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X7375

Sigma-Aldrich

Xanthine

≥99%

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Synonym(s):
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

biological source

synthetic (organic)

Quality Level

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

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1 of 4

This Item
X4002X06261720203
vibrant-m

X7375

Xanthine

vibrant-m

X4002

Xanthine

vibrant-m

X0626

Xanthine

vibrant-m

1720203

Xanthone

Quality Level

300

Quality Level

200

Quality Level

400

Quality Level

-

assay

≥99%

assay

≥99%

assay

≥99.5% (HPLC)

assay

-

form

powder

form

powder

form

powder

form

-

solubility

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

solubility

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

solubility

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

solubility

-

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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


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Uric acid ≥99%, crystalline

Sigma-Aldrich

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Uric acid

Transport Assays in Aspergillus nidulans
Krypotou E and Diallinas G
Molecular Microbiology, 3(22), 1-5 (2013)
Biosensing methods for xanthine determination: a review
Pundir CS and Devi R
Enzyme and Microbial Technology, 57, 55-62 (2014)
Fish gill damage by the dinoflagellate Alexandrium catenella from Chilean fjords: synergistic action of ROS and PUFA
Mardones JI, et al.
Harmful Algae, 49(22), 40-49 (2015)
Xanthine scaffold: scope and potential in drug development
Singh N, et al.
Heliyon, 4(10), e00829-e00829 (2018)
D L Krebs et al.
Methods in cell science : an official journal of the Society for In Vitro Biology, 21(1), 57-68 (2000-03-25)
Murine B cell lines such as WEHI-231, BAL17 and M12.4.1 are frequently used as model systems to study signal transduction, cell cycle regulation, and apoptosis. Dissection of these processes often involves expressing exogenous genes in these cells. Electroporation is an

Articles

Uric acid is not a direct additive to any of the classical cell culture media. However, it is present in animal sera. Consequently, uric acid is typically present in complete serum-supplemented classical cell culture systems.

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.

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