X0626

Xanthine

≥99.5% (HPLC), purified by recrystallization

• Synonym(s): 2,6-Dioxopurine, 3,7-Dihydropurine-2,6-dione, Xanthin, 2,6-Dihydroxypurine
• 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: 24902122
• NACRES: NA.51

Properties

• 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

Description

General description

Xanthine is an important component of the various natural and synthetic medicinal active compounds.[1] Various forms of xanthine such as caffeine, theobromine, and theophylline are found in chocolate, cocoa, tea, yeast, potatoes, animal organs, and coffee.[2] Xanthine is a purine-based natural heterocyclic alkaloid [2] composed of a central nitrogen atom and a pyrimidine ring that is fused with an imidazole ring.[1] 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.[3]

Biochem/physiol Actions

Xanthine participates in the catabolism of nucleic acids and nucleotides and is a precursor of uric acid.[2] 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.[1] Xanthine acts as a biomarker for detecting gout.[4]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves