1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, [1aR-(1aα,7α,7aα,7bα)]-
- Formula: C15H24
- Molecular weight: 204.3511
- IUPAC Standard InChIKey: MBIPADCEHSKJDQ-ADBWKJQBSA-N
- CAS Registry Number: 17334-55-3
- 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:
- [1aR-(1a,R,7R,7aR,7bR)]-1a,2,3,5,6,7,7a,7bocta-hydro-1,1,7,7a-tetramethyl-1H-cyclopropa[a]naphthalene
- 1(10)-Aristolene
- β-Calarene
- 1H-Cycloprop[a]naphthalene, 1a,2,3,5,6,7a,7b-octahydro-1,1,7,7a-tetramethyl, [1aR,1aα,7α,7bβ]
- 1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7a,7b-octahydro-1,1,7,7a-tetramethyl-, 1aR-1aα,7α,7aα,7bβ
- 1aα,7α,7aα,7bα-1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl
- Other names: 1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-, (1aR,7R,7aR,7bS)-(+)-; (1aR,7R,7aR,7bS)-1,1,7,7a-Tetramethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[a]naphthalene; β-Gurjunene; δ1(10)-Aristolene; Calarene; 1(10)-Aristolene, (+)-; (+)-Calarene; δ-Aristol-1(10)-ene; (+)-1(10)-Aristolene; (+)-δ1(10)-Aristolene; 1(10)-Aristolene; β-Gurjenene; Calarene (= β-gurjunene); Aristol-1(10)-ene; 1aα,7α,7aα,7bα-1H-Cyclopropa[a]naphthalene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl; β-Gurjurene; Calarene (β-gurjunene); β-Gurjunene (calarene); [1aR-(1aα,7α,7aα,7bα)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,7,7a-tetramethyl-1H-cyclopropa[a]naphthalene
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Normal alkane 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
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-Wax | DB-Wax | HP Innowax | Supelcowax-10 | DB-Wax |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | Helium | Helium | Helium | He | He |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.50 | 0.25 | 0.25 |
Tstart (C) | 40. | 60. | 60. | 50. | 50. |
Tend (C) | 230. | 250. | 260. | 250. | 250. |
Heat rate (K/min) | 4. | 10. | 3. | 2. | 3. |
Initial hold (min) | 2. | 2. | |||
Final hold (min) | 4.5 | 10. | 10. | ||
I | 1652. | 1604. | 1559. | 1622. | 1601. |
Reference | Zeng, Xie, et al., 2011 | Guo, Wu, et al., 2008 | Capetanos, Saroglou, et al., 2007 | Raal, Orav, et al., 2007 | Havlik, Kokoska, et al., 2006 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | Carbowax 20M | HP-20M | Carbowax 20M | BP-20 | BP-20 |
Column length (m) | 50. | 50. | 50. | 25. | 25. |
Carrier gas | He | N2 | Nitrogen | ||
Substrate | |||||
Column diameter (mm) | 0.2 | 0.2 | 0.25 | 0.50 | 0.33 |
Phase thickness (μm) | 0.25 | 0.2 | 0.25 | 0.25 | 0.5 |
Tstart (C) | 60. | 70. | 90. | 60. | 80. |
Tend (C) | 250. | 180. | 220. | 200. | 220. |
Heat rate (K/min) | 2. | 4. | 3. | 5. | 5. |
Initial hold (min) | 60. | 4. | |||
Final hold (min) | 10. | ||||
I | 1652. | 1567. | 1596. | 1600. | 1606. |
Reference | Fernandez, Lizzani-Cuvelier, et al., 2005 | Mastelic and Jerkovic, 2003 | Priestap, van Baren, et al., 2003 | Mallavarapu, Rao, et al., 2000 | Dunlop, Bignell, et al., 1999 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | DB-Wax | BP-20 | DB-Wax | BP-20 | BP-20 |
Column length (m) | 60. | 25. | 30. | 25. | 25. |
Carrier gas | He | H2 | N2 | H2 | H2 |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.33 | 0.25 | 0.33 | 0.33 |
Phase thickness (μm) | 0.25 | 0.5 | 0.25 | 0.5 | 0.5 |
Tstart (C) | 60. | 80. | 45. | 80. | 80. |
Tend (C) | 240. | 220. | 220. | 220. | 220. |
Heat rate (K/min) | 4. | 5. | 3. | 5. | 5. |
Initial hold (min) | |||||
Final hold (min) | |||||
I | 1617. | 1606. | 1617. | 1606. | 1606. |
Reference | Ngassoum, Yonkeu, et al., 1999 | Bignell, Dunlop, et al., 1998 | Molleken U., Sinnwell V., et al., 1998 | Bignell, Dunlop, et al., 1997 | Bignell, Dunlop, et al., 1997, 2 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | BP-20 | BP-20 | BP-20 | BP-20 | DB-Wax |
Column length (m) | 25. | 25. | 25. | 25. | 30. |
Carrier gas | H2 | H2 | H2 | He | |
Substrate | |||||
Column diameter (mm) | 0.33 | 0.33 | 0.33 | 0.33 | 0.32 |
Phase thickness (μm) | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
Tstart (C) | 80. | 80. | 80. | 80. | 40. |
Tend (C) | 220. | 220. | 220. | 220. | 210. |
