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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.
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 ]
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.
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)
[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 phenolic unit can be found dimerized or further polymerized, creating a new class of polyphenol. For example, ellagic acid is a dimer of gallic acid and forms the class of ellagitannins, or a catechin and a gallocatechin can combine to form the red compound theaflavin, a process that also results in the large class of brown thearubigins in tea.
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.