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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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Khairia M. Youssef, et al
Medicinal Chemistry Research, 11, 481-503 (2003)
Sh. Joshi
Oxidation Communications, 32, 714-723 (2009)
Raymond Javan Chan et al.
Radiation oncology (London, England), 7, 121-121 (2012-08-02)
Radiation-induced skin reaction (RISR) is one of the most common and distressing side effects of radiotherapy in patients with cancer. It is featured with swelling, redness, itching, pain, breaks in skin, discomfort, and a burning sensation. There is a lack
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
Adviye A Tolun et al.
Annals of epidemiology, 22(12), 892-894 (2012-10-16)
Oxidative stress has been implicated in Down syndrome (DS) pathology. This study compares DS individuals and controls on their urinary levels of allantoin and 2,3-dinor-iPF2α-III; these biomarkers have been previously validated in a clinical model of oxidative stress. Urine samples

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