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Chemical Compound Review

MENTHONE     5-methyl-2-propan-2-yl- cyclohexan-1-one

Synonyms: Isomenthone, Neomenthone, p-Menthone, DL-Menthone, cis-Menthone, ...
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Disease relevance of MENTHONE


High impact information on MENTHONE

  • An X-ray diffraction study of 6b reveals that the isopropyl group of the menthone ketal influences the position of the syn-pseudoaxial phenyl group in the TADDOL structure [3].
  • This early biosynthetic process is followed by a second, later oil maturation program (approximately coincident with flower initiation) in which the C3-carbonyl of menthone is reduced to yield (-)-(3R)-menthol and (+)-(3S)-neomenthol by two distinct NADPH-dependent ketoreductases [4].
  • Addition of either menthol or menthone to LA-N-5 cultures induced neurite outgrowth, cellular clustering, and reduction of cell growth in a dose-dependent fashion that correlated with the ability of these compounds to inhibit the DHP-insensitive Ca2+ influx [5].
  • Menthol and menthone cause loosening of the SC lipid bilayer due to breaking of hydrogen bonding between ceramides, resulting in penetration of water into the lipids of the SC lipid bilayer that leads to creation of new aqueous channels and is responsible for increased hydrophilicity of SC [6].
  • In ex vivo studies, both linoleic acid and menthone in combination with iontophoresis showed a synergistic enhancement of insulin permeation [7].

Biological context of MENTHONE


Anatomical context of MENTHONE


Associations of MENTHONE with other chemical compounds


Gene context of MENTHONE


Analytical, diagnostic and therapeutic context of MENTHONE


  1. Short-term toxicity study in rats dosed with menthone. Madsen, C., Würtzen, G., Carstensen, J. Toxicol. Lett. (1986) [Pubmed]
  2. Biofilm in water pipelines; a potential source for off-flavours in the drinking water. Skjevrak, I., Lund, V., Ormerod, K., Due, A., Herikstad, H. Water Sci. Technol. (2004) [Pubmed]
  3. Metallophosphite-catalyzed asymmetric acylation of alpha,beta-unsaturated amides. Nahm, M.R., Potnick, J.R., White, P.S., Johnson, J.S. J. Am. Chem. Soc. (2006) [Pubmed]
  4. Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint. Davis, E.M., Ringer, K.L., McConkey, M.E., Croteau, R. Plant Physiol. (2005) [Pubmed]
  5. Menthol blocks dihydropyridine-insensitive Ca2+ channels and induces neurite outgrowth in human neuroblastoma cells. Sidell, N., Verity, M.A., Nord, E.P. J. Cell. Physiol. (1990) [Pubmed]
  6. Effect of lipid bilayer alteration on transdermal delivery of a high-molecular-weight and lipophilic drug: studies with paclitaxel. Panchagnula, R., Desu, H., Jain, A., Khandavilli, S. Journal of pharmaceutical sciences. (2004) [Pubmed]
  7. Transdermal delivery of insulin from poloxamer gel: ex vivo and in vivo skin permeation studies in rat using iontophoresis and chemical enhancers. Pillai, O., Panchagnula, R. Journal of controlled release : official journal of the Controlled Release Society. (2003) [Pubmed]
  8. Transdermal drug delivery of imipramine hydrochloride. I. Effect of terpenes. Jain, A.K., Thomas, N.S., Panchagnula, R. Journal of controlled release : official journal of the Controlled Release Society. (2002) [Pubmed]
  9. In vitro percutaneous absorption enhancement of propranolol hydrochloride through porcine epidermis by terpenes/ethanol. Zhao, K., Singh, J. Journal of controlled release : official journal of the Controlled Release Society. (1999) [Pubmed]
  10. Effect of sucrose on the perceived flavor intensity of chewing gum. Davidson, J.M., Linforth, R.S., Hollowood, T.A., Taylor, A.J. J. Agric. Food Chem. (1999) [Pubmed]
  11. In vivo and in vitro destruction of rat liver cytochrome P-450 by a monoterpene ketone, pulegone. Madyastha, P., Moorthy, B., Vaidyanathan, C.S., Madyastha, K.M. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
  12. Membrane fluidity response to odorants as seen by 2H-NMR and infrared spectroscopy. Bouchard, M., Boudreau, N., Auger, M. Biochim. Biophys. Acta (1996) [Pubmed]
  13. Different stereoselectivity in the reduction of pulegone by Mentha species. Fuchs, S., Beck, T., Mosandl, A. Planta Med. (2001) [Pubmed]
  14. Enhanced iontophoretic delivery of buspirone hydrochloride across human skin using chemical enhancers. Meidan, V.M., Al-Khalili, M., Michniak, B.B. International journal of pharmaceutics. (2003) [Pubmed]
  15. Functional MRI of congenital hyposmia: brain activation to odors and imagination of odors and tastes. Henkin, R.I., Levy, L.M. Journal of computer assisted tomography. (2002) [Pubmed]
  16. Structural investigation of amylose complexes with small ligands: inter- or intra-helical associations? Rondeau-Mouro, C., Le Bail, P., Buléon, A. Int. J. Biol. Macromol. (2004) [Pubmed]
  17. Terpene penetration enhancers in propylene glycol/water co-solvent systems: effectiveness and mechanism of action. Yamane, M.A., Williams, A.C., Barry, B.W. J. Pharm. Pharmacol. (1995) [Pubmed]
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