β-Bisabolene

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m0/s1
IUPAC Standard InChIKey: XZRVRYFILCSYSP-HNNXBMFYSA-N
CAS Registry Number: 495-61-4
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.
Stereoisomers:
- (E)- β-Bisabolene
- Bisabolene
Other names: Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexenyl)-, (S)-; 1,5-Heptadiene, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-, (S)-(-)-; l-β-Bisabolene; (+,-)-β-Bisabolene; 1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)-1-cyclohexene-, (4S)-; beta-Bisabolene; (-)-β-bisabolene; 1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)-(S)-cyclohexene; (S)-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene; Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexen-1-yl)-, (4S)-
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Kovats' RI, non-polar column, temperature ramp

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5MS	DB-5	BP-1	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	60.	60.	40.
T_end (C)	280.	280.		220.	210.
Heat rate (K/min)	5.	2.	3.	5.	2.
Initial hold (min)	3.	8.			2.
Final hold (min)		30.		3.	33.
I	1503.	1506.	1509.	1503.	1512.
Reference	Allegrone, Belliardo, et al., 2006	Hazzit, Baaliouamer, et al., 2006	Lucero, Fredrickson, et al., 2006	Srivastava, Srivastava, et al., 2006	Sylvestre, Pichette, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	HP-5MS	DB-5	SPB-1	HP-5MS
Column length (m)	30.	30.		30.	30.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.25	0.25		0.32	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	50.	50.	60.	50.	60.
T_end (C)	240.	250.	240.	250.	200.
Heat rate (K/min)	3.	3.	3.	2.	4.
Initial hold (min)		10.		2.	1.
Final hold (min)		5.		5.	15.
I	1547.	1511.	1509.	1490.	1506.
Reference	Tepe, Askin Akpulat, et al., 2006	Asuming, Beauchamp, et al., 2005	Shatar S., 2005	Behera, Nagarajan, et al., 2004	Juliani, Zygadlo, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	DB-5	DB-5	HP-5MS	HP-5MS
Column length (m)	30.	25.	50.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25		0.25	0.25	0.25
T_start (C)	60.	40.	50.	50.	60.
T_end (C)	260.	280.	280.	280.	280.
Heat rate (K/min)	3.	3.	5.	4.	3.
Initial hold (min)		5.	2.	2.
Final hold (min)		5.	10.	10.
I	1509.	1506.	1525.	1517.	1489.
Reference	Lopes, Strobl, et al., 2004	Amparo Blázquez, Pérez, et al., 2003	Baranauskiene, Venskutonis, et al., 2003	Baranauskiene, Venskutonis, et al., 2003, 2	Gkinis, Tzakou, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	BP-1	SPB-1	HP-5	DB-1
Column length (m)	25.	25.	30.	30.	25.
Carrier gas	He	N2	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.25	0.2
Phase thickness (μm)	0.15	0.25	0.25	0.25
T_start (C)	50.	60.	60.	60.	60.
T_end (C)	230.	220.	225.	200.	220.
Heat rate (K/min)	3.	5.	2.	4.	3.
