Trans-4,5-Epoxy-(E)-2-decenal: Difference between revisions
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'''''trans''-4,5-Epoxy-(''[[E-Z notation|E]]'')-2-decenal''' is an oxygenated α,β-unsaturated [[aldehyde]] found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.<ref>{{cite web|url=http://phys.org/news/2014-11-odor-blood-component-powerful-trigger.html|title=Odor that smells like blood: Single component powerful trigger for large carnivores|date=11 November 2014|publisher=Physorg|accessdate=11 November 2014}}</ref> Humans can smell it at a concentration of 1.5 pg/l in air,<ref name="Lin2001">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=2001|title=Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay|journal=Lipids|volume=36|issue=7|pages=749–756|issn=0024-4201|doi=10.1007/s11745-001-0781-x}}</ref> at 15 ng/L in water and 1.3μg/L in oil.<ref name="Lin1999">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=1999|title=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|journal=Lipids|volume=34|issue=10|pages=1117–1126|issn=0024-4201|doi=10.1007/s11745-999-0463-8}}</ref> It is permitted as a [[Flavor#Flavorants or flavorings|food flavouring]] in the [[European Union|EU]].{{citation needed}} |
'''''trans''-4,5-Epoxy-(''[[E-Z notation|E]]'')-2-decenal''' is an oxygenated α,β-unsaturated [[aldehyde]] found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.<ref>{{cite web|url=http://phys.org/news/2014-11-odor-blood-component-powerful-trigger.html|title=Odor that smells like blood: Single component powerful trigger for large carnivores|date=11 November 2014|publisher=Physorg|accessdate=11 November 2014}}</ref> Humans can smell it at a concentration of 1.5 pg/l in air,<ref name="Lin2001">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=2001|title=Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay|journal=Lipids|volume=36|issue=7|pages=749–756|issn=0024-4201|doi=10.1007/s11745-001-0781-x}}</ref> at 15 ng/L in water and 1.3μg/L in oil.<ref name="Lin1999">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=1999|title=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|journal=Lipids|volume=34|issue=10|pages=1117–1126|issn=0024-4201|doi=10.1007/s11745-999-0463-8}}</ref> It is permitted as a [[Flavor#Flavorants or flavorings|food flavouring]] in the [[European Union|EU]].{{citation needed|date=November 2015}} |
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It can be formed during baking fats that contain [[linoleic acid]]. 13-Hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.<ref name="Gassenmeier1994">{{cite journal|last=Gassenmeier|first=Klaus|author2=Peter Schieberle|year=1994|title=Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats|journal=Journal of the American Oil Chemists’ Society|volume=71|issue=12|pages=1315–1319|issn=0003-021X|doi=10.1007/BF02541347}}</ref> The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.<ref name="Konopka1991">{{cite journal|last=Konopka|first=Ute Christine|author2=Werner Grosch|year=1991|title=Potent odorants causing the warmed-over flavour in boiled beef|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=193|issue=2|pages=123–125|issn=0044-3026|doi=10.1007/BF01193360}}</ref> It is also an important part of the smell of raw and cooked [[mutton]].<ref name="Rota2005">{{cite journal|last=Rota|first=Valerie|author2=Peter Schieberle|year=2005|title=Changes in Key Odorants of Sheep Meat Induced by Cooking|volume=920|pages=73–83|issn=1947-5918|doi=10.1021/bk-2005-0920.ch006}}</ref> |
It can be formed during baking fats that contain [[linoleic acid]]. 13-Hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.<ref name="Gassenmeier1994">{{cite journal|last=Gassenmeier|first=Klaus|author2=Peter Schieberle|year=1994|title=Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats|journal=Journal of the American Oil Chemists’ Society|volume=71|issue=12|pages=1315–1319|issn=0003-021X|doi=10.1007/BF02541347}}</ref> The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.<ref name="Konopka1991">{{cite journal|last=Konopka|first=Ute Christine|author2=Werner Grosch|year=1991|title=Potent odorants causing the warmed-over flavour in boiled beef|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=193|issue=2|pages=123–125|issn=0044-3026|doi=10.1007/BF01193360}}</ref> It is also an important part of the smell of raw and cooked [[mutton]].<ref name="Rota2005">{{cite journal|last=Rota|first=Valerie|author2=Peter Schieberle|year=2005|title=Changes in Key Odorants of Sheep Meat Induced by Cooking|volume=920|pages=73–83|issn=1947-5918|doi=10.1021/bk-2005-0920.ch006}}</ref> |
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Revision as of 22:00, 15 November 2015
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| Names | |
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| Other names
3-[(2R,3R)-3-Pentyloxiranyl]-2E-propenal; Epoxy-2-decenal
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H16O2 | |
| Molar mass | 168.236 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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trans-4,5-Epoxy-(E)-2-decenal is an oxygenated α,β-unsaturated aldehyde found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.[1] Humans can smell it at a concentration of 1.5 pg/l in air,[2] at 15 ng/L in water and 1.3μg/L in oil.[3] It is permitted as a food flavouring in the EU.[citation needed]
It can be formed during baking fats that contain linoleic acid. 13-Hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.[4] The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.[5] It is also an important part of the smell of raw and cooked mutton.[6]
References
- ^ "Odor that smells like blood: Single component powerful trigger for large carnivores". Physorg. 11 November 2014. Retrieved 11 November 2014.
- ^ Lin, Jianming; Laurent B. Fay; Dieter H. Welti; Imre Blank (2001). "Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay". Lipids. 36 (7): 749–756. doi:10.1007/s11745-001-0781-x. ISSN 0024-4201.
- ^ Lin, Jianming; Laurent B. Fay; Dieter H. Welti; Imre Blank (1999). "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. 34 (10): 1117–1126. doi:10.1007/s11745-999-0463-8. ISSN 0024-4201.
- ^ Gassenmeier, Klaus; Peter Schieberle (1994). "Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats". Journal of the American Oil Chemists’ Society. 71 (12): 1315–1319. doi:10.1007/BF02541347. ISSN 0003-021X.
- ^ Konopka, Ute Christine; Werner Grosch (1991). "Potent odorants causing the warmed-over flavour in boiled beef". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 193 (2): 123–125. doi:10.1007/BF01193360. ISSN 0044-3026.
- ^ Rota, Valerie; Peter Schieberle (2005). "Changes in Key Odorants of Sheep Meat Induced by Cooking". 920: 73–83. doi:10.1021/bk-2005-0920.ch006. ISSN 1947-5918.
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