trans-4,5-Epoxy-(E)-2-decenal

Formula: C₁₀H₁₆O₂
Molecular weight: 168.2328
IUPAC Standard InChI: InChI=1S/C10H16O2/c1-2-3-4-6-9-10(12-9)7-5-8-11/h5,7-10H,2-4,6H2,1H3/b7-5+/t9-,10+/m0/s1
IUPAC Standard InChIKey: HIOMEXREAUSUBP-IUUOVRRDSA-N
CAS Registry Number: 134454-31-2
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:
- 4,5-epoxydec-2-enal
Other names: 4,5-epoxy-(E)-2-decenal; (E)-4,5-Epoxy-(E)-2-decenal; trans-4,5-Epoxy-2(E)-decenal; (E)-2-Decenal, 4,5-epoxy; tr-4,5-Epoxy-(E)-dec-2-enal; trans-4,5-epoxy-(E)-dec-2-enal; (E)-4,5-epoxydec-2-enal; trans-4,5-epoxy-(E)-2-decanal; trans-(E)-2-Decenal, 4,5-epoxy; tr-4,5-Epoxy-(E)-2-decenal; trans-4,5-epoxy-(E)-2-decenale; 4,5-epoxy-(E)-dec-2-enal; 2-Decenal, (E)-, 4,5-(E)-epoxy-
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Van Den Dool and Kratz RI, polar column, custom temperature program

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	FFAP	FFAP	DB-Wax	FFAP	FFAP
Column length (m)	30.	30.		30.	30.
Carrier gas				He	He
Substrate
Column diameter (mm)	0.32	0.32		0.25	0.32
Phase thickness (μm)	0.25	0.25		0.25	0.25
Program	40C(2min) => 6C/min => 150C => 20C/min => 230C	40C(2min) => 6C/min => 150C => 20C/min => 230C	not specified	40C(1min) => 40C/min => 50C(2min) => 6C/min => 240C	35C (2min) => 60C/min => 50C (2min) => 6C/min => 240C (10min)
I	1986.	2006.	2006.	2000.	2006.
Reference	Schuh and Schieberle, 2006	Schuh and Schieberle, 2006	Elston, Lin, et al., 2005	Jezussek, Juliano, et al., 2002	Kirchhoff and Schieberle, 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	FFAP	FFAP	FFAP	DB-FFAP	DB-FFAP
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He
Substrate
Column diameter (mm)	0.32	0.32	0.32	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	35C (2min) => 60C/min => 50C (2min) => 6C/min => 240C (10min)	35C(2min) => 40C/min => 60C(2min) => 6C/min => 180C => 10C/min=230C(10min)	40C(2min) => 40C/min => 60C(2min) => 6C/min => 240C(10min)	40C(2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 240C(5min)	40C(2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 240C (5min)
I	2006.	2006.	2006.	2018.	1979.
Reference	Kirchhoff and Schieberle, 2002	Buettner and Schieberle, 2001	Kirchhoff and Schieberle, 2001	Munk, Johansen, et al., 2001	Munk, Munch, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-FFAP	FFAP	FFAP	FFAP	FFAP
Column length (m)	30.	25.	30.	30.	30.
Carrier gas		He	He	He	He
Substrate
Column diameter (mm)	0.32	0.32	0.25	0.32	0.32
Phase thickness (μm)	0.25		0.25	0.25	0.25
Program	40C(2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 240C (5min)	35C (2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 240C	35C(2min) => 40C/min => 60C => 6C/min => 180C 20C/min => 240C(10min)	35C (2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 230C (10min)	35C (2min) => 40C/min => 60C => 4C/min => 230C (10min)
I	1978.	2007.	2025.	2000.	1995.
Reference	Munk, Munch, et al., 2000	Steinhaus and Schieberle, 2000	Zimmermann and Schieberle, 2000	Buettner and Schieberle, 1999	Derail, Hofmann, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	FFAP	DB-Wax	FFAP	DB-FFAP	FFAP
Column length (m)	30.	30.	30.	30.	25.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.32	0.32	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.5
Program	35C (2min) => 40C/min => 60C => 4C/min => 230C (10min)	20C(1min) => 70C/min => 60C => 6C/min => 180C => 10C/min => 240C(15min)	20C(2min) => 40C/min => 50C => 4C/min => 150C => 10C/min => 240C(15min)	40C(2min) => 40C/min => 60C(2min) => 6C/min => 230C(10min)	35C (2min) => 40C/min => 60C => 6C/min => 230C (10min)
I	1995.	1993.	2010.	2011.	2011.
Reference	Derail, Hofmann, et al., 1999	Lin J.M., Fay L.B., et al., 1999	Lin J.M., Fay L.B., et al., 1999	Mutti and Grosch, 1999	Fickert and Schieberle, 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	FFAP
Column length (m)	30.
Carrier gas	He
Substrate
Column diameter (mm)	0.32
Phase thickness (μm)	0.25
Program	35C(2min) => 40C/min => 60C(2min) => 6C/min => 180C => 10C/min => 230C(10 min)
I	2000.
Reference	Hinterholzer, Lemos, et al., 1998
Comment	MSDC-RI

