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:
- 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-
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | SE-54 | SE-54 | DB-5 | DB-5 | DB-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 25. |
| 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 | 40C(2min) => 6C/min => 150C => 20C/min => 230C | 40C(2min) => 6C/min => 150C => 20C/min => 230C | 20C => 70C/min => 50C => 4C/min => 180C => 10C/min => 240C(10min) | 40C(1min) => 40C/min => 50C(2min) => 6C/min => 240C | 35C (2min) => 40C/min => 50C (2min) => 4C/min => 240C (10min) |
| I | 1374. | 1379. | 1379. | 1380. | 1381. |
| Reference | Schuh and Schieberle, 2006 | Schuh and Schieberle, 2006 | Lin and Blank, 2003 | 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 | DB-5 | DB-5 | DB-5 | DB-5 | DB-5 |
| Column length (m) | 25. | 30. | 30. | 30. | 25. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.25 | 0.32 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Program | 35C (2min) => 40C/min => 50C (2min) => 4C/min => 240C (10min) | 35 C (2 min) 40 C/min -> 50 C (2 min) 4 C/min -> 230 C | 20C => 70C/min => 50C => 4C/min => 180C => 10C/min => 240C(10min) | 35C(2min) => 40C/min => 50C(2min) => 6C/min => 180C => 10C/min=230C(10min) | 35C(2min) => 40C/min => 50C(2min) => 4C/min => 240C(10min) |
| I | 1381. | 1378. | 1381. | 1381. | 1381. |
| Reference | Kirchhoff and Schieberle, 2002 | Zehentbauer and Reineccius, 2002 | Blank, Lin, et al., 2001 | Buettner and Schieberle, 2001 | Kirchhoff and Schieberle, 2001 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | DB-5 | CP Sil 8 CB | SE-54 | SE-54 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Program | 40C(2min) => 40C/min => 50C (1min) => 6C/min => 180C => 10C/min => 240C (5min) | 40C(2min) => 40C/min => 50C (1min) => 6C/min => 180C => 10C/min => 240C (5min) | 35C (2min) => 40C/min => 50C (2min) => 6C/min => 180C => 10C/min => 240C | 35C(2min) => 40C/min => 60C => 6C/min => 180C 20C/min => 240C(10min) | 35C (2min) => 40C/min => 50C (2min) => 6C/min => 180C => 10C/min => 230C (10min) |
| I | 1380. | 1380. | 1375. | 1382. | 1380. |
| Reference | Munk, Munch, et al., 2000 | Munk, Munch, et al., 2000 | Steinhaus and Schieberle, 2000 | Zimmermann and Schieberle, 2000 | Buettner and Schieberle, 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | SE-54 | DB-5 | SE-54 | SE-54 | SE-54 |
| Column length (m) | 30. | 30. | 60. | 25. | 30. |
| 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 | 0.5 | 0.25 |
| Program | 35C (2min) => 40C/min => 50C => 4C/min => 230C (10min) | 20C => 70C/min => 50C => 4C/min => 180C => 10C/min => 240C(10min) | 40C(2min) => 5C/min => 70C(2min) => 6C/min => 250C(10min) | 35C (2min) => 4C/min => 150C => 10C/min => 240C | 35C(2min) => 40C/min => 50C(2min) => 6C/min => 180C => 10C/min => 230C(10 min) |
| I | 1362. | 1378. | 1384. | 1380. | 1380. |
| Reference | Derail, Hofmann, et al., 1999 | Lin J.M., Fay L.B., et al., 1999 | Mutti and Grosch, 1999 | Fickert and Schieberle, 1998 | Hinterholzer, Lemos, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|
| Active phase | SE-54 | DB-5MS | DB-5 | SE-54 |
| Column length (m) | 30. | 30. | 30. | |
| Carrier gas | He | He | ||
| Substrate | ||||
| Column diameter (mm) | 0.32 | 0.25 | 0.25 | |
| Phase thickness (μm) | 0.25 | 0.5 | 1. | |
| Program | 35C(2min) => 40C/min => 50C(2min) => 6C/min => 180C => 10C/min => 230C(10min) | 40C(2min) => 6C/min => 180C => 10C/min => 250C | 35C (2min) => 40C/min => 50C (1min) => 6C/min => 250C (10min) | 35C (2min) => 40C/min => 50C (1min) => 6C/min => 250C (10min) |
| I | 1380. | 1383. | 1384. | 1382. |
| Reference | Hinterholzer and Schieberie, 1998 | Milo and Reineccius, 1997 | Triqui and Reineccius, 1995 | Triqui and Reineccius, 1995 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Van Den Dool and Kratz RI, non-polar column, custom temperature program, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Lin and Blank, 2003
Lin, J.; Blank, I.,
Odorans generated by thermally induced degradation of phospholipids,
J. Agric. Food Chem., 2003, 51, 15, 4364-4369, https://doi.org/10.1021/jf034300m
. [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]
Zehentbauer and Reineccius, 2002
Zehentbauer, G.; Reineccius, G.A.,
Determination of key aroma components of cheddar cheese using dynamic headspace dilution assay,
Flavour Fragr. J., 2002, 17, 4, 300-305, https://doi.org/10.1002/ffj.1102
. [all data]
Blank, Lin, et al., 2001
Blank, I.; Lin, J.; Arce Vera, F.; Welti, D.H.; Fay, L.B.,
Identification of potent odorants formed by autoxidation of arachidonic acid: structure elucidation and synthesis of (E,Z,Z)-2,4,7-tridecatrienal,
J. Agric. Food Chem., 2001, 49, 6, 2959-2965, https://doi.org/10.1021/jf010160+
. [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, 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]
Hinterholzer and Schieberie, 1998
Hinterholzer, A.; Schieberie, P.,
Identification of the most odour-active volatiles in fresh, hand-extracted juice of valencia late oranges by odour dilution techniques,
Flavour Fragr. J., 1998, 13, 1, 49-55, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<49::AID-FFJ691>3.0.CO;2-S
. [all data]
Milo and Reineccius, 1997
Milo, C.; Reineccius, G.A.,
Identification and quantification of potent odorants in regular-fat and low-fat mild cheddar cheese,
J. Agric. Food Chem., 1997, 45, 9, 3590-3594, https://doi.org/10.1021/jf970152m
. [all data]
Triqui and Reineccius, 1995
Triqui, R.; Reineccius, G.A.,
Changes in flavor profiles with ripening of anchovy (Engraulis encrasicholus),
J. Agric. Food Chem., 1995, 43, 7, 1883-1889, https://doi.org/10.1021/jf00055a024
. [all data]
Notes
Go To: Top, Van Den Dool and Kratz RI, non-polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.