(1S,2E,6E,10R)-3,7,11,11-Tetramethylbicyclo[8.1.0]undeca-2,6-diene

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-11-6-5-7-12(2)10-14-13(9-8-11)15(14,3)4/h6,10,13-14H,5,7-9H2,1-4H3/b11-6+,12-10+
IUPAC Standard InChIKey: VPDZRSSKICPUEY-BFPRWLMKSA-N
CAS Registry Number: 24703-35-3
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:
Other names: Bicyclo[8.1.0]undeca-2,6-diene, 3,7,11,11-tetramethyl-, (1S,2E,6E,10R)-; Bicyclo[8.1.0]undeca-2,6-diene, 3,7,11,11-tetramethyl-, (E,E)-(1S,10R)-(+)-; Bicyclo[8.1.0]undeca-2,6-diene, 3,7,11,11-tetramethyl-, [1S-(1R*,2E,6E,10S*)]-; (+)-Bicyclogermacrene; Bicyclogermacren; Bicyclogermacrene; β-Cyclogermacrane; Bicylogermacrene
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Other data available:
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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-5MS	HP-5MS	HP-5MS	DB-5MS	HP-1
Column length (m)	30.	30.	60.	30.	60.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	40.	60.	60.
T_end (C)	180.	280.	250.	280.	200.
Heat rate (K/min)	3.	2.	3.	3.	4.
Initial hold (min)		8.	1.		5.
Final hold (min)	15.	30.	20.	30.	25.
I	1488.	1495.	1518.	1470.	1502.
Reference	Angioni, Barra, et al., 2006	Hazzit, Baaliouamer, et al., 2006	Jalali-Heravi, Zekavat, et al., 2006	Marongiu, Porcedda, et al., 2006	Meccia G., Rosquete C., et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	DB-5	HP-5MS	HP-5MS	BP-5
Column length (m)	25.	30.	30.	30.	50.
Carrier gas			He	He	He
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.33	0.25	0.25	0.25	0.25
T_start (C)	60.	40.	50.	50.	50.
T_end (C)	240.	210.	240.	250.	260.
Heat rate (K/min)	3.	2.	3.	3.	5.
Initial hold (min)		2.		10.	2.
Final hold (min)		33.		5.	5.
I	1495.	1496.	1533.	1498.	1499.
Reference	Oliveira, Leitao, et al., 2006	Sylvestre, Pichette, et al., 2006	Tepe, Askin Akpulat, et al., 2006	Asuming, Beauchamp, et al., 2005	Baranauskiene, Venskutonis, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5MS	DB-5	HP-5MS	HP-5MS	DB-1
Column length (m)	30.	30.	30.	30.	50.
Carrier gas	He	He	He	He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	70.	70.	95.
T_end (C)	240.	300.	250.	250.	240.
Heat rate (K/min)	3.	5.	3.	3.	4.
Initial hold (min)			5.	5.
Final hold (min)
I	1495.	1486.	1486.	1501.	1492.
Reference	Maia, Andrade, et al., 2005	Santos, Lopes, et al., 2004	Siani, Garrido, et al., 2004	Siani, Garrido, et al., 2004	Velasco-Negueruela, Sanz, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	DB-5	HP-5	BP-1	DB-5
Column length (m)	25.	25.	30.	30.	30.
Carrier gas	H2	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.32	0.26
Phase thickness (μm)	0.15	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	60.	60.	60.
T_end (C)	230.	240.	200.	220.	240.
Heat rate (K/min)	3.	3.	4.	5.	3.
Initial hold (min)			1.
Final hold (min)			15.	13.
I	1497.	1480.	1496.	1486.	1494.
Reference	Ogunwande, Olawore, et al., 2003	El-Ghorab, Fadel, et al., 2002	Juliani and Simon, 2002	Shawl, Srivastava, et al., 2002	Adams, 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-30	BP-5	DB-5	CP Sil 5 CB	DB-5
Column length (m)	25.	25.	30.	25.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.22	0.25	0.26	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	70.	60.	60.	60.	60.
T_end (C)	220.	200.	246.	280.	240.
Heat rate (K/min)	5.	3.	3.	5.	3.
Initial hold (min)
Final hold (min)
I	1484.	1497.	1499.	1494.	1496.
Reference	Kardali, Velasco-Negueruela, et al., 2000	Weissbecker B., Van Loon J.J.A., et al., 2000	Adams, 1999	Kaul, Gujral, et al., 1999	da Silva, Andrade, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	BP-1	BP-1	CP Sil 8 CB	DB-5
Column length (m)	30.	50.	50.	25.	30.
Carrier gas	He			Ar	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.15	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.12	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	240.	260.	260.	220.	240.
Heat rate (K/min)	4.	2.	2.	3.	3.
Initial hold (min)
Final hold (min)
I	1497.	1498.	1500.	1493.	1495.
Reference	da Silva, Zoghbi, et al., 1999	Vera and Chane-Ming, 1999	Vera and Chane-Ming, 1999	Szafranek, Malinski, et al., 1998	Tellez, Estell, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	OV-101
Column length (m)	30.	30.	30.	25.
Carrier gas				N2
Substrate
Column diameter (mm)				0.25
Phase thickness (μm)
T_start (C)	40.	40.	40.	50.
T_end (C)	210.	210.	210.	200.
Heat rate (K/min)	2.	2.	2.	5.
Initial hold (min)	2.	2.	2.
Final hold (min)	120.	120.	120.
I	1490.	1497.	1497.	1496.
Reference	Loayza, Abujder, et al., 1995	Loayza, Abujder, et al., 1995	Loayza, Abujder, et al., 1995	Menut, Molangui, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Angioni, Barra, et al., 2006
Angioni, A.; Barra, A.; Coroneo, V.; Dessi, S.; Cabras, P., Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers, J. Agric. Food Chem., 2006, 54, 12, 4364-4370, https://doi.org/10.1021/jf0603329 . [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]

