Glycidamide information

Glycidamide
Names
	Preferred IUPAC name Oxiranecarboxamide
	Other names Glycidic acid amide; Oxirane-2-carboxamide
Identifiers
CAS Number	5694-00-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	82664;
ECHA InfoCard	100.024.694
PubChem CID	91550;
UNII	6G5ELX5XYN ;
CompTox Dashboard (EPA)	DTXSID2031374 ;
	InChI InChI=1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5);
	SMILES C1C(O1)C(=O)N;
Properties
Chemical formula	C3H5NO2
Molar mass	87.078 g·mol−1
Density	1.404 g/cm3
Melting point	32–34 °C (90–93 °F; 305–307 K)
Pharmacology
	Pharmacokinetics:
Biological half-life	5 hours
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glycidamide is an organic compound with the formula H₂NC(O)C₂H₃O. It is a colorless oil. Structurally, it contains adjacent amides and epoxide functional groups. It is a bioactive, potentially toxic or even carcinogenic metabolite of acrylonitrile and acrylamide.^[2]^[3] It is a chiral molecule.

^ Hemgesberg, Melanie N.; Bonck, Thorsten; Merz, Karl-Heinz; Sun, Yu; Schrenk, Dieter (2016). "Crystal Structure of Glycidamide: The Mutagenic and Genotoxic Metabolite of Acrylamide". Acta Crystallographica Section E. 72 (8): 1179–1182. doi:10.1107/S2056989016010859. PMC 4971867. PMID 27536408.
^ Friedman, Mendel (2003). "Chemistry, Biochemistry, and Safety of Acrylamide. A Review". Journal of Agricultural and Food Chemistry. 51 (16): 4504–4526. doi:10.1021/jf030204+. PMID 14705871.
^ Mendel Friedman, Don Mottram, ed. (2005). Chemistry and Safety of Acrylamide in Food. ISBN 978-1-4419-3672-1.

[1] Hemgesberg, Melanie N.; Bonck, Thorsten; Merz, Karl-Heinz; Sun, Yu; Schrenk, Dieter (2016). "Crystal Structure of Glycidamide: The Mutagenic and Genotoxic Metabolite of Acrylamide". Acta Crystallographica Section E. 72 (8): 1179–1182. doi:10.1107/S2056989016010859. PMC 4971867. PMID 27536408.

[2] Friedman, Mendel (2003). "Chemistry, Biochemistry, and Safety of Acrylamide. A Review". Journal of Agricultural and Food Chemistry. 51 (16): 4504–4526. doi:10.1021/jf030204+. PMID 14705871.

[3] Mendel Friedman, Don Mottram, ed. (2005). Chemistry and Safety of Acrylamide in Food. ISBN 978-1-4419-3672-1.

Glycidamide information

and 6 Related for: Glycidamide information

Glycidamide

Acrylamide

Glycidol

Asparagine

Glycidic acid

C3H5NO2

Names

Preferred IUPAC name Oxiranecarboxamide
Other names Glycidic acid amide Oxirane-2-carboxamide
Identifiers
CAS Number	5694-00-8^Y
3D model (JSmol)	Interactive image
ChemSpider	82664
ECHA InfoCard	100.024.694
PubChem CID	91550
UNII	6G5ELX5XYN^Y
CompTox Dashboard (EPA)	DTXSID2031374
InChI InChI=1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5)
SMILES C1C(O1)C(=O)N
Properties
Chemical formula	C₃H₅NO₂
Molar mass	87.078 g·mol⁻¹
Density	1.404 g/cm³^[1]
Melting point	32–34 °C (90–93 °F; 305–307 K)
Pharmacology
Pharmacokinetics:
Biological half-life	5 hours
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references