Caryophyllene oxide

• Formula: C₁₅H₂₄O
• Molecular weight: 220.3505
• IUPAC Standard InChI: InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12+,13-,15+/m1/s1 Copy

  
• IUPAC Standard InChIKey: NVEQFIOZRFFVFW-COMQUAJESA-N Copy
• CAS Registry Number: 1139-30-6
• 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:
  • Isocaryophyllene oxide
  • cis-Caryophyllene epoxide
  • trans-caryophyllene oxide
  • (+)(-)-caryophyllene oxide
  • (-)-Caryophyllene oxide
  • Isocaryophyllene, 5,6-epoxide
  • trans-β-Caryophyllene oxide
  • Cariophyllene oxide II
• Other names: 5-Oxatricyclo[8.2.0.0(4,6)-]dodecane, 4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-; 5-Oxatricyclo(8.2.0.0(4,6))dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-; Caryophylene oxide; Caryophyllene epoxide; (-)-β-Caryophyllene epoxide; β-Caryophyllene oxide; Epoxycaryophyllene; (-)-Epoxydihydrocaryophyllene; 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane, (1R,4R,6R,10S)-; (-)-5-Oxatricyclo[8.2.0.0(4,6)]dodecane,4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-; β-Caryophyllene epoxide; (-)-β-Caryophyllene oxide; Caryophyllene oxyde; 4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.]dodecane (caryophyllene oxide); Cariophyllene epoxide; [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Normal alkane RI, polar column, temperature ramp
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
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Normal alkane RI, polar column, temperature ramp

Go To: Top, References, Notes

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

References

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

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

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Neves, Rosa, et al., 2010
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Karlsson, Birgersson, et al., 2009
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Wannes, Mhamdi, et al., 2009
Wannes, W.A.; Mhamdi, B.; Marzouk, B., GC comparative analysis of least essential oils from two Myrtle varieties at different phenological stages, Chromatographia, 2009, 69, 1/2, 145-150, https://doi.org/10.1365/s10337-008-0818-9 . [all data]

Charoensiddhi and Anprung, 2008
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Paolini, Tomi, et al., 2008
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Capetanos, Saroglou, et al., 2007
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Cheraif, Ben Jannet, et al., 2007
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Chyau, Tsai, et al., 2007
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Hachicha, Skanji, et al., 2007
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Hymete, Rohloff, et al., 2007
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Raal, Orav, et al., 2007
Raal, A.; Orav, A.; Arak, E.; Kailas, T.; Müürisepp, M., Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia, Proc. Est. Acad. Sci. Chem., 2007, 56, 2, 67-74. [all data]

Sylvestre, Longtin, et al., 2007
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Vichi, Riu-Aumatell, et al., 2007
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Boti, Muselli, et al., 2006
Boti, J.B.; Muselli, A.; Tomi, F.; Koukoua, G.; N'Guessan, T.Y.; Costa, J.; Casanova, J., Combined analysis of Cymbopogon giganteus Chiov. leaf oil from Ivory Coast by GC/RI, GC/MS and ¹³C-NMR, C.R. Chim., 2006, 9, 1, 164-168, https://doi.org/10.1016/j.crci.2005.10.003 . [all data]

Boti, Yao, et al., 2006
Boti, J.B.; Yao, P.A.; Koukoua, G.; N'Guessan, T.Y.; Casanova, J., Components and chemical variability of Isolona campanulata Engler Diels leaf oil, Flavour Fragr. J., 2006, 21, 1, 166-170, https://doi.org/10.1002/ffj.1555 . [all data]

Cai, Lin, et al., 2006
Cai, J.; Lin, P.; Zhu, X.; Su, Q., Comparative analysis of clary sage (S. sclarea L.) oil volatiles by GC-FTIR and GC-MS, Food Chem., 2006, 99, 2, 401-407, https://doi.org/10.1016/j.foodchem.2005.07.041 . [all data]

Cavaleiro, Pinto, et al., 2006
Cavaleiro, C.; Pinto, E.; Gonsales, M.J.; Salguero, L., Antifungal activity of Juniperus essential oils agains dermatophyte, Asrgillus and Candida strains, J. Appl. Microbiol., 2006, 100, 6, 1333-1338, https://doi.org/10.1111/j.1365-2672.2006.02862.x . [all data]