Heat rate (K/min) | 5. | 5. | 5. | 5. | 3. |
Initial hold (min) | 1. | ||||
Final hold (min) | 25. | ||||
I | 1606. | 1606. | 1606. | 1606. | 1583. |
Reference | Bignell, Dunlop, et al., 1997, 3 | Bignell, Dunlop, et al., 1997, 4 | Bignell, Dunlop, et al., 1997, 5 | Bignell, Dunlop, et al., 1997, 6 | Pollak and Berger, 1996 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary |
---|---|---|---|
Active phase | Supelcowax-10 | Supelcowax-10 | Supelcowax-10 |
Column length (m) | 60. | 30. | 30. |
Carrier gas | He | He | |
Substrate | |||
Column diameter (mm) | 0.32 | ||
Phase thickness (μm) | |||
Tstart (C) | 60. | 50. | 50. |
Tend (C) | 220. | 240. | 240. |
Heat rate (K/min) | 2. | 4. | 4. |
Initial hold (min) | 1. | 2. | 2. |
Final hold (min) | 10. | 10. | |
I | 1616. | 1593. | 1593. |
Reference | Loughrin, Hamilton-Kemp, et al., 1990 | Ramaswami, Briscese, et al., 1988 | Ramaswami, Briscese, et al., 1986 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane 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.
Zeng, Xie, et al., 2011
Zeng, Z.; Xie, R.; Zhang, T.; Zhang, H.; Chen, J.Y.,
Analysis of volatile compositions of Magnolia biondii Pamp by steam distillation and Headspace solid phase micro-extraction,
J. Oleo Sci., 2011, 60, 12, 591-596, https://doi.org/10.5650/jos.60.591
. [all data]
Guo, Wu, et al., 2008
Guo, L.; Wu, J.-Z.; Han, T.; Cao, T.; Rahman, K.; Qin, L.-P.,
Chemical composition, antifungal and antitumor properties of ether extracts of Scapania verrucosa Heeg. and its endophytic fungus Chaetomium fusiforme,
Molecules, 2008, 13, 9, 2114-2125, https://doi.org/10.3390/molecules13092114
. [all data]
Capetanos, Saroglou, et al., 2007
Capetanos, C.; Saroglou, V.; Marin, P.D.; Simic, A.; Skaltsa, H.D.,
Essential oil snalysis of two endemic Eringium species from Serbia,
J. Serb. Chem. Soc., 2007, 72, 10, 961-965, https://doi.org/10.2298/JSC0710961C
. [all data]
Raal, Orav, et al., 2007
Raal, A.; Orav, A.; Arak, E.; Kailas, T.; Müürisepp, M.,
Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia,
Proc. Est. Acad. Sci. Chem., 2007, 56, 2, 67-74. [all data]
Havlik, Kokoska, et al., 2006
Havlik, J.; Kokoska, L.; Vasickova, S.; Valterova, I.,
Chemical composition of essential oil from the seeds of Nigella arvensis L. and assessment of its actimicrobial activity,
Flavour Fragr. J., 2006, 21, 4, 713-717, https://doi.org/10.1002/ffj.1713
. [all data]
Fernandez, Lizzani-Cuvelier, et al., 2005
Fernandez, X.; Lizzani-Cuvelier, L.; Loiseau, A.-M.; Perichet, C.; Delbecque, C.; Arnaudo, J.-F.,
Chemical composition of the essential oils from Turkish and Honduras Styrax,
Flavour Fragr. J., 2005, 20, 1, 70-73, https://doi.org/10.1002/ffj.1370
. [all data]
Mastelic and Jerkovic, 2003
Mastelic, J.; Jerkovic, I.,
Application of co-distillation with superheated pentane vapour to the isolation of unstable essential oils,
Flavour Fragr. J., 2003, 18, 6, 521-526, https://doi.org/10.1002/ffj.1261
. [all data]
Priestap, van Baren, et al., 2003
Priestap, H.A.; van Baren, C.M.; Lira, P.D.L.; Coussio, J.D.; Bandoni, A.L.,
Volatile constituents of Aristolochia argentina,
Phytochemistry, 2003, 63, 2, 221-225, https://doi.org/10.1016/S0031-9422(02)00751-3
. [all data]
Mallavarapu, Rao, et al., 2000
Mallavarapu, G.R.; Rao, L.; Ramesh, S.,
Volatile constituents of the leaf and fruit oils of Murraya koenigii Spreng.,
L. Ess. Oil Res., 2000, 12, 6, 766-768, https://doi.org/10.1080/10412905.2000.9712211
. [all data]
Dunlop, Bignell, et al., 1999
Dunlop, P.J.; Bignell, C.M.; Brooker, M.I.H.; Brophy, J.J.; Hibbert, D.B.,
Use of gas chromatograms of essential leaf oils to compare eight taxa of genus Angophora (Myrtaceae): possible relationships to the genus Eucalyptus,
Biochem. Syst. Ecol., 1999, 27, 8, 815-830, https://doi.org/10.1016/S0305-1978(99)00022-8
. [all data]
Ngassoum, Yonkeu, et al., 1999
Ngassoum, M.B.; Yonkeu, S.; Jirovetz, L.; Buchbauer, G.; Schmaus, G.; Hammerschmidt, F.-J.H.,
Chemical composition of essential oils of Lantana camara leaves and flowers from Cameroon and Madagascar,
