Bicyclogermacrene

• Formula: C₁₅H₂₄
• Molecular weight: 204.3511
• IUPAC Standard InChI: InChI=1S/C15H24/c1-11-6-5-7-12(2)10-14-13(9-8-11)15(14,3)4/h6,10,13-14H,5,7-9H2,1-4H3/b11-6-,12-10+ Copy

  
• IUPAC Standard InChIKey: VPDZRSSKICPUEY-QVIJUPDLSA-N Copy
• CAS Registry Number: 67650-90-2
• Chemical structure:
  This structure is also available as a 2d Mol file
• Species with the same structure:
  • Lepidozene
• Stereoisomers:
  • (1S,2E,6E,10R)-3,7,11,11-Tetramethylbicyclo[8.1.0]undeca-2,6-diene
  • Isobicyclogermacrene
  • cis-Bicyclogermacradiene
  • trans-Bicyclogermacradiene
  • Isolepidozene
• Information on this page:
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
• Options:
  • Switch to SI units

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Pripdeevech and Saansoomchai, 2013
Pripdeevech, P.; Saansoomchai, J., Antibacterial activity and chemical composition of essential oil and various extracts of Fagraea fragrans Roxb. flowers, Chiang Mai J. Sci., 2013, 40, 2, 214-223. [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]

Dutra, Pittella, et al., 2012
Dutra, R.C.; Pittella, F.; Dittz, D.; Marcon, R.; Pimenta, D.S.; Lopes, M.T.P.; Raposo, N.R.B., Chemical composition and cytotoxicity activity of the essential oil of Pterodon emarginatus, Braz. J. of Pharmacognosy, 2012, 22, 5, 971-978. [all data]

Jian-Yu, Zhu, et al., 2012
Jian-Yu, S.; Zhu, L.; Tian, Y.-J., Chemical composition and antimicrobial activities of essential oil of Matricaria songarica, Int. J. Agriculture Biology, 2012, 14, 1, 107-110. [all data]

Silva, Suzuki, et al., 2012
Silva, P.S.; Suzuki, E.Y.; Moreira, A.P.; Raposo, N.R.B.; Alves, T.M.A.; Viccini, L.F., Stachytarpheta gesnerioides Cham.: chemical composition of hexane fraction and essential oil, antioxidant and antimicrobial activities, Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas, 2012, 11, 6, 542-548. [all data]

Zouari, Ayadi, et al., 2012
Zouari, N.; Ayadi, I.; Fakhfakh, N.; Rebai, A.; Zouari, S., Variations of chemical composition of essential oils in wild-populations of Thymus algeriensis Boiss et Reut., a North African endemic species, Lipids in Health and Desease, 2012, 11, 1, 28-39, https://doi.org/10.1186/1476-511X-11-28 . [all data]

Alizadeh, Khosh-Khui, et al., 2011
Alizadeh, A.; Khosh-Khui, M.; Javidnia, K.; Firuzi, O.; Jokar, S.M., Chemical composition of the essential oil, total phenolic content and antioxidant activity in Origanum maiorana L. (Lamiaceae) cultivated in Iran, Adv. Environ. Biol., 2011, 5, 8, 2326-2331. [all data]

Ameen, Usman, et al., 2011
Ameen, O.M.; Usman, L.A.; Oganija, F.S.; Hamid, A.A.; Muhammed, N.O.; Zubair, M.F.; Adebayo, S.A., Chemical composition of leaf essential oil of Annona senegalensis Pers. (Annonaceae) growing in North Central Nigeria, Int. J. Biol. Chem. Sci., 2011, 5, 1, 375-379. [all data]

Andrade, Cardoso, et al., 2011
Andrade, M.A.; Cardoso, M.G.; Batista, L.R.; Freire, J.M.; Nelson, D.L., Antimicrobial activity and chemical composition of essential oil of Pelargonium odoratissimum, Braz. J. Pharmacognosy, 2011, 21, 1, 47-52. [all data]

Bertoli, Lepnardi, et al., 2011
Bertoli, A.; Lepnardi, M.; Krzyzanowska, J.; Oleszek, W.; Pistelli, L., Mentha longifolia in vitro cultures as safe source of flavouring ingradients, Acta Biochem. Polonica, 2011, 58, 4, 581-587. [all data]

