1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, [3aS-(3aα,3bβ,4β,7α,7aS*)]-

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13?,14?,15?/m0/s1
IUPAC Standard InChIKey: FSRZGYRCMPZNJF-PBWBXLIUSA-N
CAS Registry Number: 13744-15-5
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:
- 6-epi-β-Cubebene
Other names: 1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, 2,3,3aα,3bα,4,5,6,7-octahydro-4α-isopropyl-7β-methyl-3-methylene-; β-Cubebene; β-Cuvebene; 1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3aα,3bα,4α,7β,7aR*)-; 1H-Cyclopenta[1,3]cyclopropa[1,2]benzene, octahydro-7-methyl-3-methylene-4-(1-methylethyl)-, (3aS,3bR,4S,7R,7aR)-; beta cubebene
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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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-5	HP-5	BP-1	DB-5	HP-5MS
Column length (m)	30.	25.	25.	30.	30.
Carrier gas	He		N2	He	He
Substrate
Column diameter (mm)	0.25	0.2	0.32	0.26	0.25
Phase thickness (μm)	0.25	0.33	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	50.
T_end (C)		240.	220.	246.	250.
Heat rate (K/min)	3.	3.	5.	3.	3.
Initial hold (min)					10.
Final hold (min)			13.		5.
I	1391.	1390.	1389.	1390.	1388.
Reference	Lucero, Fredrickson, et al., 2006	Oliveira, Leitao, et al., 2006	Raina, Verma, et al., 2006	Adams and Nguyen, 2005	Asuming, Beauchamp, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-5	DB-5	BP-1	HP-5
Column length (m)	30.	25.	30.	25.	30.
Carrier gas	He	He	He	N2	He
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)	60.	60.	60.	60.	60.
T_end (C)	200.	180.	300.	220.	200.
Heat rate (K/min)	4.	5.	5.	5.	4.
Initial hold (min)	1.	6.			1.
Final hold (min)	15.	15.		15.	15.
I	1388.	1387.	1381.	1395.	1390.
Reference	Juliani, Zygadlo, et al., 2004	Merle, Morón, et al., 2004	Santos, Lopes, et al., 2004	Raina, Srivastava, et al., 2003	Juliani and Simon, 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	HP-5MS	BP-1	PTE-5	DB-1
Column length (m)	60.	30.	30.	60.	30.
Carrier gas	N2	He	N2	H2	He
Substrate
Column diameter (mm)	0.32	0.25	0.32	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.39	0.25
T_start (C)	60.	50.	60.	60.	40.
T_end (C)	220.	250.	220.	285.	260.
Heat rate (K/min)	5.	3.	5.	4.3	2.
Initial hold (min)					5.
Final hold (min)			13.		20.
I	1383.	1390.	1384.	1389.	1390.
Reference	Raina, Lal, et al., 2002	Salido, Altarejos, et al., 2002	Shawl, Srivastava, et al., 2002	Gudzic, Dordevic, et al., 2001	Senatore and Rigano, 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-54	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He		He
Substrate
Column diameter (mm)	0.25	0.26	0.26	0.26	0.26
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	280.	246.	240.	246.	246.
Heat rate (K/min)	3.	3.	3.	3.	3.
Initial hold (min)
Final hold (min)
I	1390.	1389.	1390.	1390.	1390.
Reference	Tzakou and Couladis, 2001	Adams, 2000	Adams, 2000, 2	Adams, 2000, 3	Adams, 2000, 4
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	OV-101	DB-5	Methyl Silicone	Methyl Silicone
Column length (m)	30.	25.	30.	30.	25.
Carrier gas	He		He	He	N2
Substrate
Column diameter (mm)	0.26	0.32	0.25	0.32	0.5
Phase thickness (μm)	0.25		0.25	0.25
T_start (C)	60.	50.	60.	60.	60.
T_end (C)	246.	200.	240.	250.	220.
Heat rate (K/min)	3.	5.	3.	2.	5.
Initial hold (min)				2.
Final hold (min)				5.
I	1389.	1391.	1390.	1386.	1378.
Reference	Adams, 1999	Kuiate, Zollo, et al., 1999	da Silva, Andrade, et al., 1999	Adegoke, Rao, et al., 1998	Mallavarapu, Rao, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	DB-1	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.23	0.25
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	40.	40.	60.	50.	40.
T_end (C)	250.	250.	240.	200.	250.
Heat rate (K/min)	2.	2.	4.	3.	2.
Initial hold (min)	5.	5.			5.
Final hold (min)	20.	20.			20.
I	1360.	1360.	1392.	1372.	1361.
Reference	Senatore, Urrunaga Soria, et al., 1998	Senatore, 1998	Zoghbi, Andrade, et al., 1998	Fiorini, Fourasté, et al., 1997	Senatore, Urrunaga Soria, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	SE-30	DB-5	DB-5
Column length (m)	30.	25.	30.	30.
Carrier gas	He	N2
Substrate
Column diameter (mm)	0.25	0.2
Phase thickness (μm)	0.25
T_start (C)	60.	60.	40.	40.
T_end (C)	240.	180.	210.	210.
Heat rate (K/min)	3.	3.	2.	2.
Initial hold (min)		10.	2.	2.
Final hold (min)		1.	120.	120.
I	1389.	1387.	1387.	1387.
Reference	Tellez, Estell, et al., 1997	Jantan, Ahmad, et al., 1996	Loayza, Abujder, et al., 1995	Loayza, Abujder, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

