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05670

Sigma-Aldrich

Allantoin

≥98.0% (N)

Synonym(s):

NSC 7606, 5-Ureidohydantoin, Glyoxylic(acid) diureide

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About This Item

Empirical Formula (Hill Notation):
C4H6N4O3
CAS Number:
Molecular Weight:
158.12
Beilstein:
102364
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (N)

form

powder

ign. residue

≤0.2%

mp

230 °C (dec.) (lit.)

SMILES string

NC(=O)NC1NC(=O)NC1=O

InChI

1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)

InChI key

POJWUDADGALRAB-UHFFFAOYSA-N

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Application

Reactant for:
Synthesis of Mannich bases for use as antibacterial agents
Synthesis of sulofenur analogs for use as antitumor agents

Biochem/physiol Actions

Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Sh. Joshi
Oxidation Communications, 32, 714-723 (2009)
Khairia M. Youssef, et al
Medicinal Chemistry Research, 11, 481-503 (2003)
Camila G Moreira et al.
Journal of ethnopharmacology, 141(3), 1005-1011 (2012-04-17)
Pyrostegia venusta is a native Brazilian plant which has a variety of uses in traditional folk medicine including the treatment of vitiligo. However, its effectiveness on melanogenesis is not yet elucidated. This study aimed to investigate the melanogenic activity of
Peng Wang et al.
Journal of agricultural and food chemistry, 60(11), 2793-2798 (2012-03-01)
Despite increasing knowledge of allantoin as a phytochemical involved in rice, relatively little is known about its distribution and function in rice grains. In this study, allantoin was quantified in 15 Chinese rice grains, and its contents varied with grain
Juan Luis Díaz-Leal et al.
Journal of experimental botany, 63(11), 4095-4106 (2012-03-24)
The ureides allantoin and allantoate are key molecules in the transport and storage of nitrogen in ureide legumes. In shoots and leaves from Phaseolus vulgaris plants using symbiotically fixed nitrogen as the sole nitrogen source, ureide levels were roughly equivalent

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