Initial hold (min)			3.	1.
Final hold (min)		15.	5.	15.
I	1505.	1507.	1476.	1509.	1506.
Reference	Ogunwande, Olawore, et al., 2003	Raina, Srivastava, et al., 2003	Jayaprakasha, Jena, et al., 2002	Juliani and Simon, 2002	Mevy, Bessiere, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	BP-1	HP-5MS	BP-1	HP-1
Column length (m)	25.	25.	30.	30.	25.
Carrier gas	N2	N2	He	N2	He
Substrate
Column diameter (mm)	0.32	0.55	0.25	0.32	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	50.	60.	100.
T_end (C)	220.	220.	250.	220.	220.
Heat rate (K/min)	5.	5.	3.	5.	4.
Initial hold (min)
Final hold (min)	15.	15.		13.
I	1505.	1501.	1508.	1510.	1508.
Reference	Raina, Srivastava, et al., 2002	Raina, Srivastava, et al., 2002, 2	Salido, Altarejos, et al., 2002	Shawl, Srivastava, et al., 2002	Rajeswara Rao, 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	SE-54	DB-5	SE-30	OV-101
Column length (m)	30.	30.	30.	25.	25.
Carrier gas	He		He	He
Substrate
Column diameter (mm)	0.25	0.26	0.26	0.2	0.32
Phase thickness (μm)	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	50.
T_end (C)	280.	246.	246.	180.	200.
Heat rate (K/min)	3.	3.	3.	3.	5.
Initial hold (min)				10.
Final hold (min)
I	1509.	1509.	1509.	1503.	1491.
Reference	Tzakou and Couladis, 2001	Adams, 2000	Adams, 1999	Jantan I. and Ahmad A.S., 1999	Kuiate, Zollo, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	HP-5MS	Methyl Silicone	Methyl Silicone	CP Sil 5 CB
Column length (m)	30.	30.	30.	25.	30.
Carrier gas	He	He	He	N2	Ar
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.5	0.25
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	60.	70.	60.	60.	60.
T_end (C)	280.	250.	250.	220.	220.
Heat rate (K/min)	4.	3.	2.	5.	3.
Initial hold (min)		5.	2.
Final hold (min)			5.
I	1507.	1500.	1497.	1507.	1500.
Reference	Sajjadi and Ghassemi, 1999	Siani, Ramos, et al., 1999	Adegoke, Rao, et al., 1998	Mallavarapu, Rao, et al., 1998	Szafranek, Malinski, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 8 CB	SE-30	DB-1	BP-1
Column length (m)	25.	25.	28.	50.
Carrier gas	Ar	N2	He	H2
Substrate
Column diameter (mm)	0.15	0.2	0.25	0.33
Phase thickness (μm)	0.12		0.25
T_start (C)	60.	60.	50.	65.
T_end (C)	220.	180.	270.	220.
Heat rate (K/min)	3.	3.	4.	5.
Initial hold (min)		10.	1.	2.
Final hold (min)		1.
I	1507.	1498.	1498.	1506.
Reference	Szafranek, Malinski, et al., 1998	Jantan, Ahmad, et al., 1996	Saad, El-Sharkawy, et al., 1995	Ekundayo, Laakso, et al., 1988
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Allegrone, Belliardo, et al., 2006
Allegrone, G.; Belliardo, F.; Cabella, P., Comparison of volatile concentrations in hand-squeezed juices of four different lemon varieties, J. Agric. Food Chem., 2006, 54, 5, 1844-1848, https://doi.org/10.1021/jf051206s . [all data]

