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X7375

Sigma-Aldrich

Xanthine

≥99%

Synonym(s):

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:
24902156
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

300

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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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 Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5098V
WXBF4952V
WXBF4165V
WXBF4288V
WXBF3615V

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Biosensing methods for xanthine determination: a review
Pundir CS and Devi R
Enzyme and Microbial Technology, 57, 55-62 (2014)
Transport Assays in Aspergillus nidulans
Krypotou E and Diallinas G
Molecular Microbiology, 3(22), 1-5 (2013)
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)
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
Xanthine scaffold: scope and potential in drug development
Singh N, et al.
Heliyon, 4(10), e00829-e00829 (2018)
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