Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1α,7α,8aβ)]-

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/h12-13,15H,1,5-9H2,2-4H3/t12-,13+,15?/m0/s1
IUPAC Standard InChIKey: YHAJBLWYOIUHHM-IKCIUXDWSA-N
CAS Registry Number: 3691-11-0
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: (3S,3aS,5R)-3,8-Dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene; Azulene, 1,2,3,5,6,7,8,8a-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,7R,8aS)-; Guaia-1(10),11-diene; α-Bulnesene; δ-Guaiene; 5-Isopropenyl-3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulene-, [1S-(1α,7α,8aβ)]-; δ-Guaiene (α-bulnesene); δ-Guaiene (= α-bulnesene); δ-Guaijene
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Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane 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 MS	HP-5 MS	DB-5 MS	DB-1	HP-5
Column length (m)	60.	30.	30.	30.	25.
Carrier gas	Helium	Helium	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.20
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.33
T_start (C)	40.	60.	60.	50.	60.
T_end (C)	250.	220.	240.	220.	240.
Heat rate (K/min)	5.	5.	3.	4.	3.
Initial hold (min)	15.	10.		2.
Final hold (min)	15.			2.	7.
I	1509.	1506.	1502.	1513.	1508.
Reference	Mesa-Arango, Betancur-Galvis, et al., 2010	Ogunwande, Flamini, et al., 2010	Silva, Pott, et al., 2010	Xu, Tang, et al., 2010	Maridass, 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-1	HP-1	HP-5	HP-5	CP-Sil 5 CB
Column length (m)	25.	25.	60.	30.	25.
Carrier gas			He	He	Hydrogen
Substrate
Column diameter (mm)	0.32	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.17	0.17	0.25	0.25	0.15
T_start (C)	50.	50.	60.	50.	50.
T_end (C)	260.	260.	250.	300.	230.
Heat rate (K/min)	1.	1.	3.	5.	3.
Initial hold (min)	5.	5.		5.
Final hold (min)	5.	5.		5.
I	1504.	1500.	1515.	1500.	1509.
Reference	Wetwiayaklung, Thavanapong, et al., 2009	Wetwiayaklung, Thavanapong, et al., 2009	Bertrand, Comte, et al., 2006	Figuérédo, Cabassu, et al., 2006	Olawore, Usman, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-1	CP Sil 5 CB	DB-5	HP-5MS
Column length (m)	30.	50.	25.	30.	30.
Carrier gas	Hydrogen	N2		He	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
T_start (C)	70.	95.	50.	60.	60.
T_end (C)	280.	240.	230.	280.	280.
Heat rate (K/min)	4.	4.	3.	3.	3.
Initial hold (min)	4.
Final hold (min)
I	1505.	1498.	1517.	1470.	1503.
Reference	Pino, Marbot, et al., 2006	Pala-Paul, Perez-Alonso, et al., 2005	Tesso, König, et al., 2005	Tzakou and Constantinidis, 2005	Couladis, Özcan, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-1	DB-5	DB-5	DB-5MS	DB-5MS
Column length (m)	50.	30.	30.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.5	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	220.	240.	280.	240.	270.
Heat rate (K/min)	2.	3.	3.	3.	3.
Initial hold (min)
Final hold (min)	45.		30.
I	1502.	1504.	1493.	1507.	1504.
Reference	Fernandez, Lizzani-Cuvelier, et al., 2003	Zoghbi, Andrade, et al., 2003	Caredda, Marongiu, et al., 2002	Maia, Zoghbi, et al., 2002	Zoghbi, Andrade, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5	DB-5MS	SE-30	CP Sil 5 CB
Column length (m)	30.	30.	30.	25.	25.
Carrier gas		He	He	He	N2
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.2	0.32
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	45.	40.	60.	60.	50.
T_end (C)	300.	240.	240.	180.	290.
Heat rate (K/min)	15.	3.	3.	3.	4.
Initial hold (min)	2.	5.		10.
Final hold (min)	5.
I	1490.	1515.	1503.	1455.	1489.
Reference	Hedin, McKibben, et al., 2000	Novak, Novak, et al., 2000	Zoghbi, Andrade, et al., 1999	Jantan, Ahmad, et al., 1998	Bos, Woerdenbag, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	CP Sil 5 CB	DB-5	DB-5	Methyl Silicone
Column length (m)	25.	25.	30.	30.	50.
Carrier gas	N2	He	He	He	N2
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.17
T_start (C)	50.	60.	65.	65.	80.
T_end (C)	290.	300.	300.	300.	200.
Heat rate (K/min)	4.	6.	4.	4.	2.
Initial hold (min)			2.	2.
Final hold (min)
I	1489.	1489.	1489.	1504.	1502.
Reference	Bos, Woerdenbag, et al., 1997	Bos, Woerdenbag, et al., 1997, 2	Elias, Simoneit, et al., 1997	Elias, Simoneit, et al., 1997	Gopalakrishnan, Menon, et al., 1993
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Methyl Silicone	SE-54	OV-101	OV-101	SE-30
Column length (m)	50.	30.	50.	50.	30.
Carrier gas	N2	Hydrogen	N2	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.17	0.25
T_start (C)	80.	60.	80.	80.	50.
T_end (C)	200.	250.	200.	200.	240.
Heat rate (K/min)	3.	2.	2.	2.	4.
Initial hold (min)		5.			2.
Final hold (min)		2.			10.
I	1515.	1498.	1501.	1503.	1502.
Reference	Gopalakrishnan, Menon, et al., 1993	Kollmannsberger, Nitz, et al., 1992	Sugisawa, Yang, et al., 1989	Sugisawa, Yang, et al., 1989	Ramaswami, Briscese, et al., 1988
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	SE-30
Column length (m)	30.
Carrier gas
Substrate
Column diameter (mm)
Phase thickness (μm)
T_start (C)	50.
T_end (C)	240.
Heat rate (K/min)	4.
Initial hold (min)	2.
Final hold (min)	10.
I	1502.
Reference	Ramaswami, Briscese, et al., 1986
Comment	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

