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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Van Den Dool and Kratz 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 | DB-5 | SE-52 | BPX-5 | BP-5 | VF-5MS |
| Column length (m) | 30. | 30. | 25. | 25. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.22 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.15 | 0.50 | 0.25 | 0.25 |
| Program | 40C(2min) => 4C/min => 220C => 20C/min => 280C | 45C => 1C/min => 100C => 5C/min => 250C(10min) | 60 0C 6 0C/min -> 210 0C 10 0C/min -> 290 0C (20 min) | 30C(1min) => 50C/min => 105C => 1.5C/min => 150C => 30C/min => 280C (10min) | 40C(2min) => 5C/min => 200C (2min) => 30C/min => 260C |
| I | 1588. | 1582. | 1612. | 1577. | 1574. |
| Reference | Andrade, Sampaio, et al., 2007 | Bruni, Bianchi, et al., 2007 | Eyres, Marriott, et al., 2007 | Sant'Anna, Fontes, et al., 2007 | Carasek and Pawliszyn, 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | BPX-5 | DB-5MS | DB-5 | DB-5 | SE-52 |
| Column length (m) | 30. | 30. | 30. | 30. | |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.32 | |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.15 | |
| Program | 35C(5min) => 3C/min => 210C => 40C/min => 240C (4min) | 50C(3min) => 200C(2min) => 15C/min => 300C(5min) | 40C(3min) => 3C/min => 180C => 10C/min => 260C(2min) | not specified | 45C => 1C/min => 100C => 5C/min => 250C(10min) |
| I | 1605. | 1573. | 1571. | 1573. | 1583. |
| Reference | Cardeal, da Silva, et al., 2006 | Eom S.H., Yang H.S., et al., 2006 | Moon, Cliff, et al., 2006 | Özel, Gögüs, et al., 2006 | Sacchetti, Guerrini, et al., 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | SE-52 | SE-52 | CBP-5 | 5 % Phenyl methyl siloxane |
| Column length (m) | 30. | 30. | 25. | 30. | 30. |
| Carrier gas | He | He | H2 | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.32 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.15 | 0.43 | 0.25 | 0.15 |
| Program | 50C (3min) => 3C/min => 200C => 6C/min => 240C | 45C => 1C/min => 100C => 5C/min => 250C(10min) | 60C(8min) => 3C/min => 180C => 20C/min => 250C(10min) | 60C => 3C/min => 240C => 10C/min => 280C(10min) | 45C => 1C/min => 100C => 5C/min => 250C (10min) |
| I | 1583. | 1584. | 1581. | 1582. | 1583. |
| Reference | Akpulat, Tepe, et al., 2005 | Bruni, Pellati, et al., 2005 | Lorenzo, Paz, et al., 2005 | Oliveira, Campos, et al., 2005 | Sacchetti, Maietti, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | SE-52 | CP Sil 8 CB | DB-5 | CBP-5 |
| Column length (m) | 30. | 30. | 50. | 30. | 50. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.52 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.1 | 0.15 | 0.25 | 0.25 | |
| Program | 40C(5min) => 20C/min => 100C => 2C/min => 160C => 40C/min => 250C (5min) | 45C => 1C/min => 100C => 5C/min => 250C (10min) | 60C (2min) => 5C/min => 160C (1min) => 10C/min => 250C (2min) | 60C(2min) => 3C/min => 240C => 10C/min => 270C (4.5min) | 60C(2min) => 3C/min => 240C => 10C/min => 280C(10min) |
| I | 1534.1 | 1583. | 1581. | 1578. | 1577. |
| Reference | Helmig, Bocquet, et al., 2004 | Sacchetti, Medici, et al., 2004 | Mockute and Judzentiene, 2003 | Passos X.S., Castro A.C.M., et al., 2003 | Azevedo, Campos, et al., 2002 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | HP-5 | SE-52 | BP-1 | SE-52 |
