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X0626

Sigma-Aldrich

Xanthine

≥99.5% (HPLC), purified by recrystallization

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Synonym(s):
2,6-Dioxopurine, 3,7-Dihydropurine-2,6-dione, Xanthin, 2,6-Dihydroxypurine
Empirical Formula (Hill Notation):
C5H4N4O2
CAS Number:
Molecular Weight:
152.11
Beilstein/REAXYS Number:
8733
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

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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1 of 4

This Item
X4002X73751720203
vibrant-m

X0626

Xanthine

vibrant-m

X4002

Xanthine

vibrant-m

X7375

Xanthine

vibrant-m

1720203

Xanthone

assay

≥99.5% (HPLC)

assay

≥99%

assay

≥99%

assay

-

form

powder

form

powder

form

powder

form

-

solubility

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

solubility

1 M NaOH: 0.1 M, clear, colorless to light yellow

solubility

1 M NaOH: soluble 50 mg/mL, clear to slightly hazy, NH4OH: freely soluble, NaOH: freely soluble

solubility

-

purified by

recrystallization

purified by

-

purified by

-

purified by

-

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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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


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Xanthine sodium salt ≥99%

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Xanthine sodium salt

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)
Bioactive chemical constituents of Stereospermum kunthianum (Bignoniaceae)
Island, W
Research Journal of Phytochemistry, 3, 35-43 (2009)
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)
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)

Articles

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

Enzymatic Assay of Superoxide Dismutase

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