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X0750

Sigma-Aldrich

Xanthosine dihydrate

≥99%

Synonym(s):

9-β-D-Ribofuranosylxanthine

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O6 · 2H2O
CAS Number:
5968-90-1
Molecular Weight:
320.26
EC Number:
205-679-9
MDL number:
MFCD00149347
UNSPSC Code:
41106305
PubChem Substance ID:
24902123
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

100

Assay

≥99%

form

powder

solubility

1 M NH4OH: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

O.O.OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3C(=O)NC(=O)Nc23

InChI

1S/C10H12N4O6.2H2O/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18;;/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19);2*1H2/t3-,5-,6-,9-;;/m1../s1

InChI key

ZCCPXSQIUORWCO-LGVAUZIVSA-N

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General description

Xanthosine comprises xanthine ring. It is derived from a purine metabolite and is a caffeine biosynthesis intermediate.

Application

Xanthosine dihydrate has been used as a test compound in one dimensional liquid chromatography analysis (1D-LC ).

Biochem/physiol Actions

Xanthosine plays a key role in purine metabolism. High levels of xanthosine excretion is observed in breast cancer.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Comprehensive Natural Products II, 1, 977-1007 (2010)
Ewa Kulikowska et al.
Acta biochimica Polonica, 51(2), 493-531 (2004-06-26)
The 6-oxopurine xanthine (Xan, neutral form 2,6-diketopurine) differs from the corresponding 6-oxopurines guanine (Gua) and hypoxanthine (Hyp) in that, at physiological pH, it consists of a approximately 1:1 equilibrium mixture of the neutral and monoanionic forms, the latter due to
Lucas Willmann et al.
Scientific reports, 5, 13374-13374 (2015-08-22)
Cancer cells show characteristic effects on cellular turnover and DNA/RNA modifications leading to elevated levels of excreted modified nucleosides. We investigated the molecular signature of different subtypes of breast cancer cell lines and the breast epithelial cell line MCF-10A. Prepurification
Lucas Willmann et al.
Analytical and bioanalytical chemistry, 407(13), 3555-3566 (2015-03-05)
Modified nucleosides derived from the RNA metabolism constitute an important chemical class, which are discussed as potential biomarkers in the detection of mammalian breast cancer. Not only the variability of modifications, but also the complexity of biological matrices such as

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