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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:
89-78-1
Molecular Weight:
156.27
Beilstein:
3194263
EC Number:
201-939-0
MDL number:
MFCD00001484
UNSPSC Code:
12352212
PubChem Substance ID:
24896764
NACRES:
NA.25

vapor pressure

0.8 mmHg ( 20 °C)

Quality Level

200

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

human ... TRPA1(8989) , TRPM8(79054)

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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

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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(−)-Menthol puriss., meets analytical specification of Ph. Eur., BP, USP, 98.0-102.0%

Sigma-Aldrich

15785

(−)-Menthol

Thymol ≥98.5%

Sigma-Aldrich

T0501

Thymol

(−)-Menthol primary reference standard

00580590

(−)-Menthol

Ethyl benzoate ≥99%

Sigma-Aldrich

E12907

Ethyl benzoate

(−)-Menthone 90%

Sigma-Aldrich

218235

(−)-Menthone

(-)-Menthol for synthesis

Sigma-Aldrich

8.14113

(-)-Menthol

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)
TRP channel mediated neuronal activation and ablation in freely behaving zebrafish
Chen S, et al.
Nature Methods, 13(2), 147-147 (2015)
Spontaneous rapid odor source localization behavior requires interhemispheric communication
Rabell JE, et al.
Current Biology, 27(10), 1542-1548 (2017)
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)
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)
View All Related Papers

Articles

GC Analysis of Spearmint Essential Oil on SLB®-IL59

-Cymene; Linalool; Menthol; α-Terpineol; Menthyl acetate

Protocols

Essential Oil on SLB®-5ms

-Pinocarveol; Menthol; (+)-Terpinen-4-ol; α-Terpineol; (±)-α-Terpinyl acetate, predominantly α-isomer; Germacrene D

GC Analysis of Peppermint Essential Oil on SLB®-IL59

Cymene; 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran; Linalool; Menthol; Menthone; Menthyl acetate; Germacrene D; Bicyclogermacrene; Thymol

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