• Bulletin of the Korean Chemical Society
• /
• v.33 no.4
• /
• pp.1333-1336
• /
• 2012

• Journal of the Korean Society of Tobacco Science
• /
• v.25 no.2
• /
• pp.160-166
• /
• 2003

The majority of ι-menthol is still obtained by freezing the oil of Mentha arvensis to crystallize the menthol present. This 'natural' menthol is then physically seperated by centrifuging the supernatant liquid away from the menthol crystal. But the price of natural ι-menthol has fluctuated widely so effort has been devoted to the production of ι-menthol by synthetic more readily available raw materials. In the 1970's, many researcher synthesised a new compounds with the menthol cooling effect. During this period many molecular structure designed and synthesised on concepts of correlation between structure and biological activity and the various types of molecule which give rise to cooling effect more than ι-menthol. Specially, N-alkyl-carboxamide group is substituted for the hydroxyl group in ι-menthol. Recently, the most active compounds synthesised is 4-methyl-3-(1-pyrrolidinyl)-2-[5H]-furanone. This compound is 35 times more powerful in the mouth and 512 times more powerful on the skin than ι-menthol. The cooling effect also lasts twice as long. While not yet commercially available, it is expected that these types of materials will be subjected to toxicological studies and will soon be sell on the market.