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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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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

Assay:

≥99.5% (HPLC)

Biological source:

synthetic

Form:

powder

Solubility:

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

Storage temp.:

2-8°C

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Properties

Product Name

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

biological source

synthetic

Quality Level

400

assay

≥99.5% (HPLC)

form

powder

purified by

recrystallization

color

white to off-white

solubility

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

storage temp.

2-8°C

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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

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