References

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

Schuh and Schieberle, 2006
Schuh, C.; Schieberle, P., Characterization of the Key Aroma Compounds in the Beverage Prepared from Darjeeling Black Tea: Quantitative Differences between Tea Leaves and Infusion, J. Agric. Food Chem., 2006, 54, 3, 916-924, https://doi.org/10.1021/jf052495n . [all data]

Elston, Lin, et al., 2005
Elston, A.; Lin, J.; Rouseff, R., Determination of the role of valencene in orange oil as a direct contributor to aroma quality, Flavour Fragr. J., 2005, 20, 4, 381-386, https://doi.org/10.1002/ffj.1578 . [all data]

Jezussek, Juliano, et al., 2002
Jezussek, M.; Juliano, B.O.; Schieberle, P., Comparison of key aroma compounds in cooked brown rice varieties based on aroma extract dilution analysis, J. Agric. Food Chem., 2002, 50, 5, 1101-1105, https://doi.org/10.1021/jf0108720 . [all data]

Kirchhoff and Schieberle, 2002
Kirchhoff, E.; Schieberle, P., Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays, J. Agric. Food Chem., 2002, 50, 19, 5378-5385, https://doi.org/10.1021/jf020236h . [all data]

Buettner and Schieberle, 2001
Buettner, A.; Schieberle, P., Aroma properties of a homologous series of 2,3-epoxyalkanals and trans-4,5-epoxyalk-2-enals, J. Agric. Food Chem., 2001, 49, 8, 3881-3884, https://doi.org/10.1021/jf0104329 . [all data]

Kirchhoff and Schieberle, 2001
Kirchhoff, E.; Schieberle, P., Determination of key aroma compounds in the crumb of a three-stage sourdough rye bread by stable isotope dilution assays and sensory studies, J. Agric. Food Chem., 2001, 49, 9, 4304-4311, https://doi.org/10.1021/jf010376b . [all data]

Munk, Johansen, et al., 2001
Munk, S.; Johansen, C.; Stahnke, L.H.; Adler-Nissen, J., Microbial survival and odor in laundry, Journal of Surfactants and Detergents, 2001, 4, 4, 385-394, https://doi.org/10.1007/s11743-001-0192-2 . [all data]

Munk, Munch, et al., 2000
Munk, S.; Munch, P.; Stahnke, L.; Adler-Nissen., J.; Schieberle, P., Primary odorants of laundry soiled with sweat/sebum: influence of lipase on the odor profile, Journal of Surfactants and Detergents, 2000, 3, 4, 505-515, https://doi.org/10.1007/s11743-000-0150-z . [all data]

Steinhaus and Schieberle, 2000
Steinhaus, M.; Schieberle, P., Comparison of the most odor-active compounds in fresh and dried hop cones (Humulus lupulus L. variety Spalter Select) based on GC-olfactometry and odor dilution techniques, J. Agric. Food Chem., 2000, 48, 5, 1776-1783, https://doi.org/10.1021/jf990514l . [all data]

Zimmermann and Schieberle, 2000
Zimmermann, M.; Schieberle, P., Important odorants of sweet bell pepper powder (Capsicum annuum cv. annuum): differences between samples of Hungarian and Morrocan origin, Eur. Food Res. Technol., 2000, 211, 3, 175-180, https://doi.org/10.1007/s002170050019 . [all data]

Buettner and Schieberle, 1999
Buettner, A.; Schieberle, P., Characterization of the most odor-active volatiles in fresh, hand squeezed juice of grapefruit (Citrus paradise Macfayden), J. Agric. Food Chem., 1999, 47, 12, 5189-5193, https://doi.org/10.1021/jf990071l . [all data]

Derail, Hofmann, et al., 1999
Derail, C.; Hofmann, T.; Schieberle, P., Differences in key odorants of handmade juice of yellow-flesh peaches (Prunus persica L.) induced by the workup procedure, J. Agric. Food Chem., 1999, 47, 11, 4742-4745, https://doi.org/10.1021/jf990459g . [all data]

Lin J.M., Fay L.B., et al., 1999
Lin J.M.; Fay L.B.; Welti D.H.; Blank I., Synthesis of trans-4,5-epoxy-(E)-2-decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization, Lipids, 1999, 34, 10, 1117-1126, https://doi.org/10.1007/s11745-999-0463-8 . [all data]

Mutti and Grosch, 1999
Mutti, B.; Grosch, W., Potent odorants of boiled potatoes, Nahrung, 1999, 43, 5, 302-306, https://doi.org/10.1002/(SICI)1521-3803(19991001)43:5<302::AID-FOOD302>3.0.CO;2-8 . [all data]

Fickert and Schieberle, 1998
Fickert, B.; Schieberle, P., Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses, Nahrung, 1998, 42, 6, 371-375, https://doi.org/10.1002/(SICI)1521-3803(199812)42:06<371::AID-FOOD371>3.0.CO;2-V . [all data]

Hinterholzer, Lemos, et al., 1998
Hinterholzer, A.; Lemos, T.; Schieberle, P., Identification of the key odorants in raw French beans and changes during cooking, Z. Lebensm. Unters. Forsch. A, 1998, 207, 3, 219-222, https://doi.org/10.1007/s002170050322 . [all data]

Notes

Go To: Top, Van Den Dool and Kratz RI, polar column, custom temperature program, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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