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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Kovats' 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
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Stabilwax | BP-20 | Supelcowax-10 | DB-Wax | DB-Wax |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | N2 | N2 | H2 | He | |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 1. | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 50. | 60. | 40. | 40. | 40. |
| Tend (C) | 220. | 220. | 210. | 260. | 220. |
| Heat rate (K/min) | 2. | 5. | 2. | 4. | 3. |
| Initial hold (min) | 3. | 2. | 2. | 5. | |
| Final hold (min) | 15. | 14. | 33. | 15. | |
| I | 2014. | 2006. | 1971. | 2013. | 1953. |
| Reference | Hazzit, Baaliouamer, et al., 2006 | Khan, Verma, et al., 2006 | Sylvestre, Pichette, et al., 2006 | Avato, Raffo, et al., 2004 | Lopes, Strobl, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Innowax | Innowax | Supelcowax-10 | Carbowax 20M | Carbowax 20M |
| Column length (m) | 30. | 30. | 30. | 50. | 50. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.2 | 0.2 |
| Tstart (C) | 40. | 50. | 75. | 60. | 60. |
| Tend (C) | 190. | 250. | 230. | 260. | 260. |
| Heat rate (K/min) | 5. | 0.5 | 3. | 2. | 2. |
| Initial hold (min) | 5. | ||||
| Final hold (min) | 5. | 10. | |||
| I | 2000. | 2008. | 1983. | 1985. | 2000. |
| Reference | Mahmood, Kaul, et al., 2004 | Viña and Murillo, 2003 | Tzakou and Couladis, 2001 | Vera and Chane-Ming, 1999 | Vera and Chane-Ming, 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | Supelcowax-10 | Supelcowax-10 | Supelcowax-10 | Carbowax 20M |
| Column length (m) | 25. | 30. | 30. | 30. | 50. |
| Carrier gas | N2 | He | |||
| Substrate | |||||
| Column diameter (mm) | 0.5 | 0.28 | |||
| Phase thickness (μm) | |||||
| Tstart (C) | 60. | 40. | 40. | 40. | 70. |
| Tend (C) | 200. | 210. | 210. | 210. | 190. |
| Heat rate (K/min) | 5. | 2. | 2. | 2. | 2. |
| Initial hold (min) | 2. | 2. | 2. | ||
| Final hold (min) | 120. | 120. | 120. | ||
| I | 1994. | 2005. | 1963. | 1963. | 1966. |
| Reference | Mallavarapu, Rao, et al., 1998 | Loayza, Abujder, et al., 1995 | Loayza, Abujder, et al., 1995 | Loayza, Abujder, et al., 1995 | Tressl, Friese, et al., 1978 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary |
|---|---|
| Active phase | Carbowax 20M |
| Column length (m) | 50. |
| Carrier gas | He |
| Substrate | |
| Column diameter (mm) | 0.28 |
| Phase thickness (μm) | |
| Tstart (C) | 70. |
| Tend (C) | 190. |
| Heat rate (K/min) | 2. |
| Initial hold (min) | |
| Final hold (min) | |
| I | 1964. |
| Reference | Tressl, Friese, et al., 1978, 2 |
| Comment | MSDC-RI |
References
Go To: Top, Kovats' 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.
Hazzit, Baaliouamer, et al., 2006
Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G.,
Composition of the Essential Oils of Thymus and Origanum Species from Algeria and Their Antioxidant and Antimicrobial Activities,
J. Agric. Food Chem., 2006, 54, 17, 6314-6321, https://doi.org/10.1021/jf0606104
. [all data]
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]
Sylvestre, Pichette, et al., 2006
Sylvestre, M.; Pichette, A.; Longtin, A.; Nagau, F.; Legault, J.,
Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe,
J. Ethnopharmacol., 2006, 103, 1, 99-102, https://doi.org/10.1016/j.jep.2005.07.011
. [all data]
Avato, Raffo, et al., 2004
Avato, P.; Raffo, F.; Aldouri, N.A.; Vartanian, S.T.,
Essential oils of varthemia iphionoides from Jordan,
Flavour Fragr. J., 2004, 19, 6, 559-561, https://doi.org/10.1002/ffj.1351
. [all data]
Lopes, Strobl, et al., 2004
Lopes, D.; Strobl, H.; Kolodziejczyk, P.,
14-Methylpentadecano-15-lactone (Muscolide): a new macrocyclic lactone from the oil of Angelica archangelica L.,
Chemistry and Biodiversity, 2004, 1, 12, 1880-1887, https://doi.org/10.1002/cbdv.200490144
. [all data]
Mahmood, Kaul, et al., 2004
Mahmood, U.; Kaul, V.K.; Acharya, R.,
Volatile constituents of Capillipedium parviflorum,
Phytochemistry, 2004, 65, 14, 2163-2166, https://doi.org/10.1016/j.phytochem.2004.04.003
. [all data]
Viña and Murillo, 2003
Viña, A.; Murillo, E.,
Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Columbia,
J. Braz. Chem. Soc., 2003, 14, 5, 744-749, https://doi.org/10.1590/S0103-50532003000500008
. [all data]
Tzakou and Couladis, 2001
Tzakou, O.; Couladis, M.,
The essential oil of Micromeria graeca (L.) Bentham et Reichenb. growing in Greece,
Flavour Fragr. J., 2001, 16, 2, 107-109, https://doi.org/10.1002/ffj.955
. [all data]
Vera and Chane-Ming, 1999
Vera, R.R.; Chane-Ming, J.,
Chemical composition of the essential oil of marjoram (Origanum majorana L.) from Reunion Island,
Food Chem., 1999, 66, 2, 143-145, https://doi.org/10.1016/S0308-8146(98)00018-1
. [all data]
Mallavarapu, Rao, et al., 1998
Mallavarapu, G.R.; Rao, B.R.R.; Kaul, P.N.; Ramesh, S.; Bhattacharya, A.K.,
Volatile constituents of the essential oils of the seeds and the herb of palmarosa (Cymbopogon martinii (Roxb.) Wats. var. motia Burk.),
Flavour Fragr. J., 1998, 13, 3, 167-169, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<167::AID-FFJ719>3.0.CO;2-B
. [all data]
Loayza, Abujder, et al., 1995
Loayza, I.; Abujder, D.; Aranda, R.; Jakupovic, J.; Collin, G.; Deslauriers, H.; Jean, F.-I.,
Essential oils of Baccharis salicifolia, B. latifolia and B. dracunculifolia,
Phytochemistry, 1995, 38, 2, 381-389, https://doi.org/10.1016/0031-9422(94)00628-7
. [all data]
Tressl, Friese, et al., 1978
Tressl, R.; Friese, L.; Fendesack, F.; Köppler, H.,
Gas chromatographic--mass spectrometric investigation of hop aroma constituents in beer,
J. Agric. Food Chem., 1978, 26, 6, 1422-1426, https://doi.org/10.1021/jf60220a037
. [all data]
Tressl, Friese, et al., 1978, 2
Tressl, R.; Friese, L.; Fendesack, F.; Köppler, H.,
Studies of the volatile composition of hops during storage,
J. Agric. Food Chem., 1978, 26, 6, 1426-1430, https://doi.org/10.1021/jf60220a036
. [all data]
Notes
Go To: Top, Kovats' RI, polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.