(1R,9R,E)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene

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+/m1/s1
IUPAC Standard InChIKey: NPNUFJAVOOONJE-BLOBHPOZSA-N
CAS Registry Number: 68832-35-9
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- 2-epi-(E)-β-Caryophyllene
Stereoisomers:
Other names: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9R)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9R*)]-; (+)-9-epi-β-Caryophyllene; 9-epi-(E)-Caryophyllene; 9-epi-trans-Caryophyllene; 9-epi-β-Caryophyllene; epi-β-Caryophyllene; 9-epi-(E)-Caryophillene
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1466.	Adams, González Elizondo, et al., 2006	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1457.	Marongiu, Piras, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min, 240. C @ 30. min; T_start: 60. C
Capillary	DB-5	1455.	Marongiu, Piras, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min, 240. C @ 30. min; T_start: 60. C
Capillary	HP-5	1465.	Tzakou and Couladis, 2001	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1470.	Benkaci-Ali, Baaliouamer, et al., 2007	30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 30. min
Capillary	DB-5	1467.	Telascrea, de Araujo, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1463.	Yu, Liao, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min, 250. C @ 10. min; T_start: 50. C
Capillary	DB-5	1466.	Su, Ho, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 2. min, 5. K/min; T_end: 250. C
Capillary	DB-1	1429.	Dob, Dahmane, et al., 2005	30. m/0.32 mm/0.25 μm, 50. C @ 8. min, 2. K/min; T_end: 250. C
Capillary	HP-5MS	1465.	Pino, Mesa, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	HP-5	1468.	Macchioni, Cioni, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	HP-5MS	1467.	Demetzos, Angelopoulou, et al., 2002	30. m/0.25 mm/0.25 μm, 50. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	HP-5	1466.	Aligiannis, Kalpoutzakis, et al., 2001	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; T_end: 280. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	1471.	Cardeal, da Silva, et al., 2006	30. m/0.25 mm/0.25 μm; Program: 35C(5min) => 3C/min => 210C => 40C/min => 240C (4min)
Capillary	SE-52	1475.	Lorenzo, Paz, et al., 2005	25. m/0.32 mm/0.43 μm, H2; Program: 60C(8min) => 3C/min => 180C => 20C/min => 250C(10min)

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1563.	Lorenzo, Paz, et al., 2005	25. m/0.32 mm/0.25 μm, H2; Program: 40C(8min) => 3C/min => 180C => 20C/min => 230C(10min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5 MS	1472.	Noudogbessi, Yedomonhan, et al., 2008	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 300. C @ 5. min
Capillary	DB-5	1467.	Pontes, de Olivera, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen, 4. K/min; T_start: 50. C; T_end: 250. C
Capillary	DB-5	1462.	Sylvestre, Pichette, et al., 2007	30. m/0.25 mm/0.25 μm, 2. K/min, 250. C @ 33. min; T_start: 40. C
Capillary	DB-5	1451.	Apel, Sobral, et al., 2006	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 300. C
Capillary	DB-5	1467.	Rout, Naik, et al., 2006	30. m/0.25 mm/0.25 μm, He, 2. K/min, 200. C @ 60. min; T_start: 60. C
Capillary	Methyl Silicone	1467.	Chalchat and Özcan, 2005	He, 3. K/min; Column length: 60. m; Column diameter: 0.3 mm; T_start: 50. C; T_end: 240. C
Capillary	HP-5	1457.	Jovanovic, Kitic, et al., 2005	25. m/0.32 mm/0.52 μm, H2, 4. K/min; T_start: 40. C; T_end: 240. C
Capillary	HP-5MS	1474.	Melkani, Dev, et al., 2005	30. m/0.25 mm/0.25 μm, 50. C @ 10. min, 3. K/min, 250. C @ 5. min
Capillary	RTX-1	1462.	Sonboli A., Fakhari A.R., et al., 2005	60. m/0.25 mm/0.25 μm, He, 5. K/min, 250. C @ 10. min; T_start: 60. C
Capillary	DB-5MS	1457.	Marongiu, Porcedda, et al., 2004	30. m/0.25 mm/0.25 μm, He, 3. K/min, 280. C @ 30. min; T_start: 60. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1467.	Pontes, de Olivera, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen; Program: not specified
Capillary	Methyl Silicone	1465.	Demyttenaere, Morina, et al., 2003	He; Program: 60 0C 3 0C/min -> 200 0C 15 0C/min -> 250 0C (5 min)
Capillary	HP-5MS	1465.	Demyttenaere, Moriña, et al., 2002	25. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 8C/min => 160C => 15C/min => 250C(3min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	1630.	Sylvestre, Pichette, et al., 2007	30. m/0.25 mm/0.25 μm, 2. K/min, 250. C @ 33. min; T_start: 40. C
Capillary	DB-Wax	1572.	Paniandy, Chane-Ming, et al., 2000	60. m/0.32 mm/0.25 μm, Helium, 50. C @ 2. min, 5. K/min; T_end: 230. C

References

Go To: Top, Gas Chromatography, Notes

Adams, González Elizondo, et al., 2006
Adams, R.P.; González Elizondo, M.S.; González Elizondo, M.; Slinkman, E., DNA fingerprinting and terpenoid analysis of Juniperus blancoi var. huehuentensis (Cupressaceae), a new subalpine variety from Durango, Mexico, Biochem. Syst. Ecol., 2006, 34, 3, 205-211, https://doi.org/10.1016/j.bse.2005.11.004 . [all data]

Marongiu, Piras, et al., 2003
Marongiu, B.; Piras, A.; Pani, F.; Porcedda, S.; Ballero, M., Extraction, separation and isolation of essential oils from natural matrices by supercritical CO₂, Flavour Fragr. J., 2003, 18, 6, 505-509, https://doi.org/10.1002/ffj.1258 . [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]

Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 2007, 22, 2, 148-153, https://doi.org/10.1002/ffj.1773 . [all data]

Telascrea, de Araujo, et al., 2007
Telascrea, M.; de Araujo, C.C.; Marques, M.O.M.; Facanali, R.; de Moraes, P.L.R.; Cavalheiro, A.J., Essential oil from leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability, Biochem. Syst. Ecol., 2007, 35, 4, 222-232, https://doi.org/10.1016/j.bse.2006.09.015 . [all data]

Yu, Liao, et al., 2007
Yu, J.Q.; Liao, Z.X.; Cai, X.Q.; Lei, J.C.; Zou, G.L., Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima, Environmental Toxicology and Pharmacology, 2007, 23, 2, 162-167, https://doi.org/10.1016/j.etap.2006.08.004 . [all data]

Su, Ho, et al., 2006
Su, Y.C.; Ho, C.L.; Wang, E.I.C., Analysis of leaf essential oils from the indigenous five conifers of Taiwan, Flavour Fragr. J., 2006, 21, 3, 447-452, https://doi.org/10.1002/ffj.1685 . [all data]

Dob, Dahmane, et al., 2005
Dob, T.; Dahmane, D.; Berramdane, T.; Chelghoum, C., Chemical composition of the essential oil of Artemisia campestris L. from Algeria, Pharm. Biol., 2005, 43, 6, 512-514, https://doi.org/10.1080/13880200500220664 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Macchioni, Cioni, et al., 2003
Macchioni, F.; Cioni, P.L.; Flamini, G.; Morelli, I.; Maccioni, S.; Ansaldi, M., Chemical composition of essential oils from needles, branches and cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from central Italy, Flavour Fragr. J., 2003, 18, 2, 139-143, https://doi.org/10.1002/ffj.1178 . [all data]

Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D., A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece), Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4 . [all data]

Aligiannis, Kalpoutzakis, et al., 2001
Aligiannis, N.; Kalpoutzakis, E.; Chinou, I.B.; Mitaku, S.; Gikas, E.; Tsarbopoulos, A., Composition and antimicrobial activity of the essential oils of five taxa of Sideritis from Greece, J. Agric. Food Chem., 2001, 49, 2, 811-815, https://doi.org/10.1021/jf001018w . [all data]

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, Rapid Commun. Mass Spectrom., 2006, 20, 19, 2823-2836, https://doi.org/10.1002/rcm.2665 . [all data]

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 . [all data]

Noudogbessi, Yedomonhan, et al., 2008
Noudogbessi, J.-P.; Yedomonhan, P.; Sohounhloue, D.C.K.; Chalchat, J.-C.; Figueredo, G., Chemical composition of essential oil of syzygium guineense (Willd.) DC. var. guineense (Myrtaceae) from Benin, Rec. Nat. Prod., 2008, 33-38. [all data]

