X7375

Xanthine

≥99%

• Synonym(s): 2,6-Dihydroxypurine
• Empirical Formula (Hill Notation): C₅H₄N₄O₂
• CAS Number: 69-89-6
• Molecular Weight: 152.11
• Beilstein: 8733
• EC Number: 200-718-6
• MDL number: MFCD00078453
• UNSPSC Code: 41106305
• PubChem Substance ID: 24902156
• NACRES: NA.51

Properties

• biological source: synthetic (organic)
• Assay: ≥99%
• form: powder
• solubility: 1 M NaOH: soluble 50 mg/mL, clear to slightly hazy; NH₄OH: freely soluble; NaOH: freely soluble
• 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 synthesized from guanine in the presence of guanine deaminase. Xanthine oxidase catalyzes the production of xanthine from hypoxanthine and its subsequent breakdown to uric acid. Xanthine derivatives are present in coffee, tea and cocoa seeds. Xanthine has been proposed as a lead for the generation of pharmacologically active compounds.

Application

Xanthine has been used in a nonradiolabled substrate mix in an Aspergillus nidulans transport assay. It has also been used as a substrate for xanthine oxidase for superoxide anion generation in gill cells and algal cells.

Biochem/physiol Actions

A high level of xanthine is implicated in metabolic disorders like Lesch-Nyhan syndrome. A xanthine-based biosensor may be useful for detecting xanthine in food and clinical samples. Blood and urine samples of patients with renal failure, gout and xanthinuria show high levels of xanthine.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves