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Chemical Compound Review

Carene     3,7,7- trimethylbicyclo[4.1.0]hept- 3-ene

Synonyms: d3-carene, S-3-Carene, CHEMBL506854, ACMC-1ADO8, AG-D-70852, ...
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Disease relevance of Monoterpenes


Psychiatry related information on Monoterpenes

  • The effect of water on the initial secondary organic aerosol (SOA) formation from gas-phase ozonolysis of limonene, delta3-carene, and alpha-pinene (-3 and approximately 1.5 x 10(11) molecule cm(-3) reacted) has been investigated in a flow reactor at controlled relative humidity (RH), temperature (298 +/- 0.4 K), and reaction time (270 +/- 2 s) [5].

High impact information on Monoterpenes


Chemical compound and disease context of Monoterpenes


Biological context of Monoterpenes


Anatomical context of Monoterpenes


Associations of Monoterpenes with other chemical compounds


Gene context of Monoterpenes

  • Our results suggest that monoterpenes induce growth arrest of colon cancer cells through the up-regulation of p21(Waf1/Cip1) and the down-expression of cyclin D1 and its partner cdk4 [26].
  • Further kinetic analysis revealed that CYP2B6 exhibited the highest activity for Delta(3)-carene 10-hydroxylation [27].
  • Given that some substrates of type I GGPTase, such as RhoA and Rac1, have transforming properties, the possibility that the inhibition of type I GGPTase will change the cellular location and functionality of these proteins and thus contribute to the chemoprevention activity of monoterpenes, is discussed [17].
  • Metabolism of Delta(3)-carene by human cytochrome p450 enzymes: identification and characterization of two new metabolites [27].
  • OBJECTIVE: The present study was undertaken to test more rigorously the hypothesis that monoterpenes raise HDL concentrations in men with hypoalphalipoproteinemia [19].

