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
CAS Number	2216-51-5 (levomenthol) ; 89-78-1 (racementhol) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15409 ;
ChEMBL	ChEMBL470670 ;
ChemSpider	15803 ;
DrugBank	DB00825 ;
ECHA InfoCard	100.016.992
EC Number	218-690-9;
IUPHAR/BPS	2430;
KEGG	C00400;
PubChem CID	16666;
RTECS number	OT0350000, racemic;
UNII	BZ1R15MTK7 (levomenthol) ; YS08XHA860 (racementhol) ;
CompTox Dashboard (EPA)	DTXSID1022180 ;
	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 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;
	SMILES O[C@H]1[C@H](C(C)C)CC[C@@H](C)C1;
Properties
Chemical formula	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)
Solubility in water	Slightly soluble, (−)-isomer
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant, flammable
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

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 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 congestion.^[3]^[4]

Menthol also acts as a weak κ-opioid receptor agonist.

^ "l-Menthol". pubchem.ncbi.nlm.nih.gov.
^ "Safety Data Sheet" (PDF). Reckitt Benckiser. 27 October 2016. Retrieved 3 August 2018.
^ Eccles R (1 May 2003). "Menthol: Effects on nasal sensation of airflow and the drive to breathe". Current Allergy and Asthma Reports. 3 (3): 210–214. doi:10.1007/s11882-003-0041-6. ISSN 1534-6315.
^ BUTLER DB, IVY AC (1 October 1943). "Effects of Nasal Inhalers on Erectile Tissues of the Nose: Quantitative Studies". Archives of Otolaryngology. 38 (4): 309–317. doi:10.1001/archotol.1943.00670040323001. ISSN 0276-0673.

[1] "l-Menthol". pubchem.ncbi.nlm.nih.gov.

[2] "Safety Data Sheet" (PDF). Reckitt Benckiser. 27 October 2016. Retrieved 3 August 2018.

[3] Eccles R (1 May 2003). "Menthol: Effects on nasal sensation of airflow and the drive to breathe". Current Allergy and Asthma Reports. 3 (3): 210–214. doi:10.1007/s11882-003-0041-6. ISSN 1534-6315.

[4] BUTLER DB, IVY AC (1 October 1943). "Effects of Nasal Inhalers on Erectile Tissues of the Nose: Quantitative Studies". Archives of Otolaryngology. 38 (4): 309–317. doi:10.1001/archotol.1943.00670040323001. ISSN 0276-0673.

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