2',3',5'-Tri-O-acetyluridine
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
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)
Safety Information
- Safety Statements
- 24/25
- WGK Germany
- 3
- HS Code
- 29349990
MSDS
- Language:English Provider:SigmaAldrich
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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2',3',5'-Tri-O-acetyluridine(4105-38-8)Related Product Information
- 1-beta-D-Arabinofuranosyluracil
- Doxifluridine
- Floxuridine
- Sodium triacetoxyborohydride
- Trifluridine
- 2',3',5'-Triacetylguanosine
- uridine diphosphate glucose {= UDP-glucose}
- 2',3',5'-TRI-O-BENZOYLURIDINE
- Diethyleneglycol diformate
- 2'-Deoxyuridine
- 2'-O-Methyluridine
- (2-ISOPROPOXYETHYL) ACETATE
- TETRAHYDROFURFURYL ACETATE
- Uridine
- Diethyleneglycol diacetate
- Uracil
- 3'-DEOXYURIDINE
- 1-amino-3-methoxy-propan-2-ol