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M2772

Sigma-Aldrich

Menthol

99%

Synonym(s):

2-Isopropyl-5-methylcyclohexanol, Hexahydrothymol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
Molecular Weight:
156.27
Beilstein:
3194263
EC Number:
MDL number:
UNSPSC Code:
12352212
PubChem Substance ID:
NACRES:
NA.25

vapor pressure

0.8 mmHg ( 20 °C)

Quality Level

Assay

99%

bp

216 °C (lit.)

mp

34-36 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

CC(C)C1CCC(C)CC1O

InChI

1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3

InChI key

NOOLISFMXDJSKH-UHFFFAOYSA-N

Gene Information

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General description

Menthol (C10H20O) is a terpenoid compound. It is extracted from the plants belonging to Mentha genus in the Lamiaceae family.
Menthol is a cyclic monoterpene alcohol, which is extracted from essential oils of Mentha canadensis and Mentha x piperita. It possesses antimicrobial, anticancer and anti-inflammatory properties. Menthol acts as a transient receptor potential cation channel (TRPM8) agonist. It also exhibits analgesic, antipruritic, anesthetic and cooling effects.

Application

Menthol has been used:
  • to test its antifungal susceptibility
  • to determine its efficacy as an anesthetic in fish
  • to activate transient receptor potential cation channel (TRPM8)
  • as an odorant for measuring sniffing dynamics

Biochem/physiol Actions

Menthol exhibits antifungal action on the membrane permeability and the cell wall consistency, this might leads to cell death or inhibition of the C. albicans filamentation. Therefore, it can be used as a potential therapeutic agent for candidiasis. In addition to antifungal activity, menthol also exhibits anesthetic, antispasmodic, anti-ulcer and antiviral properties. It is considered as a safe compound for animal life. Therefore, Menthol is widely used in pharmaceuticals, cosmetics and food industries.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

204.8 °F

Flash Point(C)

96 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Inhibitory effect of menthol on expression of aspartyl proteinase 1 in fluconazole-resistant Candida albicans
Shahrzad S and Alireza k
Journal of HerbMed Pharmacology, 8(1) (2019)
Cancer treatment-related neuropathic pain: proof of concept study with menthol?a TRPM8 agonist
Fallon MT, et al
Supportive Care in Cancer : Official Journal of the Multinational Association of Supportive Care in Cancer, 23(9), 2769-2777 (2015)
Inhibitory effect of menthol on expression of aspartyl proteinase 1 in fluconazole-resistant Candida albicans
Shahrzad S and Alireza K
Journal of HerbMed Pharmacology, 8(1) (2019)
Efficacy of Benzocaine, Eugenol, and Menthol as Anesthetics for Freshwater Angelfish
Romaneli RD et al.
Journal of Aquatic Animal Health, 30(3), 210-216 (2018)
Guy P P Kamatou et al.
Phytochemistry, 96, 15-25 (2013-09-24)
Menthol is a cyclic monoterpene alcohol which possesses well-known cooling characteristics and a residual minty smell of the oil remnants from which it was obtained. Because of these attributes it is one of the most important flavouring additives besides vanilla

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