Caryophyllene
- Formula: C15H24
- Molecular weight: 204.3511
- IUPAC Standard InChI: InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m0/s1
- IUPAC Standard InChIKey: NPNUFJAVOOONJE-IOMPXFEGSA-N
- CAS Registry Number: 87-44-5
- Chemical structure:
This structure is also available as a 2d Mol file - Species with the same structure:
- Stereoisomers:
- Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-,[1R-(1R*,4Z,9S*)]-
- Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-
- (1R,9R,E)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
- 9-epi-Caryophyllene
- cis-Caryophyllene
- (+)(E)-Caryophyllene
- 2-epi-(E)- β-Caryophyllene
- 9-epi-β-Caryophyllene
- cis-Caryophyllene
- 2-epi-(E)-β-Caryophyllene
- β-cis-Caryophyllene
- Isocaryophyllene
- Other names: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-; β-Caryophyllen; β-Caryophyllene; trans-Caryophyllene; L-Caryophyllene; Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-; 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene, (1R,4E,9S)-; beta-Caryophyllene; β-(E)-Caryophyllene; β-trans-Caryophyllene; Caryophyllene, (E); E-β-Caryophyllene; (E)-Caryophyllene; trans-β-Caryophyllene; (-)-(E)-Caryophyllene; Caryophyllene B; NSC 11906; t-β-caryophyllene; β-Caryophillene; 4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene; β-cariofillene; β-caryophellene; bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-[1R-(4E,9S)]; (E)-β-Caryophylene
- Information on this page:
- Other data available:
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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 | HP-Wax | DB-Wax |
| Column length (m) | 30. | 30. | 30. | 50. | 30. |
| Carrier gas | N2 | N2 | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.2 | 0.32 |
| Phase thickness (μm) | 1. | 0.25 | 0.25 | 0.4 | 0.25 |
| Tstart (C) | 50. | 60. | 40. | 60. | 40. |
| Tend (C) | 220. | 220. | 210. | 230. | 220. |
| Heat rate (K/min) | 2. | 5. | 2. | 4. | 3. |
| Initial hold (min) | 3. | 2. | 5. | ||
| Final hold (min) | 15. | 14. | 33. | 30. | |
| I | 1620. | 1615. | 1589. | 1625. | 1576. |
| Reference | Hazzit, Baaliouamer, et al., 2006 | Khan, Verma, et al., 2006 | Sylvestre, Pichette, et al., 2006 | Gauvin, Lecomte, 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 | DB-Wax | Innowax | Innowax | Supelcowax-10 |
| Column length (m) | 30. | 30. | 30. | 50. | 30. |
| Carrier gas | He | He | He | He | |
| 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 |
| Tstart (C) | 40. | 40. | 50. | 50. | 75. |
| Tend (C) | 190. | 240. | 250. | 180. | 230. |
| Heat rate (K/min) | 5. | 2. | 0.5 | 2.5 | 3. |
| Initial hold (min) | 5. | 5. | |||
| Final hold (min) | 5. | 40. | 10. | ||
| I | 1617. | 1570. | 1585. | 1575. | 1599. |
| Reference | Mahmood, Kaul, et al., 2004 | Nébié, Yaméogo, et al., 2004 | Viña and Murillo, 2003 | Yáñez, Pinzón, et al., 2002 | Tzakou and Couladis, 2001 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax |
| Column length (m) | 50. | 50. | 25. | 25. | 30. |
| Carrier gas | N2 | N2 | Ar | ||
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.25 | 0.5 | 0.25 |
| Phase thickness (μm) | 0.2 | 0.2 | 0.25 | ||
| Tstart (C) | 60. | 60. | 60. | 60. | 50. |
| Tend (C) | 260. | 260. | 200. | 200. | 220. |
| Heat rate (K/min) | 2. | 2. | 5. | 5. | 4. |
| Initial hold (min) | |||||
| Final hold (min) | |||||
| I | 1617. | 1632. | 1581. | 1584. | 1617. |
| Reference | Vera and Chane-Ming, 1999 | Vera and Chane-Ming, 1999 | Kulkarni, Mallavarapu, et al., 1998 | Mallavarapu, Rao, et al., 1998 | Szafranek, Malinski, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Supelcowax-10 | Supelcowax-10 | Supelcowax-10 | Supelcowax-10 | Carbowax 20M |
| Column length (m) | 30. | 30. | 30. | 60. | 50. |
| Carrier gas | He | ||||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.22 | |||
