(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
Information on this page:
Other data available:
- Gas Chromatography
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Normal alkane RI, non-polar column, temperature ramp

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5 MS	DB-5	DB-5	DB-5	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	Hydrogen		He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	50.	40.	60.	60.
T_end (C)	300.	250.	250.	300.	200.
Heat rate (K/min)	5.	4.	2.	3.	2.
Initial hold (min)	5.
Final hold (min)	5.		33.		60.
I	1472.	1467.	1462.	1451.	1467.
Reference	Noudogbessi, Yedomonhan, et al., 2008	Pontes, de Olivera, et al., 2007	Sylvestre, Pichette, et al., 2007	Apel, Sobral, et al., 2006	Rout, Naik, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Methyl Silicone	HP-5	HP-5MS	RTX-1	DB-5MS
Column length (m)	60.	25.	30.	60.	30.
Carrier gas	He	H2		He	He
Substrate
Column diameter (mm)	0.3	0.32	0.25	0.25	0.25
Phase thickness (μm)		0.52	0.25	0.25	0.25
T_start (C)	50.	40.	50.	60.	60.
T_end (C)	240.	240.	250.	250.	280.
Heat rate (K/min)	3.	4.	3.	5.	3.
Initial hold (min)			10.
Final hold (min)			5.	10.	30.
I	1467.	1457.	1474.	1462.	1457.
Reference	Chalchat and Özcan, 2005	Jovanovic, Kitic, et al., 2005	Melkani, Dev, et al., 2005	Sonboli A., Fakhari A.R., et al., 2005	Marongiu, Porcedda, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

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]

Notes

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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