Mesa-Arango, Betancur-Galvis, et al., 2010
Mesa-Arango, A.C.; Betancur-Galvis, L.; Montiel, J.; Bueno, J.G.; Baena, A.; Duran, D.C.; Martinez, J.R.; Stashenko, E.E., Antifungal activity and chemical composition of the essential oils of Lippia alba (Miller) N.E. Brown grown in different regions of Colombia, J. Essential Oil Res., 2010, 22, 6, 568-574, https://doi.org/10.1080/10412905.2010.9700402 . [all data]

Ogunwande, Flamini, et al., 2010
Ogunwande, I.A.; Flamini, G.; Cioni, P.L.; Omikorede, O.; Azeez, R.A.; Ayodele, A.A.; Kamil, Y.O., Aromatic plants growing in Nigeria: essential oil constituents of Cassia alata (Linn.) Roxb. and Helianthus annuus L., Rec. Nat. Prod., 2010, 4, 4, 211-217. [all data]

Silva, Pott, et al., 2010
Silva, D.B.; Pott, A.; Oliveira, D.C.R., Analyses of the headspace volatile constituents of aerial parts (leaves and stems), flowers and fruits of Bidens gardneri Bak. and Bidens sulphurea (Cav.) Sch. Bip. using solid-phase microextraction, J. Essen. Oil Res., 2010, 22, 6, 560-563, https://doi.org/10.1080/10412905.2010.9700400 . [all data]

Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y., Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods, Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h . [all data]

Maridass, 2009
Maridass, M., Inter-generic relationships of Ocimum and Origanum based on GC-MS volatile oils data using software NTSPSpc version 2.0, Ethnobotanical Leaflets, 2009, 13, 83-88. [all data]

Wetwiayaklung, Thavanapong, et al., 2009
Wetwiayaklung, P.; Thavanapong, N.; Charoenteeraboon, J., Chemical constituents and antimicrobial activity os essential oil and extracts of heartwood of Aquilaria crassna obtained from water distillation and supercritical fluid carbon dioxide extraction, Silpakorn U Sci. J., 2009, 3, 1, 25-33. [all data]

