Menthol

Menthol is an organic compound made synthetically or obtained from corn mint, peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol also acts as a weak kappa opioid receptor agonist.

Structure

Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form (bottom left corner of the diagram below). The eight possible stereoisomers are:

In the natural compound, the isopropyl group is in the trans orientation to both the methyl and hydroxyl groups. Thus, it can be drawn in any of the ways shown:

The (+)- and (–)-enantiomers of menthol are the most stable among these based on their cyclohexane conformations. With the ring itself in a chair conformation, all three bulky groups can orient in equatorial positions.

Menthol (data page)

This page provides supplementary chemical data on Menthol.

Material Safety Data Sheet

The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet (MSDS) for this chemical from a reliable source such as SIRI or the links below, and follow its directions.

Structure and properties

Thermodynamic properties

Spectral data

References

Except where noted otherwise, data relate to standard ambient temperature and pressure.

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