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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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Van Den Dool and Kratz RI, 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	RTX-Wax	BP-20	BP-20	BP-20	HP-Innowax
Column length (m)	60.	50.	50.	50.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.22	0.22	0.22	0.22	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	230.	220.	220.	220.	280.
Heat rate (K/min)	2.	2.	2.	2.	3.
Initial hold (min)
Final hold (min)	30.	20.	20.	20.
I	1980.	1985.	1990.	1979.	1989.
Reference	Bendahou, Muselli, et al., 2008	Boti, Koukoua, et al., 2007	Castilho, Liu, et al., 2007	Duquesnoy, Castola, et al., 2007	Kundakovic, Fokialakis, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	RTX-Wax	RTX-Wax	RTX-Wax	BP-20
Column length (m)	50.	60.	60.	60.	50.
Carrier gas	He	He	He	He
Substrate
Column diameter (mm)	0.22	0.22	0.22	0.22	0.22
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	220.	230.	230.	230.	220.
Heat rate (K/min)	2.	2.	2.	2.	2.
Initial hold (min)
Final hold (min)	20.	30.	35.	35.	20.
I	1982.	1937.	1960.	1940.	1987.
Reference	Lesueur, de Rocca Serra, et al., 2007	Muselli, Rossi, et al., 2007	Paolini J., Costa J., et al., 2007	Paolini, Muselli, et al., 2007	Blanc, Bradesi, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	BP-20	RTX-Wax	Polyethylene Glycol	BP-20
Column length (m)	50.	50.	60.	30.	50.
Carrier gas	He	He	He	N2	He
Substrate
Column diameter (mm)	0.22	0.25	0.22	0.32	0.22
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	50.	60.
T_end (C)	220.	220.	230.	230.	220.
Heat rate (K/min)	2.	2.	2.	2.	2.
Initial hold (min)				10.
Final hold (min)	20.	20.	45.	15.	20.
I	1989.	1985.	1976.	2001.	1981.
Reference	Boti, Bighelli, et al., 2006	Bousmaha, Boti, et al., 2006	Cavalli, Tomi, et al., 2006	Dob, Dahmane, et al., 2006	Duquesnoy, Dinh, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Wax	BP-20	DB-Wax	Supelcowax-10	PEG-20M
Column length (m)	30.	50.	60.	30.	25.
Carrier gas	N2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.22	0.32	0.2	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.2	0.3
T_start (C)	60.	60.	35.	70.	50.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)	5.	2.	3.	3.	3.
Initial hold (min)	10.				1.
Final hold (min)		20.		15.	5.
I	1966.	1987.	1988.	1968.	1965.
Reference	Flamini, Tebano, et al., 2006	Gonny, Cavaleiro, et al., 2006	Pala-Paul, Copeland, et al., 2006	Pinto, Pina-Vaz, et al., 2006	Rubiolo P., Matteodo M., et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Supelcowax-10	FFAP	BP-20	DB-Wax	RTX-Wax
Column length (m)	30.	20.	50.	60.	60.
Carrier gas	He	He	He	N2
Substrate
Column diameter (mm)	0.2	0.25	0.22	0.25	0.22
Phase thickness (μm)	0.2	0.25	0.25	0.25	0.25
T_start (C)	70.	90.	60.	70.	60.
T_end (C)	220.	220.	220.	230.	220.
Heat rate (K/min)	3.	4.	2.	2.	2.
Initial hold (min)		2.		2.
Final hold (min)	15.		20.	20.	20.
I	1968.	2036.	1986.	1990.	1964.
Reference	Salgueiro L.R., Pinto E., et al., 2006	Agnihotri, Agarwal, et al., 2005	Boti J.B., Koukoua G., et al., 2005	Choi, 2005	Cozzani, Muselli, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	RTX-Wax	PEG-20M	BP-20	DB-Wax
Column length (m)	60.	60.		50.	30.
Carrier gas	N2	He		He	N2
Substrate
Column diameter (mm)	0.25	0.22		0.22	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	70.	60.	50.	60.	60.
T_end (C)	230.	230.	250.	230.	220.
Heat rate (K/min)	2.	2.	4.	2.	5.
Initial hold (min)	2.				10.
Final hold (min)	20.	35.		35.
