trans-4,5-Epoxy-(E)-2-decenal
Names | |
---|---|
Other names
3-[(2R,3R)-3-Pentyloxiranyl]-2E-propenal; Epoxy-2-decenal
| |
Identifiers | |
3D model (JSmol)
|
|
ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C10H16O2 | |
Molar mass | 168.236 g·mol−1 |
water | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
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.
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 (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.
{{cite journal}}
: Unknown parameter|coauthors=
ignored (|author=
suggested) (help) - ^ Lin, Jianming (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.
{{cite journal}}
: Unknown parameter|coauthors=
ignored (|author=
suggested) (help) - ^ Gassenmeier, Klaus (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.
{{cite journal}}
: Unknown parameter|coauthors=
ignored (|author=
suggested) (help) - ^ Konopka, Ute Christine (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.
{{cite journal}}
: Unknown parameter|coauthors=
ignored (|author=
suggested) (help) - ^ Rota, Valerie (2005). "Changes in Key Odorants of Sheep Meat Induced by Cooking". 920: 73–83. doi:10.1021/bk-2005-0920.ch006. ISSN 1947-5918.
{{cite journal}}
: Cite journal requires|journal=
(help); Unknown parameter|coauthors=
ignored (|author=
suggested) (help)