A monoterpene with diverse biological activities
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(–)-Menthol

Item No. 30384

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2S,5R)-5-methyl-2-(1-methylethyl)-cyclohexanol
CAS Number
2216-51-5
Synonyms
  • L-Menthol
  • (1R,2S,5R)-(−)-Menthol
  • NSC 62788
Molecular Formula
C10H20O
Formula Weight
156.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 10 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.33 mg/ml
SMILES
CC(C)[C@H]1[C@H](O)C[C@H](C)CC1
InChi Code
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
Origin
Plant/Mentha arvensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    Product Description

    (–)-Menthol is a monoterpene that has been found in cornmint oil and has diverse biological activities.1 It inhibits acetylcholinesterase (AChE; Ki = 1.25 mM for the bovine enzyme).2 (–)-Menthol (1.6 mM) decreases expression of the genes encoding topoisomerase I, IIα, and Iiβ in, and cell viability of, SNU-5 gastric cancer cells.3 It reduces acetic acid-induced writhing and increases latency to paw licking in a hot plate test in mice when administered at doses ranging from 3-10 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamatou, G.P., Vermaak, I., Viljoen, A.M., et al. Menthol: A simple monoterpene with remarkable biological properties. Phytochemistry 96, 15-25 (2013).

    2. Miyazawa, M., Watanabe, H., and Kameoka, H. Inhibition of acetylcholinesterase activity by monoterpenoids with a p-menthane skeleton. J. Agric. Food Chem. 45(3), 677-679 (1997).

    3. Lin, J.P., Lu, H.F., Lee, J.H., et al. (−)-Menthol inhibits DNA topoisomerases I, II α and β and promotes NF-Î B expression in human gastric cancer SNU-5 cells. Anticancer Res. 25(3B), 2069-2074 (2005).

    4. Galeotti, N., Di Cesare Mannelli, L., Mazzanti, G., et al. Menthol: A natural analgesic compound. Neurosci. Lett. 322(3), 145-148 (2002).