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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:
69-89-6
Molecular Weight:
152.11
Beilstein:
8733
EC Number:
200-718-6
MDL number:
MFCD00078453
UNSPSC Code:
41106305
PubChem Substance ID:
24902122
NACRES:
NA.51

Quality Level

400

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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P Leanderson et al.
Carcinogenesis, 17(3), 545-550 (1996-03-01)
The formation of DNA-strand breaks was studied in cultured human lung cells (A 549) subjected to iron, either in the form of iron(III) citrate or in combination with the metal chelators ethylene diamine tetra-acetic acid (EDTA), nitrilo triacetic acid (NTA)
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)
Bioactive chemical constituents of Stereospermum kunthianum (Bignoniaceae)
Island, W
Research Journal of Phytochemistry, 3, 35-43 (2009)
S A Back et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(16), 6241-6253 (1998-08-11)
Death of oligodendrocyte (OL) precursors can be triggered in vitro by cystine deprivation, a form of oxidative stress that involves depletion of intracellular glutathione. We report here that OLs demonstrate maturation-dependent differences in survival when subjected to free radical-mediated injury
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Articles

HPLC Analysis of Xanthines on Purospher® STAR RP-18 endcapped

Xanthine is a purine base found in most human body tissues and fluids as well as in other organisms. Methylated xanthines (methylxanthines), which include caffeine, paraxanthine, theobromine, and theophylline, commonly used for their effects as mild stiµlants and as bronchodilators, notably in the treatment of asthma symptoms. This application shows the efficient separation of several common xanthines and may be applied their analysis in any number of desired matrices.

Protocols

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