed that this is due to the high cost of producing, purifying and solubilizing the material.
In addition to the background information obtained for this patent, NewsRx journalists also obtained the inventors' summary information for this patent: "The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Neoisomers of other derivatives including menthyl esters, menthyl ethers, menthanecarboxy esters and other N-substituted menthanecarboxamides are also prepared and demonstrated to be useful as coolants."
URL and more information on this patent, see: Yelm,
Keywords for this news article include: Esters, Dentistry, Dentifrices, Cyclohexanes, Hydrocarbons, Cycloparaffins, Carboxylic Acids, Organic Chemicals,
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