An in silico investigation of menthol metabolism

Abstract

Prevalence of mentholated products for consumption has brought great importance to studies on menthol’s metabolic pathways to ensure safety, design more potent derivatives, and identify therapeutic benefits. Proposed pathways of (-)-menthol metabolism based on metabolites found experimentally in previous works by Yamaguchi, Caldwell & Farmer, Madyastha & Srivatsan and Hiki et al. were not in agreement. This in silico approach is based on the three in vivo studies and aims to resolve the discrepancies. Reactions in the pathways are conjugation with glucuronic acid/sulfate, oxidation to alcohol, aldehyde & carboxylic acid, and formation of a four-membered/five-membered ring. Gas-phase structures, standard Gibbs energies and SMD solvation energies at B3LYP/6-311++G(d,p) level were obtained for 102 compounds in the pathways. This study provides a more complete picture of menthol metabolism by combining information from three experimental studies and filling missing links in previously published pathways.

Geometric and energetic data from ab initio calculations of haloethene, haloimine, halomethylenephosphine, haloiminophosphine, halodiazene, halodiphosphene and halocyclopropane

“…Q-Chem input files (.inp) were generated partly by using a Unix shell script previously described elsewhere [[6], [7], [8]]. The ab initio calculations were performed using the Q-Chem 5.1 program package [9] to optimize the structures at HF, B3LYP, MP2 and CCSD levels of theory on 6-311++G(d,p) basis set.…”

Geometric and Energetic Data from Ab Initio Calculations of Haloethene, Haloimine, Halomethylphosphine, Haloiminophosphine, Halodiazene, Halodiphosphene and Halocyclopropane

“…Q-Chem input files (.inp) were generated using shell scripts previously described elsewhere [7][8][9]. The ab initio calculations were performed using the Q-Chem 5.1 program package [10] to optimize the structures at HF, B3LYP, MP2 and CCSD levels of theory on 6-311++G(d,p) basis set.…”

The Use of Menthol in Skin Wound Healing—Anti-Inflammatory Potential, Antioxidant Defense System Stimulation and Increased Epithelialization

“…Menthol is an agonist of transient receptor potential melastatin-8 channels, cold receptors in the sensory nerves of the skin. For this reason, menthol exerts a cooling sensation when applied to the skin and mucosal membranes [13]. The activation of TRPM8 channels does not influence skin wound healing [14].…”