α-Guaiene

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m1/s1
IUPAC Standard InChIKey: ADIDQIZBYUABQK-UPJWGTAASA-N
CAS Registry Number: 3691-12-1
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.
Other names: Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1α,4α,7α)]-; (1S,4S,7R)-1,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene; Guaia-1(5),11-diene; 7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene-, [1S-(1α,4α,7α)]-; Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-; (Z)-β-Guaiene; α-Guajene; α-quaiene; α-Guaiaene; β-Guaiene, cis-
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Other data available:
- Mass spectrum (electron ionization)
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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	DB-5	DB-5	CP Sil 5 CB	HP-5
Column length (m)	30.	30.		25.	30.
Carrier gas		Helium		H2	He
Substrate
Column diameter (mm)	0.25	0.25		0.25	0.25
Phase thickness (μm)	0.25	0.25		0.15	1.
T_start (C)	40.	60.	60.	50.	40.
T_end (C)	210.	255.	240.	230.	250.
Heat rate (K/min)	2.	3.	3.	3.	5.
Initial hold (min)	2.				1.
Final hold (min)	33.
I	1438.	1440.	1439.	1442.	1457.
Reference	Sylvestre, Pichette, et al., 2006	Medina, Lucero, et al., 2005	Shatar S., 2005	Ogunwande, Olawore, et al., 2004	Bouzouita, Kachouri, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	HP-5	BP-1	SPB-1
Column length (m)	30.	60.	30.	25.	30.
Carrier gas	He	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.55	0.32
Phase thickness (μm)	0.25	1.	0.25	0.25	0.25
T_start (C)	50.	40.	60.	60.	50.
T_end (C)	250.	230.	200.	220.	250.
Heat rate (K/min)	0.5	3.	4.	5.	2.
Initial hold (min)	5.	5.	1.		3.
Final hold (min)	10.	2.	15.	15.	5.
I	1439.	1452.	1440.	1451.	1441.
Reference	Viña and Murillo, 2003	Buchin, Salmon, et al., 2002	Juliani and Simon, 2002	Raina, Srivastava, et al., 2002	John, Rao, et al., 1999
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	SE-30	SE-30
Column length (m)	30.	30.	30.	25.	25.
Carrier gas	He	He	He	N2	N2
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.2	0.2
Phase thickness (μm)	0.25	0.25	0.25
T_start (C)	70.	60.	40.	60.	60.
T_end (C)	250.	240.	250.	180.	180.
Heat rate (K/min)	3.	3.	2.	3.	3.
Initial hold (min)	5.		5.	10.	10.
Final hold (min)			20.	1.	1.
I	1433.	1443.	1428.	1455.	1455.
Reference	Siani, Ramos, et al., 1999	da Silva, Andrade, et al., 1999	Senatore, Urrunaga Soria, et al., 1998	Jantan, Ahmad, et al., 1996	Jantan, Ali, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

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]

Medina, Lucero, et al., 2005
Medina, A.L.; Lucero, M.E.; Holguin, F.O.; Estell, R.E.; Posakony, J.J.; Simon, J.; O'Connell, M.A., Composition and antimicrobial activity of Anemopsis californica leaf oil, J. Agric. Food Chem., 2005, 53, 22, 8694-8698, https://doi.org/10.1021/jf0511244 . [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]

Ogunwande, Olawore, et al., 2004
Ogunwande, I.A.; Olawore, N.O.; Adeleke, K.A.; Ekundayo, O.; König, W.A., Rare terpenoid esters from Hyparrhenia rufa (Nees) Stapf. growing wild in Nigeria, Flavour Fragr. J., 2004, 19, 3, 239-243, https://doi.org/10.1002/ffj.1295 . [all data]

Bouzouita, Kachouri, et al., 2003
Bouzouita, N.; Kachouri, F.; Hamdi, M.; Chaabouni, M.M., Antimicrobial activity of essential oils from Tunisian aromatic plants, Flavour Fragr. J., 2003, 18, 5, 380-383, https://doi.org/10.1002/ffj.1200 . [all data]

Viña and Murillo, 2003
Viña, A.; Murillo, E., Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Columbia, J. Braz. Chem. Soc., 2003, 14, 5, 744-749, https://doi.org/10.1590/S0103-50532003000500008 . [all data]

Buchin, Salmon, et al., 2002
Buchin, S.; Salmon, J.-C.; Carnat, A.-P.; Berger, T.; Bugaud, C.; Bosset, J.O., Identification de composés monoterpéniques, sesquiterpéniques et benzéniques dans un lait d'alpage très riche en ces substances, Mitt. Lebensmittelunters. Hyg., 2002, 93, 199-216. [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, Srivastava, et al., 2002
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]

John, Rao, et al., 1999
John, K.S.; Rao, L.J.M.; Bhat, S.G.; Rao, U.J.S.P., Characterization of aroma components of sap from different Indian mango varieties, Phytochemistry, 1999, 52, 5, 891-894, https://doi.org/10.1016/S0031-9422(99)00296-4 . [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]

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]

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]

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]

Jantan, Ali, et al., 1995
Jantan, I.; Ali, N.A.M.; Ahmad, A.S.; Ahmad, A.R., Constituents of the essential oil of Leptospermum javanicum blume from peninsular Malaysia, Flavour Fragr. J., 1995, 10, 4, 255-258, https://doi.org/10.1002/ffj.2730100406 . [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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