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156361

Sigma-Aldrich

Hydantoin

98%

Synonym(s):

2,4-Imidazolidinedione, Glycolylurea

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About This Item

Empirical Formula (Hill Notation):
C3H4N2O2
CAS Number:
461-72-3
Molecular Weight:
100.08
Beilstein/REAXYS Number:
110598
EC Number:
207-313-3
MDL number:
MFCD00005259
UNSPSC Code:
12352100
PubChem Substance ID:
24849609
NACRES:
NA.22

assay

98%

form

powder

mp

218-220 °C (lit.)

SMILES string

O=C1CNC(=O)N1

InChI

1S/C3H4N2O2/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)

InChI key

WJRBRSLFGCUECM-UHFFFAOYSA-N

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Application

Reactant for synthesis of:
N-benzyl aplysinopsin analogs as anticancer agents
D-glutamic acid based inhibitors
Antidiabetic chromonyl-2,4-thiazolidinediones
GSK-3β inhibitors with brain permeability
Thiazolidinedione derivatives as 15-PGDH inhibitors
Radio-sensitizing agents
The product has been used as a substrate (at 40 °C and pH 9.0) to determine the D-hydantoinase activity in adzuki bean extract.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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June Izquierdo et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(53), 12431-12438 (2019-07-19)
A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid
Effect of treatment with compressed CO2 and propane on D-hydantoinase activity
Andrade JM, et al.
Journal of Supercritical Fluids, 46(2), 342-350 (2008)
Y Thirupathi Reddy et al.
Bioorganic & medicinal chemistry letters, 20(2), 600-602 (2009-12-17)
A series of (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-dione (9a-9m) and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (10a-10i) derivatives that incorporate a variety of aromatic substituents in both the indole and N-benzyl moieties have been synthesized. These analogs were evaluated for their radiosensitization activity against the HT-29 cell line. Three
Lixuan Zhan et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(1), 1313-1329 (2018-08-28)
Hypoxic preconditioning (HPC) alleviates the selective and delayed neuronal death in the hippocampal CA1 region induced by transient global cerebral ischemia (tGCI). This type of cell death may include different programmed cell death mechanisms, namely, apoptosis and necroptosis. Although apoptotic
I Hauksson et al.
The British journal of dermatology, 174(2), 371-379 (2015-10-20)
Formaldehyde is a well-known contact sensitizer. Formaldehyde releasers are widely used preservatives in skincare products. It has been found that formaldehyde at concentrations allowed by the European Cosmetics Directive can cause allergic contact dermatitis. However, we still lack information on
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