Menthol

Not to be confused with Methanol or Methanal.

Menthol
(−)-Menthol
(−)-Menthol
Ball-and-stick model of (−)-menthol
Ball-and-stick model of (−)-menthol
Menthol crystals.jpg
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 InfoCard 100.016.992 Edit this at Wikidata
EC 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 checkY
    Key: NOOLISFMXDJSKH-KXUCPTDWSA-N checkY
  • 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
C10H20O
Molar mass 156.269 g·mol−1
Appearance White or colorless crystalline solid
Odor mint-licorice
Density 0.890 g·cm−3, solid
(racemic or (−)-isomer)
Melting point 36–38 °C (97–100 °F; 309–311 K) racemic
42–45 °C, (−)-isomer, α crystalline form
Boiling point 214.6 °C (418.3 °F; 487.8 K)
Slightly soluble, (−)-isomer
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant, flammable
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 93 °C (199 °F; 366 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related alcohols
 Cyclohexanol, Pulegol,
Dihydrocarveol, Piperitol
Related compounds
 Menthone, Menthene, Menthane,Thymol,
p-Cymene, Citronellal
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).
☒N verify (what is checkY☒N ?)

Menthol is an organic compound, specifically a monoterpenoid, that occurs naturally in the oils of several 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 also acts as a weak κ-opioid receptor agonist.

  1. ^ "l-Menthol". pubchem.ncbi.nlm.nih.gov.
  2. ^ "Safety Data Sheet" (PDF). Reckitt Benckiser. 27 October 2016. Retrieved 3 August 2018.