2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-, (E)-

Formula: C₁₃H₁₈O
Molecular weight: 190.2814
IUPAC Standard InChI: InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
IUPAC Standard InChIKey: POIARNZEYGURDG-FNORWQNLSA-N
CAS Registry Number: 23726-93-4
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.
Species with the same structure:
Stereoisomers:
Other names: β-Damascenone; trans-β-Damascenone; Damascenone; Damascenone, trans-; 2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene; (2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one; β-(E)-Damascenone; 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, trans-; (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one; (E)-β-Damascenone; trans-Damascenone; 36649-63-5; 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one (β-damascenone); (2 E)-1-(2,6,6-trimethylcyclohexane-1,3-dien-1-yl)but-2-en-1-one (β-damascenone); (E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- 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	Optima-5	PTE-5	HP-5 MS	SE-54	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	Helium	Helium		Nitrogen
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	80.	70.	0.	40.
T_end (C)	246.	300.	200.	200.	230.
Heat rate (K/min)	3.	7.	3.	6.	2.
Initial hold (min)	1.	3.	2.	2.
Final hold (min)		5.	18.
I	1384.	1385.	1388.	1389.	1385.
Reference	Al-Qudah, Muhaidat, et al., 2012	Fabri, Coimbra, et al., 2012	Jerkovic, Hegic, et al., 2010	Laselan, Buettner, et al., 2009	Scrivanti, Anton, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5 MS	DB-1	HP-5	SLB-5MS	HP-5
Column length (m)	30.	30.	30.	10.	30.
Carrier gas	Helium	He	Helium	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.18	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.18
T_start (C)	50.	30.	100.	40.	70.
T_end (C)	280.	210.	240.	295.	240.
Heat rate (K/min)	4.	5.	5.	10.	5.
Initial hold (min)			2.	1.5
Final hold (min)			5.
I	1386.	1373.	1380.	1384.	1389.
Reference	Zhao, Zeng, et al., 2009	Kumazawa, Itobe, et al., 2008	Lago, Romoff, et al., 2008	Risticevic, Carasek, et al., 2008	Asekun, Olusegun, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	HP-5MS	DB-5	ZB-5	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He		Helium
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)	60.	60.	40.	60.	60.
T_end (C)	280.	250.	240.	220.	220.
Heat rate (K/min)	3.	2.	3.	4.	4.
Initial hold (min)		8.		5.
Final hold (min)		15.		20.
I	1367.	1379.	1378.	1378.	1386.
Reference	Basta, Tzakou, et al., 2007	Ferhat, Tigrine-Kordjani, et al., 2007	Machado, Bastos, et al., 2007	Mohottalage, Tabacchi, et al., 2007	Morteza-Semnani, Saeedi, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	RTX-5	DB-5	DB-1	HP-101	HP-5
Column length (m)	10.	60.	60.	25.	30.
Carrier gas	He	He		He	Helium
Substrate
Column diameter (mm)	0.18	0.32	0.25	0.2	0.32
Phase thickness (μm)	0.2		0.25	0.2	0.25
T_start (C)	40.	60.	60.	70.	40.
T_end (C)	275.	250.	250.	200.	240.
Heat rate (K/min)	50.	4.	5.	3.	4.
Initial hold (min)	0.5	5.		2.
Final hold (min)	0.5		10.	15.	5.
I	1394.	1375.	1368.	1364.	1373.
Reference	Setkova, Risticevic, et al., 2007	Fadel, Mageed, et al., 2006	Hadian, Sonboli, et al., 2006	Mastelic, Jerkovic, et al., 2006	Miyazawa and Kawata, 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	HP-5 MS	HP-5MS
Column length (m)	30.	30.	13.5	30.	30.
Carrier gas	He	He	He	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	60.	40.	35.	60.	60.
T_end (C)	220.	260.	225.	250.	280.
Heat rate (K/min)	4.	2.	6.	2.	3.
Initial hold (min)		5.	3.	8.
Final hold (min)		20.		15.
I	1387.	1382.	1383.	1379.	1359.
Reference	Morteza-Semnani, Akbarzadeh, et al., 2006	Senatore, Landolfi, et al., 2006	de Souza, Vásquez, et al., 2006	Tigrine-Kordiani, Meklati, et al., 2006	Tzakou, Said, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	HP-5	HP-5	HP-5MS	HP-1
Column length (m)	30.	30.	30.	30.	50.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.5
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	250.	260.	260.	280.	250.
Heat rate (K/min)	10.	5.	5.	3.	2.
Initial hold (min)	2.	2.	2.
Final hold (min)	10.	14.	14.		60.
I	1394.	1380.	1385.	1360.	1361.
Reference	Wang, Yang, et al., 2006	Yayli, Gülec, et al., 2006	Yayli, Gülec, et al., 2006	Basta, Tzakou, et al., 2005	Bendimerad and Bendiab, 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-5	HP-5	DB-5	DB-5	DB-1
Column length (m)	30.	60.	30.	30.	50.
Carrier gas	He	He	He	He	N2
Substrate
Column diameter (mm)	0.53	0.32	0.25	0.25	0.25
Phase thickness (μm)		0.25	0.25	0.25	0.25
T_start (C)	100.	30.	60.	60.	95.
T_end (C)	250.	260.	220.	220.	240.
Heat rate (K/min)	5.	2.	4.	4.	4.
Initial hold (min)		2.	5.	4.
Final hold (min)		28.
I	1402.	1390.9	1385.	1387.	1371.
Reference	Kilic, Kollmannsberger, et al., 2005	Leffingwell and Alford, 2005	Morteza-Semnani, Akbarzadeh, et al., 2005	Morteza-Semnani and Saeedi, 2005	Pala-Paul, Perez-Alonso, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5	HP-5MS	HP-5MS	DB-1
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	60.	60.	60.	50.
T_end (C)	260.	260.	280.	280.	265.
Heat rate (K/min)	2.	5.	3.	3.	2.5
Initial hold (min)	5.	2.			1.
Final hold (min)	20.	13.			20.
I	1382.	1385.	1383.	1381.	1351.
Reference	Senatore, Apostolides Arnold, et al., 2005	Yayli, Yasar, et al., 2005	Malencic, Couladis, et al., 2004	Mimica-Dukic, Bozin, et al., 2004	Sarkhail, Amin, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-54	SPB-5	OV-101	HP-1	DB-5
Column length (m)	30.	30.	12.	50.	30.
Carrier gas	N2	He		He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.2	0.25
Phase thickness (μm)	0.25	0.25	0.32	0.5	0.25
T_start (C)	40.	40.	35.	60.	60.
T_end (C)	200.	220.	225.	220.	240.
Heat rate (K/min)	5.	5.	6.	2.	3.
Initial hold (min)	4.	1.	3.
Final hold (min)	10.	20.		40.
I	1380.	1386.	1361.	1358.	1382.
Reference	Tura, Prenzler, et al., 2004	Ledauphin, Guichard, et al., 2003	Murakami, Goldstein, et al., 2003	Valette, Fernandez, et al., 2003	Flamini, Ertugrul, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	Optima-1	DB-5MS
Column length (m)	30.	30.	30.	25.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.20	0.53
Phase thickness (μm)	0.25	0.25	0.25	0.25	1.5
T_start (C)	60.	40.	40.	50.	40.
T_end (C)	240.	290.	230.	250.	225.
Heat rate (K/min)	3.	7.	6.	3.	6.
Initial hold (min)			2.	3.	5.
Final hold (min)			5.		30.
I	1381.	1390.	1395.	1363.	1396.
