Menthol Inhibitor CAS No. 15356-70-4

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Chemical Characteristic

Product Name	Menthol
CAS No.	15356-70-4
Molecular Weight	156.27
Formula	C₁₀H₂₀O
Chemical Structure

Biological activities

Menthol is a naturally occurring compound of plant origin, which gives plants of the Mentha species the typical minty smell and flavour.^[1] Menthol is a noncompetitive antagonist of 5-HT3 receptor. Menthol also nonselectively activates transient receptor potential vanilloid 3 (TRPV3) with an EC50 of 20 mM and inhibits mouse transient receptor potential A1 (TRPA1) with an IC50 of 68 µM. Menthol reversibly inhibited 5-HT (1 µM)-evoked currents recorded by two-electrode voltage clamp technique in a concentration-dependent manner, with an IC50 of 163 µM. Menthol increases intracellular Ca2+ levels and activates various Ca2+ sensitive kinases (PKC).^[2] Menthol inhibits 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanol (NNAL) O-glucuronidation and N-glucuronidation with IC50 of 410 and 260 µM, respectively.^[3] Menthol is present in the volatile oil of several species of mint plants such as peppermint Mentha piperita and cornmint oil Mentha arvensis. Menthol is widely used as flavouring for toothpaste, other oral hygiene products and chewing-gum. Among the optical isomers, (-)-menthol is the one that occurs most widely in nature. (-)-Menthol (3-10 mg kg-1 p.o.) produces a dose-dependent increase in the pain threshold in the mouse hot-plate.^[1] (-)-Menthol inhibits the growth of rat liver epithelial tumor cells. (-)-Menthol acts as a potent chemopreventive agent during dimethylbenzanthracene (DMBA) initiation of rat mammary tumors. (-)-Menthol induces human promyelocytic leukemia HL-60 cell death through the Ca2+ release from the endoplasmic reticulum.^[4]

Protocols

In vitro, (-)-menthol is dissolved in a vehicle of 1:4 solution of DMSO in H2O.^[1]

References

[1] Galeotti N, et al. Menthol: a natural analgesic compound. Neurosci Lett. 2002, 322(3): 145-148. [2] Ashoor A, et al. MENTHOL INHIBITS 5-HT3 RECEPTOR-MEDIATED CURRENTS. J Pharmacol Exp Ther. 2013. [3] Muscat JE, et al. Effects of menthol on tobacco smoke exposure, nicotine dependence, and NNAL glucuronidation. Cancer Epidemiol Biomarkers Prev. 2009, 18(1): 35-41. [4] Lu HF, et al. (-)-Menthol inhibits WEHI-3 leukemia cells in vitro and in vivo. In Vivo. 2007, 21(2): 285-289.

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