Analytical, diagnostic and therapeutic context of Monoterpenes


  1. Biotransformation of monoterpenes, bile acids, and other isoprenoids in anaerobic ecosystems. Hylemon, P.B., Harder, J. FEMS Microbiol. Rev. (1998) [Pubmed]
  2. Increased mannose 6-phosphate/insulin-like growth factor II receptor and transforming growth factor beta 1 levels during monoterpene-induced regression of mammary tumors. Jirtle, R.L., Haag, J.D., Ariazi, E.A., Gould, M.N. Cancer Res. (1993) [Pubmed]
  3. Effect of monoterpenes on the formation and activation of osteoclasts in vitro. Dolder, S., Hofstetter, W., Wetterwald, A., Mühlbauer, R.C., Felix, R. J. Bone Miner. Res. (2006) [Pubmed]
  4. The capacity for thermal protection of photosynthetic electron transport varies for different monoterpenes in Quercus ilex. Copolovici, L.O., Filella, I., Llusià, J., Niinemets, U., Peñuelas, J. Plant Physiol. (2005) [Pubmed]
  5. Impact of humidity on the ozone initiated oxidation of limonene, delta3-carene, and alpha-pinene. Jonsson, A.M., Hallquist, M., Ljungström, E. Environ. Sci. Technol. (2006) [Pubmed]
  6. Formation of monoterpenes in Antirrhinum majus and Clarkia breweri flowers involves heterodimeric geranyl diphosphate synthases. Tholl, D., Kish, C.M., Orlova, I., Sherman, D., Gershenzon, J., Pichersky, E., Dudareva, N. Plant Cell (2004) [Pubmed]
  7. (E)-beta-ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: function and expression of three terpene synthase genes of a new terpene synthase subfamily. Dudareva, N., Martin, D., Kish, C.M., Kolosova, N., Gorenstein, N., Fäldt, J., Miller, B., Bohlmann, J. Plant Cell (2003) [Pubmed]
  8. Autocrine interleukin-1beta production in leukemia: evidence for the involvement of mutated RAS. Beaupre, D.M., Talpaz, M., Marini, F.C., Cristiano, R.J., Roth, J.A., Estrov, Z., Albitar, M., Freedman, M.H., Kurzrock, R. Cancer Res. (1999) [Pubmed]
  9. Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Wattenberg, L.W., Sparnins, V.L., Barany, G. Cancer Res. (1989) [Pubmed]
  10. Mechanisms of antibacterial action of three monoterpenes. Trombetta, D., Castelli, F., Sarpietro, M.G., Venuti, V., Cristani, M., Daniele, C., Saija, A., Mazzanti, G., Bisignano, G. Antimicrob. Agents Chemother. (2005) [Pubmed]
  11. Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase. Bohlmann, J., Martin, D., Oldham, N.J., Gershenzon, J. Arch. Biochem. Biophys. (2000) [Pubmed]
  12. Effect of limonene and sobrerol on monocrotaline-induced lung alterations and pulmonary hypertension. Touvay, C., Vilain, B., Carré, C., Mencia-Huerta, J.M., Braquet, P. Int. Arch. Allergy Immunol. (1995) [Pubmed]
  13. Mono and diterpene production in Escherichia coli. Reiling, K.K., Yoshikuni, Y., Martin, V.J., Newman, J., Bohlmann, J., Keasling, J.D. Biotechnol. Bioeng. (2004) [Pubmed]
  14. Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells. Raphael, T.J., Kuttan, G. J. Exp. Clin. Cancer Res. (2003) [Pubmed]
  15. Biosynthesis of monoterpenes. Stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (-)-endo-fenchol. Croteau, R., Satterwhite, D.M., Wheeler, C.J., Felton, N.M. J. Biol. Chem. (1988) [Pubmed]
  16. Differential timing of spider mite-induced direct and indirect defenses in tomato plants. Kant, M.R., Ament, K., Sabelis, M.W., Haring, M.A., Schuurink, R.C. Plant Physiol. (2004) [Pubmed]
  17. Modulation of small G protein isoprenylation by anticancer monoterpenes in in situ mammary gland epithelial cells. Ren, Z., Gould, M.N. Carcinogenesis (1998) [Pubmed]
  18. Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. Wise, M.L., Savage, T.J., Katahira, E., Croteau, R. J. Biol. Chem. (1998) [Pubmed]
  19. Plant monoterpenes do not raise plasma high-density-lipoprotein concentrations in humans. Cooke, C.J., Nanjee, M.N., Dewey, P., Cooper, J.A., Miller, G.J., Miller, N.E. Am. J. Clin. Nutr. (1998) [Pubmed]
  20. Prenylated proteins and lymphocyte proliferation: inhibition by d-limonene related monoterpenes. Schulz, S., Bühling, F., Ansorge, S. Eur. J. Immunol. (1994) [Pubmed]
  21. Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita) and spearmint (Mentha spicata). Alonso, W.R., Rajaonarivony, J.I., Gershenzon, J., Croteau, R. J. Biol. Chem. (1992) [Pubmed]
  22. Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol. Satterwhite, D.M., Wheeler, C.J., Croteau, R. J. Biol. Chem. (1985) [Pubmed]
  23. Dimethylallyl diphosphate and geranyl diphosphate pools of plant species characterized by different isoprenoid emissions. Nogués, I., Brilli, F., Loreto, F. Plant Physiol. (2006) [Pubmed]
  24. Purification and characterization of a Baeyer-Villiger mono-oxygenase from Rhodococcus erythropolis DCL14 involved in three different monocyclic monoterpene degradation pathways. Van Der Werf, M.J. Biochem. J. (2000) [Pubmed]
  25. Perillyl alcohol selectively induces G0/G1 arrest and apoptosis in Bcr/Abl-transformed myeloid cell lines. Sahin, M.B., Perman, S.M., Jenkins, G., Clark, S.S. Leukemia (1999) [Pubmed]
  26. Monoterpenes inhibit proliferation of human colon cancer cells by modulating cell cycle-related protein expression. Bardon, S., Foussard, V., Fournel, S., Loubat, A. Cancer Lett. (2002) [Pubmed]
  27. Metabolism of Delta(3)-carene by human cytochrome p450 enzymes: identification and characterization of two new metabolites. Duisken, M., Benz, D., Peiffer, T.H., Blömeke, B., Hollender, J. Curr. Drug Metab. (2005) [Pubmed]
  28. Altered host plant volatiles are proxies for sex pheromones in the gall wasp Antistrophus rufus. Tooker, J.F., Koenig, W.A., Hanks, L.M. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  29. Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association. Ruch, R.J., Sigler, K. Carcinogenesis (1994) [Pubmed]
  30. Effect of selected monoterpenes on methane oxidation, denitrification, and aerobic metabolism by bacteria in pure culture. Amaral, J.A., Ekins, A., Richards, S.R., Knowles, R. Appl. Environ. Microbiol. (1998) [Pubmed]
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