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X4002

Sigma-Aldrich

Xanthine

BioUltra, ≥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:
24902144
NACRES:
NA.51

biological source

synthetic (organic)

product line

BioUltra

Assay

≥99%

form

powder

impurities

≤0.0005% Phosphorus (P)
≤0.1% Insoluble matter

ign. residue

≤0.1%

solubility

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

anion traces

sulfate (SO42-): <0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
NH4+: ≤0.05%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

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 a purine that can be produced in the purine metabolic pathway via different precursors:
  • Guanine deamination by guanine deaminase
  • Hypoxanthine conversion by xanthine oxidoreductase
Xanthine or its derivatives are naturally present in animal organs, yeast, potatoes, coffee beans, and tea.

Application

Xanthine has been used as a substrate for the determination of xanthine oxidase (XOD) inhibitory activity. It has also been used in the following systems:
  • yeast culture
  • human cell line culture
  • recombinant viruses cloned as bacterial artificial chromosomes in Escherichia coli

Biochem/physiol Actions

Xanthine and xanthine oxidase are used to generate superoxide radicals to measure the activity of superoxide dismutase.

Features and Benefits

  • Tested for trace metal content (fuller details in Properties section and on Specification Sheet)
  • Tested for trace sulfate content (fuller details in Properties section and on Specification Sheet)

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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Gavin C Higgins et al.
Free radical biology & medicine, 53(10), 1960-1967 (2012-09-18)
Neurons can undergo a diverse range of death responses under oxidative stress, encompassing apoptosis (caspase-dependent, programmed cell death) to various forms of caspase-independent death, including necrosis. We recently showed that primary murine cortical neurons exposed acutely to hydrogen peroxide undergo
Sergey Dikalov et al.
Biochemical pharmacology, 76(5), 589-596 (2008-07-22)
Honokiol, a compound extracted from Magnolia officinalis, has antitumor and antiangiogenic properties in several tumor models in vivo. Among the downstream pathways inhibited by honokiol is nuclear factor kappa beta (NFkappabeta). A prime physiologic stimulus of NFkappabeta is reactive oxygen
R Hille et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 9(11), 995-1003 (1995-08-01)
Xanthine oxidase and xanthine dehydrogenase are enzymes involved in the metabolism of purines and pyrimidines in various organisms. Their relationship to one another has been the subject of considerable debate, primarily because of their proposed roles in ischemia/reperfusion damage in
Avery G Frey et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(22), 8031-8036 (2014-05-21)
Although cells express hundreds of metalloenzymes, the mechanisms by which apoenzymes receive their metal cofactors are largely unknown. Poly(rC)-binding proteins PCBP1 and PCBP2 are multifunctional adaptor proteins that bind iron and deliver it to ferritin for storage or to prolyl
Carolyn F Deacon et al.
Expert opinion on investigational drugs, 19(1), 133-140 (2009-12-02)
Type 2 diabetes is a progressive disease for which current treatments are often unsatisfactory with respect to achieving therapeutic goals and unwanted side effects. Preclinical and clinical studies of linagliptin, a new oral antidiabetic agent, including data presented at Scientific
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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.

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