146-80-5

Basic information

• Product Name: XANTHOSINE
• Synonyms: XANTHINE RIBOSIDE;XANTHINE-9-RIBOFURANOSIDE;XANTHOSINE;XANTHOSINE HYDRATE;9-B-D-RIBOFURANOSYLXANTHINE;9-BETA-D-RIBOFURANOSYLXANTHINE;9-[3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-3H-PURINE-2,6-DIONE;XANTHOSINE MIN 99%
• CAS NO: 146-80-5
• Molecular Formula: C₁₀H₁₂N₄O₆
• Molecular Weight: 284.23
• EINECS: 205-679-9
• Product Categories: Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Amines;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 146-80-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 174～176℃
• Boiling Point: 828.2 °C at 760 mmHg
• Flash Point: 454.7 °C
• Appearance: /
• Density: 2.25 g/cm³
• Vapor Pressure: 4.6E-29mmHg at 25°C
• Refractive Index: -52 ° (C=8, 0.3mol/L NaOH)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: pK1:<2.5(+1);pK2:5.67(0);pK3:12.00(-1) (25°C)
• Merck: 14,10065
• CAS DataBase Reference: XANTHOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: XANTHOSINE(146-80-5)
• EPA Substance Registry System: XANTHOSINE(146-80-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 146-80-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 146-80-5 differently. You can refer to the following data:
1. The deamination product of Guanosine. Potential biomarker for detecting radiation exposure. XANTHOSINE is used in the amplification of DNA isothermal strand displacement.
2. Xanthosine-13C5, is the labeled analogue of Xanthosine (X742100), the deamination product of Guanosine. It is also a potential biomarker for detecting radiation exposure.

Definition

ChEBI: A purine nucleoside in which xanthine is attached to ribofuranose via a beta-N9-glycosidic bond.

InChI:InChI=1/C10H12N4O6/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)/t3-,5-,6-,9-/m1/s1

Upstream product

• 1448782-32-8 C₃₁H₂₄N₄O₉ 
• 18551-03-6 9-trimethylsilanyl-2,6-bis-trimethylsilanyloxy-9H-purine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 73024-64-3 C₃₁H₂₄N₄O₉ 
• 1203555-53-6 2′,3′,5′-tris-O-(tert-butyldimethylsilyl)-6-O-[2-(4-nitrophenyl)ethyl]guanosine 
• 72409-24-6 2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine 
• 197437-76-6 5-amino-1-(5′-O-tert-butyldimethylsilyl-2′,3′-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 118-00-3 G 
• 5383-06-2 N¹-hydroxyinosine 

Downstream Products

• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 86013-99-2 7-<(4-amino-1,2-dimethyl-5-pyrimidinio)methyl>xanthine perchlorate 
• 132194-28-6 9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-xanthosine 
• 88010-99-5 2-O-(R)-Formyl-(xanthin-9-yl)methyl-(R)-glyceraldehyde 
• 146-80-5 9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3,9-dihydro-purine-2,6-dione 
• 69-89-6 xanthine 
• 69-89-6 xanthin 
• 523-98-8 L-xanthosine 5’-monophosphate 
• 58-63-9 Inosine 
• 50-69-1 D-ribose 
• 61444-45-9 2',3',5'-tri-O-acetyl-β-xanthosine 
• 523-98-8 XMP 
• 80106-09-8 8-nitroxanthine 

Related news

Functionally Nonequivalent Interactions of Guanosine 5 -Triphosphate, Inosine 5 -Triphosphate, and XANTHOSINE (cas 146-80-5) 5 -Triphosphate with the Retinal G-Protein, Transducin, and with G i -Proteins in HL-60 Leukemia Cell Membranes09/30/2019

G-proteins mediate signal transfer from receptors to effector systems. In their guanosine 5 -triphosphate (GTP)-bound form, G-protein α-subunits activate effector systems. Termination of G-protein activation is achieved by the high-affinity GTPase [E.C. 3.6.1.-] of their α-subunits. Like G...detailed

Chelate Adsorption for Trace Voltammetric Determination of XANTHOSINE (cas 146-80-5) 5′-Monophosphate and XANTHOSINE (cas 146-80-5) 5′-Diphosphate09/29/2019

. Square-wave cathodic adsorptive stripping voltammetry based on adsorptive accumulation is a very sensitive technique for the trace determination of xanthosine 5′-monophosphate (5′-XMP) and xanthosine 5′-diphosphate (5′-XDP). The determination is based on the strong interaction of the adsor...detailed

Relevant articles and documents

A new synthesis of oxanosine and 2'-deoxyoxanosine

An easy and more efficient synthesis of oxanosine and 2'-deoxyoxanosine has been developed, a key step in the reported synthesis is a new photochemical transformation by UV irradiation of 1-hydroxy derivatives of inosine.

2'-Deoxyisoinosine: Synthesis of a highly fluorescent nucleoside and its incorporation into oligonucleotides

The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'- dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.

Inhibition of Guanosine Monophosphate Synthetase by the Substrate Enantiomer L-XMP

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Formation of 2-chloroinosine from guanosine by treatment of HNO2 in the presence of NaCl

We investigated the reaction of Guo with nitrous acid in the presence of NaCl. When 1 mM Guo was incubated with 100 mM NaNO2 and 2 M NaCl in sodium acetate buffer at pH 3.2 and 37°C, 2-chloroinosine (2-Cl-Ino) was produced in addition to oxanosine (Oxo) and xanthosine (Xao). The yield of 2-Cl-Ino was 0.033 mM at an incubation time of 2 h. Under the same reaction conditions, GMP and dGuo gave rise to the corresponding 2-chloro derivatives with comparable yields. All the 2-chloro derivatives were fairly stable (t1/2>360 h) at physiological pH and temperature. To elucidate the reaction mechanism of the chlorination, the diazoate derivative of Guo, a reaction intermediate of the Guo-HNO2 system, was employed as a starting compound. When the diazoate was incubated with 2 M NaCl in a neutral solution, 2-Cl-Ino was produced in addition to Oxo and Xao. These results suggest that the 2-chloro derivatives can be produced from foodstuffs in the human stomach and may have potential importance as a carcinogen causing gastric cancer.