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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:
p-Menthane-3,8-diol, also known as para-menthane-3,8-diol, PMD, or menthoglycol, is an organic compound classified as a diol and a terpenoid.It is colorless. Its name reflects the hydrocarbon backbone, which is that of p-menthane.
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)
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 ...
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.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters.The reaction mainly applies to primary and secondary alcohols.
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.
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 ]