Bicyclosesquiphellandrene

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,12-14H,3,5-8H2,1-2,4H3
IUPAC Standard InChIKey: RNDFUOKDULDZPR-UHFFFAOYSA-N
CAS Registry Number: 54324-03-7
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- cis-Muurola-4(15),5-diene
Stereoisomers:
Other names: (1S,4R,4aR)-1-Isopropyl-4-methyl-7-methylene-1,2,3,4,4a,5,6,7-octahydronaphthalene; Naphthalene, 1,2,3,4,4a,5,6,7-octahydro-4-methyl-7-methylene-1-(1-methylethyl)-, (1S,4R,4aR)-; Naphthalene, 1,2,3,4,4a,5,6,7-octahydro-4-methyl-7-methylene-1-(1-methylethyl)-, [1S-(1α,4β,4aα)]-; (-)-Bicyclosesquiphellandrene; trans-?Muurola-?4(15)?,?5-?diene; (+)epi-Bicyclosesquiphellandrene
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Gas Chromatography

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

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

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1488.	Stashenko, Jaramillo, et al., 2004	50. m/0.2 mm/0.2 μm, He, 35. C @ 15. min, 3. K/min, 250. C @ 40. min
Capillary	MS5	1470.	Shao, Marriott, et al., 2003	25. m/0.25 mm/0.25 μm, 3. K/min; T_start: 40. C; T_end: 180. C
Capillary	BP-1	1489.	Rezzi, Cavaleiro, et al., 2001	50. m/0.22 mm/0.25 μm, 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	1498.7	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)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	CP Sil 5 CB	1493.	Ayoub, Al-Azizi, et al., 2006	He, 10. K/min; Column length: 25. m; T_start: 80. C; T_end: 270. C
Capillary	HP-5	1491.	Figuérédo, Cabassu, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 300. C @ 5. min
Capillary	BPX-5	1495.	Dickschat, Martens, et al., 2005	25. m/0.22 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min; T_end: 320. C
Capillary	CP Sil 5 CB	1490.	Olawore, Ogunwande, et al., 2005	25. m/0.25 mm/0.15 μm, 3. K/min; T_start: 50. C; T_end: 230. C
Capillary	HP-5	1489.	Stashenko, Jaramillo, et al., 2003	60. m/0.25 mm/0.25 μm, 40. C @ 15. min, 5. K/min; T_end: 250. C
Capillary	HP-5	1489.	Stashenko, Jaramillo, et al., 2003	60. m/0.25 mm/0.25 μm, 40. C @ 15. min, 5. K/min; T_end: 250. C
Capillary	HP-5	1490.	Stashenko, Jaramillo, et al., 2003	60. m/0.25 mm/0.25 μm, 40. C @ 15. min, 5. K/min; T_end: 250. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1481.	Parker, Pollnitz, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 50C(1min) => 3C/min => 250C(10min) => 20C/min => 280C (5min)
Capillary	HP-5MS	1521.	Yu, Huang, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 40C(3min) => 6C/min => 160C => 10C/min => 300C (10min)
Capillary	DB-5	1471.	Hamm, Bleton, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 40C(1min) => 9C/min => 130C => 2C/min => 230C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	1760.	Stashenko, Jaramillo, et al., 2003	50. m/0.2 mm/0.2 μm, 50. C @ 5. min, 4. K/min; T_end: 220. C
Capillary	HP-Innowax	1760.	Stashenko, Jaramillo, et al., 2003	50. m/0.2 mm/0.2 μm, 50. C @ 5. min, 4. K/min; T_end: 220. C
Capillary	HP-Innowax	1760.	Stashenko, Jaramillo, et al., 2003	50. m/0.2 mm/0.2 μm, 50. C @ 5. min, 4. K/min; T_end: 220. C
Capillary	DB-Wax	1706.	Christoph, 2001	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 45. C; T_end: 240. C
Capillary	DB-Wax	1748.	Molleken U., Sinnwell V., et al., 1998	30. m/0.25 mm/0.25 μm, N2, 3. K/min; T_start: 45. C; T_end: 220. C

