1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-, [1S-(1α,2α,3aβ,4α,8aβ,9R*)]-

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-13(2)6-5-7-14(3)9-8-10-12(11(9)13)15(10,14)4/h9-12H,5-8H2,1-4H3
IUPAC Standard InChIKey: WCEIQUQVIOGRBF-UHFFFAOYSA-N
CAS Registry Number: 1137-12-8
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.
Species with the same structure:
- 1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-, [1S-(1a`,2a`,3aa',4a`,8aa',9R*)]-
Other names: Longicyclene; 1,2,4-Methenoazulene, decahydro-1,5,5,8a-tetramethyl-, [1S-(1α,2α,3aβ,4α,8aβ,9R)]-; (1S,2R,3aR,4R,8aS,9S)-1,5,5,8a-Tetramethyldecahydro-1,2,4-(epimethanetriyl)azulene; α-Longicyclene; [1S-(1α,2α,3aβ,4α,8aβ,9R*)]-decahydro-1,5,5,8a-tetramethyl-1,2,4-methenoazulene
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SE-30	100.	1399.1	Tudor, 1997	40. m/0.35 mm/0.35 μm
Packed	SF-96	170.	1409.	Andersen, Bissonette, et al., 1977	Column length: 7.3 m
Packed	SE-30	130.	1371.	Andersen and Falcone, 1969	He, Chromosorb G

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1374.	Juliani, Zygadlo, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 1. min, 4. K/min, 200. C @ 15. min

Kovats' RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1368.	Mevy, Bousquet-Melou, et al., 2006	30. m/0.25 mm/0.25 μm, He; Program: 50C(2min) => 2C/min => 160C(5min) => 50C/min => 270C (6min)

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Carbowax 20M	150.	1558.5	Andersen, Bissonette, et al., 1977	Column length: 7.3 m
Packed	Carbowax 20M	150.	1558.5	Andersen, Bissonette, et al., 1977	Column length: 7.3 m
Packed	Carbowax 20M	165.	1580.	Andersen, Bissonette, et al., 1977	Column length: 7.3 m
Packed	Carbowax 20M	150.	1554.5	Andersen, Bissonette, et al., 1977	Column length: 7.3 m
Packed	Carbowax 20M	132.	1519.	Andersen and Falcone, 1969
Packed	Carbowax 20M	132.	1519.	Andersen and Falcone, 1969
Packed	Carbowax 20M	165.	1554.	Andersen and Falcone, 1969

