(-)-β-Bourbonene

• Formula: C₁₅H₂₄
• Molecular weight: 204.3511
• IUPAC Standard InChI: InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12?,13?,14?,15-/m1/s1 Copy

  
• IUPAC Standard InChIKey: YIRAHEODBQONHI-XTLGRWLVSA-N Copy
• CAS Registry Number: 5208-59-3
• 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.
• Stereoisomers:
  • Bourbonene
  • 1,2,3a,3b'a,4,5,6,6aa',6ba'-Decahydro-1a'-isopropyl-3aa'-methyl-6-methylenecyclobuta[1,2:3,4]dicyclopentene
  • 1,5-di-epi-β-Bourbonene
  • (E)-β-Bourbonene
  • 1,5-di-epi-β-Bourbonene
• Other names: Cyclobuta[1,2:3,4]dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, [1S-(1α,3aα,3bβ,6aβ,6bα)]-; β-Bourbonene; Cyclobuta[1,2:3,4]dicyclopentene, 1,2,3,3a,3bβ,4,5,6,6aβ,6bα-decahydro-1α-isopropyl-3aα-methyl-6-methylene-; Cyclobuta[1,2:3,4]dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1α,3aα,3bβ,6aβ,6bα)-; [1S-[1α,3aα,3bβ,6aβ,6bα]]-Cyclobuta[1,2:3,4]dicyclopentene-decahydro-3a-methyl-6-methylene-1-[1-methylethyl]; (1S,3aS,3bR,6aS,6bR)-1-Isopropyl-3a-methyl-6-methylenedecahydrocyclobuta[1,2:3,4]di[5]annulene; β-bourbenene; Cyclobuta[1,2:3,4]dicyclopentene, decahydro-3a-methyl-6-methylene-1-(1-methylethyl)-, (1S,3aS,3bR,6aS,6bR)-; beta-bourbonene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Van Den Dool and Kratz RI, polar column, temperature ramp
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Options:
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Van Den Dool and Kratz RI, polar column, temperature ramp

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

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

Lesueur, de Rocca Serra, et al., 2007
Lesueur, D.; de Rocca Serra, D.; Bighelli, A.; Hoi, T.M.; Ban, N.K.; Thai, T.H.; Casanova, J., Chemical composition and antibacterial activity of the essential oil of Michelia foveolata Merryll ex Dandy from Vietnam, Flavour Fragr. J., 2007, 22, 4, 317-321, https://doi.org/10.1002/ffj.1799 . [all data]

Paolini J., Costa J., et al., 2007
Paolini J.; Costa J.; Bernardini A.F., Analysis of the essential oil from the roots of Eupatorium cannabinum subsp corsicum (L.) by GC, GC-MS and C-13-NMR, Phytochem. Anal., 2007, 18, 3, 235-244, https://doi.org/10.1002/pca.977 . [all data]

Flamini, Tebano, et al., 2006
Flamini, G.; Tebano, M.; Cioni, P.L.; Bagci, Y.; Dural, H.; Ertugrul, K.; Uysal, T.; Savran, A., A multivariate statistical approach to Centaurea classification using essential oil composition data of some species from Turkey, Pl. Syst. Evol., 2006, 261, 1-4, 217-228, https://doi.org/10.1007/s00606-006-0448-3 . [all data]

Pinto, Pina-Vaz, et al., 2006
Pinto, E.; Pina-Vaz, C.; Salgueiro, L.; Goncalves, M.J.; Costa-de-Oliveira, S.; Cavaleiro, C.; Palmeira, A.; Rodrigues, A.; Martinez-de-Oliveira, J., Antifuncal activity of the essential oil Thymus pulegioides on Candida, Aspergillus and dermatophyte species, Journal of Medical Microbiology, 2006, 55, 10, 1367-1373, https://doi.org/10.1099/jmm.0.46443-0 . [all data]

