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M2772

Sigma-Aldrich

Menthol

99%

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Synonym(s):
2-Isopropyl-5-methylcyclohexanol, Hexahydrothymol
Empirical Formula (Hill Notation):
C10H20O
CAS Number:
Molecular Weight:
156.27
Beilstein/REAXYS Number:
3194263
EC Number:
MDL number:
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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This Item
15785M278063670
Menthol 99%

M2772

Menthol

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

15785

(−)-Menthol

(1R,2S,5R)-(−)-Menthol ReagentPlus®, 99%

M2780

(1R,2S,5R)-(−)-Menthol

(±)-Menthol racemic, ≥98.0% (GC)

63670

(±)-Menthol

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

pharmaceutical (small molecule)

application(s)

-

application(s)

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

vapor pressure

0.8 mmHg ( 20 °C)

vapor pressure

-

vapor pressure

0.8 mmHg ( 20 °C)

vapor pressure

0.8 mmHg ( 20 °C)

bp

216 °C (lit.)

bp

-

bp

212 °C (lit.)

bp

216 °C (lit.)

mp

34-36 °C (lit.)

mp

41-44 °C

mp

41-45 °C (lit.)

mp

34-36 °C (lit.)

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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

204.8 °F

flash_point_c

96 °C

ppe

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

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)
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)
TRP channels in brown and white adipogenesis from human progenitors: new therapeutic targets and the caveats associated with the common antibiotic, streptomycin
Goralczyk A, et al
Faseb Journal, 31(8), 3251-3266 (2017)
TRP channel mediated neuronal activation and ablation in freely behaving zebrafish
Chen S, et al.
Nature Methods, 13(2), 147-147 (2015)

Articles

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

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