Jalali-Heravi, Zekavat, et al., 2006
Jalali-Heravi, M.; Zekavat, B.; Sereshti, H., Characterization of essential oil components of Iranian geranium oil using gas chromatography-mass spectrometry combined with chemometric resolution techniques, J. Chromatogr. A, 2006, 1114, 1, 154-163, https://doi.org/10.1016/j.chroma.2006.02.034 . [all data]

Marongiu, Porcedda, et al., 2006
Marongiu, B.; Porcedda, S.; Piras, A.; Sanna, G.; Murreddu, M.; Loddo, R., Extraction of Juniperus communis L. ssp. nana Willd. essential oil by supercritical carbon dioxide, Flavour Fragr. J., 2006, 21, 1, 148-154, https://doi.org/10.1002/ffj.1549 . [all data]

Meccia G., Rosquete C., et al., 2006
Meccia G.; Rosquete C.; Rojas L.B.; San Felician A., New labdane derivative from the essential oil of Acalypha plicata Mull.Arg., Flavour Fragr. J., 2006, 21, 3, 559-561, https://doi.org/10.1002/ffj.1679 . [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]

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]

Baranauskiene, Venskutonis, et al., 2005
Baranauskiene, R.; Venskutonis, R.P.; Demyttenaere, J.C.R., Sensory and instrumental evaluation of sweet marjoram (Origanum majorana L.) aroma, Flavour Fragr. J., 2005, 20, 5, 492-500, https://doi.org/10.1002/ffj.1478 . [all data]

Maia, Andrade, et al., 2005
Maia, J.G.S.; Andrade, E.H.A.; da Silva, A.C.M.; Oliveira, J.; Carreira, L.M.M.; Araújo, J.S., Leaf volatile oils from four Brazilian Xylopia species, Flavour Fragr. J., 2005, 20, 5, 474-477, https://doi.org/10.1002/ffj.1499 . [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]

