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1 2012

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Adaszyńska M., Swarcewicz M.

Wiadomości Chemiczne

2012

[Z] 66, 5-6

543-562

Menthol and new cooling compounds are widely used to improve modern toothpastes, gums, breath fresheners, cosmetic lotions, deodorants, shaving gels, and shaving aid composites. This paper reviews the use of menthol and new classes of cooling agents, that have been discovered since the 1970s, in cosmetic preparations. We have presented here 57 chemical structures. In addition, we briefly touch upon cold receptors and mechanism of action. Finally, we add up, recent findings on the production of cooling ingredients in the world. The underlying process in thermoreception depends on ion transport across cellular membranes. Thermoreceptors belong to a class of transient receptor potential (TRP) channels. Among them are temperature-sensitive thermoreceptors TRPM8 or TRPA 1. Certain types of chemical agonists activate the same thermoTRP channels, as for example menthol or icilin. Only the (–)-menthol enantiomer possesses clean, desirable minty odor and intense cooling properties (Fig. 1). Natural menthol is normally about 99.0% to 99.6% pure, with the remaining impurities being other constituents found in the cornmit oil. Synthetic (–)-menthol is normally about 99.8% pure and has less of the minty top note than the natural menthol. The other natural and synthetic compounds being menthol-related coolants are showed in Figure 3, as for example, menthone 1,2-glycerol ketal (17). From among 3-carboxamide-p-menthane derivatives as commercial cooling agents (Fig. 4), there are for example N-ethyl-pmenthane- 3-carboxamide (25) as WS-3 and [ethyl 3-(p-menthane-3-carboxamido) acetate] as WS-5, which is currently the coldest of all commercial cooling agents (27). Other examples of recently discovered carboxamide coolants belong to a series of analogs of WS-23 (28). Of particular interest are various aryl p-menthane-3- carboxamides, such as N-benzo[1,3]dioxol-5-yl-3-p-menthanecarboxamide (36), which was reported to have 100 times more cooling intensity than menthol (Fig. 6). In 2010, Furrer disclosed a series of new p-menthane carboxamide and WS-23 analogs as cooling agents [56]. Three particularly potential cooling agents 50, 51 and 52 are shown in Figure 9.