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Chemical Compound Review

MENTHOL     (1R,2S,5R)-5-methyl-2-propan- 2-yl...

Synonyms: Racementol, levomentol, Levomenthol, Racementhol, Levomentholum, ...
 
 
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Disease relevance of MENTHOL

  • Repeated oral administration (800 mg/kg of body weight/day) of l-menthol to rats for 3 days resulted in the increase of both liver microsomal cytochrome P-450 content and NADPH-cytochrome c reductase activity by nearly 80% [1].
  • We investigated the effects of l-menthol on cultured dorsal root ganglion (DRG) cells, instead of free nerve endings of sensory fibers [2].
  • Lytic activity of l-menthol derivatives against the snow blight disease fungus, Micronectriella nivalis [3].
  • A 13-wk comparative nose-only smoke inhalation toxicity study was conducted using an American-style, cellulose acetate-filtered, non-menthol reference cigarette and a similarly blended test cigarette containing 5000 ppm synthetic l-menthol tobacco [4].
  • Bacteria were screened for alpha-anomer-selective glucosylation activity toward l-menthol, resulting in the isolation of two strains, Xanthomonas campestris WU-9701 and Stenotrophomonas maltophilia WU-9702, from independent soil samples [5].
 

Psychiatry related information on MENTHOL

  • In 6 experiments that used a variety of psychometric techniques, the authors experimentally isolated the modality by which l-menthol is detected in the upper airways (the nose and mouth) [6].
 

High impact information on MENTHOL

 

Chemical compound and disease context of MENTHOL

 

Biological context of MENTHOL

 

Anatomical context of MENTHOL

  • Exposure of the nasal cavity to l-menthol markedly enhances this ventilatory inhibition; considering the stimulatory effect of l-menthol on cold receptors, these results suggest a predominant role of nasal cold receptors in this response [10].
  • These results suggest that TRPM8 protein is present in sensory lingual nerve fibers mainly projected from TG and might work as cold and l-menthol receptors on tongue [9].
  • When the emulsion containing 3% l-menthol was applied, a sufficient skin concentration (47 microg/cm3 in dermis) was obtained [14].
 

Associations of MENTHOL with other chemical compounds

  • After topical anesthesia of the nasal cavity with 2% lidocaine, cold air and l-menthol no longer stimulated the EN [15].
  • The purpose of the present study was to clarify the mechanism for l-menthol whisker growth. l-Menthol was mixed with an excipient, and the interaction was examined by IR measurement, thermal analysis and powder X-ray diffraction [16].
  • The apparent 1-octanol/buffer partition coefficient (log K(p)) of ddC was significantly (P<0.05) increased in presence of l-menthol and was also independent of the enhancer concentration [17].
  • The lipase immobilized on EP-400 polyethylene was found to be effective in transesterification using tributyrin or triacetin as acyl donors with l-menthol as acceptor [18].
  • Skin penetration of methyl, ethyl, propyl and butyl parabens through excised guinea pig dorsal skin was examined, and effects of the penetration enhancers, l-menthol plus ethanol itself and N-dodecyl-2-pyrrolidone, were observed [19].
 

Analytical, diagnostic and therapeutic context of MENTHOL

  • Constant flows (400 ml/min) of room air (20 degrees C), warm air (45 degrees C), room air containing l-menthol, and cold air (-5 degrees C) were directed into the nasal cavity in the inspiratory direction via a nasopharyngeal catheter in the anesthetized guinea pigs breathing spontaneously through a tracheostomy [15].
  • A simple analytical method for l-menthol by high-performance liquid chromatography with a polarized photometric detector was established [20].
  • A change in the IR spectra of stratum corneum after treatment with l-menthol was observed at the CH band, and the peaks representative of the lipid structure in the X-ray diffraction patterns decreased in intensity [21].
  • The melting properties of lidocaine and l-menthol binary systems were studied using differential scanning calorimetry (DSC) [22].
  • The racemate was converted to diastereomeric esters of l-menthol; these were separated by recycling HPLC into two optically active diastereomers that were then hydrolyzed with p-TsOH to two optically active enantiomers of 5,7-Cl(2)-2-IPA [23].

