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X4002

Sigma-Aldrich

Xanthine

BioUltra, ≥99%

Synonym(s):

2,6-Dihydroxypurine

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O2
CAS Number:
69-89-6
Molecular Weight:
152.11
Beilstein/REAXYS Number:
8733
EC Number:
200-718-6
MDL number:
MFCD00078453
UNSPSC Code:
41106305
PubChem Substance ID:
24902144
NACRES:
NA.51

biological source

synthetic (organic)

product line

BioUltra

assay

≥99%

form

powder

impurities

≤0.0005% Phosphorus (P)
≤0.1% Insoluble matter

ign. residue

≤0.1%

solubility

1 M NaOH: 0.1 M, clear, colorless to light yellow

anion traces

sulfate (SO42-): <0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

SMILES string

O=C1NC(=O)c2nc[nH]c2N1

InChI

1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)

InChI key

LRFVTYWOQMYALW-UHFFFAOYSA-N

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General description

Xanthine is a purine that can be produced in the purine metabolic pathway via different precursors:
  • Guanine deamination by guanine deaminase
  • Hypoxanthine conversion by xanthine oxidoreductase
Xanthine or its derivatives are naturally present in animal organs, yeast, potatoes, coffee beans, and tea.

Application

Xanthine has been used as a substrate for the determination of xanthine oxidase (XOD) inhibitory activity. It has also been used in the following systems:
  • yeast culture
  • human cell line culture
  • recombinant viruses cloned as bacterial artificial chromosomes in Escherichia coli

Biochem/physiol Actions

Xanthine and xanthine oxidase are used to generate superoxide radicals to measure the activity of superoxide dismutase.

Features and Benefits

  • Tested for trace metal content (fuller details in Properties section and on Specification Sheet)
  • Tested for trace sulfate content (fuller details in Properties section and on Specification Sheet)

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Insights from multispectral and molecular docking investigation on the xanthine oxidase inhibition by 1, 4-dicaffeoylquinic acid
Cao W, et al.
Journal of Molecular Structure, 1219, 128475-128475 null
Optimization of total phenolic contents, antioxidant, and in-vitro xanthine oxidase inhibitory activity of sunflower head
Mehmood A, et al.
CYTA-journal of Food, 16, 957-964 null
Raffaello Castoria et al.
Phytopathology, 93(5), 564-572 (2008-10-24)
ABSTRACT We detected the generation of the reactive oxygen species (ROS) superoxide anion ( O.(-) (2)) and hydrogen peroxide (H(2)O(2)) in apple wounds 2 immediately after wounding, and assessed the relationships between (i) timely colonization of apple wounds by biocontrol
Avery G Frey et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(22), 8031-8036 (2014-05-21)
Although cells express hundreds of metalloenzymes, the mechanisms by which apoenzymes receive their metal cofactors are largely unknown. Poly(rC)-binding proteins PCBP1 and PCBP2 are multifunctional adaptor proteins that bind iron and deliver it to ferritin for storage or to prolyl
Ken Okamoto et al.
Current pharmaceutical design, 19(14), 2606-2614 (2012-11-03)
Xanthine oxidoreductase (XOR), a complex flavoprotein, catalyzes the metabolic reactions leading from hypoxanthine to xanthine and from xanthine to urate, and both reactions take place at the molybdenum cofactor. The enzyme is a target of drugs for therapy of gout
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