| Column length (m) | 50. | 50. | 30. | 50. | 25. |
| Carrier gas | He | He | H2 | H2 | |
| Substrate | |||||
| Column diameter (mm) | 0.2 | 0.2 | 0.32 | 0.22 | 0.32 |
| Phase thickness (μm) | 0.33 | 0.33 | 0.42 | 0.25 | 0.40 |
| Program | 50C(2min) => 5C/min => 150C => 10C/min => 250C(30min) | 50C(2min) => 5C/min => 150C => 10C/min => 250C(30min) | 60C(8min) => 3C/min => 180C => 20C/min => 250C(10min) | not specified | 60 0C (8 min) 3 K/min -> 180 0C 20 K/min -> 250 0C (10 min) |
| I | 1575. | 1580. | 1572. | 1576. | 1576. |
| Reference | García, Alvarez, et al., 2002 | García, Alvarez, et al., 2002 | Lorenzo, Paz, et al., 2002 | Cavalli, Ranarivelo, et al., 2001 | Lorenzo, Dellacassa, et al., 2001 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary |
|---|---|---|
| Active phase | SE-52 | HP-5 |
| Column length (m) | 30. | 30. |
| Carrier gas | H2 | |
| Substrate | ||
| Column diameter (mm) | 0.32 | 0.25 |
| Phase thickness (μm) | 0.40 | 0.25 |
| Program | 60 0C (8 min) 3 K/min -> 180 0C 20 K/min -> 250 0C (10 min) | 40C(1min) => 3C/min => 120C => 5C/min => 280C |
| I | 1579. | 1582. |
| Reference | Lorenzo, Paz, et al., 2001 | Isidorov, Krajewska, et al., 2000 |
| Comment | MSDC-RI | MSDC-RI |
References
Go To: Top, Van Den Dool and Kratz 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.
Andrade, Sampaio, et al., 2007
Andrade, M.S.; Sampaio, T.S.; Nogueira, P.C.L.; Ribeiro, A.S.; Bittrich, V.; Amaral, M.C.E.,
Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae),
Flavour Fragr. J., 2007, 22, 1, 49-52, https://doi.org/10.1002/ffj.1751
. [all data]
Bruni, Bianchi, et al., 2007
Bruni, R.; Bianchi, A.; Bellardi, M.G.,
Essential oil composition of Agastache anethiodora Britton (Lamiaceae) infected by cucumber mosaic virus (CMV),
Flavour Fragr. J., 2007, 22, 1, 66-70, https://doi.org/10.1002/ffj.1760
. [all data]
Eyres, Marriott, et al., 2007
Eyres, G.T.; Marriott, P.J.; Dufour, J.-P.,
Comparison of Odor-Active Compounds in the Spicy Fraction of Hop (Humulus lupulus L.) Essential Oil from Four Different Varieties,
J. Agric. Food Chem., 2007, 55, 15, 6252-6261, https://doi.org/10.1021/jf070739t
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Sant'Anna, Fontes, et al., 2007
Sant'Anna, B.M.P.; Fontes, S.P.; Pinto, A.C.; Rezende, C.M.,
Characterization of woody odorant contributors in copaiba oil (Copaifera multijuga Hayne),
J. Braz. Chem. Soc., 2007, 18, 5, 984-989, https://doi.org/10.1590/S0103-50532007000500016
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Carasek and Pawliszyn, 2006
Carasek, E.; Pawliszyn, J.,
Screening of Tropical Fruit Volatile Compounds Using Solid-Phase Microextraction (SPME) Fibers and Internally Cooled SPME Fiber,
J. Agric. Food Chem., 2006, 54, 23, 8688-8696, https://doi.org/10.1021/jf0613942
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Cardeal, da Silva, et al., 2006
Cardeal, Z.L.; da Silva, M.D.R.G.; Marriott, P.J.,
Comprehensive two-dimensional gas chromatography/mass spectrometric analysis of pepper volatiles,
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Eom S.H., Yang H.S., et al., 2006
Eom S.H.; Yang H.S.; Weston L.A.,
An evaluation of the allelopathic potential of selected perennial groundcovers: Foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth,
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Moon, Cliff, et al., 2006
Moon, S.-Y.; Cliff, M.A.; Li-Chan, E.C.Y.,