Hazzit, Baaliouamer, et al., 2006
Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G., Composition of the Essential Oils of Thymus and Origanum Species from Algeria and Their Antioxidant and Antimicrobial Activities, J. Agric. Food Chem., 2006, 54, 17, 6314-6321, https://doi.org/10.1021/jf0606104 . [all data]

Lucero, Fredrickson, et al., 2006
Lucero, M.E.; Fredrickson, E.L.; Estell, R.E.; Morrison, A.A.; Richman, D.B., Volatile Composition of Gutierrezia sarothrae (Broom Snakeweed) as Determined by Steam Distillation and Solid Phase Microextraction, J. Essent. Oil Res., 2006, 18, 2, 121-125, https://doi.org/10.1080/10412905.2006.9699039 . [all data]

Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V., Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India, Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680 . [all data]

Sylvestre, Pichette, et al., 2006
Sylvestre, M.; Pichette, A.; Longtin, A.; Nagau, F.; Legault, J., Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe, J. Ethnopharmacol., 2006, 103, 1, 99-102, https://doi.org/10.1016/j.jep.2005.07.011 . [all data]

Tepe, Askin Akpulat, et al., 2006
Tepe, B.; Askin Akpulat, H.; Sokmen, M.; Daferera, D.; Yumrutas, O.; Aydin, E.; Polissiou, M.; Sokmen, A., Screening of the antioxidative and antimicrobial properties of the essential oils of Pimpinella anisetum and Pimpinella flabellifolia from Turkey, Food Chem., 2006, 97, 4, 719-724, https://doi.org/10.1016/j.foodchem.2005.05.045 . [all data]

Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005 . [all data]

Shatar S., 2005
Shatar S., Essential oil of Ferula ferulaoides from Western Mongolia, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 5, 607-608, https://doi.org/10.1007/s10600-005-0222-8 . [all data]

Behera, Nagarajan, et al., 2004
Behera, S.; Nagarajan, S.; Rao, L.J.M., Microwave heating and conventional roasting of cumin seeds (Cuminum cyminum L.) and effect on chemical composition of volatiles, Food Chem., 2004, 87, 1, 25-29, https://doi.org/10.1016/j.foodchem.2003.10.012 . [all data]

Juliani, Zygadlo, et al., 2004
Juliani, H.R.; Zygadlo, J.A.; Scrivanti, R.; de la Sota, E.; Simon, J.E., The essential oil of Anemia tomentosa (Savigny) Sw. var. anthriscifolia (Schrad.) Mickel, Flavour Fragr. J., 2004, 19, 6, 541-543, https://doi.org/10.1002/ffj.1341 . [all data]

Lopes, Strobl, et al., 2004
Lopes, D.; Strobl, H.; Kolodziejczyk, P., 14-Methylpentadecano-15-lactone (Muscolide): a new macrocyclic lactone from the oil of Angelica archangelica L., Chemistry and Biodiversity, 2004, 1, 12, 1880-1887, https://doi.org/10.1002/cbdv.200490144 . [all data]

Amparo Blázquez, Pérez, et al., 2003
Amparo Blázquez, M.; Pérez, I.; Boira, H., Essential oil analysis of Teucrium libanitis and T. turredanum by GC and GC-MS, Flavour Fragr. J., 2003, 18, 6, 497-501, https://doi.org/10.1002/ffj.1256 . [all data]

Baranauskiene, Venskutonis, et al., 2003
Baranauskiene, R.; Venskutonis, R.P.; Demyttenaere, J.C.R., Sensory and instrumental evaluation of catnip (Nepeta cataria L.) aroma, J. Agric. Food Chem., 2003, 51, 13, 3840-3848, https://doi.org/10.1021/jf021187b . [all data]

Baranauskiene, Venskutonis, et al., 2003, 2
Baranauskiene, R.; Venskutonis, P.R.; Viskelis, P.; Dambrauskiene, E., Influence of nitrogen fertilizers on the yield and composition of thyme (Thymus vulgaris), J. Agric. Food Chem., 2003, 51, 26, 7751-7758, https://doi.org/10.1021/jf0303316 . [all data]

Gkinis, Tzakou, et al., 2003
Gkinis, G.; Tzakou, O.; Iliopoulou, D.; Roussis, V., Chemical Composition and Biological Activity of Nepeta parnassica Oils and Isolated Nepetalactones, Z. Naturforsch. C:, 2003, 58, 681-686. [all data]

Ogunwande, Olawore, et al., 2003
Ogunwande, I.A.; Olawore, N.O.; Adeleke, K.A.; Ekundayo, O.; Koenig, W.A., Chemical composition of the leaf volatile oil of Psidium guajava L. growing in Nigeria, Flavour Fragr. J., 2003, 18, 2, 136-138, https://doi.org/10.1002/ffj.1175 . [all data]

Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Syamasunder, K.V., Essential oil composition of Acorus calamus L. from the lower region of the Himalayas, Flavour Fragr. J., 2003, 18, 1, 18-20, https://doi.org/10.1002/ffj.1136 . [all data]