Reference	Kobaisy, Tellez, et al., 2002	Lin, Rouseff, et al., 2002	Sanz, Czerny, et al., 2002	Brun, Bessière, et al., 2001	Cadwallader and Heo, 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	DB-5MS	DB-5MS	DB-5	DB-5
Column length (m)	30.	60.	30.	30.	30.
Carrier gas	N2	He	He	H2	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.5	0.25
T_start (C)	60.	40.	40.	60.	60.
T_end (C)	220.	200.	195.	245.	240.
Heat rate (K/min)	5.	2.	5.	3.	3.
Initial hold (min)	10.	5.	5.	3.
Final hold (min)		30.	40.	20.
I	1381.	1384.	1391.	1395.	1383.
Reference	Campeol, Flamini, et al., 2001	Lee, Suriyaphan, et al., 2001	Suriyaphan, Drake, et al., 2001	Kotseridis and Baumes, 2000	Tellez, Dayan, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-5	HP-1	OV-101	HP-1	HP-1
Column length (m)	50.	25.	10.	25.	25.
Carrier gas	He		Helium
Substrate
Column diameter (mm)	0.32	0.20	0.25	0.32	0.32
Phase thickness (μm)	1.		0.52
T_start (C)	40.	35.	35.	35.	35.
T_end (C)	190.	250.	225.	250.	250.
Heat rate (K/min)	2.	4.	6.	4.	4.
Initial hold (min)	5.		3.
Final hold (min)
I	1393.	1356.	1349.	1356.	1356.
Reference	Lopez, Ferreira, et al., 1999	Ong and Acree, 1999	Deibler, Acree, et al., 1998	Ong and Acree, 1998	Ong, Acree, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	OV-101	OV-101	OV-101	OV-101	DB-5
Column length (m)	12.	12.	15.	15.	30.
Carrier gas			He	He	H2
Substrate
Column diameter (mm)	0.32	0.32	0.32	0.32	0.32
Phase thickness (μm)					1.
T_start (C)	35.	35.	35.	35.	40.
T_end (C)	225.	225.	250.	250.	220.
Heat rate (K/min)	6.	6.	6.	6.	3.
Initial hold (min)	3.	3.	3.	3.
Final hold (min)
I	1352.	1353.	1356.	1360.	1390.
Reference	Roberts and Acree, 1996	Roberts and Acree, 1996	Chisholm, Guiher, et al., 1995	Chisholm, Guiher, et al., 1995	Moio, Dekimpe, et al., 1993
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Packed	Capillary	Capillary	Capillary	Capillary
Active phase	SE-54	DB-1	DB-1	DB-1	HP-5
Column length (m)	3.	60.	60.	60.	50.
Carrier gas				He	H2
Substrate	Chromosorb G AW DMCS (100-120 mesh)
Column diameter (mm)		0.32		0.25	0.3
Phase thickness (μm)
T_start (C)	50.	50.	30.	30.	80.
T_end (C)	230.	230.	200.	200.	250.
Heat rate (K/min)	6.	4.	4.	4.	16.
Initial hold (min)	2.		25.	25.
Final hold (min)	10.	10.	30.	5.
I	1389.	1360.	1360.	1360.	1371.
Reference	Schieberle, 1991	Binder, Turner, et al., 1990	Buttery, Takeoka, et al., 1990	Buttery, Teranishi, et al., 1990	Spadone, Takeoka, et al., 1990
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	OV-101	OV-101	DB-5	DB-1
Column length (m)	50.	50.	50.	30.	50.
Carrier gas	H2	N2	N2	Hydrogen
Substrate
Column diameter (mm)	0.3	0.25	0.25	0.35	0.32
Phase thickness (μm)				1.0
T_start (C)	80.	80.	80.	45.	0.
T_end (C)	250.	200.	200.	220.	250.
Heat rate (K/min)	16.	2.	2.	2.	3.
Initial hold (min)
Final hold (min)
I	1397.	1360.	1367.	1396.	1360.
Reference	Spadone, Takeoka, et al., 1990	Yang and Sugisawa, 1990	Yang and Sugisawa, 1990	Georgilopoulos and Gallois, 1988	Habu, Flath, et al., 1985
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	DB-1
Column length (m)	50.
Carrier gas
Substrate
Column diameter (mm)	0.32
Phase thickness (μm)
T_start (C)	50.
T_end (C)	250.
Heat rate (K/min)	3.
Initial hold (min)
Final hold (min)
I	1360.
Reference	Habu, Flath, et al., 1985
Comment	MSDC-RI