References

  1. Studies on the metabolism of l-menthol in rats. Madyastha, K.M., Srivatsan, V. Drug Metab. Dispos. (1988) [Pubmed]
  2. l-Menthol-induced [Ca2+]i increase and impulses in cultured sensory neurons. Okazawa, M., Terauchi, T., Shiraki, T., Matsumura, K., Kobayashi, S. Neuroreport (2000) [Pubmed]
  3. Lytic activity of l-menthol derivatives against the snow blight disease fungus, Micronectriella nivalis. Miyazawa, M., Kawazoe, H., Sumi, Y., Hyakumachi, M. J. Agric. Food Chem. (2003) [Pubmed]
  4. 13-week inhalation toxicity study of menthol cigarette smoke. Gaworski, C.L., Dozier, M.M., Gerhart, J.M., Rajendran, N., Brennecke, L.H., Aranyi, C., Heck, J.D. Food Chem. Toxicol. (1997) [Pubmed]
  5. Alpha-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701. Nakagawa, H., Dobashi, Y., Sato, T., Yoshida, K., Tsugane, T., Shimura, S., Kirimura, K., Kino, K., Usami, S. J. Biosci. Bioeng. (2000) [Pubmed]
  6. Psychophysical isolation of the modality responsible for detecting multimodal stimuli: a chemosensory example. Nagata, H., Dalton, P., Doolittle, N., Breslin, P.A. Journal of experimental psychology. Human perception and performance. (2005) [Pubmed]
  7. Topical menthol--a human model for cold pain by activation and sensitization of C nociceptors. Wasner, G., Schattschneider, J., Binder, A., Baron, R. Brain (2004) [Pubmed]
  8. Nasal inhalation of l-menthol reduces respiratory discomfort associated with loaded breathing. Nishino, T., Tagaito, Y., Sakurai, Y. Am. J. Respir. Crit. Care Med. (1997) [Pubmed]
  9. TRPM8 protein localization in trigeminal ganglion and taste papillae. Abe, J., Hosokawa, H., Okazawa, M., Kandachi, M., Sawada, Y., Yamanaka, K., Matsumura, K., Kobayashi, S. Brain Res. Mol. Brain Res. (2005) [Pubmed]
  10. Upper airway cooling and l-menthol reduce ventilation in the guinea pig. Orani, G.P., Anderson, J.W., Sant'Ambrogio, G., Sant'Ambrogio, F.B. J. Appl. Physiol. (1991) [Pubmed]
  11. Effect of chiral enhancers on the permeability of optically active and racemic metoprolol across hairless mouse skin. Kommuru, T.R., Khan, M.A., Reddy, I.K. Chirality. (1999) [Pubmed]
  12. Menthol inhibits the perception of warmth. Green, B.G. Physiol. Behav. (1986) [Pubmed]
  13. Combined effect of cyclic monoterpenes and ethanol on percutaneous absorption of diclofenac sodium. Obata, Y., Takayama, K., Machida, Y., Nagai, T. Drug design and discovery. (1991) [Pubmed]
  14. Preparation of griseofulvin for topical application using N-methyl-2-pyrrolidone. Fujii, M., Bouno, M., Fujita, S., Yoshida, M., Watanabe, Y., Matsumoto, M. Biol. Pharm. Bull. (2000) [Pubmed]
  15. Nasal receptors responding to cold and l-menthol airflow in the guinea pig. Sekizawa, S., Tsubone, H., Kuwahara, M., Sugano, S. Respiration physiology. (1996) [Pubmed]
  16. Whisker growth of l-menthol in coexistence with various excipients. Yuasa, H., Ooi, M., Takashima, Y., Kanaya, Y. International journal of pharmaceutics. (2000) [Pubmed]
  17. Transbuccal permeation of a nucleoside analog, dideoxycytidine: effects of menthol as a permeation enhancer. Shojaei, A.H., Khan, M., Lim, G., Khosravan, R. International journal of pharmaceutics. (1999) [Pubmed]
  18. Immobilization of lipase from Candida cylindraceae and its use in the synthesis of menthol esters by transesterification. Gray, C.J., Narang, J.S., Barker, S.A. Enzyme Microb. Technol. (1990) [Pubmed]
  19. Skin permeation of parabens in excised guinea pig dorsal skin, its modification by penetration enhancers and their relationship with n-octanol/water partition coefficients. Kitagawa, S., Li, H., Sato, S. Chem. Pharm. Bull. (1997) [Pubmed]
  20. Determination of l-menthol in pharmaceutical products by high performance liquid chromatography with polarized photometric detection. Hamasaki, K., Kato, K., Watanabe, T., Yoshimura, Y., Nakazawa, H., Yamamoto, A., Matsunaga, A. Journal of pharmaceutical and biomedical analysis. (1998) [Pubmed]
  21. Comparison of skin permeation enhancement by 3-l-menthoxypropane-1,2-diol and l-menthol: the permeation of indomethacin and antipyrine through Yucatan micropig skin and changes in infrared spectra and X-ray diffraction patterns of stratum corneum. Fujii, M., Takeda, Y., Yoshida, M., Utoguchi, N., Matsumoto, M., Watanabe, Y. International journal of pharmaceutics. (2003) [Pubmed]
  22. Physicochemical studies of lidocaine-menthol binary systems for enhanced membrane transport. Kang, L., Jun, H.W., McCall, J.W. International journal of pharmaceutics. (2000) [Pubmed]
  23. Synthesis, absolute configuration and biological activities of both enantiomers of 2-(5,7-Dichloro-3-indolyl)propionic acid: a novel dichloroindole auxin and antiauxin. Katayama, M., Kato, Y., Marumo, S. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
 
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