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1372.	Benkaci-Ali, Baaliouamer, et al., 2007	30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 30. min
Capillary	BP-1	1376.	Duquesnoy, Castola, et al., 2007	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	HP-5MS	1377.2	Zeng, Zhao, et al., 2007	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 80. C; T_end: 300. C
Capillary	DB-1	1362.	Dob T., Berramdane T., et al., 2005	30. m/0.32 mm/0.25 μm, N2, 50. C @ 3. min, 2. K/min, 260. C @ 5. min
Capillary	DB-5	1372.	Adams, Habte, et al., 2004	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	HP-5	1371.	Isidorov, Vinogorova, et al., 2003	25. C @ 5. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 150. C
Capillary	HP-5	1375.	Macchioni, Cioni, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	HP-5	1376.	Skaltsa, Demetzos, et al., 2003	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	CP Sil 8 CB	1392.	Oruna-Concha, Ames, et al., 2002	60. m/0.25 mm/0.25 μm, He, 40. C @ 8. min, 4. K/min, 250. C @ 10. min
Capillary	DB-5	1371.	Bortolomeazzi, Berno, et al., 2001	30. m/0.25 mm/0.25 μm, He, 60. C @ 3. min, 5. K/min; T_end: 300. C
Capillary	DB-5	1371.	Bortolomeazzi, Pizzale, et al., 2000	30. m/0.25 mm/0.25 μm, He, 60. C @ 3. min, 5. K/min; T_end: 300. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1374.	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	1496.	Duquesnoy, Castola, et al., 2007	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	DB-5	1371.	Yang, Zhang, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 1. min, 10. K/min, 250. C @ 3. min
Capillary	HP-5	1373.	Lago, Romoff, et al., 2008	30. m/0.32 mm/0.25 μm, Helium, 100. C @ 2. min, 5. K/min, 240. C @ 5. min
Capillary	ZB-1	1370.	Mierendorff, Stahl-Biskup, et al., 2008	30. m/0.25 mm/0.25 μm, Nitrogen, 3. K/min; T_start: 45. C; T_end: 230. C
Capillary	DB-1	1368.	Pala-Paul J., Perez-Alonso M.J., et al., 2006	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 95. C; T_end: 240. C
Capillary	ZB-5	1401.	Dötterl, Wolfe, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 7. min, 6. K/min, 250. C @ 1. min
Capillary	ZB-1	1370.	Mierendorff, Stahl-Biskup, et al., 2003	30. m/0.25 mm/0.25 μm, N2, 3. K/min; T_start: 45. C; T_end: 230. C
Capillary	5 % Phenyl methyl siloxane	1374.	Cicció and Gómez-Laurito, 2002	30. m/0.25 mm/0.25 μm, He, 75. C @ 4. min, 3. K/min, 200. C @ 8. min
Capillary	SPB-5	1376.	Doneanu and Anitescu, 1998	50. m/0.32 mm/0.25 μm, He, 3. K/min, 240. C @ 20. min; T_start: 60. C
Capillary	DB-5	1378.	Elias, Simoneit, et al., 1997	30. m/0.25 mm/0.25 μm, He, 65. C @ 2. min, 4. K/min; T_end: 300. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 8 CB	1374.	Nivinskienë, Butkienë, et al., 2005	50. m/0.32 mm/0.25 μm, He; Program: 60C(1min) => 5C/min => 160C => 5C/min => 250C(3min)
Capillary	DB-5	1380.	Hamm, Bleton, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 9C/min => 130C => 2C/min => 230C
Capillary	SE-30	1378.	Vinogradov, 2004	Program: not specified
Capillary	Methyl Silicone	1378.	Zenkevich, 1996	Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	TC-FFAP	1494.	Kurose, Okamura, et al., 2007	He, 3. K/min, 220. C @ 30. min; Column diameter: 0.25 mm; Phase thickness: 0.25 μm; T_start: 60. C
Capillary	PEG-20M	1497.	Yao, Guo, et al., 2005	60. C @ 10. min, 3. K/min, 180. C @ 30. min; Column length: 30. m; Column diameter: 0.25 mm

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1554.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Andersen, Bissonette, et al., 1977
Andersen, N.H.; Bissonette, P.; Liu, C.-B.; Shunk, B.; Ohta, Y.; Tseng, C.-L.W.; Moore, A.; Huneck, S., Sesquiterpenes of nine European liverworts from the genera, Anastrepta, Bazzania, Jungermannia, Lepidozia, and Scapania, Phytochemistry, 1977, 16, 11, 1731-1751, https://doi.org/10.1016/0031-9422(71)85081-1 . [all data]

Andersen and Falcone, 1969
Andersen, N.H.; Falcone, M.S., The identification of sesquiterpene hydrocarbons from gas-liquid chromatography retention data, J. Chromatogr., 1969, 44, 52-59, https://doi.org/10.1016/S0021-9673(01)92497-5 . [all data]

Juliani, Zygadlo, et al., 2004
Juliani, H.R.; Zygadlo, J.A.; Scrivanti, R.; de la Sota, E.; Simon, J.E., The essential oil of Anemia tomentosa (Savigny) Sw. var. anthriscifolia (Schrad.) Mickel, Flavour Fragr. J., 2004, 19, 6, 541-543, https://doi.org/10.1002/ffj.1341 . [all data]

Mevy, Bousquet-Melou, et al., 2006
Mevy, J.P.; Bousquet-Melou, A.; Greff, S.; Millogo, J.; Fernandez, C., Chemical composition of the volatile oil of Laggera aurita Schulz from Burkina-Faso, Biochem. Syst. Ecol., 2006, 34, 11, 815-818, https://doi.org/10.1016/j.bse.2006.06.005 . [all data]

Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 2007, 22, 2, 148-153, https://doi.org/10.1002/ffj.1773 . [all data]

Duquesnoy, Castola, et al., 2007
Duquesnoy, E.; Castola, V.; Casanova, J., Composition and chemical variability of the twig oil of Abies alba Miller from Corsica, Flavour Fragr. J., 2007, 22, 4, 293-299, https://doi.org/10.1002/ffj.1796 . [all data]

Zeng, Zhao, et al., 2007
Zeng, Y.-X.; Zhao, C.-X.; Liang, Y.-Z.; Yang, H.; Fang, H.-Z.; Yi, L.-Z.; Zeng, Z.-D., Comparative analysis of volatile components from Clematis species growing in China, Anal. Chim. Acta., 2007, 595, 1-2, 328-339, https://doi.org/10.1016/j.aca.2006.12.022 . [all data]

Dob T., Berramdane T., et al., 2005
Dob T.; Berramdane T.; Chelghoum C., Analysis of essential oil from the needles of Pinus pinaster growing in Algeria, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 5, 545-548, https://doi.org/10.1007/s10600-005-0202-z . [all data]

Adams, Habte, et al., 2004
Adams, R.P.; Habte, M.; Park, S.; Dafforn, M.R., Preliminary comparison of vetiver root essential oils from cleansed (bacteria- and fungus-free) versus non-cleansed (normal) vetiver plants, Biochem. Syst. Ecol., 2004, 32, 12, 1137-1144, https://doi.org/10.1016/j.bse.2004.03.013 . [all data]

Isidorov, Vinogorova, et al., 2003
Isidorov, V.A.; Vinogorova, V.T.; Rafalowski, K., HS-SPME analysis of volatile organic compounds of coniferous needle litter, Atmos. Environ., 2003, 37, 33, 4645-4650, https://doi.org/10.1016/j.atmosenv.2003.07.005 . [all data]

Macchioni, Cioni, et al., 2003
Macchioni, F.; Cioni, P.L.; Flamini, G.; Morelli, I.; Maccioni, S.; Ansaldi, M., Chemical composition of essential oils from needles, branches and cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from central Italy, Flavour Fragr. J., 2003, 18, 2, 139-143, https://doi.org/10.1002/ffj.1178 . [all data]

Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M., Essential oil analysis and antimicrobial activity of eight Stachys species from Greece, Phytochemistry, 2003, 64, 3, 743-752, https://doi.org/10.1016/S0031-9422(03)00386-8 . [all data]

Oruna-Concha, Ames, et al., 2002
Oruna-Concha, M.J.; Ames, J.M.; Bakker, J., Comparison of the volatile components of eight cultivars of potato after microwave baking, Lebensm. Wiss. Technol., 2002, 35, 1, 80-86, https://doi.org/10.1006/fstl.2001.0819 . [all data]

Bortolomeazzi, Berno, et al., 2001
Bortolomeazzi, R.; Berno, P.; Pizzale, L.; Conte, L.S., Sesquiterpene, alkene, and alkane hydrocarbons in virgin olive oils of different varieties and geographical origins, J. Agric. Food Chem., 2001, 49, 7, 3278-3283, https://doi.org/10.1021/jf001271w . [all data]

Bortolomeazzi, Pizzale, et al., 2000
Bortolomeazzi, R.; Pizzale, L.; Vichi, S.; Piasenzotto, L.; Conte, L.S., GC-MS Characterization of sesquiterpenic hydrocarbons in virgin olive oils, Proceedings 23rd ISCC; CD-ROM, 2000, retrieved from http://www.richrom.com/assets/CD23PDF. [all data]

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

Yang, Zhang, et al., 2010
Yang, X.; Zhang, H.; Zhang, Y.; Zhao, H.; Dong, A.; Xu, L.; Yang, L.; Ma, Y.; Wang, J., Analysis if the essential oils of pine cones of Pinus koraiensis Steb. et Zucc. and P. sylvestris L. from China, J. Essen. Oil Res., 2010, 22, 5, 446-448, https://doi.org/10.1080/10412905.2010.9700368 . [all data]

