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Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form (bottom left corner of the diagram below). The eight possible stereoisomers are: In the natural compound, the isopropyl group is in the trans orientation to both the methyl and hydroxyl groups. Thus, it can be drawn in any of the ways shown:
[15] [16] Menthol, hinokitiol and thymol are also used in oral hygiene products. Thymol also has antiseptic and disinfectant properties. [17] Volatile monoterpenes produced by plants can attract or repel insects, thus some of them are used in insect repellents, such as citronellol, eucalyptol, limonene, linalool, hinokitiol, menthol and thymol ...
The importance of this observation was that, in theory, if a half equivalent of (−)-menthol had been used, a highly enantioenriched sample of (−)-mandelic acid could have been prepared. This observation led to the successful kinetic resolution of other chiral acids, the beginning of the use of kinetic resolution in organic chemistry.
The following other wikis use this file: Usage on af.wikipedia.org Mentol; Usage on bg.wikipedia.org Ментол; Usage on bs.wikipedia.org Mentol
Phase behavior Triple point? K (? °C), ? Pa Critical point? K (? °C), ? Pa Std enthalpy change of fusion, Δ fus H o? kJ/mol Std entropy change of fusion, Δ fus S oJ/(mol·K)
The following other wikis use this file: Usage on ar.wikipedia.org مركب ذو رائحة; Usage on bs.wikipedia.org Mentol; Usage on el.wikipedia.org
Menthoxypropanediol (also known as Cooling agent 10 [tradename of Takasago]), is a synthetic derivative of menthol.While the cooling strength of 3-(l-menthoxy)propane-1,2-diol is accepted as being about 20–25% that of menthol, it is also noted that "in a Vaseline ointment, 3-(l-menthoxy)propane-1,2-diol shows a cool feeling 2.0 to 2.5 times stronger than that of l-menthol".
The Haworth synthesis is a classic method for the synthesis of polycyclic aromatic hydrocarbons. In this reaction, an arene is reacted with succinic anhydride, the subsequent product is then reduced in either a Clemmensen reduction or a Wolff-Kishner reduction. Lastly, a second Friedel-Crafts acylation takes place with addition of acid.