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

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 was permitted as a food flavouring in the EU until it was prohibited on 11 July 2017.[4]

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
UNII
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H319, H336 EUH066
P210, P261, P264, P280, P303+361+353, P304+340, P305+351+338, P312, P337+313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[5] The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.[6] It is also an important part of the smell of raw and cooked mutton.[7]

Humans are more sensitive to the smell of trans-4,5-Epoxy-(E)-2-decenal than mice.[8]

References
  1. "Odor that smells like blood: Single component powerful trigger for large carnivores". Physorg. 11 November 2014. Retrieved 11 November 2014.
  2. 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. PMID 11521974.
  3. 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. PMID 10580339.
  4. "COMMISSION REGULATION (EU) 2017/1250 of 11 July 2017 amending Annex I to Regulation (EC) No 1334/2008 of the European Parliament and of the Council as regards removal from the Union list of the flavouring substance 4,5-epoxydec-2(trans)-enal". Official Journal of the European Union. 11 July 2017.
  5. 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.
  6. 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.
  7. Rota, Valerie; Peter Schieberle (2005). "Changes in Key Odorants of Sheep Meat Induced by Cooking". Food Lipids. ACS Symposium Series. 920. pp. 73–83. doi:10.1021/bk-2005-0920.ch006. ISBN 0-8412-3896-0. ISSN 1947-5918.
  8. McGann, John P. (11 May 2017). "Poor human olfaction is a 19th-century myth". Science. 356 (6338): eaam7263. doi:10.1126/science.aam7263.
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