Flavour Fragr. J., 1999, 14, 4, 245-250, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<245::AID-FFJ819>3.0.CO;2-X
. [all data]
Bignell, Dunlop, et al., 1998
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series 1). Part XIX,
Flavour Fragr. J., 1998, 13, 2, 131-139, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<131::AID-FFJ710>3.0.CO;2-X
. [all data]
Molleken U., Sinnwell V., et al., 1998
Molleken U.; Sinnwell V.; Kubeczka K.H.,
TThe essential oil composition of fruits from Smyrnium perfoliatum,
Phytochemistry, 1998, 47, 6, 1079-1083, https://doi.org/10.1016/S0031-9422(98)80076-9
. [all data]
Bignell, Dunlop, et al., 1997
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.; Fookes, C.J.R.,
Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XIV: Subgenus Monocalyptus,
Flavour Fragr. J., 1997, 12, 3, 177-183, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<177::AID-FFJ626>3.0.CO;2-9
. [all data]
Bignell, Dunlop, et al., 1997, 2
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XV: Subgenus symphyomyrtus, section bisectaria, series levispermae,
Flavour Fragr. J., 1997, 12, 3, 185-193, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<185::AID-FFJ627>3.0.CO;2-B
. [all data]
Bignell, Dunlop, et al., 1997, 3
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVI: Subgenus symphyomyrtus, section bisectaria, series cneorifoliae, series porantherae and series falcatae,
Flavour Fragr. J., 1997, 12, 261-267. [all data]
Bignell, Dunlop, et al., 1997, 4
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVII: Subgenus symphyomyrtus (i) section bisectaria, series calycogonae and (ii) section dumaria, series dumosae, series rigentes and series ovulares,
Flavour Fragr. J., 1997, 12, 269-275. [all data]
Bignell, Dunlop, et al., 1997, 5
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some Queensland and Norther Australian species of the genus Eucalyptus (Series II) Part II. Subgenera (a) Blakella, (b) Corymbia, (c) Unnamed, (d) Idiogenes, (e) Monocalyptus and (f) Symphyomyrtus,
Flavour Fragr. J., 1997, 12, 4, 277-284, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<277::AID-FFJ642>3.0.CO;2-B
. [all data]
Bignell, Dunlop, et al., 1997, 6
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.,
Volatile leaf oils of some south-western and southern Australian speices of the genus Eucalyptus (Series I). Part XVIII. A. Subgenus monocalyptus. B. Subgenus Symphyomyrtus: (i) section Guilfoyleanae; (ii) section bisectaria, series accedentes, series occidentales, series levispermae, series loxophlebae, series macrocarpae, series orbifoliae, series calycogonae; (iii) section dumaria, series incrassatae and series ovulares,
Flavour Fragr. J., 1997, 12, 423-432. [all data]
Pollak and Berger, 1996
Pollak, F.C.; Berger, R.G.,
Geosmin and Related Volatiles in Bioreactor-Cultured Streptomyces citreus CBS 109.60,
Appl. Environ. Microbiol., 1996, 62, 4, 1295-1299. [all data]
Loughrin, Hamilton-Kemp, et al., 1990
Loughrin, J.H.; Hamilton-Kemp, T.R.; Andersen, R.A.; Hildebrand, D.F.,
Headspace compounds from flowers of Nicotiana tabacum and related species,
J. Agric. Food Chem., 1990, 38, 2, 455-460, https://doi.org/10.1021/jf00092a027
. [all data]
Ramaswami, Briscese, et al., 1988
Ramaswami, S.K.; Briscese, P.; Gargiullo, R.J.; von Geldern, T.,
Sesquiterpene hydrocarbons: from mass confusion to orderly line-up
in Flavors and Fragrances: A World Perspective. Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Lawrence,B.M.; Mookherjee,B.D.; Willis,B.J., ed(s)., Elsevier, New York, 1988, 951-980. [all data]
Ramaswami, Briscese, et al., 1986
Ramaswami, S.K.; Briscese, P.; Gargiullo, R.J.; von Geldern, T.,
Sesquiterpene hydrocarbons: from mass confusion to orderly line-up
in Flavors and Fragrances: A World Perspective, Lawrence,B.M.; Mookherjee,B.D.; Willis,B.J., ed(s)., Proceedings of the 10th International Congress of Essential Oils, Fragrances, and Flavors, Washington, DC, 1986, 951-959. [all data]
Notes
Go To: Top, Normal alkane 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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