Pontes, de Olivera, et al., 2007
Pontes, W.J.T.; de Olivera, J.C.G.; da Camara, C.A.G.; Lopes, A.C.H.R.; Gondim Jr.; de Olivera, J.V.; Barros, R.; Schwartz, M.O.E., Chemical composition and acaridical activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl.) Marchand (Burseraceae), Acta Amazonica, 2007, 37, 1, 103-110, https://doi.org/10.1590/S0044-59672007000100012 . [all data]

Sylvestre, Pichette, et al., 2007
Sylvestre, M.; Pichette, A.; Longtin, A.; Martin, M.-A.C.; Bercion, S.R.; Legault, J., Chemical composition of leaf essential oil of Hedyosmum arborescens and evaluation of its anticancer activity, Natural Product Communications, 2007, 2, 12, 1269-1272. [all data]

Apel, Sobral, et al., 2006
Apel, M.A.; Sobral, M.; Zuanazzi, J.A.S.; Henriques, A.T., Essential oil composition of four Plinia species (Myrtaceae), Flavour Fragr. J., 2006, 21, 3, 565-567, https://doi.org/10.1002/ffj.1638 . [all data]

Rout, Naik, et al., 2006
Rout, P.K.; Naik, S.N.; Rao, Y.R., Composition of the concrete, absolute, headspace and essential oil of the flowers of Michelia champaca Linn., Flavour Fragr. J., 2006, 21, 6, 906-911, https://doi.org/10.1002/ffj.1742 . [all data]

Chalchat and Özcan, 2005
Chalchat, J.-C.; Özcan, M., Constituents of the essential oil of Sideritis erythantha Boiss. Heldr. Var. erythrantha, Gen. Appl. Plant Physiology, 2005, 31, 1-2, 65-70. [all data]

Jovanovic, Kitic, et al., 2005
Jovanovic, T.; Kitic, D.; Palic, R.; Stojanovic, G.; Ristic, M., Chemical composition and antimicrobial activity of the essential oil of Acinos arvensis (Lam.) Dandy from Serbia, Flavour Fragr. J., 2005, 20, 3, 288-290, https://doi.org/10.1002/ffj.1409 . [all data]

Melkani, Dev, et al., 2005
Melkani, A.B.; Dev, V.; Beauchamp, P.S.; Negi, A.; Mehta, S.P.S.; Melkani, K.B., Constituents of the essential oil of a new chemotype of Elsholtzia strobilifera Benth., Biochem. Syst. Ecol., 2005, 33, 4, 419-425, https://doi.org/10.1016/j.bse.2004.10.009 . [all data]

Sonboli A., Fakhari A.R., et al., 2005
Sonboli A.; Fakhari A.R.; Sefidkon F., Chemical composition of the essential oil of Salvia macilenta from Iran, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 2, 168-170, https://doi.org/10.1007/s10600-005-0104-0 . [all data]

Marongiu, Porcedda, et al., 2004
Marongiu, B.; Porcedda, A.P.S.; Casu, R.; Pierucci, P., Chemical composition of the oil and supercritical CO₂ extract of Schinus molle L., Flavour Fragr. J., 2004, 19, 6, 554-558, https://doi.org/10.1002/ffj.1350 . [all data]

Demyttenaere, Morina, et al., 2003
Demyttenaere, J.C.R.; Morina, R.M.; Sandra, P., Monitoring and fast detection of mycotoxin-producing fungi based on headspace solid-phase microextraction and headspace sorptive extraction of the volatile metabolites, J. Chromatogr. A, 2003, 985, 1-2, 127-135, https://doi.org/10.1016/S0021-9673(02)01417-6 . [all data]

Demyttenaere, Moriña, et al., 2002
Demyttenaere, J.C.R.; Moriña, R.M.; Sandra, P.; Schelfaut, M., Monitoring and fast detection of mycotoxin-producing fungi based on headspace solid-phase microextraction and headspace sorptive extraction of the volatile metabolites in 25th International Symposium on Capillary Chromatography, 2002, 1-12. [all data]

Paniandy, Chane-Ming, et al., 2000
Paniandy, J.-C.; Chane-Ming, J.; Pierbattesti, J.-C., Chemical Composition of the Essential Oil and Headspace Solid-Phase Microextraction of the Guava Fruit (Psidium guajava L.), J. Essent. Oil Res., 2000, 12, 153-158. [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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