References

Go To: Top, Gas Chromatography, Notes

Stashenko, Jaramillo, et al., 2004
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity, J. Chromatogr. A, 2004, 1025, 1, 93-103, https://doi.org/10.1016/j.chroma.2003.10.058 . [all data]

Shao, Marriott, et al., 2003
Shao, Y.; Marriott, P.; Shellie, R.; Hügel, H., Solid-phase micro-extraction-comprehensive two-dimensional gas chromatography of ginger (Zingiber officinale) volatiles, Flavour Fragr. J., 2003, 18, 1, 5-12, https://doi.org/10.1002/ffj.1133 . [all data]

Rezzi, Cavaleiro, et al., 2001
Rezzi, S.; Cavaleiro, C.; Bighelli, A.; Salgueiro, L.; da Cunha, A.P.; Casanova, J., Intraspecific chemical variability of the leaf essential oil of Juniperus phoenicea subsp. turbinata from Corsica, Biochem. Syst. Ecol., 2001, 29, 2, 179-188, https://doi.org/10.1016/S0305-1978(00)00044-2 . [all data]

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

Ayoub, Al-Azizi, et al., 2006
Ayoub, N.; Al-Azizi, M.; König, W.; Kubeczka, K.-H., Essential oils and a novel polyacetylene from Eryngium yuccifolium Michaux. (Apiaceae), Flavour Fragr. J., 2006, 21, 6, 864-868, https://doi.org/10.1002/ffj.1631 . [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]

Dickschat, Martens, et al., 2005
Dickschat, J.S.; Martens, T.; Brinkhoff, T.; Simon, M.; Schulz, S., Volatiles released by a Streptomyces species isolated from the North Sea, Chemistry and Biodiversity, 2005, 2, 7, 837-865, https://doi.org/10.1002/cbdv.200590062 . [all data]

Olawore, Ogunwande, et al., 2005
Olawore, N.O.; Ogunwande, I.A.; Ekundayo, O.; Adeleke, K.A., Chemical composition of the leaf and fruit essential oils of Murraya paniculata (L.) Jack. (Syn. Murraya exotica Linn.), Flavour Fragr. J., 2005, 20, 1, 54-56, https://doi.org/10.1002/ffj.1365 . [all data]

Stashenko, Jaramillo, et al., 2003
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparación de la composición química y de la actividad antioxidante in vitro de los metabolitos secundarios volátiles de plantas de la familia verbenaceae, Rev. Acad. Colomb. Cienc. Exactas Fis. Nat., 2003, 27, 105, 579-597. [all data]

Parker, Pollnitz, et al., 2007
Parker, M.; Pollnitz, A.P.; Cozzolino, D.; Leigh Francis, I.; Herderich, M.J., Identification and Quantification of a Marker Compound for 'Pepper' Aroma and Flavor in Shiraz Grape Berries by Combination of Chemometrics and Gas Chromatography-Mass Spectrometry, J. Agric. Food Chem., 2007, 55, 15, 5948-5955, https://doi.org/10.1021/jf0705320 . [all data]

Yu, Huang, et al., 2007
Yu, Y.; Huang, T.; Yang, B.; Liu, X.; Duan, G., Development of gas chromatography-mass spectrometry with microwave distillation and simultaneous solid-phase microextraction for rapid determination of volatile constituents in ginger, J. Pharm. Biomed. Anal., 2007, 43, 1, 24-31, https://doi.org/10.1016/j.jpba.2006.06.037 . [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]

Christoph, 2001
Christoph, F., Chemische Zuzammensetzung und antimikrobielle Eigenschaften der ätherischen Öle von Leptospermum scoparium J. R. et G. Forst. und anderer Teebaumöle der Gattungen Kunzea, Leptospermum und Melaleuca unter besonderer Berücksichtigung von Handelsölen, Dissertation, University of Hamburg, Germany, 2001, 196. [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]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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