Salgueiro L.R., Pinto E., et al., 2006
Salgueiro L.R.; Pinto E.; Goncalves M.J.; Costa I.; Palmeira A.; Cavaleiro C.; Pina-Vaz C.; Rodrigues A.G.; Martinez-De-Oliveira J., Antifungal activity of the essential oil of Thymus capitellatus against Candida, Aspergillus and dermatophyte strains, Flavour Fragr. J., 2006, 21, 5, 749-753, https://doi.org/10.1002/ffj.1610 . [all data]

Skocibusic, Bezic, et al., 2006
Skocibusic, M.; Bezic, N.; Dunkic, V., Phytochemical composition and antimicrobial activities of the essential oils from Satureja subspicata Vis. growing in Croatia, Food Chem., 2006, 96, 1, 20-28, https://doi.org/10.1016/j.foodchem.2005.01.051 . [all data]

Fanciullino, Gancel, et al., 2005
Fanciullino, A.-L.; Gancel, A.-L.; Froelicher, Y.; Luro, F.; Ollitrault, P.; Brillouet, J.-M., Effects of Nucleo-cytoplasmic Interactions on Leaf Volatile Compounds from Citrus Somatic Diploid Hybrids, J. Agric. Food Chem., 2005, 53, 11, 4517-4523, https://doi.org/10.1021/jf0502855 . [all data]

Gancel, Ollitrault, et al., 2005
Gancel, A.-L.; Ollitrault, P.; Froelicher, Y.; Tomi, F.; Jacquemond, C.; Luro, F.; Brillouet, J.-M., Leaf volatile compounds of six citrus somatic allotetraploid hybrids originating from various combinations of lime, lemon, citron, sweet orange, and grapefruit, J. Agric. Food Chem., 2005, 53, 6, 2224-2230, https://doi.org/10.1021/jf048315b . [all data]

Lee, Lee, et al., 2005
Lee, J.-G.; Lee, C.-G.; Kwag, J.-J.; Buglass, A.J.; Lee, G.-H., Determination of optimum conditions for the analysis of volatile components in pine needles by double-shot pyrolysis-gas chromatography-mass spectrometry, J. Chromatogr. A, 2005, 1089, 1-2, 227-234, https://doi.org/10.1016/j.chroma.2005.06.060 . [all data]

Paolini, Costa, et al., 2005
Paolini, J.; Costa, J.; Bernardini, A., Analysis of the essential oil from aerial parts of Eupatorium cannabinum subsp. corsicum (L.) by gas chromatography with electron impact and chemical ionization mass spectrometry, J. Chromatogr. A, 2005, 1076, 1-2, 170-178, https://doi.org/10.1016/j.chroma.2005.03.131 . [all data]

Vellutini, Baldovini, et al., 2005
Vellutini, M.; Baldovini, N.; de Rocca Serra, D. Tomi; Casanova, J., β-Cyclolavandulyl and β-isocyclolavandulyl esters from Peucedanum paniculatum L., an endemic species to Corsica, Phytochemistry, 2005, 66, 16, 1956-1962, https://doi.org/10.1016/j.phytochem.2005.07.001 . [all data]

Bertoli, Menichini, et al., 2004
Bertoli, A.; Menichini, F.; Noccioli, C.; Morelli, I.; Pistelli, L., Volatile constituents of different organs of Psoralea bituminosa L., Flavour Fragr. J., 2004, 19, 2, 166-171, https://doi.org/10.1002/ffj.1315 . [all data]

Cavaleiro, Salgueiro, et al., 2004
Cavaleiro, C.; Salgueiro, L.R.; Miguel, M.G.; da Cunha, A.P., Analysis by gas chromatography?mass spectrometry of the volatile components of Teucrium lusitanicum and Teucrium algarbiensis, J. Chromatogr. A, 2004, 1033, 1, 187-190, https://doi.org/10.1016/j.chroma.2004.01.005 . [all data]

Flamini, Luigi Cioni, et al., 2004
Flamini, G.; Luigi Cioni, P.; Morelli, I., Essential oils of Galeopsis pubescens and G. tetrahit from Tuscany (Italy), Flavour Fragr. J., 2004, 19, 4, 327-329, https://doi.org/10.1002/ffj.1307 . [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]

