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Menthol is manufactured as a single enantiomer (94% e.e.) on the scale of 3,000 tonnes per year by Takasago International Corporation. [15] The process involves an asymmetric synthesis developed by a team led by Ryōji Noyori, who won the 2001 Nobel Prize for Chemistry in recognition of his work on this process:
Thus, the two substrates of this enzyme are (−)-menthol and NADP +, whereas its 3 products are (−)-menthone, NADPH, and H +. This enzyme belongs to the family of oxidoreductases, specifically those acting on the CH-OH group of donor with NAD + or NADP + as acceptor. The systematic name of this enzyme class is (−)-menthol:NADP ...
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)
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[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 ...
Chiral auxiliaries are incorporated into synthetic routes to control the absolute configuration of stereogenic centers. David A. Evans' synthesis of the macrolide cytovaricin, considered a classic, utilizes oxazolidinone chiral auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting the absolute stereochemistry of nine stereocenters.
Menthone was first synthesized by oxidation of menthol in 1881, [6] [needs update] [7] before being found as a component in essential oils in 1891. [ citation needed ] Of the isomers possible for this chemical structure (see below), the one termed l -menthone —formally, the (2 S ,5 R )- trans -2-isopropyl-5-methylcyclohexanone (see infobox ...
The process generates a range of alcohols that are separated by distillation. Many higher alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene , as is common, one typically obtains a linear alcohol: [ 25 ]