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]

Oliveira, Leitao, et al., 2006
Oliveira, D.R.; Leitao, G.G.; Santos, S.S.; Bizzo, H.R.; Lopes, D.; Alviano, C.S.; Alviano, D.S.; Leitao, S.G., Ethnopharmacological study of two Lippia species from Oriximina, Brazil, J. Ethnopharmacol., 2006, 108, 1, 103-108, https://doi.org/10.1016/j.jep.2006.04.018 . [all data]

Raina, Verma, et al., 2006
Raina, V.K.; Verma, S.C.; Dhawan, S.; Khan, M.; Ramesh, S.; Singh, S.C.; Yadav, A.; Srivastava, S.K., Essential oil composition of Murraya exotica from the plains of northern India, Flavour Fragr. J., 2006, 21, 1, 140-142, https://doi.org/10.1002/ffj.1547 . [all data]

Adams and Nguyen, 2005
Adams, R.P.; Nguyen, S., Infra-specific variation in Juniperus deppeana and F. Sperryi in the Davis Mountains of Texas: variation in leaf essential oils and random amplified polymorphic DNAS (RAPDS), Phytologia, 2005, 87, 2, 96-108. [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]

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]

Merle, Morón, et al., 2004
Merle, H.; Morón, M.; Blázquez, A.; Boira, H., Taxonomical contribution of essential oils in mandarins cultivars, Biochem. Syst. Ecol., 2004, 32, 5, 491-497, https://doi.org/10.1016/j.bse.2003.09.010 . [all data]

Santos, Lopes, et al., 2004
Santos, A.P.; Lopes, M.C.; Limberger, R.P.; Apel, M.A.; Henriques, A.T.; Moreno, P.R.H., Analysis of the volatile oil from Pilocarpus pennatifolius Lemmaire (Rutaceae) leaves by GC-MS, Flavour Fragr. J., 2004, 19, 4, 325-326, https://doi.org/10.1002/ffj.1306 . [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]

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]

Raina, Lal, et al., 2002
Raina, V.K.; Lal, R.K.; Tripathi, S.; Khan, M.; Syamasundar, K.V.; Srivastava, S.K., Erratum. Essential oil composition of genetically diverse stocks of Murraya koenigii from India, Flavour Fragr. J., 2002, 17, 5, 404, https://doi.org/10.1002/ffj.1139 . [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]

Gudzic, Dordevic, et al., 2001
Gudzic, B.; Dordevic, S.; Palic, R.; Stojanovic, G., Essential oils of Hypericum olympicum L. and Hypericum perforatum L., Flavour Fragr. J., 2001, 16, 3, 201-203, https://doi.org/10.1002/ffj.978 . [all data]

