α-Pinene

• Formula: C₁₀H₁₆
• Molecular weight: 136.2340
• IUPAC Standard InChI: InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3 Copy

  
• IUPAC Standard InChIKey: GRWFGVWFFZKLTI-UHFFFAOYSA-N Copy
• CAS Registry Number: 80-56-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Species with the same structure:
  • α-Pinene
• Stereoisomers:
  • (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  • (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Other names: Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-; 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; Pinene, α; 2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene; 2,6,6-Trimethylbicyclo[3.1.1]-2-heptene; Acintene A; 4,6,6-Trimethylbicyklo(3,1,1)hept-3-en; UN 2368; alpha-Pinene; PC 500; Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-; Sylvapine A; (.+/-.)-α-Pinene; NSC 7727; Pinene; (+)-α-pinene; 2,6,6-trimethylbicyclo[3,1,1]-heptene (α-pinene); α-Pinene [1R-(+), 1S-(-) ]; 2,6,6-trimethylbicyclo-[3,1,1]-2-heptene (α-pinene); pin-2(3)-ene
• Information on this page:
  • Kovats' RI, non-polar column, custom temperature program
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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Kovats' RI, non-polar column, custom temperature program

Go To: Top, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

References

Go To: Top, Kovats' RI, non-polar column, custom temperature program, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

de Marchese, de Heluani, et al., 2007
de Marchese, M.J.A.; de Heluani, C.S.; Catalán, C.A.N.; Griffin, C.A.; Vaughn, J.B., Jr.; Herz, W., Incisol, an alcohol with a novel sesquiterpene skeleton from Xenophyllum incisum, Biochem. Syst. Ecol., 2007, 35, 3, 169-175, https://doi.org/10.1016/j.bse.2006.10.006 . [all data]

Khan, Verma, et al., 2006
Khan, M.; Verma, S.C.; Srivastava, S.K.; Shawl, A.S.; Syamsundar, K.V.; Khanuja, S.P.S.; Kumar, T., Essential oil composition of Taxus wallichiana Zucc. from the Northern Himalayan region of India, Flavour Fragr. J., 2006, 21, 5, 772-775, https://doi.org/10.1002/ffj.1682 . [all data]

Lima, Barros, et al., 2005
Lima, M.A.S.; Barros, M.C.P.; Pinheiro, S.M.; do Nascimento, R.F.; de Abreu Matos, F.J.; Silveira, E.R., Volatile compositions of two Asteraceae from the north-east of Brazil: Ageratum conyzoides and Acritopappus confertus (Eupatorieae), Flavour Fragr. J., 2005, 20, 6, 559-561, https://doi.org/10.1002/ffj.1483 . [all data]

Radusiene, Judzentiene, et al., 2005
Radusiene, J.; Judzentiene, A.; Bernotiene, G., Essential oil composition and variability of Hypericum perforatum L. growing in Lithuania, Biochem. Syst. Ecol., 2005, 33, 2, 113-124, https://doi.org/10.1016/j.bse.2004.06.010 . [all data]

Tuberoso, Kowalczyk, et al., 2005
Tuberoso, C.I.G.; Kowalczyk, A.; Coroneo, V.; Russo, M.T.; Dessì, S.; Cabras, P., Chemical Composition and Antioxidant, Antimicrobial, and Antifungal Activities of the Essential Oil of Achillea ligustica All., J. Agric. Food Chem., 2005, 53, 26, 10148-10153, https://doi.org/10.1021/jf0518913 . [all data]

Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A., Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India, Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333 . [all data]

Araújo, Silveira, et al., 2003
Araújo, E.C.C.; Silveira, E.R.; Lima, M.A.S.; Neto, M.A.; de Andrade, I.L.; Lima, M.A.A.; Santiago, G.M.P.; Mesquita, A.L.M., Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth, J. Agric. Food Chem., 2003, 51, 13, 3760-3762, https://doi.org/10.1021/jf021074s . [all data]

Daferera, Ziogas, et al., 2003
Daferera, D.J.; Ziogas, B.N.; Polissiou, M.G., The effectiveness of plant essential oils on the growth of Botrytis cinerea, Fusarium sp. and Clavibacter michiganensis subsp. michiganensis, Crop Prot., 2003, 22, 1, 39-44, retrieved from http://www.elsevier.com/gej-ng/10/25/40/84/25/31/article.pdf, https://doi.org/10.1016/S0261-2194(02)00095-9 . [all data]

Khan, Srivastava, et al., 2003
Khan, M.; Srivastava, S.K.; Jain, N.; Syamasundar, K.V.; Yadav, A.K., Chemical composition of fruit and stem essential oils of Lantana camara from northern India, Flavour Fragr. J., 2003, 18, 5, 376-379, https://doi.org/10.1002/ffj.1197 . [all data]

Shellie and Marriott, 2003
Shellie, R.A.; Marriott, P.J., Comprehensive two-dimensional gas chromatography-mass spectrometry analysis of Pelargonium graveolens essential oil using rapid scanning quadrupole mass spectrometry, Analyst, 2003, 128, 7, 879-883, https://doi.org/10.1039/b304371a . [all data]

