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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)
Rufus Turner et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 891-892, 85-89 (2012-03-09)
Allantoin is the major oxidation product of urate in humans and is a potential biomarker of oxidative stress. Several methods are used to measure allantoin in biological samples but they have inherent issues that can include lack of specificity and
Dora Il'yasova et al.
Clinica chimica acta; international journal of clinical chemistry, 413(19-20), 1446-1453 (2012-06-12)
Oxidative damage produced by reactive oxygen species (ROS) has been implicated in the etiology and pathology of many health conditions, including a large number of chronic diseases. Urinary biomarkers of oxidative status present a great opportunity to study redox balance
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

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