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Chemical Compound Review

CARVONE     2-methyl-5-prop-1-en-2-yl- cyclohex-2-en-1-one

Synonyms: Carvol, Carvon, Karvon, D-Cavone, dl-Carvone, ...
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Disease relevance of Carvol


High impact information on Carvol

  • Treatment with increasing concentrations of the odorant, l-carvone, induced a time- and dose-dependent dramatic increase in GnRH protein release (1000-fold increase) and gene expression [5].
  • [reaction: see text] The first enantioselective total synthesis of valeriananoids A-C (-)-1-3 is reported starting from the readily available monoterpene (R)-carvone, employing a tandem intermolecular Michael addition-intramolecular Michael addition-alkylation sequence and an electron-transfer-mediated 6-endo-trig cyclization as key steps [6].
  • (S)-3,4,4-Trimethylcarvone (7), obtained from (R)-carvone, was transformed into the bicyclo[2.2.2]octanone 13 via regioselective intramolecular alkylation of the allyl bromide 11 [7].
  • The synthesis of l-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells [3].
  • The sensitizing potential of l-carvone has been considered low, but it has occasionally caused contact allergy in users of spearmint toothpaste and chewing gum. l-Carvone is also an oxidation product of d-limonene that occurs in solvents used increasingly in industry [8].

Anatomical context of Carvol

  • This mechanism was supported by the data recorded from a single olfactory cilium, showing that a single cell has both receptors for l-carvone and d-carvone and that the response to d-carvone appeared after the response to l-carvone was adapted [9].

Analytical, diagnostic and therapeutic context of Carvol


  1. Plant compounds that induce polychlorinated biphenyl biodegradation by Arthrobacter sp. strain B1B. Gilbert, E.S., Crowley, D.E. Appl. Environ. Microbiol. (1997) [Pubmed]
  2. Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Naigre, R., Kalck, P., Roques, C., Roux, I., Michel, G. Planta Med. (1996) [Pubmed]
  3. The synthesis of l-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. Chen, J., Lu, M., Jing, Y., Dong, J. Bioorg. Med. Chem. (2006) [Pubmed]
  4. Bioactivities of l-carvone, d-carvone, and dihydrocarvone toward three stored product beetles. Tripathi, A.K., Prajapati, V., Kumar, S. J. Econ. Entomol. (2003) [Pubmed]
  5. Sex steroids and odorants modulate gonadotropin-releasing hormone secretion in primary cultures of human olfactory cells. Barni, T., Maggi, M., Fantoni, G., Granchi, S., Mancina, R., Gulisano, M., Marra, F., Macorsini, E., Luconi, M., Rotella, C., Serio, M., Balboni, G.C., Vannelli, G.B. J. Clin. Endocrinol. Metab. (1999) [Pubmed]
  6. Enantioselective total synthesis of valeriananoids A-C. Srikrishna, A., Satyanarayana, G. Org. Lett. (2004) [Pubmed]
  7. An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes. Srikrishna, A., Anebouselvy, K. J. Org. Chem. (2001) [Pubmed]
  8. Carvone: an overlooked contact allergen cross-reacting with sesquiterpene lactones? Paulsen, E., Andersen, K.E., Carlsen, L., Egsgaard, H. Contact Derm. (1993) [Pubmed]
  9. Temperature increase abolishes ability of turtle olfactory receptors to discriminate similar odorant. Hanada, T., Kashiwayanagi, M., Kurihara, K. Am. J. Physiol. (1994) [Pubmed]
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