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X0626

Sigma-Aldrich

Xanthine

≥99.5% (HPLC), purified by recrystallization

Synonym(s):

2,6-Dioxopurine, 3,7-Dihydropurine-2,6-dione, Xanthin, 2,6-Dihydroxypurine

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O2
CAS Number:
Molecular Weight:
152.11
Beilstein:
8733
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

Assay

≥99.5% (HPLC)

form

powder

purified by

recrystallization

solubility

1 M NaOH: soluble 50 mg/mL, clear, colorless to faintly yellow

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 an important component of the various natural and synthetic medicinal active compounds. Various forms of xanthine such as caffeine, theobromine, and theophylline are found in chocolate, cocoa, tea, yeast, potatoes, animal organs, and coffee. Xanthine is a purine-based natural heterocyclic alkaloid composed of a central nitrogen atom and a pyrimidine ring that is fused with an imidazole ring. Xanthine is produced from several different precursors in the purine metabolic pathway: deamination of guanine-by-guanine deaminase and conversion of hypoxanthine by xanthine oxidoreductase.

Biochem/physiol Actions

Xanthine participates in the catabolism of nucleic acids and nucleotides and is a precursor of uric acid. It is a versatile compound that shows therapeutic effects in several pharmacological conditions related to respiratory tract, central nervous system (CNS), kidney, stomach, smooth muscle cells, and heart. Xanthine acts as a biomarker for detecting gout.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Physiological acclimation to gradients of solar irradiance within mats of the filamentous green macroalga Chaetomorpha linum from southern Spain.
Bischof, Kai, et al.
Marine Ecology Progress Series, 306, 165-175 (2006)
Different processed milk with residual xanthine oxidase activity and risk of increasing serum uric acid level
Sha W, et al.
Food Bioscience, 40, 100892-100892 (2021)
Recent Advances in the Synthesis of Xanthines: A Short Review
Kapri A, et al.
Scientifica, 2022 (2022)
Bioactive chemical constituents of Stereospermum kunthianum (Bignoniaceae)
Island, W
Research Journal of Phytochemistry, 3, 35-43 (2009)
Oxidative stress and enzymatic scavenging of superoxide radicals induced by solar UV-B radiation in Ulva canopies from southern Spain.
Bischof, Kai, et al.
Scientia Marina, 67, 353-359 (2003)

Protocols

Enzymatic Assay of Superoxide Dismutase

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