X0626

Xanthine

Name: Xanthine
Brand: SIGMA

≥99.5% (HPLC), powder

Synonym(s):

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

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All Photos(5)

About This Item

Empirical Formula (Hill Notation):

C₅H₄N₄O₂

CAS Number:

69-89-6

Molecular Weight:

152.11

NACRES:

NA.51

PubChem Substance ID:

24902122

UNSPSC Code:

41106305

EC Number:

200-718-6

MDL number:

MFCD00078453

Beilstein/REAXYS Number:

8733

Product Name

Xanthine, ≥99.5% (HPLC), purified by recrystallization

InChI key

LRFVTYWOQMYALW-UHFFFAOYSA-N

InChI

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

SMILES string

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

biological source

synthetic

assay

≥99.5% (HPLC)

form

powder

purified by

recrystallization

solubility

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

storage temp.

2-8°C

Quality Level

400

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Biochemicals

Nucleosides and Nucleotides

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000518457

0000482851

0000511035

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Bioactive chemical constituents of Stereospermum kunthianum (Bignoniaceae)

Island, W

Research Journal of Phytochemistry, 3, 35-43 (2009)

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)

Recent Advances in the Synthesis of Xanthines: A Short Review

Kapri A, et al.

Scientifica, 2022 (2022)

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)

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)

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