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
- IUPAC Standard InChIKey: NVEQFIOZRFFVFW-COMQUAJESA-N
- 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:
- 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
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Kovats' RI, non-polar column, custom temperature program
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
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | BP-1 | HP-5MS | CP Sil 8 CB | DB-5MS | BP-1 |
| Column length (m) | 30. | 30. | 50. | 30. | 25. |
| Carrier gas | N2 | He | He | He | N2 |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Program | 60C => 5C/min => 220C (5min) => 3C/min => 245C(5min) | 50C(2min) => 2C/min => 160C(5min) => 50C/min => 270C (6min) | 60C(1min) => 3C/min => 70C => 15C/min => 170C(8min) => 5C/min => 250C | 60C(5min) => 2C/min => 140C= 5C/min => 250C(5min) | 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min) |
| I | 1567. | 1578. | 1580. | 1594. | 1576. |
| Reference | Khan, Verma, et al., 2006 | Mevy, Bousquet-Melou, et al., 2006 | Radusiene, Judzentiene, et al., 2005 | Tuberoso, Kowalczyk, et al., 2005 | Dwivedi, Khan, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | DB-5 | HP-5 | BP-1 | BP-1 |
| Column length (m) | 30. | 30. | 30. | 25. | 25. |
| Carrier gas | He | He | He | N2 | N2 |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Program | 40C(10min) => 3C/min => 200C => 2C/min => 220C | 35C => 4C/min => 180C => 20C/min => 280C | 40C (3min) => 3C/min => 180C => 30C/min => 270C (5min) | 60C => 5C/min => 220C (5min) => 3C/min => 245 C (5min) | 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min) |
| I | 1583. | 1561. | 1583. | 1577. | 1584. |
| Reference | Sibanda, Chigwada, et al., 2004 | Araújo, Silveira, et al., 2003 | Daferera, Ziogas, et al., 2003 | Khan, Srivastava, et al., 2003 | Raina, Srivastava, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | BP-1 | BP-1 | DB-5 | HP-5 | AT-5 |
| Column length (m) | 30. | 30. | 30. | 60. | |
| Carrier gas | N2 | N2 | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.25 | |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Program | 60C => 5.5C/min => 220C => 3.5C/min => 245C | 60 C 5 C/min -> 220 C (5 min) 3 C/min -> 245 C (5 min) | not specified | 50 0C 5 K/min -> 140 0C 2 K/min -> 170 0C | 60 C 4K/min -> 200 C 10 K/min -> 280 C |
| I | 1571. | 1577. | 1581. | 1587. | 1582. |
| Reference | Rao, Kaul, et al., 2003 | Khan, Srivastava, et al., 2002 | Bizzo, Lopes, et al., 2001 | Novak, Zitterl-Eglseer, et al., 2001 | Khouri, Usubillaga, et al., 2000 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5MS | AT-5 | DB-5 | DB-5 | DB-5 |
| Column length (m) | 30. | 60. | 30. | 30. | 30. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.26 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Program | 40C => 2C/min => 60C => 4C/min => 260C | 60 C (1 min) 4 K/min -> 200 C 10 K/min -> 280 C | not specified | 50C(5min) => 2C/min => 250C (60min) => 2C/min => 270C => 1C/min => 290C | 40C => 2C/min => 60C => 4C/min => 240C |
| I | 1581. | 1603. | 1581. | 1565. | 1580. |
| Reference | Maia, Andrade, et al., 2000 | Rojas and Usubillaga, 2000 | Adams, 1998 | Roscigno, 1998 | Santos, Andrade, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Kovats' RI, non-polar column, custom temperature program, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Khan, Verma, et al., 2006
Khan, M.; Verma, S.C.; Srivastava, S.K.; Shawl, A.S.; Syamsundar, K.V.; Khanuja, S.P.S.; Kumar, T.,
Essential oil composition of Taxus wallichiana Zucc. from the Northern Himalayan region of India,
Flavour Fragr. J., 2006, 21, 5, 772-775, https://doi.org/10.1002/ffj.1682
. [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]
Radusiene, Judzentiene, et al., 2005
Radusiene, J.; Judzentiene, A.; Bernotiene, G.,
Essential oil composition and variability of Hypericum perforatum L. growing in Lithuania,
Biochem. Syst. Ecol., 2005, 33, 2, 113-124, https://doi.org/10.1016/j.bse.2004.06.010
. [all data]
Tuberoso, Kowalczyk, et al., 2005
Tuberoso, C.I.G.; Kowalczyk, A.; Coroneo, V.; Russo, M.T.; Dessì, S.; Cabras, P.,
Chemical Composition and Antioxidant, Antimicrobial, and Antifungal Activities of the Essential Oil of Achillea ligustica All.,
J. Agric. Food Chem., 2005, 53, 26, 10148-10153, https://doi.org/10.1021/jf0518913
. [all data]
Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A.,
Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India,
Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333
. [all data]
Sibanda, Chigwada, et al., 2004
Sibanda, S.; Chigwada, G.; Poole, M.; Gwebu, E.T.; Noletto, J.A.; Schmidt, J.M.; Rea, A.I.; Setzer, W.N.,
Composition and bioactivity of the leaf essential oil of Heteropyxis dehniae from Zimbabwe,
J. Ethnopharmacol., 2004, 92, 1, 107-111, https://doi.org/10.1016/j.jep.2004.02.010
. [all data]
Araújo, Silveira, et al., 2003
Araújo, E.C.C.; Silveira, E.R.; Lima, M.A.S.; Neto, M.A.; de Andrade, I.L.; Lima, M.A.A.; Santiago, G.M.P.; Mesquita, A.L.M.,
Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth,
J. Agric. Food Chem., 2003, 51, 13, 3760-3762, https://doi.org/10.1021/jf021074s
. [all data]
Daferera, Ziogas, et al., 2003
Daferera, D.J.; Ziogas, B.N.; Polissiou, M.G.,
The effectiveness of plant essential oils on the growth of Botrytis cinerea, Fusarium sp. and Clavibacter michiganensis subsp. michiganensis,
Crop Prot., 2003, 22, 1, 39-44, retrieved from http://www.elsevier.com/gej-ng/10/25/40/84/25/31/article.pdf, https://doi.org/10.1016/S0261-2194(02)00095-9
. [all data]
Khan, Srivastava, et al., 2003
Khan, M.; Srivastava, S.K.; Jain, N.; Syamasundar, K.V.; Yadav, A.K.,
Chemical composition of fruit and stem essential oils of Lantana camara from northern India,
Flavour Fragr. J., 2003, 18, 5, 376-379, https://doi.org/10.1002/ffj.1197
. [all data]
Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Aggarwal, K.K.; Syamasunder, K.V.; Khanuja, S.P.S.,
Essential oil composition of Cymbopogon martinii from different places in India,
Flavour Fragr. J., 2003, 18, 4, 312-315, https://doi.org/10.1002/ffj.1222
. [all data]
Rao, Kaul, et al., 2003
Rao, B.R.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S.,
Comparative composition of decanted and recovered essential oils of Eucalyptus citriodora Hook,
Flavour Fragr. J., 2003, 18, 2, 133-135, https://doi.org/10.1002/ffj.1157
. [all data]
Khan, Srivastava, et al., 2002
Khan, M.; Srivastava, S.K.; Syamasundar, K.V.; Singh, M.; Naqvi, A.A.,
Chemical composition of leaf and flower essential oil of Lantana camara from India,
Flavour Fragr. J., 2002, 17, 1, 75-77, https://doi.org/10.1002/ffj.1047
. [all data]
Bizzo, Lopes, et al., 2001
Bizzo, H.R.; Lopes, D.; Abdala, R.V.; Pimentel, F.A.; de Souza, J.A.; Pereira, M.V.G.; Bergter, L.; Guimaraes, E.F.,
Sarisan from leaves of Piper affinis hispidinervum C. DC (long pepper),
Flavour Fragr. J., 2001, 16, 2, 113-115, https://doi.org/10.1002/ffj.957
. [all data]
Novak, Zitterl-Eglseer, et al., 2001
Novak, J.; Zitterl-Eglseer, K.; Deans, S.G.; Franz, C.M.,
Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity,
Flavour Fragr. J., 2001, 16, 4, 259-262, https://doi.org/10.1002/ffj.993
. [all data]
Khouri, Usubillaga, et al., 2000
Khouri, N.; Usubillaga, A.; Rojas, L.B.; Galarraga, F.,
The essential oil of Espeletia weddellii Sch. Bip. ex Wedd.,
Flavour Fragr. J., 2000, 15, 4, 263-265, https://doi.org/10.1002/1099-1026(200007/08)15:4<263::AID-FFJ907>3.0.CO;2-Q
. [all data]
Maia, Andrade, et al., 2000
Maia, J.G.S.; Andrade, E.H.A.; Zoghbi, M.G.B.,
Volatile constituents of the leaves, fruits and flowers of cashew ( Anacardium occidentaleL.),
J. Food Comp. Anal., 2000, 13, 3, 227-232, https://doi.org/10.1006/jfca.2000.0894
. [all data]
Rojas and Usubillaga, 2000
Rojas, L.B.; Usubillaga, A.,
Composition of the essential oil fo Satureja brownei (SW.) Briq. from Venezuela,
Flavour Fragr. J., 2000, 15, 1, 21-22, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<21::AID-FFJ861>3.0.CO;2-G
. [all data]
Adams, 1998
Adams, R.P.,
The essential oils and chemotaxonomy of Juniperus sect. Juniperus,
Biochem. Syst. Ecol., 1998, 26, 6, 637-645, https://doi.org/10.1016/S0305-1978(98)00020-9
. [all data]
Roscigno, 1998
Roscigno, G.,
Estrazione supercritica di principi farmaceutici e biopesticidi, Tesi di Laurea, Universita degli Studi di Salerno, Salerno, Italy, 1998, 121. [all data]
Santos, Andrade, et al., 1998
Santos, A.S.; Andrade, E.H.A.; Zoghbi, M.G.B.; Maia, J.G.S.,
Volatile constituents of fruits of Annona glabra L. from Brazil,
Flavour Fragr. J., 1998, 13, 3, 148-150, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<148::AID-FFJ711>3.0.CO;2-Y
. [all data]
Notes
Go To: Top, Kovats' RI, non-polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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