Jayaprakasha, Jena, et al., 2002
Jayaprakasha, G.K.; Jena, B.S.; Negi, P.S.; Sakariah, K.K., Evaluation of antioxidant activities and antimutagenicity of turmeric oil: a byproduct from curcumin production, Z. Naturforsch. C:, 2002, 57c, 828-835, retrieved from http://www.znaturforsch.com/57c/s57c0828.pdf. [all data]

Juliani and Simon, 2002
Juliani, H.R.; Simon, J.E., Antioxidant acitivity of basil in Trends in new crops and new uses, Janick,J.; Whipkey,A., ed(s)., ASHA Press, Alexandria, Va, 2002, 575-579. [all data]

Mevy, Bessiere, et al., 2002
Mevy, J.P.; Bessiere, J.-M.; Dherbomez, M.; Viano, J., Composition and some biological activities of the essential oils from an African pasture grass: Elionurus elegans Kunth., J. Agric. Food Chem., 2002, 50, 15, 4240-4243, https://doi.org/10.1021/jf0115140 . [all data]

Raina, Srivastava, et al., 2002
Raina, V.K.; Srivastava, S.K.; Syamasunder, K.V., The essential oil of 'greater galangal' [Alpinia galanga (L.) Willd.] from the lower Himalayan region of India, Flavour Fragr. J., 2002, 17, 5, 358-360, https://doi.org/10.1002/ffj.1105 . [all data]

Raina, Srivastava, et al., 2002, 2
Raina, V.K.; Srivastava, S.K.; Jain, N.; Ahmad, A.; Syamasundar, K.V.; Aggarwal, K.K., Essential oil composition of Curcuma longa L. cv. Roma from the plains of northern India, Flavour Fragr. J., 2002, 17, 2, 99-102, https://doi.org/10.1002/ffj.1053 . [all data]

Salido, Altarejos, et al., 2002
Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A.; Pannecouque, C.; Witvrouw, M.; De Clercq, E., Chemical studies of essential oils of Juniperus oxycedrus ssp. badia, J. Ethnopharmacol., 2002, 81, 1, 129-134, https://doi.org/10.1016/S0378-8741(02)00045-4 . [all data]

Shawl, Srivastava, et al., 2002
Shawl, A.S.; Srivastava, S.K.; Syamasundar, K.V.; Tripathi, S.; Raina, V.K., Essential oil composition of Achillea millefolium L. growing wild in Kashmir, India, Flavour Fragr. J., 2002, 17, 3, 165-168, https://doi.org/10.1002/ffj.1074 . [all data]

Rajeswara Rao, 2001
Rajeswara Rao, B.R., Biomass and essential oil yields of rainfed palmarosa (Cymbopogon martinii (Roxb.) Wats. var. motia Burk.) supplied with different levels of organic manure and fertilizer nitrogen in semi-arid tropical climate, Ind. Crops Prod., 2001, 14, 3, 171-178, https://doi.org/10.1016/S0926-6690(01)00081-4 . [all data]

Tzakou and Couladis, 2001
Tzakou, O.; Couladis, M., The essential oil of Micromeria graeca (L.) Bentham et Reichenb. growing in Greece, Flavour Fragr. J., 2001, 16, 2, 107-109, https://doi.org/10.1002/ffj.955 . [all data]

Adams, 2000
Adams, R.P., Systematics of the one seeded Juniperus of the eastern hemisphere based on leaf essential oils and random amplified polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 6, 529-543, https://doi.org/10.1016/S0305-1978(99)00096-4 . [all data]

Adams, 1999
Adams, R.P., Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 1999, 27, 7, 709-725, https://doi.org/10.1016/S0305-1978(99)00016-2 . [all data]

Jantan I. and Ahmad A.S., 1999
Jantan I.; Ahmad A.S., Oleoresins of three pinus species from malaysian pine plantations, ASEAN Review of BiodiversityEnvironment Conservation, 1999, November-December, 1-9. [all data]

