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2',3',5'-Tri-O-acetyluridine

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2',3',5'-Tri-O-acetyluridine Basic information

Product Name:
2',3',5'-Tri-O-acetyluridine
Synonyms:
  • RG 2133
  • Tri-O-acetyl uridine
  • Uridine triacetate
  • Vistonuridine
  • 1-((2R,3R,4R,5R)-3,4-Diacetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione
  • 2',3',5'-Tri-O-acetyl-rU
  • (2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  • 1-((2R,3R,4R,5R)-3,4-Diacetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)tetrahydrofuran-2-yl)pyrimid
CAS:
4105-38-8
MF:
C15H18N2O9
MW:
370.31
EINECS:
223-881-5
Mol File:
4105-38-8.mol
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2',3',5'-Tri-O-acetyluridine Chemical Properties

Melting point:
127.0 to 131.0 °C
Density 
1.43±0.1 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
form 
Solid
pka
9.39±0.10(Predicted)
color 
Off-White
InChI
InChI=1S/C15H18N2O9/c1-7(18)23-6-10-12(24-8(2)19)13(25-9(3)20)14(26-10)17-5-4-11(21)16-15(17)22/h4-5,10,12-14H,6H2,1-3H3,(H,16,21,22)/t10-,12-,13-,14-/m1/s1
InChIKey
AUFUWRKPQLGTGF-QRMSVCKNSA-N
SMILES
C(OC(=O)C)[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](OC(=O)C)[C@@H]1OC(=O)C
CAS DataBase Reference
4105-38-8(CAS DataBase Reference)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29349990

MSDS

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2',3',5'-Tri-O-acetyluridine Usage And Synthesis

Description

Uridine triacetate is an orally available pro-drug of uridine approved by the FDA for the treatment of the rare autosomal recessive disorder called hereditary orotic aciduria. The drug was also approved for treating overdose of two chemotherapies (fluorouracil and capecitabine). Uridine triacetate was developed by Wellstat Therapeutics and licensed to BTG.

Chemical Properties

White or almost white crystalline powder

Uses

2’,3’,5’-Triacetyluridine is used in the treatment of Alzheimer’s disease in mice and provide neuroprotective effects. Shown to also decrease depressive symptoms and increases in brain pH bipolar patients.

Definition

ChEBI: Uridine triacetate is an acetate ester that is uracil in which the three hydroxy hydrogens are replaced by acetate group. A prodrug for uridine, it is used for the treatment of hereditary orotic aciduria and for management of fluorouracil toxicity. It has a role as a prodrug, a neuroprotective agent and an orphan drug. It is a member of uridines and an acetate ester.

Synthesis

Commercially available uridine (167) was treated with acetic anhydride in the presence of catalytic boron trifluoride-etherate, and the crude product was recrystallized from ethanol to give uridine triacetate (XX) in 74-78% yield.

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