Siani, Garrido, et al., 2004
Siani, A.C.; Garrido, I.S.; Monteiro, S.S.; Carvalho, E.S.; Ramos, M.F.S., Protium icicariba as a source of volatile essences, Biochem. Syst. Ecol., 2004, 32, 5, 477-489, https://doi.org/10.1016/j.bse.2003.11.003 . [all data]

Velasco-Negueruela, Sanz, et al., 2004
Velasco-Negueruela, A.; Sanz, J.; Pérez-Alonso, M.J.; Palá-Paúl, J., The volatile components of the aerial parts of Melittis melissophyllum L. subsp. melissophyllum gathered in Spain, Botanica Complutensis, 2004, 28, 133-136. [all data]

Ogunwande, Olawore, et al., 2003
Ogunwande, I.A.; Olawore, N.O.; Kasali, A.A.; König, W.A., Chemical composition of the leaf volatile oils of Callitris intratropica R.T. Baker H.G. Smith from Nigeria, Flavour Fragr. J., 2003, 18, 5, 387-389, https://doi.org/10.1002/ffj.1214 . [all data]

El-Ghorab, Fadel, et al., 2002
El-Ghorab, A.H.; Fadel, H.M.; El-Massry, K.F., The Egyptian Eucalyptus camaldulensis var. brevirostris: chemical compositions of the fruit volatile oil and antioxidant activity, Flavour Fragr. J., 2002, 17, 4, 306-312, https://doi.org/10.1002/ffj.1085 . [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]

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]

Adams, 2000
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]

Kardali, Velasco-Negueruela, et al., 2000
Kardali, M.; Velasco-Negueruela, A.; Pérez-Alonso, M., Essential Oil Constituents of Sideritis ibanyezii Pau, Botanica Complutensis, 2000, 24, 101-106. [all data]

Weissbecker B., Van Loon J.J.A., et al., 2000
Weissbecker B.; Van Loon J.J.A.; Posthumus M.A.; Bouwmeester H.J.; Dicke M., Identification of volatile potato sesquiterpenoids and their olfactory detection by the two-spotted stinkbug Perillus bioculatus, J. Chem. Ecol., 2000, 26, 6, 1433-1445, https://doi.org/10.1023/A:1005535708866 . [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]

Kaul, Gujral, et al., 1999
Kaul, V.K.; Gujral, R.K.; Singh, B., Volatile constituents of the essential oil of flowers of Rosa brunonii Lindl, Flavour Fragr. J., 1999, 14, 1, 9-11, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<9::AID-FFJ761>3.0.CO;2-C . [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]

da Silva, Zoghbi, et al., 1999
da Silva, M.H.L.; Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., The essential oils of Peperomia pellucida Kunth and P. circinnata link var. circinnata, Flavour Fragr. J., 1999, 14, 5, 312-314, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<312::AID-FFJ835>3.0.CO;2-B . [all data]

Vera and Chane-Ming, 1999
Vera, R.R.; Chane-Ming, J., Chemical composition of the essential oil of marjoram (Origanum majorana L.) from Reunion Island, Food Chem., 1999, 66, 2, 143-145, https://doi.org/10.1016/S0308-8146(98)00018-1 . [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]

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]

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]

Menut, Molangui, et al., 1995
Menut, C.; Molangui, T.; Lamaty, G.E.; Bessière, J.-M.; Habimana, J.-B. Menut.; Molangui, T.; Lamaty, G.E.; Bessière, J.-M.; Habimana, J.-B., Aromatic plants of tropical Central Africa. 23. Chemical composition of leaf essential oils of Eucalyptus goniocalyx F. Muell. and Eucalyptus patens Benth. grown in Rwanda, J. Agric. Food Chem., 1995, 43, 5, 1267-1271, https://doi.org/10.1021/jf00053a026 . [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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