| Phase thickness (μm) | |||||
| Tstart (C) | 40. | 40. | 40. | 35. | 80. |
| Tend (C) | 210. | 210. | 210. | 200. | 200. |
| Heat rate (K/min) | 2. | 2. | 2. | 3. | 2. |
| Initial hold (min) | 2. | 2. | 2. | 5. | |
| Final hold (min) | 120. | 120. | 120. | 20. | |
| I | 1579. | 1579. | 1588. | 1598. | 1617. |
| Reference | Loayza, Abujder, et al., 1995 | Loayza, Abujder, et al., 1995 | Loayza, Abujder, et al., 1995 | Wong and Tie, 1993 | Nishimura, Yamaguchi, et al., 1989 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Supelcowax-20M | DB-Wax | Carbowax 20M | BP-20 | Carbowax 20M |
| Column length (m) | 23. | 60. | 50. | 25. | 50. |
| Carrier gas | H2 | He | H2 | ||
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.25 | 0.3 | 0.332 | 0.3 |
| Phase thickness (μm) | 0.30 | 0.15 | |||
| Tstart (C) | 50. | 40. | 70. | 70. | 70. |
| Tend (C) | 200. | 220. | 210. | 200. | 210. |
| Heat rate (K/min) | 3. | 2. | 2. | 4. | 2. |
| Initial hold (min) | 1. | 10. | 2. | ||
| Final hold (min) | |||||
| I | 1587. | 1585. | 1581. | 1617. | 1577. |
| Reference | Bicchi, Frattini, et al., 1988 | Umano and Shibamoto, 1988 | Randriamiharisoa and Gaydou, 1987 | Wyllie, Cook, et al., 1987 | Gaydou, Randriamiharisoa, et al., 1986 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M |
| Column length (m) | 100. | 100. | 50. | 50. | 150. |
| Carrier gas | He | ||||
| Substrate | |||||
| Column diameter (mm) | 0.28 | 0.28 | 0.23 | 0.23 | 0.64 |
| Phase thickness (μm) | |||||
| Tstart (C) | 80. | 80. | 80. | 80. | 50. |
| Tend (C) | 200. | 200. | 200. | 200. | 170. |
| Heat rate (K/min) | 3. | 3. | 2. | 2. | 1. |
| Initial hold (min) | 30. | ||||
| Final hold (min) | |||||
| I | 1570. | 1570. | 1580. | 1581. | 1570. |
| Reference | Bernhard, Shibamoto, et al., 1983 | Bernhard, Shibamoto, et al., 1983 | Toda, Mihara, et al., 1983 | Toda, Mihara, et al., 1983 | Buttery, Kamm, et al., 1982 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M | Carbowax 20M |
| Column length (m) | 150. | 50. | 50. | 50. | 50. |
| Carrier gas | N2 | He | |||
| Substrate | |||||
| Column diameter (mm) | 0.64 | 0.28 | 0.28 | 0.28 | 0.28 |
| Phase thickness (μm) | |||||
| Tstart (C) | 50. | 80. | 80. | 80. | 70. |
| Tend (C) | 170. | 200. | 200. | 200. | 190. |
| Heat rate (K/min) | 1. | 2. | 2. | 2. | 2. |
| Initial hold (min) | 30. | ||||
| Final hold (min) | |||||
| I | 1570. | 1568. | 1570. | 1642. | 1594. |
| Reference | Buttery, Ling, et al., 1982 | Toda, Yamaguchi, et al., 1982 | Toda, Yamaguchi, et al., 1982 | Shibamoto, Kamiya, et al., 1981 | Tressl, Friese, et al., 1978 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | 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]
Gauvin, Lecomte, et al., 2004
Gauvin, A.; Lecomte, H.; Smadja, J.,
Comparative investigations of the essential oils of two scented geranium (Pelargonium spp.) cultivars grown on Reunion Island,
Flavour Fragr. J., 2004, 19, 5, 455-460, https://doi.org/10.1002/ffj.1354
. [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]
Nébié, Yaméogo, et al., 2004
Nébié, R.H.C.; Yaméogo, R.T.; Bélanger, A.; Sib, F.S.,
Composition chimique des huiles essentielles d'Ageratum conyzoïdes du Burkina Faso,
C.R. Chim., 2004, 7, 10-11, 1019-1022, https://doi.org/10.1016/j.crci.2003.12.027
. [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]
Yáñez, Pinzón, et al., 2002
Yáñez, X.; Pinzón, M.L.; Solano, F.; Sánchez, L.R.,
Chemical composition of the essential oil of Psidium caudatum McVaugh,
Molecules, 2002, 7, 9, 712-716, https://doi.org/10.3390/70900712
. [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]
Kulkarni, Mallavarapu, et al., 1998
Kulkarni, R.N.; Mallavarapu, G.R.; Baskaran, K.; Ramesch, S.; Kumar, S.,
Composition of the essential oils of two isomenthone-rich variants of geranium (Pelargonium sp.),