Skocibusic and Bezic, 2004
Skocibusic, M.; Bezic, N., Phytochemical Analysis and In vitro Antimicrobial Activity of Two Satureja Species Essential Oils, Phytother. Res., 2004, 18, 12, 967-970, https://doi.org/10.1002/ptr.1489 . [all data]

Yu, Kim, et al., 2004
Yu, E.J.; Kim, T.H.; Kim, K.H.; Lee, H.J., Aroma-active compounds of Pinus densiflora (red pine) needles, Flavour Fragr. J., 2004, 19, 6, 532-537, https://doi.org/10.1002/ffj.1337 . [all data]

Bader, Caponi, et al., 2003
Bader, A.; Caponi, C.; Cioni, P.L.; Flamini, G.; Morelli, I., Composition of the essential oil of Ballota undulata, B. nigra ssp. foetida and B. saxatilis, Flavour Fragr. J., 2003, 18, 6, 502-504, https://doi.org/10.1002/ffj.1257 . [all data]

Gancel, Ollitrault, et al., 2003
Gancel, A.-L.; Ollitrault, P.; Froelicher, Y.; Tomi, F.; Jacquemond, C.; Luro, F.; Brillouet, J.-M., Leaf volatile compounds of seven citrus somatic tetraploid hybrids sharing willow leaf mandarin (Citrus deliciosa Ten.) as their common parent, J. Agric. Food Chem., 2003, 51, 20, 6006-6013, https://doi.org/10.1021/jf0345090 . [all data]

Jerkovic, Mastelic, et al., 2003
Jerkovic, I.; Mastelic, J.; Milos, M.; Juteau, F.; Masotti, V.; Viano, J., Chemical variability of Artemisia vulgaris L. essential oils originated from the Mediterranean area of France and Croatia, Flavour Fragr. J., 2003, 18, 5, 436-440, https://doi.org/10.1002/ffj.1246 . [all data]

Radonic and Milso, 2003
Radonic, A.; Milso, M., Chemical Composition and In Vitro Evaluation of Antioxidant Effect of Free Volatile Compounds From Satureja montana L., Free Radical Research, 2003, 37, 6, 673-679, https://doi.org/10.1080/1071576031000105643 . [all data]

Skocibusic and Bezic, 2003
Skocibusic, M.; Bezic, N., Chemical composition and antidiarrhoeal activities of winter savory (Satureja montana L.) essential oil, Pharm. Biol., 2003, 41, 8, 622-626, https://doi.org/10.1080/13880200390502180 . [all data]

Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatile in Cosa Rican Guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit, J. Agric. Food Chem., 2002, 50, 21, 6023-6026, https://doi.org/10.1021/jf011456i . [all data]

Milos, Radonic, et al., 2001
Milos, M.; Radonic, A.; Bezic, N.; Dunkic, V., Localities and seasonal variations in the chemical composition of essential oils of Satureja montana L. and S. cuneifolia Ten, Flavour Fragr. J., 2001, 16, 3, 157-160, https://doi.org/10.1002/ffj.965 . [all data]

Brophy, Goldsack, et al., 2000
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., Essential oils of the genus Lophostemon (Myrtaceae), Flavour Fragr. J., 2000, 15, 1, 17-20, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<17::AID-FFJ859>3.0.CO;2-D . [all data]

Brophy, Goldsack, et al., 2000, 2
Brophy, J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 6. Leptospermum polygalifolium and allies, Flavour Fragr. J., 2000, 15, 4, 271-277, https://doi.org/10.1002/1099-1026(200007/08)15:4<271::AID-FFJ910>3.0.CO;2-E . [all data]

Brophy, Goldsack, et al., 2000, 3
Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Bean, A.R.; Forster, P.I.; Lepschi, B.J.; Doran, J.C.; Rozefelds, A.C., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 7. Leptospermum petersonii, L. liversidgei and allies, Flavour Fragr. J., 2000, 15, 5, 342-351, https://doi.org/10.1002/1099-1026(200009/10)15:5<342::AID-FFJ924>3.0.CO;2-V . [all data]

