Glycidamide

Structural formula
	( R ) -enantiomer (left) and ( S ) -enantiomer (right)
General
Surname	Glycidamide
other names	(±) -2,3-epoxypropanamide; (±) -Glycidamide; ( RS ) glycidamide; ( R ) -glycidamide; ( S ) -Glycidamide; ( RS ) -oxirane-2-carboxamide ( IUPAC );
Molecular formula	C 3 H 5 NO 2
Brief description	light orange crystals
External identifiers / databases
EC number	227-163-2
ECHA InfoCard	100,024,694
PubChem	91550
Wikidata	Q1532444
properties
Molar mass	87.08 g mol −1
Physical state	firmly
density	1.39 g cm −3
Melting point	32-34 ° C
boiling point	72-73 ° C (20 Pa)
Vapor pressure	38 m Pa (25 ° C)
safety instructions
H and P phrases	H: 302-315-317-319-335-350
	P: 201-261-280-305 + 351 + 338-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The glycidamide belongs to the chemical groups of amides and oxiranes . Glycidamide is classified as a highly carcinogenic substance that occurs in highly heated foods . It is formed from acrylamide through a reaction with unsaturated fatty acids and oxygen, but it is much more dangerous than this, because even small amounts can lead to mutations in cells . Another biologically relevant synthesis pathway takes place in the metabolism in the liver , where acrylamide is converted to glycidamide.

synthesis

The reaction of acrylonitrile with hydrogen peroxide results in racemic glycidamide. The selectivity and yield of glycidamide can be increased by continuously adding sodium hydroxide solution to the reaction mixture.

Stereoisomerism

Glycidamide is chiral . There are two enantiomers of this compound: ( R ) -glycidamide and the mirror image of ( S ) -glycidamide. The racemate ( RS ) -glycidamide is a 1: 1 mixture of ( R ) -glycidamide and ( S ) -glycidamide and is meant in the scientific literature and in this article when glycidamide is mentioned without a prefix .

Web links

Report from August 18, 2008 at Analytik-News.de

literature

Nicole Puppel: Studies on the genotoxicity of acrylamide and glycidamide on mammalian cells . Karlsruhe 2007, DNB 986721964 , urn : nbn: de: swb: 90-73268 (dissertation, University of Karlsruhe).

Individual evidence

↑ ^a ^b ^c ^d data sheet Glycidamide at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
↑ ^a ^b Entry on glycidamide. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
^ GB Payne: Reactions of Hydrogen Peroxide. VI. Alkaline Epoxidation of Acrylonitrile , in: J. Org. Chem. 1961 , 26 , 651-659. doi: 10.1021 / jo01062a003
↑ M. Granvogl, P. Koehler, L. Latzer, P. Schieberle: Development of a Stable Isotope Dilution Assay for the Quantitation of Glycidamide and Its Application to Foods and Model Systems , in: Journal of Agricultural and Food Chemistry 2008 , 56 , 6087-6092. doi: 10.1021 / jf800280b
↑ S. Sugiyama, S. Ohigashi, R. Sawa, H. Hayashi: Selective preparation of 2,3-epoxypropanamide and its facile conversion to 2,3-dihydroxypropanamide with acidic resins , in: Bull. Chem. Soc. Jpn. 1989 , 62 , 3202-3206. doi: 10.1246 / bcsj.62.3202 .

[Sigma-1] ta sheet Glycidamide at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).

[roempp-2] Entry on glycidamide. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[PAYNE-3] GB Payne: Reactions of Hydrogen Peroxide. VI. Alkaline Epoxidation of Acrylonitrile , in: J. Org. Chem. 1961 , 26 , 651-659. doi: 10.1021 / jo01062a003

[Granvogl-4] M. Granvogl, P. Koehler, L. Latzer, P. Schieberle: Development of a Stable Isotope Dilution Assay for the Quantitation of Glycidamide and Its Application to Foods and Model Systems , in: Journal of Agricultural and Food Chemistry 2008 , 56 , 6087-6092. doi: 10.1021 / jf800280b

[SUGIYAMA-5] S. Sugiyama, S. Ohigashi, R. Sawa, H. Hayashi: Selective preparation of 2,3-epoxypropanamide and its facile conversion to 2,3-dihydroxypropanamide with acidic resins , in: Bull. Chem. Soc. Jpn. 1989 , 62 , 3202-3206. doi: 10.1246 / bcsj.62.3202 .