Hymete, Rohloff, et al., 2006
Hymete, A.; Rohloff, J.; Iversen, T.-H., Essential oil from seeds and husks of Aframomum corrorima from Ethiopia, Flavour Fragr. J., 2006, 21, 4, 642-644, https://doi.org/10.1002/ffj.1634 . [all data]

Kitchlu, Bakshi, et al., 2006
Kitchlu, S.; Bakshi, S.K.; Kaul, M.K.; Bhan, M.K.; Thapa, R.K.; Agarwal, S.G., Tanacetum gracile Hook. f T. A new source of lavandulol from Ladakh Himalaya (India), Flavour Fragr. J., 2006, 21, 4, 690-692, https://doi.org/10.1002/ffj.1674 . [all data]

Lattoo, Dhar, et al., 2006
Lattoo, S.K.; Dhar, R.S.; Dhar, A.K.; Sharma, P.R.; Agarwal, S.G., Dynamics of essential oil biosynthesis in relation to inflorescence and glandular ontogeny in Salvia sclarea, Flavour Fragr. J., 2006, 21, 5, 817-821, https://doi.org/10.1002/ffj.1733 . [all data]

Martin, Joseph, et al., 2006
Martin, M.A.C.K.; Joseph, H.; Bercion, S.; Menut, C., Chemical composition of essential oils from aerial parts of Aframomum exscapum (Sims) Hepper collected in Guadeloupe, French West Indies, Flavour Fragr. J., 2006, 21, 6, 902-905, https://doi.org/10.1002/ffj.1741 . [all data]

Marzouk, Mansour, et al., 2006
Marzouk, Z.; Mansour, H.B.; Chraief, I.; Mosrati, R.; Cheriaa, J.; Neffati, A.; Marzouk, B.; Sfari, M.; Boukef, K.; Barillies, D.; Ghedira, L.C., Chemical composition, antibacterial and antimutagenic activities of four populations of Rosmarinus officinalis L. oils from Tunisia, J. Food Agriculture Environment, 2006, 4, 2, 89-94. [all data]

Marzouk, Neffati, et al., 2006
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Orav, Raal, et al., 2006
Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T., Composition of the essential oil of Artemisia absinthium L. of different geographical origin, Proc. Est. Acad. Sci. Chem., 2006, 55, 3, 155-165. [all data]

Sawamura, Onishi, et al., 2006
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Wong, Sivasothy, et al., 2006
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Bendimerad and Bendiab, 2005
Bendimerad, N.; Bendiab, S.A.T., Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria, J. Agric. Food Chem., 2005, 53, 8, 2947-2952, https://doi.org/10.1021/jf047937u . [all data]

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Ferretti, Maggi, et al., 2005
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Gauvin and Smadja, 2005
Gauvin, A.; Smadja, J., Essential oil composition of four Psiadia species from Reunion Island: A chemotaxonomic study, Biochem. Syst. Ecol., 2005, 33, 7, 705-714, https://doi.org/10.1016/j.bse.2004.12.013 . [all data]

Jirovetz, Buchbauer, et al., 2005
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Ka, Choi, et al., 2005
Ka, M.-H.; Choi, E.H.; Chun, H.-S.; Lee, K.-G., Antioxidative Activity of Volatile Extracts Isolated from Angelica tenuissimae Roots, Peppermint Leaves, Pine Needles, and Sweet Flag Leaves, J. Agric. Food Chem., 2005, 53, 10, 4124-4129, https://doi.org/10.1021/jf047932x . [all data]

Lee, Umano, et al., 2005
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Palá-Paúl, Pérez-Alonso, et al., 2005
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Stevanovic, Garneau, et al., 2005
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Vichi, Riu-Aumatell, et al., 2005
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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]

Agnihotri, Thappa, et al., 2004
Agnihotri, V.K.; Thappa, R.K.; Meena, B.; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N.; Agarwal, S.G., Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India), Phytochemistry, 2004, 65, 16, 2411-2413, https://doi.org/10.1016/j.phytochem.2004.07.004 . [all data]

Blanc, Muselli, et al., 2004
Blanc, M.-C.; Muselli, A.; Bradesi, P.; Casanova, J., Chemical composition and variability of the essential oil of Inula graveolens from Corsica, Flavour Fragr. J., 2004, 19, 4, 314-319, https://doi.org/10.1002/ffj.1304 . [all data]

Choi, 2004
Choi, H.-S., Volatile constituents of satsuma mandarins growing in Korea, Flavour Fragr. J., 2004, 19, 5, 406-412, https://doi.org/10.1002/ffj.1283 . [all data]