References

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

Al-Qudah, Muhaidat, et al., 2012
Al-Qudah, M.A.; Muhaidat, R.; Trawenh, I.N.; Jaber, H.I.; Abu Zarga, M.H.; Abu Orabi, S.T., Volatile constituents of leaves and bulbs of Gynandriris Sisyrinchicum and their antimicrobial activities, Jordan J. Chem., 2012, 7, 3, 287-295. [all data]

Fabri, Coimbra, et al., 2012
Fabri, R.F.; Coimbra, E.; Almeida, A.C.; Siqueira, E.P.; Alves, T.M.A.; Zani, C.L.; Scio, E., Essential oil of Mitracarpus frigidus as a potent sourse of bioactive compounds, Annals of the Brazilian Academy of Sciences, 2012, 84, 4, 1073-1080, https://doi.org/10.1590/S0001-37652012000400021 . [all data]

Jerkovic, Hegic, et al., 2010
Jerkovic, I.; Hegic, G.; Marijanovic, Z.; Bubalo, D., Organic extractives from Mentha spp. honey and the bee-stomach: methyl syringate, vomifoliol, terpenediol I, hotrienol, and other compounds, Molecules, 2010, 15, 4, 2911-2924, https://doi.org/10.3390/molecules15042911 . [all data]

Laselan, Buettner, et al., 2009
Laselan, P.; Buettner, A.; Christlbauer, M., Investigation of the retronasal perseption of palm wine (Elaeis guineensis) aroma by application of sensory analysis and exhaled odorant measurement (EXOM), African J. of Food, Agriculture, Nutrition and development, 2009, 9, 2, 793-813. [all data]

Scrivanti, Anton, et al., 2009
Scrivanti, L.R.; Anton, A.M.; Zygadlo, J.A., Essential oil conposition of Bothriochloa Kuntze (Poaceae) from South America and their chemotaxonomy, Biochem. Systematics Ecol., 2009, 37, 3, 206-213, https://doi.org/10.1016/j.bse.2009.03.009 . [all data]

Zhao, Zeng, et al., 2009
Zhao, C.; Zeng, Y.; Wan, M.; Li, R.; Liang, Y.; Li, C.; Zeng, Z.; Chau, F.-T., Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods, J. Sep. Sci., 2009, 32, 4, 660-670, https://doi.org/10.1002/jssc.200800484 . [all data]

Kumazawa, Itobe, et al., 2008
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Risticevic, Carasek, et al., 2008
Risticevic, S.; Carasek, E.; Pawliszyn, J., Headspace solid-phase microextraction-gas chromatographic-time-of-flight mass spectrometric methodology for geographical origin verification of coffee, Anal. Chim. Acta, 2008, 617, 1-2, 72-84, https://doi.org/10.1016/j.aca.2008.04.009 . [all data]

Asekun, Olusegun, et al., 2007
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Basta, Tzakou, et al., 2007
Basta, A.; Tzakou, O.; Couladis, M.; Yannitsaros, A., Essential oil composition of Prasium majus L. from Greece, Flavour Fragr. J., 2007, 22, 5, 347-349, https://doi.org/10.1002/ffj.1802 . [all data]

Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F., Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device, Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5 . [all data]

Machado, Bastos, et al., 2007
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Mohottalage, Tabacchi, et al., 2007
Mohottalage, S.; Tabacchi, R.; Guerin, P.M., Components from Sri Lankan Piper betle L. leaf oil and their analogues showing toxicity against the housefly, Musca domestica, Flavour Fragr. J., 2007, 22, 2, 130-138, https://doi.org/10.1002/ffj.1770 . [all data]

Morteza-Semnani, Saeedi, et al., 2007
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Setkova, Risticevic, et al., 2007
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Fadel, H.H.M.; Mageed, M.A.A.; Lotfy, S.N., Quality and flavour stability of coffee substitute prepared by extrusion of wheat germ and chicory roots, Amino Acids, 2006, https://doi.org/10.1007/s007260200008 . [all data]

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Hadian, J.; Sonboli, A.; Ebrahimi, S.N.; Mirjalili, M.H., Essential oil composition of Nepeta satureioides from Iran, Chem. Nat. Compd. (Engl. Transl.), 2006, 42, 2, 175-177, https://doi.org/10.1007/s10600-006-0071-0 . [all data]

Mastelic, Jerkovic, et al., 2006
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Cadwallader and Heo, 2001
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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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