3-Isopropyl-6,8a-dimethyl-1,2,4,5,8,8a-hexahydroazulene

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-11(2)13-8-10-15(4)9-7-12(3)5-6-14(13)15/h7,11H,5-6,8-10H2,1-4H3
IUPAC Standard InChIKey: MGMBZNCFUFRSSP-UHFFFAOYSA-N
CAS Registry Number: 16661-00-0
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Azulene, 2,3,3a,4,7,8-hexahydro-3a,6-dimethyl-1-(1-methylethyl)-; Azulene, 1,2,4,5,8,8a-hexahydro-3-isopropyl-6,8a-dimethyl-; Azulene, 1,2,4,5,8,8a-hexahydro-6,8a-dimethyl-3-(1-methylethyl)-; Daucene; Dauca-4,8-diene (Daucene)
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	SE-54	1380.	Adams, 2000	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1378.	da Silva, Zoghbi, et al., 1999	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 60. C; T_end: 240. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1382.	Duquesnoy, Dinh, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	OV-1	1379.	Rubiolo P., Matteodo M., et al., 2006	25. m/0.25 mm/0.25 μm, He, 50. C @ 1. min, 3. K/min, 220. C @ 5. min
Capillary	CP Sil 5 CB	1380.	Ziegenbein, Hanssen, et al., 2006	H2, 10. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 270. C
Capillary	CP Sil 5 CB	1380.	Ziegenbein, Hanssen, et al., 2006, 2	25. m/0.25 mm/0.4 μm, He, 10. K/min; T_start: 80. C; T_end: 270. C
Capillary	HP-5MS	1358.	Tzakou, Vagias, et al., 2004	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-5	1380.	Bader, Caponi, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min, 240. C @ 30. min; T_start: 60. C
Capillary	RTX-5	1382.	Shellie, Marriott, et al., 2003	30. m/0.25 mm/0.25 μm, He, 45. C @ 6. min, 3. K/min; T_end: 250. C
Capillary	RTX-5	1380.	Shellie, Mondello, et al., 2002	30. m/0.25 mm/0.25 μm, He, 45. C @ 6. min, 3. K/min; T_end: 250. C
Capillary	RTX-5	1384.	Shellie, Mondello, et al., 2002	30. m/0.25 mm/0.25 μm, He, 45. C @ 6. min, 3. K/min; T_end: 250. C
Capillary	BP-1	1380.	Mazzoni, Tomi, et al., 1999	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1385.3	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BP-20	1487.	Duquesnoy, Dinh, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	PEG-20M	1495.	Rubiolo P., Matteodo M., et al., 2006	25. m/0.25 mm/0.3 μm, He, 50. C @ 1. min, 3. K/min, 220. C @ 5. min
Capillary	BP-20	1486.	Mazzoni, Tomi, et al., 1999	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	RTX-1	1380.	Bendiabdellah, El Amine Dib, et al., 2012	60. m/0.22 mm/0.25 μm, Helium, 2. K/min, 230. C @ 5. min; T_start: 60. C
Capillary	CP-Sil 5 CB	1384.	Hnawia, Menut, et al., 2009	30. m/0.25 mm/0.25 μm, Nitrogen, 5. K/min; T_start: 50. C; T_end: 200. C
Capillary	DB-5	1387.	Porto, Decorti, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 45. C @ 3. min, 3. K/min, 250. C @ 5. min
Capillary	Methyl Silicone	1380.	Ozcan and Chalchat, 2007	Helium, 3. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 50. C; T_end: 240. C
Capillary	DB-1	1370.	Pala-Paul, Brophy, et al., 2007	50. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 95. C; T_end: 240. C
Capillary	DB-5	1379.	Askari and Sefidkon, 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; T_end: 260. C
Capillary	DB-5	1378.	Javidnia, Miri, et al., 2006	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 260. C
Capillary	DB-1	1370.	Palá-Paúl, Pérez-Alonso, et al., 2005	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 95. C; T_end: 240. C
Capillary	DB-1	1370.	Pala-Paul, Perez-Alonso, et al., 2005	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 95. C; T_end: 240. C
Capillary	CP Sil 5 CB	1377.	Baser, Özek, et al., 2000	25. m/0.25 mm/0.4 μm, He, 60. C @ 40. min, 5. K/min; T_end: 260. C
Capillary	DB-5MS	1382.	Zoghbi, Andrade, et al., 1999	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	RTX-1	1379.	Bendiabdellah, El Amine Dib, et al., 2012	60. m/0.22 mm/0.25 μm, Helium; Program: not specified
Capillary	DB-5	1384.	Porto, Decorti, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	CP-Sil 8CB-MS	1381.	Profitt, Schatz, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C(3 min) 3 0C/min -> 100 0C 2.7 0C/min -> 140 0C 2.4 0C/min -> 180 0C 6 0C/min -> 260 0C
Capillary	CP-Sil	1364.	Proffit, 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (3 min) 3 0C/min -> 100 0C 2.7 0C/min -> 140 0C 2.4 0C/min -> 180 0C 6 0C/min -> 250 0C
Capillary	CP-Sil	1381.	Proffit, 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (3 min) 3 0C/min -> 100 0C 2.7 0C/min -> 140 0C 2.4 0C/min -> 180 0C 6 0C/min -> 250 0C
Capillary	CP-Sil	1381.	Proffit, 2007	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (3 min) 3 0C/min -> 100 0C 2.7 0C/min -> 140 0C 2.4 0C/min -> 180 0C 6 0C/min -> 250 0C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Innowax	1504.	Baser, Özek, et al., 2000	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min, 4. K/min, 220. C @ 10. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Innowax FSC	1504.	Tosun, Kürkcüoglu, et al., 2006	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C