Odour-active components of simulated beef flavour analysed by solid phase microextraction and gas chromatography-mass spectrometry and -olfactometry,
Food Res. Int., 2006, 39, 3, 294-308, https://doi.org/10.1016/j.foodres.2005.08.002
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Özel, Gögüs, et al., 2006
Özel, M.Z.; Gögüs, F.; Lewis, A.C.,
Determination of Teucrium chamaedrys volatiles by using direct thermal desorption-comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry,
J. Chromatogr. A, 2006, 1114, 1, 164-169, https://doi.org/10.1016/j.chroma.2006.02.036
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Sacchetti, Guerrini, et al., 2006
Sacchetti, G.; Guerrini, A.; Noriega, P.; Bianchi, A.; Bruni, R.,
Essential oil of wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) leaves from Amazonian Ecuador,
Flavour Fragr. J., 2006, 21, 4, 674-676, https://doi.org/10.1002/ffj.1648
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Akpulat, Tepe, et al., 2005
Akpulat, H.A.; Tepe, B.; Sokmen, A.; Daferera, D.; Polissiou, M.,
Composition of the essential oils of Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum and Tanacetum parthenium (L.) Schultz Bip. (Asteraceae) from Turkey,
Biochem. Syst. Ecol., 2005, 33, 5, 511-516, https://doi.org/10.1016/j.bse.2004.10.006
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Bruni, Pellati, et al., 2005
Bruni, R.; Pellati, F.; Grazia Bellardi, M.; Benvenuti, S.; Paltrinieri, S.; Bertaccini, A.; Bianchi, A.,
Herbal drug quality and phytochemical composition of Hypericum perforatum L. affected by ash yellows phytoplasma infection,
J. Agric. Food Chem., 2005, 53, 4, 964-968, https://doi.org/10.1021/jf0487654
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Lorenzo, Paz, et al., 2005
Lorenzo, D.; Paz, D.; Davies, P.; Villamil, J.; Vila, R.; Canigueral, S.; Dellacassa, E.,
Application of Multidimensional Gas Chromatography to the Enantioselective Characterisation of the Essential Oil of Eupatorium buniifolium Hooker et Arnott,
Phytochem. Anal., 2005, 16, 1, 39-44, https://doi.org/10.1002/pca.808
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Oliveira, Campos, et al., 2005
Oliveira, M.J.; Campos, I.F.P.; Oliveira, C.B.A.; Santos, M.R.; Souza, P.S.; Santos, S.C.; Seraphin, J.C.; Ferri, P.H.,
Influence of growth phase on the essential oil composition of Hyptis suaveolens,
Biochem. Syst. Ecol., 2005, 33, 3, 275-285, https://doi.org/10.1016/j.bse.2004.10.001
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Sacchetti, Maietti, et al., 2005
Sacchetti, G.; Maietti, S.; Muzzoli, M.; Scaglianti, M.; Manfredini, S.; Radice, M.; Bruni, R.,
Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods,
Food Chem., 2005, 91, 4, 621-632, https://doi.org/10.1016/j.foodchem.2004.06.031
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Helmig, Bocquet, et al., 2004
Helmig, D.; Bocquet, F.; Pollmann, J.; Revermann, T.,
Analytical techniques for sesquiterpene emission rate studies in vegetation enclosure experiments,
Atmos. Environ., 2004, 38, 4, 557-572, https://doi.org/10.1016/j.atmosenv.2003.10.012
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Sacchetti, Medici, et al., 2004
Sacchetti, G.; Medici, A.; Maietti, S.; Radice, M.; Muzzoli, M.; Manfredini, S.; Braccioli, E.; Bruni, R.,