I	2001.	1960.	1987.	1983.	1967.
Reference	Njoroge, Koaze, et al., 2005	Paolini, Costa, et al., 2005	Simionatto, Porto, et al., 2005	Vellutini, Baldovini, et al., 2005	Bertoli, Menichini, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	Supelcowax-10	HP-Wax	BP-20	BP-20
Column length (m)	60.	30.	30.	50.	50.
Carrier gas	He	He	N2		He
Substrate
Column diameter (mm)	0.32	0.2	0.25	0.22	0.22
Phase thickness (μm)	0.25	0.2	0.25	0.25	0.25
T_start (C)	32.	70.	60.	60.	60.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)	3.	3.	5.	2.	2.
Initial hold (min)			10.
Final hold (min)		15.		20.	20.
I	1988.	1969.	1966.	1980.	1979.
Reference	Brophy, Goldsack, et al., 2004	Cavaleiro, Salgueiro, et al., 2004	Flamini, Luigi Cioni, et al., 2004	Gonny, Bradesi, et al., 2004	Tam, Thuam, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Wax	Carbowax 20M	RTX-Wax	Supelcowax	Supelcowax
Column length (m)	30.	25.	60.	25.	25.
Carrier gas	N2	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.22	0.25	0.25
Phase thickness (μm)	0.25	0.3	0.25	0.25	0.25
T_start (C)	60.	50.	60.	35.	35.
T_end (C)	220.	200.	230.	225.	225.
Heat rate (K/min)	5.	3.	2.	4.	4.
Initial hold (min)	10.	1.		5.	5.
Final hold (min)		20.	45.	10.	10.
I	1966.	1972.	1978.	2023.	2023.
Reference	Bader, Caponi, et al., 2003	Bicchi, Rubiolo, et al., 2003	Cavalli, Tomi, et al., 2003	Chisholm, Wilson, et al., 2003	Chisholm, Wilson, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Supelcowax	Supelcowax	DB-Wax	HP-20M	HP-Innowax
Column length (m)	25.	25.	60.	50.	30.
Carrier gas			N2	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.2	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.2	0.5
T_start (C)	35.	35.	70.	70.	60.
T_end (C)	225.	225.	230.	180.	260.
Heat rate (K/min)	4.	4.	2.	4.	3.
Initial hold (min)	5.	5.	2.	4.
Final hold (min)	10.	10.	20.	10.
I	2016.	2019.	1999.	1944.	1966.
Reference	Chisholm, Wilson, et al., 2003	Chisholm, Wilson, et al., 2003	Choi, 2003	Jerkovic, Mastelic, et al., 2003	Skaltsa, Demetzos, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	DB-Wax	Innowax	BP-20	RTX-Wax
Column length (m)	30.	60.	30.	50.	30.
Carrier gas	He	N2	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.22	0.25
Phase thickness (μm)	0.5	0.25	0.5	0.25	0.25
T_start (C)	60.	70.	60.	60.	45.
T_end (C)	260.	230.	260.	220.	250.
Heat rate (K/min)	3.	2.	3.	2.	3.
Initial hold (min)					6.
Final hold (min)		20.	10.	20.	10.
I	1966.	1985.	1983.	1974.	1938.
Reference	Skaltsa, Demetzos, et al., 2003	Choi, Kim. M.-S.L., et al., 2002	Couladis, Chinou, et al., 2002	Lota, de Rocca Serra, et al., 2002	Mondello, Zappia, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	AT-Wax	HP-Innowax	CP-Wax 52CB	AT-Wax	BP-20
Column length (m)	60.	30.	50.	60.	50.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.32	0.22
Phase thickness (μm)	0.25	0.50	0.2	0.25	0.25
T_start (C)	65.	60.	32.	65.	60.
T_end (C)	250.	260.	220.	250.	220.
Heat rate (K/min)	2.	3.	1.	2.	2.
Initial hold (min)	10.		1.	10.
Final hold (min)	60.	10.		60.	20.
I	1954.	2000.	1969.	1954.	1972.
Reference	Pino, Marbot, et al., 2002	Couladis, Baziou, et al., 2001	Kjeldsen, Christensen, et al., 2001	Pino, Marbot, et al., 2001	Rezzi, Bighelli, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	DB-Wax	CP-Wax 52CB	CP-Wax 52CB
Column length (m)	60.	60.	60.	25.	25.
Carrier gas	He	He	He
Substrate
Column diameter (mm)	0.50	0.53	0.53	0.25	0.25
Phase thickness (μm)	1.0	1.0	1.0	0.15	0.15
T_start (C)	60.	50.	50.	40.	40.
T_end (C)	225.	220.	220.	220.	220.
Heat rate (K/min)	3.	3.	3.	3.	3.