Chagonda, Makanda, et al., 2000
Chagonda, L.S.; Makanda, C.D.; Chalchat, J.-C., The essential oils of Ocimum canum Sims (basilic camphor) and Ocimum urticifolia Roth from Zimbabwe, Flavour Fragr. J., 2000, 15, 1, 23-26, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<23::AID-FFJ866>3.0.CO;2-W . [all data]

Kim, Thuy, et al., 2000
Kim, T.H.; Thuy, N.T.; Shin, J.H.; Baek, H.H.; Lee, H.J., Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim.), J. Agric. Food Chem., 2000, 48, 7, 2877-2881, https://doi.org/10.1021/jf000219x . [all data]

Milos and Radonic, 2000
Milos, M.; Radonic, A., Gas chromatography mass spectral analysis of free and glycosidically bound volatile compounds from Juniperus oxycedrus L. growing wild in Croatia, Food Chem., 2000, 68, 3, 333-338, https://doi.org/10.1016/S0308-8146(99)00192-2 . [all data]

Brophy, Goldsack, et al., 1999
Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Forster, P.I., The leaf essential oils of Pilidiostigma (Myrtaceae), Flavour Fragr. J., 1999, 14, 2, 143-146, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<143::AID-FFJ798>3.0.CO;2-P . [all data]

Brophy, Goldsack, et al., 1999, 2
Brophy, J.J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 5. Leptospermum continentale and allies, Flavour Fragr. J., 1999, 14, 2, 98-104, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<98::AID-FFJ797>3.0.CO;2-V . [all data]

Brophy, Forster, et al., 1998
Brophy, J.J.; Forster, P.I.; Goldsack, R.J., Esssential oils of some Australian monimiaceae, Flavour Fragr. J., 1998, 13, 4, 273-276, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<273::AID-FFJ745>3.0.CO;2-O . [all data]

Brophy, Goldsack, et al., 1998
Brophy, J.J.; Goldsack, R.J.; Forster, P.I.; Bean, A.R.; Clarkson, J.R.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in Eastern Australia. Part 1. Leptospermum brachyandrum and Leptospermum pallidum groups, Flavour Fragr. J., 1998, 13, 1, 19-25, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<19::AID-FFJ679>3.0.CO;2-9 . [all data]

Brophy, Goldsack, et al., 1998, 2
Brophy, J.J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 2. Leptospermum blakelyi and allies, Flavour Fragr. J., 1998, 13, 5, 353-358, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<353::AID-FFJ759>3.0.CO;2-1 . [all data]

Brophy, Goldsack, et al., 1997
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., The essential oils of the Australian species of Rhodomyrtus (Myrtaceae), Flavour Fragr. J., 1997, 12, 2, 103-108, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<103::AID-FFJ621>3.0.CO;2-B . [all data]

Brophy, Goldsack, et al., 1997, 2
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., The leaf essential oils of the Australian species of Rhodamnia (Myrtaceae), Flavour Fragr. J., 1997, 12, 5, 345-354, https://doi.org/10.1002/(SICI)1099-1026(199709/10)12:5<345::AID-FFJ658>3.0.CO;2-6 . [all data]

Sagrero-Nieves, Bartley, et al., 1997
Sagrero-Nieves, L.; Bartley, J.P.; Griselda Espinosa, B.; Dominguez, X.A.; Julia Verde S., Essential oil composition of Aristolochia brevipes Benth., Flavour Fragr. J., 1997, 12, 6, 401-403, https://doi.org/10.1002/(SICI)1099-1026(199711/12)12:6<401::AID-FFJ673>3.0.CO;2-D . [all data]

Notes

Go To: Top, Van Den Dool and Kratz RI, polar column, temperature ramp, References

• Symbols used in this document:
  

  Tend	Final temperature
  Tstart	Initial temperature

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