Choi, 2004, 2
Choi, H.-S., Aroma evaluation of an aquatic herb, changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME, J. Agric. Food Chem., 2004, 52, 26, 8099-8104, https://doi.org/10.1021/jf040239p . [all data]

Gauvin, Ravaomanarivo, et al., 2004
Gauvin, A.; Ravaomanarivo, H.; Smadja, J., Comparative analysis by gas chromatography?mass spectrometry of the essential oils from bark and leaves of Cedrelopsis grevei Baill, an aromatic and medicinal plant from Madagascar, J. Chromatogr. A, 2004, 1029, 1-2, 279-282, https://doi.org/10.1016/j.chroma.2003.12.012 . [all data]

González, Guerra, et al., 2004
González, S.; Guerra, P.E.; Bottaro, H.; Molares, S.; Demo, M.S.; Oliva, M.M.; Zunino, M.P.; Zygadlo, J.A., Aromatic plants from Patagonia. Part I. Antimicrobial activity and chemical composition of Schinus polygamus (Cav.) Cabrera essential oil, Flavour Fragr. J., 2004, 19, 1, 36-39, https://doi.org/10.1002/ffj.1270 . [all data]

Jiang and Kubota, 2004
Jiang, L.; Kubota, K., Differences in the volatile components and their odor characteristics of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.), J. Agric. Food Chem., 2004, 52, 13, 4197-4203, https://doi.org/10.1021/jf030663a . [all data]

Lopez Arze, Collin, et al., 2004
Lopez Arze, J.B.; Collin, G.; Garneau, F.-X.; Jean, F.-I.; Gagnon, H., Essential oils from Bolivia. II. Asteraceae: Ophryosporus heptanthus (Wedd.) H. Rob. et King, J. Essent. Oil Res., 2004, 16, 4, 374-376, https://doi.org/10.1080/10412905.2004.9698747 . [all data]

Lourens, Reddy, et al., 2004
Lourens, A.C.U.; Reddy, D.; Baser, K.H.C.; Viljoen, A.M.; Van Vuuren, S.F., In vitro Biological Activity and Essential Oil Composition of Four Indigenous South Africal Helichrysum Species, J. Ethnopharmacol., 2004, 95, 2-3, 253-258, https://doi.org/10.1016/j.jep.2004.07.027 . [all data]

Mallavarapu, Kulkarni, et al., 2004
Mallavarapu, G.R.; Kulkarni, R.N.; Baskaran, K.; Ramesh, S., The essential oil composition of anise hyssop grown in India, Flavour Fragr. J., 2004, 19, 4, 351-353, https://doi.org/10.1002/ffj.1316 . [all data]

Orav, Stulova, et al., 2004
Orav, A.; Stulova, I.; Kailas, T.; Müürisepp, M., Effect of storage on the essential oil composition of piper nigrum L. fruits of different ripening states, J. Agric. Food Chem., 2004, 52, 9, 2582-2586, https://doi.org/10.1021/jf030635s . [all data]

Palá-Paúl, Brophy, et al., 2004
Palá-Paúl, J.; Brophy, J.J.; Goldsack, R.J.; Fontaniella, B., Analysis of the volatile components of Lavandula canariensis (L.) Mill., a Canary Islands endemic species, growing in Australia, Biochem. Syst. Ecol., 2004, 32, 1, 55-62, https://doi.org/10.1016/S0305-1978(03)00177-7 . [all data]

Palá-Paúl, García-Jiménez, et al., 2004
Palá-Paúl, J.; García-Jiménez, R.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Sanz, J., Essential oil composition of the leaves and stems of Meum athamanticum Jacq., from Spain, J. Chromatogr. A, 2004, 1036, 2, 245-247, https://doi.org/10.1016/j.chroma.2004.02.064 . [all data]

Raal, Paaver, et al., 2004
Raal, A.; Paaver, U.; Arak, E.; Orav, A., Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia, Medicina (Kaunas), 2004, 40, 8, 795-800. [all data]

Agnaniet, Mounzeo, et al., 2003
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Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M., Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]

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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]

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Vernin, Lageot, et al., 2001
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Baser, Özek, et al., 2000
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Buttery, Light, et al., 2000
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Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.), J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738 . [all data]

Ajaiyeoba and Ekundayo, 1999
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Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Koca, F., Essential oils of Acinos troodi (Post) Leblebici subsp. vardaranus Leblebici and subsp. grandiflorus Hartvig Strid, Flavour Fragr. J., 1999, 14, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<50::AID-FFJ783>3.0.CO;2-7 . [all data]