Bertrand, Comte, et al., 2006
Bertrand, C.; Comte, G.; Piola, F., Solid-phase microextraction of volatile compounds from flowers of two Brunfelsia species, Biochem. Syst. Ecol., 2006, 34, 5, 371-375, https://doi.org/10.1016/j.bse.2005.12.005 . [all data]

Figuérédo, Cabassu, et al., 2006
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations. VIII. Chemical composition of essential oils of oreganos of various origins, Flavour Fragr. J., 2006, 21, 1, 134-139, https://doi.org/10.1002/ffj.1543 . [all data]

Olawore, Usman, et al., 2006
Olawore, N.O.; Usman, L.A.; Ogunwande, I.A.; Adeleke, K.A., Constituents of rhizome essential oils of two types of Cyperus articulatus L. grown in Nigeria, J. Essent Oil Res., 2006, 18, 6, 604-606, https://doi.org/10.1080/10412905.2006.9699179 . [all data]

Pino, Marbot, et al., 2006
Pino, J.A.; Marbot, R.; Payo, A.; Chao, D.; Herrera, P., Aromatic Plants from Western Cuba VII. Composition of the Leaf Oil of Psidium wrightii KRug et Urb., Lantana involucrata L., Cinnamonum montanum (Sw.) Berchtold et J. Persl. and Caesalpinia violacea (Mill.) Standley, J. Essent. Oil. Res., 2006, 18, 2, 170-174, https://doi.org/10.1080/10412905.2006.9699058 . [all data]

Pala-Paul, Perez-Alonso, et al., 2005
Pala-Paul, J.; Perez-Alonso, M.J.; Velasco-Negueruela, A.; Vadare, J.; Villa, A.M.; Sanz, J.; Brophy, J.J., Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain, J. Chromatogr. A, 2005, 1074, 1-2, 235-239, https://doi.org/10.1016/j.chroma.2005.03.036 . [all data]

Tesso, König, et al., 2005
Tesso, H.; König, W.A.; Kubeczka, K.-H.; Bartnik, M.; Glowniak, K., Secondary metabolites of Peucedanum tauricum fruits, Phytochemistry, 2005, 66, 6, 707-713, https://doi.org/10.1016/j.phytochem.2005.01.022 . [all data]

Tzakou and Constantinidis, 2005
Tzakou, O.; Constantinidis, T., Chemotaxonomic significance of volatile compounds in Thymus samius and its related species Thymus atticus and Thymus parnassicus, Biochem. Syst. Ecol., 2005, 33, 11, 1131-1140, https://doi.org/10.1016/j.bse.2005.03.008 . [all data]

Couladis, Özcan, et al., 2003
Couladis, M.; Özcan, M.; Tzakou, O.; Akgül, A., Comparative essential oil composition of various parts of the turpentine tree (Pistacia terebinthus L) growing wild in Turkey, J. Sci. Food Agric., 2003, 83, 2, 136-138, https://doi.org/10.1002/jsfa.1295 . [all data]

Fernandez, Lizzani-Cuvelier, et al., 2003
Fernandez, X.; Lizzani-Cuvelier, L.; Loiseau, A.-M.; Périchet, C.; Delbecque, C., Volatile constituents of benzoin gums: Siam and Sumatra. Part 1., Flavour Fragr. J., 2003, 18, 4, 328-333, https://doi.org/10.1002/ffj.1230 . [all data]

Zoghbi, Andrade, et al., 2003
Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.; Carreira, L.M.M.; Maia, J.G.S., Essential oils from three Myrcia species, Flavour Fragr. J., 2003, 18, 5, 421-424, https://doi.org/10.1002/ffj.1242 . [all data]

Caredda, Marongiu, et al., 2002
Caredda, A.; Marongiu, B.; Porcedda, S.; Soro, C., Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil, J. Agric. Food Chem., 2002, 50, 6, 1492-1496, https://doi.org/10.1021/jf0108563 . [all data]

Maia, Zoghbi, et al., 2002
Maia, J.G.S.; Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.L.; Luz, A.I.R.; da Silva, J.D., Essential oils composition of Eupatorium species growing wild in the Amazon, Biochem. Syst. Ecol., 2002, 30, 11, 1071-1077, https://doi.org/10.1016/S0305-1978(02)00059-5 . [all data]