References

Go To: Top, Gas Chromatography, Notes

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]

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]

Duquesnoy, Dinh, et al., 2006
Duquesnoy, E.; Dinh, N.H.; Castola, V.; Casanova, J., Composition of a Pyrolytic oil from Cupressus funebris Endl. of Vietnamese origin, Flavour Fragr. J., 2006, 21, 3, 453-457, https://doi.org/10.1002/ffj.1676 . [all data]

Rubiolo P., Matteodo M., et al., 2006
Rubiolo P.; Matteodo M.; Riccio G.; Ballero M.; Christen P.; Fleury-Souverain S.; Veuthey J.L.; Bicchi C., Analytical discrimination of poisonous and nonpoisonous chemotypes of giant fennel (Ferula communis L.) through their biologically active and volatile fractions, J. Agric. Food Chem., 2006, 54, 20, 7556-7563, https://doi.org/10.1021/jf061592t . [all data]

Ziegenbein, Hanssen, et al., 2006
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A., Secondary metabolites from Ganoderma lucidum and Spongiporus leucomallellus, Phytochemistry, 2006, 67, 2, 202-211, https://doi.org/10.1016/j.phytochem.2005.10.025 . [all data]

Ziegenbein, Hanssen, et al., 2006, 2
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A., Chemical constituents of the essential oils of three wood-rotting fungi, Flavour Fragr. J., 2006, 21, 5, 813-816, https://doi.org/10.1002/ffj.1732 . [all data]

Tzakou, Vagias, et al., 2004
Tzakou, O.; Vagias, C.; Gani, A.; Yannitsaros, A., Volatile constituents of essential oils isolated at different growth stages from three Conyza species growing in Greece, Flavour Fragr. J., 2004, 19, 425-428. [all data]

Bader, Caponi, et al., 2003
Bader, A.; Caponi, C.; Cioni, P.L.; Flamini, G.; Morelli, I., Composition of the essential oil of Ballota undulata, B. nigra ssp. foetida and B. saxatilis, Flavour Fragr. J., 2003, 18, 6, 502-504, https://doi.org/10.1002/ffj.1257 . [all data]

Shellie, Marriott, et al., 2003
Shellie, R.; Marriott, P.; Zappia, G.; Mondello, L.; Dugo, G., Interactive use of linear retention indices on polar and apolar columns with an MS-Library for reliable characterization of Australian tea tree and other Melaleuca sp. oils, J. Essent. Oil Res., 2003, 15, 5, 305-312, https://doi.org/10.1080/10412905.2003.9698597 . [all data]

Shellie, Mondello, et al., 2002
Shellie, R.; Mondello, L.; Marriott, P.; Dugo, G., Characterisation of lavender essential oils by using gas chromatography-mass spectrometry with correlation of linear retention indices and comparison with comprehensive two-dimensional gas chromatography, J. Chromatogr. A, 2002, 970, 1-2, 225-234, https://doi.org/10.1016/S0021-9673(02)00653-2 . [all data]

