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Key Documents

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:
Molecular Weight:
100.08
Beilstein:
110598
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
Meltem Ceylan-Ünlüsoy et al.
Journal of enzyme inhibition and medicinal chemistry, 25(6), 784-789 (2010-08-07)
A series of chromonyl-2,4-thiazolidinediones/imidazolidinediones/2-thioxo-imidazolidine-4-ones (IIIa-i, IVa-i) was prepared by Knoevenagel reaction of 2,4-thiazolidinedione/2,4-imidazolidinedione/2-thioxo-imidazolidine-4-one (IIa-c) with 2/3-formyl chromone (Ia-b) and then alkylation with methyl/ethyl iodide. The prepared compounds were tested for their insulinotropic activities in INS-1 cells. Compounds ıVb and ıVc
Narsimha Reddy Penthala et al.
Bioorganic & medicinal chemistry letters, 21(5), 1411-1413 (2011-02-08)
A series of novel substituted (Z)-5-((1-benzyl-1H-indol-3-yl)methylene)imidazolidin-2,4-diones (3a-f) and (Z)-5-((1-benzyl-1H-indol-3-yl)methylene)-2-iminothiazolidin-4-ones (3g-o) have been synthesized utilizing microwave irradiation. These analogs were evaluated for in vitro cytotoxicity against a panel of 60 human tumor cell lines. Compound 3i exhibits potent growth inhibition against
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)

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