Fraternale, Ricci, et al., 2011
Fraternale, D.; Ricci, D.; Flamini, G.; Giomaro, G., Volatile profile of red apple from Marche region (Italy), Rec. Nat. Prod., 2011, 5, 3, 202-207. [all data]

Hammami, Kamoun, et al., 2011
Hammami, I.; Kamoun, N.; Rebai, A., Biocontrol of Botrytis cinerea with essential oil and methanol extract of Viola odorata flowers, Archives of Appl. Sci. Res., 2011, 3, 5, 44-51. [all data]

Kahriman, Tosun, et al., 2011
Kahriman, N.; Tosun, G.; Terzioglu, S.; Karaoglu, S.A.; Yayh, N., Chemical composition and antimicrobial activity of the essential oils from the flower, leaf, and stem of Senecio pandurifolis, Rec. Nat. Prod., 2011, 5, 2, 82-91. [all data]

Karimi, Farmani, et al., 2011
Karimi, H.; Farmani, A.; Nourizadeh, H., A performance comparison of modern statistical technique for molecular descriptor selection and retention prediction of essential oil from leaves, Amer. J. Sci. Res., 2011, 38, 36-40. [all data]

Vazques, Aimar, et al., 2011
Vazques, A.M.; Aimar, M.L.; Demmel, G.I.; Criado, S.G.; Ruiz, G.M.; Cantero, J.J.; Rossi, L.I.; Velasco, M.I., Determination of volatile organic compounds of Tagetes argentina Cabrera (asteraceae) using HS-SPME analysis, Boletin Latinoamericano y del Caribe Plantas Medicinales y Aromaticas, 2011, 10, 5, 463-469. [all data]

Vazquez, Demmel, et al., 2011
Vazquez, A.M.; Demmel, G.I.; Criado, S.G.; Aimar, M.L.; Cantero, J.; Rossi, L.I.; Velasco, M.I., Phytochemistry of TAgetes minuta L. (Asteraceae) from Cordoba, Argentina: comparative study between essential oil and HS-SPME analyses, Boletin Latinoamericano y del Caribe Plantas Medicinales y Aromaticas, 2011, 10, 4, 351-362. [all data]

Yousefzadi, Heidari, et al., 2011
Yousefzadi, M.; Heidari, M.; Akbarpour, M.; Mirjalili, M.H.; Zainali, A.; Parsa, M., in vitro cytotoxic activity of the essential oil of Dorema ammoniacum D. Don., Middle-East J. Sci. Res., 2011, 7, 4, 511-514. [all data]

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]

Mishra, Chaudhary, et al., 2010
Mishra, R.K.; Chaudhary, S.; Pandey, R.; Gupta, S.; Mallavarapu, G.R.; Kumar, S., Analysis of linalool content in the inflorescence (flower) essential oil and leaf oil of Lippia alba cultivar Kavach, J. Essen. Oil Res., 2010, 22, 1, 3-7, https://doi.org/10.1080/10412905.2010.9700253 . [all data]

Miyazawa, Kawauchi, et al., 2010
Miyazawa, M.; Kawauchi, Y.; Utsumi, Y.; Takahashi, T., Character impact odorants of wild edible plant - Cacalia hastata L. var. orientalis - used in Japanese traditional food, J. Oleo Sci., 2010, 59, 10, 527-533, https://doi.org/10.5650/jos.59.527 . [all data]

Monsef-Esfahani, Miri, et al., 2010
Monsef-Esfahani, H.R.; Miri, A.; Amini, M.; Amanzadeh, Y.; Hadjiakhoondi, A.; Hajiaghaee, R.; Ajani, Y., Seasonal variations in the chemical composition, antioxidant activity and total phenolic content of Teucrium persicum Boiss. essential oils, Res. J. Biol. Sci., 2010, 5, 7, 492-498, https://doi.org/10.3923/rjbsci.2010.492.498 . [all data]

Pripdeevech, Chumpolsri, et al., 2010
Pripdeevech, P.; Chumpolsri, W.; Suttiarporn, P.; Wongpornchai, S., The chemical composition and antioxidant activities of Basil from Thailand using retention indices and comprehensive two-dimensional gas chromatography, J. Seb. Chem. Soc., 2010, 75, 11, 1503-1513, https://doi.org/10.2298/JSC100203125P . [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.S.; Dordevic, N.D.; Palic, R.M., Volatiles of Pleurospermum austriacum (L.) Hoffm. (Apiaceae), J. Serbian Chem. Soc., 2010, 75, 12, 1-11, https://doi.org/10.2298/JSC100323127R . [all data]