Kaya, Baser, et al., 1999, 2
Kaya, A.; Baser, K.H.C.; Demirci, B.; Koca, F., The essential oil of Acinos alpinus (L.) Moench growing in Turkey, Flavour Fragr. J., 1999, 14, 1, 55-59, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<55::AID-FFJ784>3.0.CO;2-Q . [all data]

Kaya, Baser, et al., 1999, 3
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [all data]

Onocha, Ekundayo, et al., 1999
Onocha, P.A.; Ekundayo, O.; Oyelola, O.; Laakso, I., Essential oils of Dacryodes edulis (G. Don) H. J. Lam (African pear), Flavour Fragr. J., 1999, 14, 2, 135-139, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<135::AID-FFJ788>3.0.CO;2-L . [all data]

Rao, Bhattacharya, et al., 1999
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Weyerstahl, Marschall, et al., 1999
Weyerstahl, P.; Marschall, H.; Thefeld, K.; Rustaiyan, A., Constituents of the essential oil of Tanacetum (syn. Chrysanthemum) fruticulosum Ledeb. from Iran, Flavour Fragr. J., 1999, 14, 2, 112-120, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<112::AID-FFJ786>3.0.CO;2-1 . [all data]

Bignell, Dunlop, et al., 1998
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series 1). Part XIX, Flavour Fragr. J., 1998, 13, 2, 131-139, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<131::AID-FFJ710>3.0.CO;2-X . [all data]

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Tümen, G.; Baser, K.H.C.; Demirci, B.; Ermin, N., The essential oils of Satureja coerulea Janka and Thymus aznavourii Velen., Flavour Fragr. J., 1998, 13, 1, 65-67, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<65::AID-FFJ695>3.0.CO;2-Q . [all data]

Bignell, Dunlop, et al., 1997
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.; Fookes, C.J.R., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XIV: Subgenus Monocalyptus, Flavour Fragr. J., 1997, 12, 3, 177-183, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<177::AID-FFJ626>3.0.CO;2-9 . [all data]

Bignell, Dunlop, et al., 1997, 2
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XV: Subgenus symphyomyrtus, section bisectaria, series levispermae, Flavour Fragr. J., 1997, 12, 3, 185-193, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<185::AID-FFJ627>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 3
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVI: Subgenus symphyomyrtus, section bisectaria, series cneorifoliae, series porantherae and series falcatae, Flavour Fragr. J., 1997, 12, 261-267. [all data]

Bignell, Dunlop, et al., 1997, 4
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVII: Subgenus symphyomyrtus (i) section bisectaria, series calycogonae and (ii) section dumaria, series dumosae, series rigentes and series ovulares, Flavour Fragr. J., 1997, 12, 269-275. [all data]

Bignell, Dunlop, et al., 1997, 5
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some Queensland and Norther Australian species of the genus Eucalyptus (Series II) Part II. Subgenera (a) Blakella, (b) Corymbia, (c) Unnamed, (d) Idiogenes, (e) Monocalyptus and (f) Symphyomyrtus, Flavour Fragr. J., 1997, 12, 4, 277-284, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<277::AID-FFJ642>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 6
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some south-western and southern Australian speices of the genus Eucalyptus (Series I). Part XVIII. A. Subgenus monocalyptus. B. Subgenus Symphyomyrtus: (i) section Guilfoyleanae; (ii) section bisectaria, series accedentes, series occidentales, series levispermae, series loxophlebae, series macrocarpae, series orbifoliae, series calycogonae; (iii) section dumaria, series incrassatae and series ovulares, Flavour Fragr. J., 1997, 12, 423-432. [all data]

Menut, Lamaty, et al., 1997
Menut, C.; Lamaty, G.; Weyerstahl, P.; Marschall, H.; Seelmann, I.; Amvam Zollo, P.H., Aromatic plants of tropical central Africa. Part XXXI. Tricyclic sesquiterpenes from the root essential oil of Echinops giganteus var. lelyi C. D. Adams, Flavour Fragr. J., 1997, 12, 6, 415-421, https://doi.org/10.1002/(SICI)1099-1026(199711/12)12:6<415::AID-FFJ666>3.0.CO;2-T . [all data]

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Notes

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• Symbols used in this document:
  

  Tend	Final temperature
  Tstart	Initial temperature

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