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Chemical Compound Review

D-alpha-PINENE     (1S,5S)-4,7,7- trimethylbicyclo[3.1.1]hept...

Synonyms: PubChem18155, CPD-8754, CCRIS 9059, P45680_ALDRICH, CHEBI:28261, ...
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Disease relevance of CHEBI:28261


Psychiatry related information on CHEBI:28261


High impact information on CHEBI:28261

  • The rearrangement of the alpha-pinene-OH adduct, a key step in the proposed mechanism of formation of acetone from alpha-pinene, is determined to possess a barrier of 11.6 kcal/mol [7].
  • The C-C bond scission reactions of the beta-hydroxyalkoxy radicals that are formed after OH addition to alpha-pinene and beta-pinene are investigated [7].
  • By using metabolically altered mutants and acrylate, novel putative intermediates of alpha-pinene metabolism by Pseudomonas putida PIN11 were detected [1].
  • Nonpolar monoterpenes may require metabolism to be active in vitro, for example, cis-verbenol, a metabolite of alpha-pinene occurring in human urine, inhibits osteoclast activity in contrast to the parent compound [8].
  • Camphor, alpha-pinene (the major component of turpentine), and thujone (a constituent in the liqueur called absinthe) produced an increase in porphyrin production in primary cultures of chick embryo liver cells [9].

Biological context of CHEBI:28261


Anatomical context of CHEBI:28261


Associations of CHEBI:28261 with other chemical compounds

  • No other tested terpene was oxidized at a significant rate. alpha-Pinene was not metabolized by cell extracts in the presence or absence of NADH or NADPH [20].
  • A partially purified and lyophilized preparation of (+)-alpha-pinene cyclase from sage (Salvia officinalis) was shown to convert geranyl pyrophosphate to the monoterpene olefins alpha-pinene, camphene, limonene, and myrcene, in hexane with the addition of 0.1 to 10% water [21].
  • Influence of organic solvent on the behaviour of camphor and alpha-pinene enantiomers in reversed-phase liquid chromatography systems with alpha-cyclodextrin as chiral additive [22].
  • In the experiments carried out at 50 Torr and 100 Torr, HPLC measurements showed that the semi-volatile products formaldehyde, acetaldehyde, acetone, campholenealdehyde and pinonaldehyde could be quantified as oxidation products for the alpha-pinene/OH reaction, with pinonaldehyde being the main product [23].
  • Capillary GC and GC-MS analysis of the essential oil from the cones of JUNIPERUS COMMUNIS L. grown wild in Greece showed a high content of alpha-pinene (ca 27%), sabinene (13%), germacrene-D (10%), and myrcene (9%) [24].

