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588733

Sigma-Aldrich

(1R,2S,5R)-(−)-Menthol

≥99%, sublimed

Synonym(s):

(−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

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About This Item

Empirical Formula (Hill Notation):
C10H20O
CAS Number:
2216-51-5
Molecular Weight:
156.27
Beilstein:
1902293
EC Number:
218-690-9
MDL number:
MFCD00062979
UNSPSC Code:
12352001
PubChem Substance ID:
24881231

vapor pressure

0.8 mmHg ( 20 °C)

Assay

≥99%

form

solid

optical activity

[α]20/D −50°, c = 10% in ethanol

bp

212 °C (lit.)

mp

41-45 °C (lit.)

density

0.89 g/mL at 25 °C (lit.)

SMILES string

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

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

InChI key

NOOLISFMXDJSKH-KXUCPTDWSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

201.2 °F - closed cup

Flash Point(C)

94 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS8277V
MKBQ0184V
MKBF5161V
79996TJ
MKBB3620

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Thomas Voets et al.
Nature chemical biology, 3(3), 174-182 (2007-02-13)
TRPM8, a member of the transient receptor potential (TRP) channel superfamily, is expressed in thermosensitive neurons, in which it functions as a cold and menthol sensor. TRPM8 and most other temperature-sensitive TRP channels (thermoTRPs) are voltage gated; temperature and ligands
A Gelal et al.
Clinical pharmacology and therapeutics, 66(2), 128-135 (1999-08-25)
Menthol is widely used in a variety of commercial products and foods, but its clinical pharmacology is not well studied. To determine the disposition kinetics and to examine subjective and cardiovascular effects of menthol, we conducted a crossover placebo-controlled study
Tibor Rohács et al.
Nature neuroscience, 8(5), 626-634 (2005-04-27)
The subjective feeling of cold is mediated by the activation of TRPM8 channels in thermoreceptive neurons by cold or by cooling agents such as menthol. Here, we demonstrate a central role for phosphatidylinositol 4,5-bisphosphate (PI(4,5)P(2)) in the activation of recombinant
Anne-Mette Haahr et al.
Physiology & behavior, 82(2-3), 531-540 (2004-07-28)
During chewing, the oral cavity functions like a bellow, forcing volatile flavour compounds into the exhaling air to the nasal compartment. Accordingly, we hypothesised that flavour release from chewing gum is predominantly governed by chewing frequency (CF), although other oral
Robert J Stein et al.
The Journal of urology, 172(3), 1175-1178 (2004-08-18)
Overactive bladder symptoms due to various etiologies have been successfully treated with capsaicin by desensitization of the temperature sensitive vanilloid receptor TRPV1. Recently another temperature sensitive receptor, TRPM8, activated by menthol and cool temperatures (8C to 28C) was described that
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