TheInfoListRev V5.1.65

Topic summary

Menthol

Menthol
Names Preferred IUPAC name
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.016.992EC Number
  • 218-690-9
KEGG
RTECS number
  • OT0350000, racemic
UNII
  • 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
  • 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
  • O[C@H]1[C@H](C(C)C)CC[C@@H](C)C1
Properties C10H20OMolar mass156.269 g·mol Appearance White or colorless crystalline solid Odormint-licorice Density0.890 g·cm, solid
(racemic or (−)-isomer) Melting point36–38 °C (97–100 °F; 309–311 K) racemic
42–45 °C, (−)-isomer, α crystalline form Boiling point214.6 °C (418.3 °F; 487.8 K) Slightly soluble, (−)-isomer Hazards Occupational safety and health (OHS/OSH):
Main hazards
Irritant, flammable GHS labelling: WarningH315, H319P264, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362NFPA 704 (fire diamond)
2
2
0
Flash point93 °C (199 °F; 366 K) Safety data sheet (SDS) External MSDSRelated compounds
Related alcohols
Cyclohexanol, ,
,
Related compounds
Menthone, , Menthane, Thymol,
p-Cymene, CitronellalPharmacology QN01AX95 (WHO) Supplementary data page Menthol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markNverify (  ?)

Menthol is a monoterpenoidorganic compound that occurs naturally in the oils of certain plants in the mint family, such as corn mint and peppermint. It is a white or clear waxy crystalline substance that 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.

For many people, menthol produces a cooling sensation when inhaled, eaten, or applied to the skin, and mint plants have been used for centuries for topical pain relief and as a food flavoring. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.

Menthol has been demonstrated to cause a subjective nasal decongestant effect without any objective decongestant action, and administration of menthol via a nasal inhaler in humans has also been shown to cause nasal decongestion.

Wikipedia source