Composition and functional properties of the essential oil of Amazonian basil, Ocimum micranthum Willd., Labiatae in comparison with commercial essential oils,
J. Agric. Food Chem., 2004, 52, 11, 3486-3491, https://doi.org/10.1021/jf035145e
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Mockute and Judzentiene, 2003
Mockute, D.; Judzentiene, A.,
Variability of the essential oils composition of Achillea millefolium ssp. millefolium growing wild in Lithuania,
Biochem. Syst. Ecol., 2003, 31, 9, 1033-1045, https://doi.org/10.1016/S0305-1978(03)00066-8
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Passos X.S., Castro A.C.M., et al., 2003
Passos X.S.; Castro A.C.M.; Pires J.S.; Garcia A.C.F.; Campos F.C.; Fernandes O.F.L.; Paula J.R.; Ferreira H.D.; Santos S.C.; Ferri P.H.; Silva M.D.R.,
Composition and antifungal activity of the essential oils of Caryocar brasiliensis,
Pharm. Biol., 2003, 41, 5, 319-324, https://doi.org/10.1076/phbi.41.5.319.15936
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Azevedo, Campos, et al., 2002
Azevedo, N.R.; Campos, I.F.P.; Ferreira, H.D.; Portes, T.A.; Seraphin, J.C.; de Paula, J.R.; Santos, S.C.; Ferri, P.H.,
Essential oil chemotypes in Hyptis suaveolens from Brazilian Cerrado,
Biochem. Syst. Ecol., 2002, 30, 3, 205-216, https://doi.org/10.1016/S0305-1978(01)00075-8
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García, Alvarez, et al., 2002
García, D.; Alvarez, A.; Tornos, P.; Fernandez, A.; Sáenz, T.,
Gas chromatographic-mass spectrometry study of the essential oils of Pimenta racemosa var. terebinthina and P. racemosa var. grisea,
Z. Naturforsch., 2002, 57c, 449-451. [all data]
Lorenzo, Paz, et al., 2002
Lorenzo, D.; Paz, D.; Dellacassa, E.; Davies, P.; Vila, R.; Cañigueral, S.,
Essential oils of Mentha pulegium and Mentha rotundifolia from Uruguay,
Braz. Arch. Biol. Technol., 2002, 45, 4, 519-524, https://doi.org/10.1590/S1516-89132002000600016
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Cavalli, Ranarivelo, et al., 2001
Cavalli, J.-F.; Ranarivelo, L.; Ratsimbason, M.; Bernardini, A.-F.; Casanova, J.,
Constituents of the essential oil of six Helichrysum species from Madagascar,
Flavour Fragr. J., 2001, 16, 4, 253-256, https://doi.org/10.1002/ffj.994
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Lorenzo, Dellacassa, et al., 2001
Lorenzo, D.; Dellacassa, E.; Bonaccorsi, I.; Mondello, L.,
Uruguayan essential oils. Composition of leaf oil of Myrcianthes cisplatensis (Camb.) Berg. ('Guayabo colorado') (Myrtaceae),
Flavour Fragr. J., 2001, 16, 2, 97-99, https://doi.org/10.1002/1099-1026(200103/04)16:2<97::AID-FFJ952>3.0.CO;2-C
. [all data]
Lorenzo, Paz, et al., 2001
Lorenzo, D.; Paz, D.; Davies, P.; Vila, R.; Canigueral, S.; Dellacassa, E.,
Composition of a new essential oil type of Lippia alba (Mill.) N.E. Brown from Uruguay,
Flavour Fragr. J., 2001, 16, 5, 356-359, https://doi.org/10.1002/ffj.1011
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Isidorov, Krajewska, et al., 2000
Isidorov, V.; Krajewska, U.; Bal, K.; Jaroszynska, J.; Niesluchowska, A.; Fuksman, I.,
GC-MS identification of multicomponent organic compounds mixtures using extra column phase equilibrium,
Chem. Anal. (Warsaw), 2000, 45, 513-520. [all data]
Notes
Go To: Top, Van Den Dool and Kratz RI, non-polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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