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

Structural formula
	Structural formula without full details of the stereochemistry
General
Surname	trans -4,5-epoxy- ( E ) -2-decenal
other names	( E ) -3 - [(2 SR , 3 RS ) -3-pentyloxiran-2-yl] prop-2-enal; FEMA 4037 ;
Molecular formula	C 10 H 16 O 2
Brief description	Liquid with a characteristic smell of blood
External identifiers / databases
PubChem	5352429
Wikidata	Q19904086
properties
Molar mass	168.24 g mol −1
Physical state	liquid
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

trans -4,5-Epoxy- ( E ) -2-decenal is an oxidized α, β-unsaturated aldehyde that is found in the blood of mammals and gives it its characteristic metallic odor. Predators use the smell of the substance to find blood or prey. Humans can smell the substance up to a concentration of 1.5 pg / L in the air, up to 15 ng / L in water and 1.3μg / L in oil. Itwasapprovedas a flavoring substance in the EU until it was banned on July 11, 2017.

It can be made by baking fats containing linolenic acid . 13-Hydroperoxy-9,11-octadecadienonic acid and 9-hydroperoxy-10,12-octadecadienonic acid are intermediate stages. In cooked beef, the aldehyde forms if left in the refrigerator for too long and gives off a rancid odor when reheated. It also plays a role in raw and cooked mutton.

Individual evidence

↑ Entry on FEMA 4037 in the database of the Flavor and Extract Manufacturers Association of the United States .
↑ ^a ^b ^c Sara Nilsson, Johanna Sjöberg u. a .: Behavioral Responses to Mammalian Blood Odor and a Blood Odor Component in Four Species of Large Carnivores. In: PLoS ONE. 9, 2014, p. E112694, doi : 10.1371 / journal.pone.0112694 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of TRANS-4,5-EPOXYDEC-2-ENAL in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 31, 2017, is reproduced from a self-classification by the distributor .
↑ Jianming Lin: Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay . In: Lipids . 36, No. 7, 2001, pp. 749-756. doi : 10.1007 / s11745-001-0781-x .
↑ Jianming Lin: 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 . In: Lipids . 34, No. 10, 1999, pp. 1117-1126. doi : 10.1007 / s11745-999-0463-8 .
↑ 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 flavoring substance 4,5-epoxydec- 2 (trans) -enal . In: Official Journal of the European Union . 11th July 2017.
↑ Klaus Gassenmeier: Formation of the intense flavor compoundtrans-4,5-epoxy- (E) -2-decenal in thermally treated fats . In: Journal of the American Oil Chemists' Society . 71, No. 12, 1994, pp. 1315-1319. doi : 10.1007 / BF02541347 .
↑ Ute Christine Konopka: Potent odorants causing the warmed-over flavor in boiled beef . In: Journal of Food Study and Research . 193, No. 2, 1991, pp. 123-125. doi : 10.1007 / BF01193360 .
^ Valerie Rota: Changes in Key Odorants of Sheep Meat Induced by Cooking . In: ACS Symposium Series . 920, 2005, pp. 73-83. doi : 10.1021 / bk-2005-0920.ch006 .

[FEMA4037-1] Entry on FEMA 4037 in the database of the Flavor and Extract Manufacturers Association of the United States .

[DOI10.1371/journal.pone.0112694-2] Sara Nilsson, Johanna Sjöberg u. a .: Behavioral Responses to Mammalian Blood Odor and a Blood Odor Component in Four Species of Large Carnivores. In: PLoS ONE. 9, 2014, p. E112694, doi : 10.1371 / journal.pone.0112694 .

[CLI-3] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of TRANS-4,5-EPOXYDEC-2-ENAL in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 31, 2017, is reproduced from a self-classification by the distributor .

[Lin2001-4] Jianming Lin: Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay . In: Lipids . 36, No. 7, 2001, pp. 749-756. doi : 10.1007 / s11745-001-0781-x .

[Lin1999-5] Jianming Lin: 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 . In: Lipids . 34, No. 10, 1999, pp. 1117-1126. doi : 10.1007 / s11745-999-0463-8 .

[6] 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 flavoring substance 4,5-epoxydec- 2 (trans) -enal . In: Official Journal of the European Union . 11th July 2017.

[Gassenmeier1994-7] Klaus Gassenmeier: Formation of the intense flavor compoundtrans-4,5-epoxy- (E) -2-decenal in thermally treated fats . In: Journal of the American Oil Chemists' Society . 71, No. 12, 1994, pp. 1315-1319. doi : 10.1007 / BF02541347 .

[Konopka1991-8] Ute Christine Konopka: Potent odorants causing the warmed-over flavor in boiled beef . In: Journal of Food Study and Research . 193, No. 2, 1991, pp. 123-125. doi : 10.1007 / BF01193360 .

[Rota2005-9] Valerie Rota: Changes in Key Odorants of Sheep Meat Induced by Cooking . In: ACS Symposium Series . 920, 2005, pp. 73-83. doi : 10.1021 / bk-2005-0920.ch006 .