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Nasycone alkohole terpenowe - właściwości i zastosowania w syntezie cieczy jonowych

Świerczek U.

Technical Issues

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2015

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nr 4

39--46

EN

Terpenes are a group of compounds having a characteristic skeleton composed of connected "head-to-tail" five-carbon isoprene units (C5H8). Their derivatives - terpenoids are more varied, including some alcohols, aldehydes, ketones and acids. In recent years, there has been an increasing interest in terpene alcohols as natural odorous compounds. Menthol, recognized as the aroma of mint, is the most popular. It exhibits an anesthetic and antiseptic activity, therefore it is widely used not only in the perfume industry, but also in cosmetic, pharmaceutical and food industry. The attractiveness of terpene alcohols makes more and more researchers use these compounds as substrates into organic synthesis. It is expected that the new compounds obtained in this way will exhibit undescribed so far interesting application properties. Ionic liquids containing (1R,2S,5R)-(−)-menthol and (1S)-endo-(−)-borneol as a component are an excellent example of this application. The presence of the optically active centers is significant, because thanks to it these terpene alcohols are a source of chirality and can be used in asymmetric synthesis.

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Wybrane substancje chłodzące stosowane w kosmetykach

Adaszyńska M., Swarcewicz M.

Wiadomości Chemiczne

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2012

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[Z] 66, 5-6

543-562

EN

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.

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Modelowanie matematyczne kinetyki ekstrakcji substancji aktywnych z roślin leczniczych w polu ultradźwiękowym

Tal-Figiel B.

Przemysł Chemiczny

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2011

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T. 90, nr 9

1689-1693

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Mentol : komponent chiralnych cieczy jonowych

Feder-Kubis J.

Przemysł Chemiczny

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2010

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T. 89, nr 11

1422-1426