Initial hold (min)				5.	5.
Final hold (min)
I	1983.	1983.	1938.	1965.	1984.
Reference	Brophy, Goldsack, et al., 2000	Brophy, Goldsack, et al., 2000, 2	Brophy, Goldsack, et al., 2000, 3	Chagonda, Makanda, et al., 2000	Chagonda, Makanda, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	Supelcowax-10	DB-Wax	DB-Wax
Column length (m)	60.	30.	30.	60.	60.
Carrier gas	N2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.53	0.53
Phase thickness (μm)	0.25	0.25	0.25
T_start (C)	70.	40.	75.	50.	50.
T_end (C)	230.	200.	200.	220.	220.
Heat rate (K/min)	2.	2.	2.5	3.	3.
Initial hold (min)	2.	5.
Final hold (min)	20.	20.
I	2001.	1955.	1969.	1983.	1983.
Reference	Choi and Sawamura, 2000	Kim, Thuy, et al., 2000	Lazari, Skaltsa, et al., 2000	Brophy, Goldsack, et al., 1999	Brophy, Goldsack, et al., 1999, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	BP-20	BP-20	Carbowax 20M	SP-1000
Column length (m)	60.	50.	50.	25.	85.
Carrier gas	He	He	He	H2	He
Substrate
Column diameter (mm)	0.25	0.22	0.22	0.25	0.5
Phase thickness (μm)		0.25	0.25	0.3
T_start (C)	32.	60.	60.	50.	60.
T_end (C)	220.	230.	220.	200.	225.
Heat rate (K/min)	2.	2.	2.	3.	3.
Initial hold (min)	1.			1.
Final hold (min)	40.	35.	20.	20.
I	1985.	1974.	1979.	1968.	1983.
Reference	Christensen, Jakobsen, et al., 1999	Lota, Serra, et al., 1999	Mazzoni, Tomi, et al., 1999	Bicchi, Rubiolo, et al., 1998	Brophy, Forster, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	Carbowax 20M	DB-Wax	SP-1000
Column length (m)	60.	60.	25.	60.	85.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.32	0.32	0.25	0.32	0.5
Phase thickness (μm)			0.3
T_start (C)	65.	35.	50.	65.	65.
T_end (C)	225.	220.	200.	225.	225.
Heat rate (K/min)	3.	3.	3.	3.	3.
Initial hold (min)			1.
Final hold (min)			20.
I	1983.	1983.	1965.	1983.	1983.
Reference	Brophy, Goldsack, et al., 1998	Brophy, Goldsack, et al., 1998, 2	Bicchi, Fresia, et al., 1997	Brophy, Goldsack, et al., 1997	Brophy, Goldsack, et al., 1997, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	BP-20	DB-Wax	DB-Wax	Carbowax 20M
Column length (m)	50.	50.	25.	60.	50.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.22	0.22	0.25	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.2
T_start (C)	60.	60.	50.	50.	30.
T_end (C)	230.	230.	240.	180.	170.
Heat rate (K/min)	2.	2.	4.	2.5	4.
Initial hold (min)			3.	5.	2.
Final hold (min)	35.	35.			20.
I	1974.	1974.	1961.	2005.	1981.
Reference	Mariotti, Costa, et al., 1997	Mariotti, Tomi, et al., 1997	Möllenbeck, König, et al., 1997	Stashenko, Prada, et al., 1996	Píry, Príbela, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-20M	DB-Wax	Carbowax 20M	Carbowax 20M	Carbowax 20M
Column length (m)	50.	30.	60.	60.	60.
Carrier gas	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.32	0.32
Phase thickness (μm)		0.5		0.25	0.25
T_start (C)	60.	40.	50.	40.	40.
T_end (C)	190.	220.	225.	230.	230.
Heat rate (K/min)	3.	3.	1.5
Initial hold (min)
Final hold (min)			80.
I	1962.	1975.	1993.	1971.	1983.
Reference	Chung, Eiserich, et al., 1993	Le Quere and Latrasse, 1990	Chen and Ho, 1988	Peppard and Ramus, 1988	Peppard and Ramus, 1988
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	Carbowax 20M	Carbowax 20M
Column length (m)	60.	60.
Carrier gas
Substrate
Column diameter (mm)	0.32	0.32
Phase thickness (μm)	0.25	0.25
T_start (C)	40.	40.
T_end (C)	230.	230.
Heat rate (K/min)
Initial hold (min)
Final hold (min)
I	1984.	1985.
Reference	Peppard and Ramus, 1988	Peppard and Ramus, 1988
Comment	MSDC-RI	MSDC-RI

