Menthol

Names

5-Methyl-2-(propan-2-yl)cyclohexan-1-ol

Other names

2-Isopropyl-5-methylcyclohexan-1-ol
2-Isopropyl-5-methylcyclohexanol
3-p-Menthanol
Hexahydrothymol
Menthomenthol
Peppermint camphor

Identifiers

CAS Number

2216-51-5 (chiral)^N
89-78-1 (racemic)^N

3D model (Jmol)

Interactive image
Interactive image

CHEBI:15409^Y

ChEMBL470670^Y

15803^Y

DB00825^Y

OT0350000, racemic

BZ1R15MTK7 (chiral)^N
YS08XHA860 (racemic)^N

InChI

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1^Y

Key: NOOLISFMXDJSKH-KXUCPTDWSA-N^Y
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
Key: NOOLISFMXDJSKH-KXUCPTDWSA-N

SMILES

O[C@H]1[C@H](C(C)C)CC[C@@H](C)C1
O[C@H]1[C@H](C(C)C)CC[C@@H](C)C1

Properties

Chemical formula

C₁₀H₂₀O

Molar mass

156.27 g·mol⁻¹

Appearance

White or colorless crystalline solid

Density

0.890 g·cm⁻³, solid
(racemic or (−)-isomer)

Melting point

36 to 38 °C (97 to 100 °F; 309 to 311 K) racemic
42–45 °C, (−)-isomer, α crystalline form

Boiling point

212 °C (414 °F; 485 K)

Solubility in water

Slightly soluble, (−)-isomer

Hazards

Main hazards

Irritant, flammable

Safety data sheet

See: data page
External MSDS

R-phrases

R37/38, R41

S-phrases

S26, S36

Flash point

93 °C (199 °F; 366 K)

Related compounds

Related alcohols

Cyclohexanol, Pulegol,
Dihydrocarveol, Piperitol

Related compounds

Menthone, Menthene,
Thymol, p-Cymene,
Citronellal

Supplementary data page

Structure and
properties

Refractive index (n),
Dielectric constant (ε_r), etc.

Thermodynamic
data

Phase behaviour
solid–liquid–gas

Spectral data

UV, IR, NMR, MS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

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.

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:

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Wikipedia