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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:
Menthone is a liquid under standard conditions, and has a density of 0.895 g/cm 3. [citation needed] Under the same conditions, [verification needed] the melting point is −6 °C, and its boiling point is 207 °C.
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 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.
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.
[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 ...
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 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 ]