Senatore and Rigano, 2001
Senatore, F.; Rigano, D., Essential oil of two Lippia spp. (Verbenaceae) growing wild in Guatemala, Flavour Fragr. J., 2001, 16, 3, 169-171, https://doi.org/10.1002/ffj.972 . [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 smooth leaf margin Juniperus of the western hemisphere based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 2000, 28, 2, 149-162, https://doi.org/10.1016/S0305-1978(99)00047-2 . [all data]

Adams, 2000, 2
Adams, R.P., Systematics of Juniperus section Juniperus based on leaf essential oils and random amplified polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 6, 515-528, https://doi.org/10.1016/S0305-1978(99)00089-7 . [all data]

Adams, 2000, 3
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, 2000, 4
Adams, R.P., The serrate leaf margined Juniperus (Section Sabina) of the western hemisphere: systematics and evolution based on leaf essential oils and Random Amplified Polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 10, 975-989, https://doi.org/10.1016/S0305-1978(00)00022-3 . [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]

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]

da Silva, Andrade, et al., 1999
da Silva, M.H.L.; Andrade, E.H.A.; Zoghbi, M.G.B.; Luz, A.I.R.; da Silva, J.D.; Maia, J.G.S., The essential oils of Lantana camara L. occurring in North Brazil, Flavour Fragr. J., 1999, 14, 4, 208-210, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<208::AID-FFJ811>3.0.CO;2-F . [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]

Senatore, Urrunaga Soria, et al., 1998
Senatore, F.; Urrunaga Soria, E.; Urrunaga Soria, R.; Porta, G.D.; de Feo, V., Essential oil from two peruvian Satureja species, Flavour Fragr. J., 1998, 13, 1, 1-4, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<1::AID-FFJ672>3.0.CO;2-4 . [all data]

Senatore, 1998
Senatore, F., Volatile constituents of Minthostachys setosa (Briq.) Epl. (Lamiaceae) from Peru, Flavour Fragr. J., 1998, 13, 4, 263-265, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<263::AID-FFJ738>3.0.CO;2-H . [all data]

Zoghbi, Andrade, et al., 1998
Zoghbi, M.G.B.; Andrade, E.H.A.; Santos, A.S.; Silva, M.H.L.; Maia, J.G.S., Essential oils of Lippia alba (Mill.) N. E. Br growing wild in the Brazilian Amazon, Flavour Fragr. J., 1998, 13, 1, 47-48, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<47::AID-FFJ690>3.0.CO;2-0 . [all data]

Fiorini, Fourasté, et al., 1997
Fiorini, C.; Fourasté, I.; David, B.; Bessière, J.M., Composition of the flower, leaf, and stem essential oils from Laurus nobilis L., Flavour Fragr. J., 1997, 12, 2, 91-93, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<91::AID-FFJ623>3.0.CO;2-3 . [all data]

Senatore, Urrunaga Soria, et al., 1997
Senatore, F.; Urrunaga Soria, E.; Urrunaga Soria, R.; Porta, G.D.; Taddeo, R.; de Feo, V., Essential oil of Eremocharis triradiata (Wolff.) Johnston (Apiaceae) growing wild in Perú, Flavour Fragr. J., 1997, 12, 4, 257-259, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<257::AID-FFJ645>3.0.CO;2-4 . [all data]

Tellez, Estell, et al., 1997
Tellez, M.R.; Estell, R.E.; Fredrickson, E.L.; Havstad, K.M., Essential oil of Dyssodia acerosa DC., J. Agric. Food Chem., 1997, 45, 8, 3276-3278, https://doi.org/10.1021/jf9701502 . [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]

Loayza, Abujder, et al., 1995
Loayza, I.; Abujder, D.; Aranda, R.; Jakupovic, J.; Collin, G.; Deslauriers, H.; Jean, F.-I., Essential oils of Baccharis salicifolia, B. latifolia and B. dracunculifolia, Phytochemistry, 1995, 38, 2, 381-389, https://doi.org/10.1016/0031-9422(94)00628-7 . [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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