Lago, Romoff, et al., 2008
Lago, J.H.G.; Romoff, P.; Favero, O.A.; Souza, F.O.; Soares, M.G.; Baraldi, P.T.; Correa, A.G., Chemical composition of male and female Baccharis trimera (Less.) DC. (Asteraceae) essential oils, Biochem. Systematics Ecol., 2008, 36, 9, 737-740, https://doi.org/10.1016/j.bse.2008.05.009 . [all data]

Mierendorff, Stahl-Biskup, et al., 2008
Mierendorff, H.-G.; Stahl-Biskup, E.; Posthumus, M.A.; van Beek, T.A., Composition of commercial Cape chamomile oil (Eriocephalus punctuatus / Eriocephalus tenuifolius), 2008, retrieved from http://www.chemische-analysen-hamburg.de/Publikationen?Cape_Chamomile_Oil/. [all data]

Pala-Paul J., Perez-Alonso M.J., et al., 2006
Pala-Paul J.; Perez-Alonso M.J.; Velasco-Negueruela A.; Ballesteros M.T.; Sanz J., Essential oil composition of Sideritis hirsuta L. from Guadalajara Province, Spain, Flavour Fragr. J., 2006, 21, 3, 410-415, https://doi.org/10.1002/ffj.1727 . [all data]

Dötterl, Wolfe, et al., 2005
Dötterl, S.; Wolfe, L.M.; Jürgens, A., Qualitative and quantitative analyses of flower scent in Silene latifolia, Phytochemistry, 2005, 66, 2, 203-213, https://doi.org/10.1016/j.phytochem.2004.12.002 . [all data]

Mierendorff, Stahl-Biskup, et al., 2003
Mierendorff, H.-G.; Stahl-Biskup, E.; Posthumus, M.A.; van Beek, T.A., Composition of commercial Cape chamomile oil (Eriocephalus punctulatus), Flavour Fragr. J., 2003, 18, 6, 510-514, https://doi.org/10.1002/ffj.1259 . [all data]

Cicció and Gómez-Laurito, 2002
Cicció, J.F.; Gómez-Laurito, J., Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica, Rev. Biol. Trop., 2002, 50, 3/4, 963-967. [all data]

Doneanu and Anitescu, 1998
Doneanu, C.; Anitescu, G., Supercritical carbon dioxide extraction of Angelica archangelica L. root oil, J. Supercrit. Fluids, 1998, 12, 1, 59-67, https://doi.org/10.1016/S0896-8446(97)00040-5 . [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]

Nivinskienë, Butkienë, et al., 2005
Nivinskienë, O.; Butkienë, R.; Mockutë, D., Chemical composition of seed (fruit) essential oils of Angelica archangelica L. growing wild in Lithuania, Chemija, 2005, 16, 3-4, 51-54. [all data]

Hamm, Bleton, et al., 2004
Hamm, S.; Bleton, J.; Tchapla, A., Headspace solid phase microextraction for screening for the presence of resins in Egyptian archaeological samples, J. Sep. Sci., 2004, 27, 3, 235-243, https://doi.org/10.1002/jssc.200301611 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Zenkevich, 1996
Zenkevich, I.G., Analytical Parameters of Components of Essential Oils for their Chromatographic and Chromato-Mass Spectral Identification. Mono- and Sesquiterpenes, Rastitelnye Resursy (Plant resources), 1996, 34, 1-2, 48-58. [all data]

Kurose, Okamura, et al., 2007
Kurose, K.; Okamura, D.; Yatagai, M., Composition of the essential oils from the leaves of nine Pinus species and the cones of three of Pinus species, Flavour Fragr. J., 2007, 22, 1, 10-20, https://doi.org/10.1002/ffj.1609 . [all data]

Yao, Guo, et al., 2005
Yao, S.-S.; Guo, W.-F.; Lu, Y.; Jiang, Y.-X., Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong, a Special Chinese Black Tea with Pine Smoking Process, J. Agric. Food Chem., 2005, 53, 22, 8688-8693, https://doi.org/10.1021/jf058059i . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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