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1
Content available Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties
100%
Janus E. , Gano M.
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2017
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tom Vol. 19, nr 3
92--98
EN
Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identified by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf2  or NPf2  were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf2  anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition.
2
Content available remote Modelowanie matematyczne kinetyki ekstrakcji substancji aktywnych z roślin leczniczych w polu ultradźwiękowym
75%
Tal-Figiel B.
Przemysł Chemiczny
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2011
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tom T. 90, nr 9
1689-1693
3
Content available Nasycone alkohole terpenowe - właściwości i zastosowania w syntezie cieczy jonowych
63%
Świerczek U.
Technical Issues
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2015
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tom 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.
4
Content available Wybrane substancje chłodzące stosowane w kosmetykach
63%
Adaszyńska M. , Swarcewicz M.
Wiadomości Chemiczne
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2012
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tom [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.
5
Content available remote Inhibition of the cardiac L-type calcium channel current by the TRPM8 agonist, (-)-menthol
63%
Baylie R. I. , Cheng H. , Langton P. D. , James A. F.
Journal of Physiology and Pharmacology
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2010
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tom 61
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nr 5
6
Biotransformation of menthol by sporulated surface cultures of Penicillium sp. and study of the pathways involved
51%
Esmaeili A. , Hoseiny Zarea A. , Sharafian S. , Safaiyan S. , Rustaiyan A.
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2009
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tom 55
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nr 1
78-83
EN
A simple and efficient method of carrying out biotransformation reactions on terpenoid compounds was developed. For these experiments, a sporulated surface culture of Penicillium sp. was inoculated on solid media in conical flasks. After a short incubation the spores germinated and a mycelia culture was formed. After a week the cultures had completely sporulated and a bioconversion reaction started. For this purpose, a known volume of menthol was added onto the sporulated surface of culture. After 7 days, a period during which transformation took place, menthol was extracted with Et2O three times. After evaporation the recognition by GC and GC/MS was followed. The main bioconverted products obtained from menthol by surface Penicillium sp. with the use of sporulated surface culture were α-pinene (18.0%), sabinene (11.6%), trans-p-menthan-1-ol (10.6%), p-menth-1-ene (5.8%), 1,8-cineole (6.4%) and limonene (3.2%). The pathways of biotransformation of menthol by Penicillium sp. to main products are also discussed.
PL
Opisano prostą i skuteczną metodę przeprowadzania reakcji biotransformacji związków terpenoidowych. W tym celu na stałej pożywce umieszczonej w kolbach zaszczepiono kulturę zarodnikową Penicillium. Po krótkim okresie inkubacji zarodniki wykiełkowały i utworzyły grzybnię. Po tygodniu kultura była całkowicie pokryta zarodnikami i rozpoczęły się reakcje biokonwersji. W tym celu na powierzchnię grzybni w kolbach dodano określoną ilość mentolu. Po 7 dniach, czyli po czasie, w którym odbywała się transformacja, za pomocą Et2O trzy razy wyekstrahowano mentol i po odparowaniu badano go za pomocą GC/MS. Podstawowymi produktami uzyskanymi z mentolu za pomocą Penicillium były α- pinen (18,0%), sabinen, trans-p-mentan-1-ol (10,6%), p-ment-1-en (5,8%), 1,8-cineol (6,4%) i limonen (3,2%) uzyskane z powierzchniowej kultury zarodnikowej. Omówiono także sposoby biotransformacji mentolu przez Penicillium do głównych produktów.
7
Effect of iron on growth and chemical composition of Japanese mint [Mentha arvensis L.]
51%
Misra A. , Bansal R. P.
Acta Physiologiae Plantarum
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1992
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tom 14
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nr 3
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