Radulovic, Dordevic, et al., 2010, 2
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R., Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae), Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962 . [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]

Takeoka, Hobbs, et al., 2010
Takeoka, G.R.; Hobbs, C.; Byeoung-Soo, P., Volatile constituents of the aerial parts of Salvia apiana Jepson, J. Essential Oil. Res., 2010, 22, 3, 241-244, https://doi.org/10.1080/10412905.2010.9700314 . [all data]

Benites, Moiteiro, et al., 2009
Benites, J.; Moiteiro, C.; Miguel, G.; Rojo, L.; Lopez, J.; Venancio, F.; Ramalho, L.; Feio, S.; Dandlen, S.; Casanova, H.; Torres, I., Composition and biological activity of the essential oil of Peruvial Lantana camara, J. Chilean Chem. Soc., 2009, 54, 4, 379-384, https://doi.org/10.4067/S0717-97072009000400012 . [all data]

Koba, Sanda, et al., 2009
Koba, K.; Sanda, K.; Guyon, C.; Raynaud, C.; Chaumont, J.-P.; Nicod, L., In vitro cytotoxic activity of Cymbopogon citratus L. and Cymbopogon nardus L. essential oils from Togo, J. Bangladesh Pharmacological Soc., 2009, 4, 29-34. [all data]

Su, Wang, et al., 2009
Su, Y.; Wang, C.; Yinlong, G., Analysis of volatile compounds from Mentha hapioealyx Briq. by GC-MS based on accurate mass measurements and retention indices, Acta Chem. Sinica, 2009, 67, 6, 546-554. [all data]

Shellie, 2008
Shellie, R.A., Comprehensive 2D GC-QPMS with differential flow modulation, LV-GC, 2008, 11, 7-18. [all data]

Ghasempour, Shirinpour, et al., 2007
Ghasempour, H.R.; Shirinpour, E.; Heidari, H., The constituents of essential oils of Ferulago angulata (Schlecht.) Boiss at two different habitats, Nevakoh and Shahoo, Agross mountain, Western Iran, Iranian J. Sci. Technol., 2007, 31, A3, 309-312. [all data]

Reza, Ebrahim, et al., 2007
Reza, G.H.; Ebrahim, S.; Hossein, H., Analysis by gas chromatography - mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss gatheres in Nevakoh and Shahoo, Zagross mountain, west of Iran, Pakistan J. Biol. Sci., 2007, 10, 5, 814-817, https://doi.org/10.3923/pjbs.2007.814.817 . [all data]

Mirza, Navaei, et al., 2006
Mirza, M.; Navaei, M.N.; Dini, M., Volatile constituents of essential oils isolated from flowers and leaves of Eupatorium cannabinum L. from Iran, Iranian J. Pharmaceutical Res., 2006, 2, 149-152. [all data]

Velickovic, Ristic, et al., 2003
Velickovic, A.S.; Ristic, M.S.; Velickovic, D.T.; Ilic, S.; Mitic, N.D., The possibilities of the application of some species of sage (Salvia L.) as auxiliaries in the treatment of some diseases, J. Serb. Chem. Soc., 2003, 68, 6, 435-445, https://doi.org/10.2298/JSC0306435V . [all data]

Bicchi, Binello, et al., 1999
Bicchi, C.; Binello, A.; D'Amato, A.; Rubiolo, P., Reliability of Van den Dool retention indices in the analysis of essential oils, J. Chromatogr. Sci., 1999, 37, 8, 288-294, https://doi.org/10.1093/chromsci/37.8.288 . [all data]

Tellez, Estell, et al., 1997
Tellez, M.R.; Estell, R.E.; Frederickson, E.L.; Havstad, K.M., Essntial oil of Flourensia cernua DC, J. Essent. Oil Res., 1997, 9, 6, 619-624, https://doi.org/10.1080/10412905.1997.9700799 . [all data]