Kuiate, Zollo, et al., 1999
Kuiate, J.-R.; Zollo, P.-H.A.; Lamaty, G.; Menut, C.; Bessière, J.-M., Composition of the essential oils from the leaves of two varieties of Aspilia africana (Pers.) C. D. Adams from Cameroon, Flavour Fragr. J., 1999, 14, 3, 167-169, https://doi.org/10.1002/(SICI)1099-1026(199905/06)14:3<167::AID-FFJ802>3.0.CO;2-O . [all data]

Sajjadi and Ghassemi, 1999
Sajjadi, S.E.; Ghassemi, N., Volatile constituents of Nepeta glomerulosa Boiss. subsp. carmanica, Flavour Fragr. J., 1999, 14, 5, 265-267, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<265::AID-FFJ822>3.0.CO;2-A . [all data]

Siani, Ramos, et al., 1999
Siani, A.C.; Ramos, M.F.S.; Menezes-de-Lima, O., Jr.; Ribeiro-dos-Santos, R.; Fernadez-Ferreira, E.; Soares, R.O.A.; Rosas, E.C.; Susunaga, G.S.; Guimarães, A.C.; Zoghbi, M.G.B.; Henriques, M.G.M.O., Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium, J. Ethnopharmacol., 1999, 66, 1, 57-69, https://doi.org/10.1016/S0378-8741(98)00148-2 . [all data]

Adegoke, Rao, et al., 1998
Adegoke, G.O.; Rao, L.J.M.; Shankaracharya, N.B., A comparison of the essential oils of Aframomum daniellii (Hook. f.) K. Schum. and Amomum subulatum Roxb, Flavour Fragr. J., 1998, 13, 5, 349-352, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<349::AID-FFJ758>3.0.CO;2-O . [all data]

Mallavarapu, Rao, et al., 1998
Mallavarapu, G.R.; Rao, B.R.R.; Kaul, P.N.; Ramesh, S.; Bhattacharya, A.K., Volatile constituents of the essential oils of the seeds and the herb of palmarosa (Cymbopogon martinii (Roxb.) Wats. var. motia Burk.), Flavour Fragr. J., 1998, 13, 3, 167-169, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<167::AID-FFJ719>3.0.CO;2-B . [all data]

Szafranek, Malinski, et al., 1998
Szafranek, B.; Malinski, E.; Szafranek, J., The sesquiterpene composition of leaf cuticular neutral lipids of ten varieties of polish Solanum tuberosum, J. Sci. Food Agric., 1998, 76, 4, 588-592, https://doi.org/10.1002/(SICI)1097-0010(199804)76:4<588::AID-JSFA994>3.0.CO;2-M . [all data]

Jantan, Ahmad, et al., 1996
Jantan, I.; Ahmad, A.S.; Ahmad, A.R.; Ali, N.A.M.; Ayop, N., Chemical composition of some citrus oils from Malaysia, J. Essent. Oil Res., 1996, 8, 6, 627-632, https://doi.org/10.1080/10412905.1996.9701030 . [all data]

Saad, El-Sharkawy, et al., 1995
Saad, H.-E.A.; El-Sharkawy, S.H.; Halim, A.F., Essential oils of Daucus carota ssp. maximus, Pharm. Acta Helv., 1995, 70, 1, 79-84, https://doi.org/10.1016/0031-6865(94)00054-Y . [all data]

Ekundayo, Laakso, et al., 1988
Ekundayo, O.; Laakso, I.; Adegbola, R.-M.; Oguntimein, B.; Sofowora, A.; Hiltunen, R., Essential oil constituents of Ashanti pepper (Piper guineense) fruits (berries), J. Agric. Food Chem., 1988, 36, 5, 880-882, https://doi.org/10.1021/jf00083a001 . [all data]

Notes

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

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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