El-Shazly, Dorai, et al., 2002
El-Shazly, A.; Dorai, G.; Wink, M., Chemical composition and biological activity of the essential oils of Senecio aegyptus var. discoideus Boiss., Z. Naturforsch., 2002, 57c, 434-439. [all data]

El-Shazly, Dorai, et al., 2002, 2
El-Shazly, A.; Dorai, G.; Wink, M., Composition and antimicrobial activity of essential oil and hexane-ether extract of Tanacetum santolinoides (DC.) Feinbr. and Fertig, Z. Naturforsch., 2002, 57c, 620-623. [all data]

Khan, Srivastava, et al., 2002
Khan, M.; Srivastava, S.K.; Syamasundar, K.V.; Singh, M.; Naqvi, A.A., Chemical composition of leaf and flower essential oil of Lantana camara from India, Flavour Fragr. J., 2002, 17, 1, 75-77, https://doi.org/10.1002/ffj.1047 . [all data]

Bizzo, Lopes, et al., 2001
Bizzo, H.R.; Lopes, D.; Abdala, R.V.; Pimentel, F.A.; de Souza, J.A.; Pereira, M.V.G.; Bergter, L.; Guimaraes, E.F., Sarisan from leaves of Piper affinis hispidinervum C. DC (long pepper), Flavour Fragr. J., 2001, 16, 2, 113-115, https://doi.org/10.1002/ffj.957 . [all data]

Frizzo, Serafini, et al., 2001
Frizzo, C.D.; Serafini, L.A.; Dellacassa, E.; Lorenzo, D.; Moyna, P., Essential oil of Baccharis uncinella DC. from Southern Brazil, Flavour Fragr. J., 2001, 16, 4, 286-288, https://doi.org/10.1002/ffj.998 . [all data]

Moreira, Sousa, et al., 2001
Moreira, D.L.; Sousa, P.O.; Pereira, N.A.; Cardoso, G.L., Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour, An. Acad. Bras. Cienc., 2001, 73, 1, 1-7, https://doi.org/10.1590/S0001-37652001000100004 . [all data]

Novak, Zitterl-Eglseer, et al., 2001
Novak, J.; Zitterl-Eglseer, K.; Deans, S.G.; Franz, C.M., Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity, Flavour Fragr. J., 2001, 16, 4, 259-262, https://doi.org/10.1002/ffj.993 . [all data]

Khouri, Usubillaga, et al., 2000
Khouri, N.; Usubillaga, A.; Rojas, L.B.; Galarraga, F., The essential oil of Espeletia weddellii Sch. Bip. ex Wedd., Flavour Fragr. J., 2000, 15, 4, 263-265, https://doi.org/10.1002/1099-1026(200007/08)15:4<263::AID-FFJ907>3.0.CO;2-Q . [all data]

Maia, Andrade, et al., 2000
Maia, J.G.S.; Andrade, E.H.A.; Zoghbi, M.G.B., Volatile constituents of the leaves, fruits and flowers of cashew ( Anacardium occidentaleL.), J. Food Comp. Anal., 2000, 13, 3, 227-232, https://doi.org/10.1006/jfca.2000.0894 . [all data]

Rojas and Usubillaga, 2000
Rojas, L.B.; Usubillaga, A., Composition of the essential oil fo Satureja brownei (SW.) Briq. from Venezuela, Flavour Fragr. J., 2000, 15, 1, 21-22, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<21::AID-FFJ861>3.0.CO;2-G . [all data]

Adams, 1998
Adams, R.P., The essential oils and chemotaxonomy of Juniperus sect. Juniperus, Biochem. Syst. Ecol., 1998, 26, 6, 637-645, https://doi.org/10.1016/S0305-1978(98)00020-9 . [all data]

Santos, Andrade, et al., 1998
Santos, A.S.; Andrade, E.H.A.; Zoghbi, M.G.B.; Maia, J.G.S., Volatile constituents of fruits of Annona glabra L. from Brazil, Flavour Fragr. J., 1998, 13, 3, 148-150, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<148::AID-FFJ711>3.0.CO;2-Y . [all data]

MacLeod, MacLeod, et al., 1988
MacLeod, A.J.; MacLeod, G.; Subramanian, G., Volatile aroma constituents of orange, Phytochemistry, 1988, 27, 7, 2185-2188, https://doi.org/10.1016/0031-9422(88)80123-7 . [all data]

Okamoto, Ellison, et al., 1981
Okamoto, R.A.; Ellison, B.O.; Kepner, R.E., Volatile terpenes in Sequoia sempervirens foliage. Changes in composition during maturation, J. Agric. Food Chem., 1981, 29, 2, 324-326, https://doi.org/10.1021/jf00104a026 . [all data]

Malingré and Maarse, 1974
Malingré, T.M.; Maarse, H., Composition of the essential oil of Mentha aquatica, Phytochemistry, 1974, 13, 8, 1531-1535, https://doi.org/10.1016/0031-9422(74)80322-5 . [all data]

Minyard, Tumlinson, et al., 1967
Minyard, J.P.; Tumlinson, J.H.; Thompson, A.C.; Hedin, P.A., Constituents of the cotton bud. The carbonyl compounds, J. Agric. Food Chem., 1967, 15, 3, 517-524, https://doi.org/10.1021/jf60151a021 . [all data]

Notes

Go To: Top, Kovats' RI, non-polar column, custom temperature program, References

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