Albano, Lima, et al., 2012
Albano, S.M.; Lima, A.S.; Miguel, M.G.; Pedro, L.G.; Barroso, J.G.; Figueiredo, A.C., Antioxidant, anti-5-lipoxygenase and antiacetylcholinesterase activities of essential oils and decoction water of some aromatic plants, Rec. Nat. Prod., 2012, 6, 1, 35-48. [all data]

Sharopov, Sulaimonova, et al., 2012
Sharopov, F.S.; Sulaimonova, V.A.; Setzer, W.N., Composition of the essential oil of Ertemisia absinthium from Tajikistan, Rec. Nat. Prod., 2012, 6, 2, 127-134. [all data]

da Silva, de Souza, et al., 2012
da Silva, A.C.; de Souza, P.E.; Machado, J. daC.; da Silva, B.M.; Pinto, J.E.B.P., Effectiveness of essential oils in the treatment of Colletotrichum truncatum-infected soybean seeds, Tropical Plant Patology, 2012, 37, 5, 305-313, https://doi.org/10.1590/S1982-56762012000500001 . [all data]

Chaverri, Diaz, et al., 2011
Chaverri, C.; Diaz, C.; Cicco, J.F., Chemical analysis of essential oils from Ocotea gomezii W.C. Burger and Ocotea morae Gomez-Laur. (Lauraceae) collected at Reserva biologica Alberto M. Brenes in Costa Rica and their cytotoxic activity on Tumor cell lines, J. Braz. Chem. Soc., 2011, 22, 4, s1-s4, https://doi.org/10.1590/S0103-50532011000400018 . [all data]

Fortes, Naves, et al., 2011
Fortes, G.A.C.; Naves, S.S.; Godoi, F.F.F.; Duarte, A.R.; Ferri, P.H.; Santos, S.C., Assessment of a maturity index in Jabuticaba fruit by the evaluation of phenolic compounds, essential oil components, sugar content and total acidity, Amer. J. Food Technol., 2011, 6, 11, 974-984, https://doi.org/10.3923/ajft.2011.974.984 . [all data]

Liu, Chu, et al., 2010
Liu, Z.L.; Chu, S.S.; Liu, Q.R., Chemical composition and insecticidial activity against Sitophilus zeamais of the essential oils of Artemisia capillaris and Artemisia mongolica, Molecules, 2010, 15, 4, 2600-2608, https://doi.org/10.3390/molecules15042600 . [all data]

Zellner, Amorim, et al., 2009
Zellner, B.D.; Amorim, A.C.L.; de Miranda A.L.P.; Alves, R.J.V.; Barbosa, J.P.; da Costa, G.L.; Rezende, C.M., Screening of the odor-activity and bioactiovity of the essential oils of leaves and flowers of Hyptis Passerina Mart. from the Brazilian Cerrado, J. Braz. Chem. Soc., 2009, 20, 2, 322-332, https://doi.org/10.1590/S0103-50532009000200018 . [all data]

Zachariah, Leela, et al., 2008
Zachariah, T.J.; Leela, N.K.; Maya, K.M.; Rema, J.; Mathew, P.A.; Vipin, T.M.; Krishnamoorthy, B., Chemical composition of leaf oils of Myristica beddomeii (King), Myristica fragrans (Houtt.) and Myristica malabarica (Lamk.), J. Spices Arom. Crops, 2008, 17, 1, 10-15. [all data]

El-Shazily, Hafez, et al., 2004
El-Shazily, A.M.; Hafez, S.S.; Wink, M., Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt, Pharmazie, 2004, 59, 226-230. [all data]

Akin, Saracoglu, et al., 2012
Akin, M.; Saracoglu, H.T.; Demirci, B.; Baser, K.H.C., Chemical composition and antibacterial activity of essential oils from different parts of Buplerum rotundifolium L., Rec. Nat. Prod., 2012, 6, 3, 316-320. [all data]

Noorizadeh, Farmany, et al., 2011
Noorizadeh, H.; Farmany, A.; Noorizadeh, M., Quantitative structure-retention relationships analysis of retention index of essential oils, Quim. Nova, 2011, 34, 2, 242-249, https://doi.org/10.1590/S0100-40422011000200014 . [all data]

Noorizadeh and Farmany, 2010
Noorizadeh, H.; Farmany, A., Exploration of linear and nonlinear modeling techniques to predict of retention index of essential oils, J. Chin. Chem. Soc., 2010, 1268-1277. [all data]

Notes

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• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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