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Merck
CN

04704

Glycidamide

analytical standard

Synonym(s):

2,3-Epoxypropanamide, Oxiranecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C3H5NO2
CAS Number:
5694-00-8
Molecular Weight:
87.08
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329747975
EC Number:
227-163-2
Beilstein/REAXYS Number:
227 163 2
MDL number:
MFCD00468053

Key Documents

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Product Name

Glycidamide, analytical standard

SMILES string

NC(=O)C1CO1

InChI

1S/C3H5NO2/c4-3(5)2-1-6-2/h2H,1H2,(H2,4,5)

InChI key

FMAZQSYXRGRESX-UHFFFAOYSA-N

grade

analytical standard

assay

≥95% (qNMR)

shelf life

limited shelf life, expiry date on the label

application(s)

environmental

format

neat

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Glycidamide may be used as an analytical standard for the determination of the analyte in human and animal biological samples by various chromatography techniques.

General description

Glycidamide, an active epoxide metabolite of acrylamide with potential biological activity, can be generated in vivo. Its mutagenic and genotoxic nature is well-known.

Other Notes

In the summer of 2008 research scientists at the Technical University of Munich besides acrylamide detected glycidamide in potato crisps. Glycidamide is a metabolite of acrylamide.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3702
BCCK2598
BCCC1244
BCCC1105
BCCB2285

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D S Barber et al.
Journal of chromatography. B, Biomedical sciences and applications, 758(2), 289-293 (2001-08-07)
Acrylamide is a widely used monomer that produces peripheral neuropathy. It is metabolized to the epoxide, glycidamide, which is also considered to be neurotoxic. A new reversed-phase high-performance liquid chromatography (HPLC) method is described that permits simultaneous determination of acrylamide
Franz Ingo Berger et al.
Molecular nutrition & food research, 55(3), 387-399 (2010-10-13)
Acrylamide (AA), classified as a genotoxic carcinogen, is generated by heating foods. We studied whether the food matrix modulates bioavailability and/or biotransformation and investigated kinetics and biological effectiveness of AA in rats. AA was given to the animals at a
Yu-Fang Huang et al.
Toxicology letters, 215(2), 92-99 (2012-10-17)
This study assesses the association of acrylamide (AA) and glycidamide (GA) hemoglobin adducts (AAVal and GAVal) and their ratios with genetic polymorphisms of the metabolic enzymes cytochrome P450 2E1 (CYP2E1), exon 3 and 4 of microsomal epoxide hydrolase (mEH3 and
Anja Olsen et al.
Toxicology, 296(1-3), 67-72 (2012-04-03)
Acrylamide is a probable human carcinogen, with industrial contact, tobacco smoking and foods processed at high temperatures as the main routes of exposure. In animal studies oral intake of acrylamide has been related to cancer development, with indications that the
Rui-Sheng Wang et al.
Toxicological sciences : an official journal of the Society of Toxicology, 117(1), 72-80 (2010-06-29)
Acrylamide (AA) is an industrial chemical, a by-product of fried starchy foods, and a mutagen and rodent carcinogen. It can also cause damage during spermatogenesis. In this study, we investigated whether AA and its metabolite glycidamide (GA) induce mutagenic effects
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