Zoghbi, Andrade, et al., 2002
Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.L.; Maia, J.G.S., Volatile constituents of Lippia lupulina Cham., Flavour Fragr. J., 2002, 17, 1, 29-31, https://doi.org/10.1002/ffj.1032 . [all data]

Hedin, McKibben, et al., 2000
Hedin, P.A.; McKibben, G.H.; Dollar, D.A., Role of ground trash volatiles in the selection of hibernation sites by boll weevils, J. Agric. Food Chem., 2000, 48, 8, 3673-3676, https://doi.org/10.1021/jf991001h . [all data]

Novak, Novak, et al., 2000
Novak, J.; Novak, S.; Bitsch, C.; Franz, C.M., Essential oil composition of underground parts of Valeriana celtica ssp. from Austria and Italy, Flavour Fragr. J., 2000, 15, 1, 40-42, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<40::AID-FFJ863>3.0.CO;2-B . [all data]

Zoghbi, Andrade, et al., 1999
Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., Volatile constituents from leaves and flowers of Alpinia speciosa K. Schum. and A. purpurata (Viell.) Schum., Flavour Fragr. J., 1999, 14, 6, 411-414, https://doi.org/10.1002/(SICI)1099-1026(199911/12)14:6<411::AID-FFJ854>3.0.CO;2-U . [all data]

Jantan, Ahmad, et al., 1998
Jantan, I.; Ahmad, A.S.; Bakar, S.A.A.; Ahmad, A.R.; Trockenbrodt, M.; Chak, C.V., Constituents of the essential oil of Baeckea frutescens L. from Malaysia, Flavour Fragr. J., 1998, 13, 4, 245-247, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<245::AID-FFJ736>3.0.CO;2-J . [all data]

Bos, Woerdenbag, et al., 1997
Bos, R.; Woerdenbag, H.J.; Hendriks, H.; Smit, H.F.; Wikström, H.V.; Scheffer, J.J.C., Composition of the essential oil from roots and rhizomes of Valeriana wallichii DC, Flavour Fragr. J., 1997, 12, 2, 123-131, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<123::AID-FFJ613>3.0.CO;2-4 . [all data]

Bos, Woerdenbag, et al., 1997, 2
Bos, R.; Woerdenbag, H.J.; Hendriks, H.; Scheffer, J.J.C., Composition of the essential oils from underground parts of Valeriana officinalis L. s.l. and several closely related taxa, Flavour Fragr. J., 1997, 12, 5, 359-370, https://doi.org/10.1002/(SICI)1099-1026(199709/10)12:5<359::AID-FFJ660>3.0.CO;2-G . [all data]

Elias, Simoneit, et al., 1997
Elias, V.O.; Simoneit, B.R.T.; Cardoso, J.N., Analysis of volatile sesquiterpenoids in environmental and geological samples, J. Hi. Res. Chromatogr., 1997, 20, 6, 305-309, https://doi.org/10.1002/jhrc.1240200602 . [all data]

Gopalakrishnan, Menon, et al., 1993
Gopalakrishnan, M.; Menon, N.; Padmakumari, K.P.; Jayalekshmy, A.; Narayanan, C.S., GC Analysis and Odor Profiles of Four New Indian Genotypes of Piper nigrum L., J. Essent. Oil Res., 1993, 5, 3, 247-253, https://doi.org/10.1080/10412905.1993.9698217 . [all data]

Kollmannsberger, Nitz, et al., 1992
Kollmannsberger, H.; Nitz, S.; Drawert, F., UBer die Aromastoffzusammensetzung von Hochdruckextrakten. I. Pfeffer (Piper nigrum, Var. muntok), Z. Lebensm. Unters Forsch., 1992, 194, 6, 545-551, https://doi.org/10.1007/BF01185481 . [all data]

Sugisawa, Yang, et al., 1989
Sugisawa, H.; Yang, R.H.; Kawabata, C.; Tamura, H., Volatile constituents in the peel oil of sudachi (Citrus sudachi), Agric. Biol. Chem., 1989, 53, 6, 1721-1723, https://doi.org/10.1271/bbb1961.53.1721 . [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, 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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