(1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene

• 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/t8-,9?/m1/s1 Copy

  
• IUPAC Standard InChIKey: GRWFGVWFFZKLTI-VEDVMXKPSA-N Copy
• CAS Registry Number: 7785-26-4
• 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:
  • (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Stereoisomers:
  • α-Pinene
  • α-Pinene
• Other names: 1S-α-Pinene; (-)-α-Pinene; L-α-Pinene; Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (1S)-; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene-, (1S,5S)-; α-Pinene, (-)-; (1S)-(-)-α-Pinene; 1S-(-)-a-pinene; (-)-pin-2(3)-ene
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Condensed phase thermochemistry data

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

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

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

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

IR Spectrum

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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

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, polar column, temperature ramp

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References

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

Auwsers, Roth, et al., 1910
Auwsers, K.; Roth, W.A.; Eisenlohr, F., III. Verbrennungswarmen von Terpenen und Styrolen, Justus Liebigs Ann. Chem., 1910, 267-290. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Gomes, Serrano, et al., 1988
Gomes, A.; Serrano, L.; Fareio, F., Solid-Liquid Equilibria in 1,8-Cineole/TErpenic Hydrocarbon Systems, J. Chem. Eng. Data, 1988, 33, 194. [all data]

Hoskovec, Grygarová, et al., 2005
Hoskovec, Michal; Grygarová, Dana; Cvacka, Josef; Streinz, Ludvík; Zima, Jirí; Verevkin, Sergey P.; Koutek, Bohumír, Determining the vapour pressures of plant volatiles from gas chromatographic retention data, Journal of Chromatography A, 2005, 1083, 1-2, 161-172, https://doi.org/10.1016/j.chroma.2005.06.006 . [all data]

Dickens, 1999
Dickens, J.C., Predator-prey interactions: olfactory adaptations of generalist and specialist predators, Agric. For. Entomol., 1999, 1, 1, 47-54, https://doi.org/10.1046/j.1461-9563.1999.00007.x . [all data]

Dickens J.C., 2000
Dickens J.C., Sexual maturation and temporal variation of neural responses in adult Colorado potato beetles to volatiles emitted by potato plants, J. Chem. Ecol., 2000, 26, 5, 1265-1279, https://doi.org/10.1023/A:1005492229377 . [all data]

Rocha, Coelho, et al., 2007
Rocha, S.M.; Coelho, E.; Zrostlikova, J.; Delgadillo, I.; Coimbra b, M.A., Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry of monoterpenoids as a powerful tool for grape origin traceability, J. Chromatogr. A, 2007, 1161, 1-2, 292-299, https://doi.org/10.1016/j.chroma.2007.05.093 . [all data]

Saroglou, Marin, et al., 2007
Saroglou, V.; Marin, P.D.; Rancic, A.; Veljic, M.; Skaltsa, H., Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia, Biochem. Syst. Ecol., 2007, 35, 3, 146-152, https://doi.org/10.1016/j.bse.2006.09.009 . [all data]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Grujic-Jovanovic, Skaltsa, et al., 2004
Grujic-Jovanovic, S.; Skaltsa, H.D.; Marin, P.; Sokovic, M., Composition and antibacterial activity of the essential oil of six Stachys species from Serbia, Flavour Fragr. J., 2004, 19, 2, 139-144, https://doi.org/10.1002/ffj.1275 . [all data]

Karioti, Hadjipavlou-Litina, et al., 2004
Karioti, A.; Hadjipavlou-Litina, D.; Mensah, M.L.K.; Fleischer, T.C.; Skaltsa, H., Composition and antioxidant activity of the essential oils of Xylopia aethiopica (Dun) A. Rich. (Annonaceae) leaves, stem bark, root bark, and fresh and dried fruits, growing in Ghana, J. Agric. Food Chem., 2004, 52, 26, 8094-8098, https://doi.org/10.1021/jf040150j . [all data]

Kjeldsen, Christensen, et al., 2003
Kjeldsen, F.; Christensen, L.P.; Edelenbos, M., Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage, J. Agric. Food Chem., 2003, 51, 18, 5400-5407, https://doi.org/10.1021/jf030212q . [all data]

Limberger, Sobral, et al., 2005
Limberger, R.P.; Sobral, M.; Henriques, A.T., Intraspecific volatile oil variation in Myrceugenia cucullata (Myrtaceae), Biochem. Syst. Ecol., 2005, 33, 3, 287-293, https://doi.org/10.1016/j.bse.2004.10.002 . [all data]

Orav, Kailas, et al., 2002
Orav, A.; Kailas, T.; Müürisepp, M., Composition of blackcurrant aroma isolated from leaves, buds, and berries of Ribes nigrum L., Proc. Est. Acad. Sci. Chem., 2002, 51, 4, 225-234. [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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