Gene context of CHEBI:28261


Analytical, diagnostic and therapeutic context of CHEBI:28261


  1. alpha-Pinene metabolism by Pseudomonas putida. Tudroszen, N.J., Kelly, D.P., Millis, N.F. Biochem. J. (1977) [Pubmed]
  2. Purification and properties of alpha-pinene oxide lyase from Nocardia sp. strain P18.3. Griffiths, E.T., Harries, P.C., Jeffcoat, R., Trudgill, P.W. J. Bacteriol. (1987) [Pubmed]
  3. Chromatographic studies of the enantiomeric composition of some therapeutic compositions applied in the treatment of liver and kidney diseases. Sybilska, D., Kowalczyk, J., Asztemborska, M., Ochocka, R.J., Lamparczyk, H. Journal of chromatography. A. (1994) [Pubmed]
  4. Alleviating effects of plant-derived fragrances on stress-induced hyperthermia in rats. Akutsu, H., Kikusui, T., Takeuchi, Y., Sano, K., Hatanaka, A., Mori, Y. Physiol. Behav. (2002) [Pubmed]
  5. Activation of soil respiration and shift of the microbial population balance in soil as a response to Lavandula stoechas essential oil. Vokou, D., Chalkos, D., Karamanlidou, G., Yiangou, M. J. Chem. Ecol. (2002) [Pubmed]
  6. Ion exchange resins as catalyst for the isomerization of alpha-pinene to camphene. Chimal-Valencia, O., Robau-Sánchez, A., Collins-Martínez, V., Aguilar-Elguézabal, A. Bioresour. Technol. (2004) [Pubmed]
  7. Reactions of the alkoxy radicals formed following OH-addition to alpha-pinene and beta-pinene. C-C bond scission reactions. Dibble, T.S. J. Am. Chem. Soc. (2001) [Pubmed]
  8. Common herbs, essential oils, and monoterpenes potently modulate bone metabolism. Mühlbauer, R.C., Lozano, A., Palacio, S., Reinli, A., Felix, R. Bone (2003) [Pubmed]
  9. Porphyrogenic properties of the terpenes camphor, pinene, and thujone (with a note on historic implications for absinthe and the illness of Vincent van Gogh). Bonkovsky, H.L., Cable, E.E., Cable, J.W., Donohue, S.E., White, E.C., Greene, Y.J., Lambrecht, R.W., Srivastava, K.K., Arnold, W.N. Biochem. Pharmacol. (1992) [Pubmed]
  10. Strain improvement of Aspergillus sp. and Penicillium sp. by induced mutation for biotransformation of alpha-pinene to verbenol. Agrawal, R., Deepika, N.U., Joseph, R. Biotechnol. Bioeng. (1999) [Pubmed]
  11. Modeling aerosol formation from alpha-pinene + NOx in the presence of natural sunlight using gas-phase kinetics and gas-particle partitioning theory. Kamens, R.M., Jaoui, M. Environ. Sci. Technol. (2001) [Pubmed]
  12. Biodegradation of alpha-pinene in model biofilms in biofilters. Miller, M.J., Allen, D.G. Environ. Sci. Technol. (2005) [Pubmed]
  13. Gas chromatographic-mass spectrometric identification of metabolites from alpha-pinene in human urine after occupational exposure to sawing fumes. Eriksson, K., Levin, J.O. J. Chromatogr. B, Biomed. Appl. (1996) [Pubmed]
  14. Uptake, distribution and elimination of alpha-pinene in man after exposure by inhalation. Falk, A.A., Hagberg, M.T., Löf, A.E., Wigaeus-Hjelm, E.M., Wang, Z.P. Scandinavian journal of work, environment & health. (1990) [Pubmed]
  15. Antispasmodic effect of the essential oil of Plectranthus barbatus and some major constituents on the guinea-pig ileum. Câmara, C.C., Nascimento, N.R., Macêdo-Filho, C.L., Almeida, F.B., Fonteles, M.C. Planta Med. (2003) [Pubmed]
  16. Changes in the Essential Oil Components during the Development of Fennel Plants from Somatic Embryoids. Miura, Y., Ogawa, K., Fukui, H., Tabata, M. Planta Med. (1987) [Pubmed]
  17. A specialist herbivore (Neotoma stephensi) absorbs fewer plant toxins than does a generalist (Neotoma albigula). Sorensen, J.S., Turnbull, C.A., Dearing, M.D. Physiol. Biochem. Zool. (2004) [Pubmed]
  18. Is alpha-pinene a substrate for permeability-glycoprotein in wood rats? Green, A.K., Haley, S.L., Barnes, D.M., Dearing, M.D., Karasov, W.H. J. Chem. Ecol. (2006) [Pubmed]
  19. Induction of hepatic P450s in rat by essential wood and leaf oils. Hiroi, T., Miyazaki, Y., Kobayashi, Y., Imaoka, S., Funae, Y. Xenobiotica (1995) [Pubmed]
  20. Bacterial metabolism of alpha-pinene: pathway from alpha-pinene oxide to acyclic metabolites in Nocardia sp. strain P18.3. Griffiths, E.T., Bociek, S.M., Harries, P.C., Jeffcoat, R., Sissons, D.J., Trudgill, P.W. J. Bacteriol. (1987) [Pubmed]
  21. Terpene cyclase catalysis in organic solvent/minimal water media: demonstration and optimization of (+)-alpha-pinene cyclase activity. Wheeler, C.J., Croteau, R. Arch. Biochem. Biophys. (1986) [Pubmed]
  22. Influence of organic solvent on the behaviour of camphor and alpha-pinene enantiomers in reversed-phase liquid chromatography systems with alpha-cyclodextrin as chiral additive. Bielejewska, A., Duszczyk, K., Sybilska, D. Journal of chromatography. A. (2001) [Pubmed]
  23. Determination of the oxidation products of the reaction between alpha-pinene and hydroxyl radicals by high-performance liquid chromatography. Vanhees, I., Van den Bergh, V., Schildermans, R., De Boer, R., Compernolle, F., Vinckier, C. Journal of chromatography. A. (2001) [Pubmed]
  24. Study of the Essential Oil from Juniperus communis "Berries" (Cones) Growing Wild in Greece. Chatzopoulou, P.S., Katsiotis, S.T. Planta Med. (1993) [Pubmed]
  25. {alpha}-Pinene Inhibits Growth and Induces Oxidative Stress in Roots. Singh, H.P., Batish, D.R., Kaur, S., Arora, K., Kohli, R.K. Ann. Bot. (2006) [Pubmed]
  26. Effect of alpha-pinene on nuclear translocation of NF-kappa B in THP-1 cells. Zhou, J.Y., Tang, F.D., Mao, G.G., Bian, R.L. Acta Pharmacol. Sin. (2004) [Pubmed]
  27. Pinic and pinonic acid formation in the reaction of ozone with alpha-pinene. Ma, Y., Willcox, T.R., Russell, A.T., Marston, G. Chem. Commun. (Camb.) (2007) [Pubmed]
  28. Union of capillary high-performance liquid chromatography and microcoil nuclear magnetic resonance spectroscopy applied to the separation and identification of terpenoids. Lacey, M.E., Tan, Z.J., Webb, A.G., Sweedle, J.V. Journal of chromatography. A. (2001) [Pubmed]
  29. The phytochemical and genetic survey of common and dwarf juniper (Juniperus communis and Juniperus nana) identifies chemical races and close taxonomic identity of the species. Filipowicz, N., Piotrowski, A., Ochocka, J.R., Asztemborska, M. Planta Med. (2006) [Pubmed]
  30. Molecular size evolution of oligomers in organic aerosols collected in urban atmospheres and generated in a smog chamber. Kalberer, M., Sax, M., Samburova, V. Environ. Sci. Technol. (2006) [Pubmed]
  31. Use of a coupled biological system to treat a chemically complex air stream. Manninen, M.R., Niemi, B.A., Kleinheinz, G.T. Arch. Environ. Contam. Toxicol. (2003) [Pubmed]
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