Mazzoni, Tomi, et al., 1999
Mazzoni, V.; Tomi, F.; Casanova, J., A daucane-type sesquiterpene from Faucus carota seed oil, Flavour Fragr. J., 1999, 14, 5, 268-272, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<268::AID-FFJ823>3.0.CO;2-Z . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Bendiabdellah, El Amine Dib, et al., 2012
Bendiabdellah, A.; El Amine Dib, M.; Djabou, N.; Allali, H.; Tabti, B.; Costa, J.; Myseli, A., Biological activities and volatile cinstituents of Daucus muricatus L. from Algeria, Chem. Centr. J., 2012, 6, 48, 1-22. [all data]

Hnawia, Menut, et al., 2009
Hnawia, E.; Menut, C.; Agrebi, A.; Cabalion, P., Wood essential oil of two endemic trees from New Caledonia: Callitris sulcata (Parl.) Schltr. and Callitris neocaledonica Dummer, Biochem. Systematics Ecol., 2009, 36, 11, 859-866, https://doi.org/10.1016/j.bse.2008.08.007 . [all data]

Porto, Decorti, et al., 2009
Porto, C.Da.; Decorti, D.; Kikic, I., Flavour compounds of Lavandula angustifolia L. to use in food manufacturing: comparison of three different extraction methods, Food Chem., 2009, 112, 4, 1072-1078, https://doi.org/10.1016/j.foodchem.2008.07.015 . [all data]

Ozcan and Chalchat, 2007
Ozcan, M.M.; Chalchat, J.C., Chemical Composition od Carrot Seeds (Daucus carota L.) Cultivated in Turkey: Characterization of the Seed Oil and Essential Oil, Grasas y Aceites, 2007, 58, 4, 359-365. [all data]

Pala-Paul, Brophy, et al., 2007
Pala-Paul, J.; Brophy, J.J.; Perez-Alonso, M.J.; Usano, J.; Soria, S.C., Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain, J. Chromatogr. A, 2007, 1175, 2, 289-293, https://doi.org/10.1016/j.chroma.2007.10.061 . [all data]

Askari and Sefidkon, 2006
Askari, F.; Sefidkon, F., Essential oil composition of Pimpinella affinis Ledeb. from two localities in Iran, Flavour Fragr. J., 2006, 21, 5, 754-756, https://doi.org/10.1002/ffj.1619 . [all data]

Javidnia, Miri, et al., 2006
Javidnia, K.; Miri, R.; Kamalinejad, M.; Mehdipour, A.R., Composition of the essential oil of Diplotaenia cachrydifolia Boiss. from Iran, J. Ess. Oil Res., 2006, 18, 1, 86-87, https://doi.org/10.1080/10412905.2006.9699393 . [all data]

Palá-Paúl, Pérez-Alonso, et al., 2005
Palá-Paúl, J.; Pérez-Alonso, M.; Velasco-Negueruela, A.; Vadaré, J.; Villa, A.M.; Sanz, J.; Brophy, J.J., Analysis of the essential oil composition from the different parts of Eryngium glaciale Boiss. from Spain, J. Chromatogr. A, 2005, 1094, 1-2, 179-182, https://doi.org/10.1016/j.chroma.2005.09.029 . [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]

Baser, Özek, et al., 2000
Baser, K.H.C.; Özek, T.; Demirci, B.; Kürkcüoglu, M.; Aytac, Z.; Duman, H., Composition of the essential oils of Zosima absinthifolia (Vent.) Link and Ferula elaeochytris Korovin from Turkey, Flavour Fragr. J., 2000, 15, 6, 371-372, https://doi.org/10.1002/1099-1026(200011/12)15:6<371::AID-FFJ919>3.0.CO;2-Z . [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]

Profitt, Schatz, et al., 2008
Profitt, M.; Schatz, B.; Bessiere, J.-M.; Chen, C.; Soler, C.; Hossaert-McKey, M., Signalling receptivity: comparison of the emission of volatile compounds by figs of Ficus hispida before, during and after the phase of receptivity to pollinators, Symbiosis, 2008, 45, 1-10. [all data]

Proffit, 2007
Proffit, M., Mediation chimique et structuration des communautes d'hymenopteres parasites du mutualisme figuier / pollinisateur (These pour obtenir le grade de Docteur de l'Universite Montpellier II) (Dissertation), 2007. [all data]

Tosun, Kürkcüoglu, et al., 2006
Tosun, A.; Kürkcüoglu, M.; Dogan, E.; Duman, H.; Baser, K.H.C., Essential oil composition of Seseli petraeum M. Bieb. and Seseli andronakii Woron. growing in Turkey, Flavour Fragr. J., 2006, 21, 2, 257-259, https://doi.org/10.1002/ffj.1572 . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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