Flavour Fragr. J., 1998, 13, 6, 389-392, https://doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<389::AID-FFJ757>3.0.CO;2-2
. [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]
Szafranek, Malinski, et al., 1998
Szafranek, B.; Malinski, E.; Szafranek, J.,
The sesquiterpene composition of leaf cuticular neutral lipids of ten varieties of polish Solanum tuberosum,
J. Sci. Food Agric., 1998, 76, 4, 588-592, https://doi.org/10.1002/(SICI)1097-0010(199804)76:4<588::AID-JSFA994>3.0.CO;2-M
. [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]
Wong and Tie, 1993
Wong, K.C.; Tie, D.Y.,
The Essential Oil of the Leaves of Murraya koenigii Spreng.,
J. Essent. Oil Res., 1993, 5, 4, 371-374, https://doi.org/10.1080/10412905.1993.9698245
. [all data]
Nishimura, Yamaguchi, et al., 1989
Nishimura, O.; Yamaguchi, K.; Mihara, S.; Shibamoto, T.,
Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree,
J. Agric. Food Chem., 1989, 37, 1, 139-142, https://doi.org/10.1021/jf00085a033
. [all data]
Bicchi, Frattini, et al., 1988
Bicchi, C.; Frattini, C.; Nano, G.M.; D'Amato, A.,
On column injection-dual channel analysis of essential oils,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1988, 11, 1, 56-60, https://doi.org/10.1002/jhrc.1240110115
. [all data]
Umano and Shibamoto, 1988
Umano, K.; Shibamoto, T.,
A new method of headspace sampling: grapefruit volatiles
in Flavors and Fragrances: A World Perspective. Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors, Lawrence,B.M.; Mookherjee,B.D.; Willis,B.J., ed(s)., Elsevier, New York, 1988, 981-998. [all data]
Randriamiharisoa and Gaydou, 1987
Randriamiharisoa, R.P.; Gaydou, E.M.,
Composition of Palmarosa (Cymbopogon martinii) essential oil from Madagascar,
J. Agric. Food Chem., 1987, 35, 1, 62-66, https://doi.org/10.1021/jf00073a015
. [all data]
Wyllie, Cook, et al., 1987
Wyllie, S.G.; Cook, D.; Brophy, J.J.; Richter, K.M.,
Volatile flavor components of Annona atemoya (custard apple),
J. Agric. Food Chem., 1987, 35, 5, 768-770, https://doi.org/10.1021/jf00077a029
. [all data]
Gaydou, Randriamiharisoa, et al., 1986
Gaydou, E.M.; Randriamiharisoa, R.; Bianchini, J.-P.,
Composition of the essential oil of ylang-ylang (Canaga odorata Hook Fil. et Thomson forma genuina) from Madagascar,
J. Agric. Food Chem., 1986, 34, 3, 481-487, https://doi.org/10.1021/jf00069a028
. [all data]
Bernhard, Shibamoto, et al., 1983
Bernhard, R.A.; Shibamoto, T.; Yamaguchi, K.; White, E.,
The volatile constituents of Schinus molle L.,
J. Agric. Food Chem., 1983, 31, 2, 463-466, https://doi.org/10.1021/jf00116a075
. [all data]
Toda, Mihara, et al., 1983
Toda, H.; Mihara, S.; Umano, K.; Shibamoto, T.,
Photochemical studies on jasmin oil,
J. Agric. Food Chem., 1983, 31, 3, 554-558, https://doi.org/10.1021/jf00117a022
. [all data]
Buttery, Kamm, et al., 1982
Buttery, R.G.; Kamm, J.A.; Ling, L.C.,
Volatile components of alfalfa flowers and pods,
J. Agric. Food Chem., 1982, 30, 4, 739-742, https://doi.org/10.1021/jf00112a028
. [all data]
Buttery, Ling, et al., 1982
Buttery, R.G.; Ling, L.C.; Wellso, S.G.,
Oat leaf volatiles: possible insect attractants,
J. Agric. Food Chem., 1982, 30, 4, 791-792, https://doi.org/10.1021/jf00112a045
. [all data]
Toda, Yamaguchi, et al., 1982
Toda, H.; Yamaguchi, K.; Shibamoto, T.,
Isolation and identification of banana-like aroma from banana shrub (Michellia figo Spreng),
J. Agric. Food Chem., 1982, 30, 1, 81-84, https://doi.org/10.1021/jf00109a017
. [all data]
Shibamoto, Kamiya, et al., 1981
Shibamoto, T.; Kamiya, Y.; Mihara, S.,
Isolation and identification of volatile compounds in cooked meat: sukiyaki,
J. Agric. Food Chem., 1981, 29, 1, 57-63, https://doi.org/10.1021/jf00103a015
. [all data]
Tressl, Friese, et al., 1978
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
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