References

Go To: Top, Van Den Dool and Kratz RI, polar column, temperature ramp, Notes

Bendahou, Muselli, et al., 2008
Bendahou, M.; Muselli, A.; Grignon-Dubois, M.; Benyoucef, M.; Desjobert, J.-M.; Bernardini, A.-F.; Costa, J., Antimicrobial activity and chemical composition of Origanum glandulosum Desf. essential oil and extract obtained by microwave extraction: Comparison with hydrodistillation, Food Chem., 2008, 106, 1, 132-139, https://doi.org/10.1016/j.foodchem.2007.05.050 . [all data]

Boti, Koukoua, et al., 2007
Boti, J.B.; Koukoua, G.; N'Guessan, T.Y.; Casanova, J., Chemical variability of Conyza sumatrensis and Microglossa pyrifolia from Côte d'Ivoire, Flavour Fragr. J., 2007, 22, 1, 27-31, https://doi.org/10.1002/ffj.1743 . [all data]

Castilho, Liu, et al., 2007
Castilho, P.; Liu, K.; Rodrigues, A.I.; Feio, S.; Tomi, F.; Casanova, J., Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira, Flavour Fragr. J., 2007, 22, 2, 139-144, https://doi.org/10.1002/ffj.1771 . [all data]

Duquesnoy, Castola, et al., 2007
Duquesnoy, E.; Castola, V.; Casanova, J., Composition and chemical variability of the twig oil of Abies alba Miller from Corsica, Flavour Fragr. J., 2007, 22, 4, 293-299, https://doi.org/10.1002/ffj.1796 . [all data]

Kundakovic, Fokialakis, et al., 2007
Kundakovic, T.; Fokialakis, N.; Kovacevic, N.; Chinou, I., Essential oil composition of Achillea lingulata and A. umbellata, Flavour Fragr. J., 2007, 22, 3, 184-187, https://doi.org/10.1002/ffj.1778 . [all data]

Lesueur, de Rocca Serra, et al., 2007
Lesueur, D.; de Rocca Serra, D.; Bighelli, A.; Hoi, T.M.; Ban, N.K.; Thai, T.H.; Casanova, J., Chemical composition and antibacterial activity of the essential oil of Michelia foveolata Merryll ex Dandy from Vietnam, Flavour Fragr. J., 2007, 22, 4, 317-321, https://doi.org/10.1002/ffj.1799 . [all data]

Muselli, Rossi, et al., 2007
Muselli, A.; Rossi, P.-G.; Desjobert, J.-M.; Bernardini, A.-F.; Berti, L.; Costa, J., Chemical composition and antibacterial activity of Otanthus maritimus (L.) Hoffmanns. Link essential oils from Corsica, Flavour Fragr. J., 2007, 22, 3, 217-223, https://doi.org/10.1002/ffj.1787 . [all data]

Paolini J., Costa J., et al., 2007
Paolini J.; Costa J.; Bernardini A.F., Analysis of the essential oil from the roots of Eupatorium cannabinum subsp corsicum (L.) by GC, GC-MS and C-13-NMR, Phytochem. Anal., 2007, 18, 3, 235-244, https://doi.org/10.1002/pca.977 . [all data]

Paolini, Muselli, et al., 2007
Paolini, J.; Muselli, A.; Bernardini, A.-F.; Bighelli, A.; Casanova, J.; Costa, J., Thymol derivatives from essential oil of Doronicum corsicum L., Flavour Fragr. J., 2007, 22, 6, 479-487, https://doi.org/10.1002/ffj.1824 . [all data]

Blanc, Bradesi, et al., 2006
Blanc, M.-C.; Bradesi, P.; Goncalves, M.J.; Salgueiro, L.; Casanova, J., Essential oil of Dittrichia viscosa ssp. viscosa: analysis by ¹³C-NMR and antimicrobial activity, Flavour Fragr. J., 2006, 21, 2, 324-332, https://doi.org/10.1002/ffj.1605 . [all data]

Boti, Bighelli, et al., 2006
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Bousmaha, Boti, et al., 2006
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Notes

Go To: Top, Van Den Dool and Kratz RI, 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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