Trans-4,5-Epoxy-(E)-2-decenal explained

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] on the grounds of possible genotoxicity, as observed from rat livers.[5]

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.[6] The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.[7] It is also an important part of the smell of raw and cooked mutton.[8]

Humans are more sensitive to the smell of trans-4,5-Epoxy-(E)-2-decenal than mice.[9]

Notes and References

  1. Web site: Odor that smells like blood: Single component powerful trigger for large carnivores. 11 November 2014. Physorg. 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. 0024-4201. 10.1007/s11745-001-0781-x. 11521974. 3979031.
  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. 0024-4201. 10.1007/s11745-999-0463-8. 10580339. 4054911.
  4. Web site: 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. 11 July 2017. Official Journal of the European Union.
  5. EFSA CEF Panel . Scientific Opinion on Flavouring Group Evaluation 226 Revision 1 (FGE.226Rev1): consideration of genotoxicity data on one α,β-unsaturated aldehyde from chemical subgroup 1.1.1(b) of FGE.19 . EFSA Journal . 2017 . 15 . 5 . 4847–4871 . 10.2903/j.efsa.2017.4847 . 32625501 . 7010128 .
  6. 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. 0003-021X. 10.1007/BF02541347. 85079936.
  7. 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. 0044-3026. 10.1007/BF01193360. 83249703.
  8. Book: Rota, Valerie. Peter Schieberle. 2005. 920. 73–83. 1947-5918. 10.1021/bk-2005-0920.ch006. Changes in Key Odorants of Sheep Meat Induced by Cooking. Food Lipids. ACS Symposium Series. 0-8412-3896-0.
  9. McGann . John P. . Poor human olfaction is a 19th-century myth . Science . 11 May 2017 . 356 . 6338 . eaam7263 . 10.1126/science.aam7263. 28495701 . 5512720 . free .

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