ChemicalBook > CAS DataBase List > 2',3',5'-Tri-O-acetyluridine

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

Product Name
2',3',5'-Tri-O-acetyluridine
CAS No.
4105-38-8
Chemical Name
2',3',5'-Tri-O-acetyluridine
Synonyms
TAU;Uridine triacetate;(2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate;MAPTL;MTBT1;RG 2133;Vistonuridine;2',3',5'-TriacetyL;Tri-O-acetyl uridine;2',3',5'-Tri-O-acety
CBNumber
CB0687805
Molecular Formula
C15H18N2O9
Formula Weight
370.31
MOL File
4105-38-8.mol
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2',3',5'-Tri-O-acetyluridine Property

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
biological source
synthetic (organic)
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

Safety Statements 
24/25
WGK Germany 
3
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SAB1306711
Product name
ANTI-TAU(C-TERMINAL) antibody produced in rabbit
Purity
IgG fraction of antiserum, buffered aqueous solution
Packaging
400μL
Price
$481
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB1306682
Product name
ANTI-TAU (MAPT) (S720) antibody produced in rabbit
Purity
affinity isolated antibody, buffered aqueous solution
Packaging
400μL
Price
$481
Updated
2024/03/01
Sigma-Aldrich
Product number
S451738
Product name
2'',3'',5''-TRIACETYLURIDINE
Purity
AldrichCPR
Packaging
250MG
Price
$179
Updated
2024/03/01
TCI Chemical
Product number
T2549
Product name
2',3',5'-Tri-O-acetyluridine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$28
Updated
2024/03/01
TCI Chemical
Product number
T2549
Product name
2',3',5'-Tri-O-acetyluridine
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$90
Updated
2024/03/01
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2',3',5'-Tri-O-acetyluridine Chemical Properties,Usage,Production

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.

Research

Administration of 200 mg/kg of 5-fluorouracil (FUra) to mice bearing human colon carcinoma DLD-1 xenografts resulted in 100% mortality. Oral administration of 2000 mg/kg of 2‘,3’,5‘-tri-O-acetyluridine (TAU), a prodrug of uridine, in combination with 120 mg/kg of 5-(benzyloxy benzyl)barbituric acid acyclonucleoside (BBBA), the most potent known inhibitor of uridine phosphorylase (UrdPase, EC 2.4.2.3), 2 hr after the administration of the same dose of FUra completely protected the mice (100% survival) from the toxicity of FUra. This combination also reduced tumor weight by 67% compared with 46% achieved by the maximum tolerated dose (50 mg/kg) of FUra alone. Similarly, administration of BBBA plus TAU 1 hr before or 4 hr after the administration of FUra reduced the tumor weight by 53 and 37%, respectively. TAU alone did not protect from FUra host toxicity. The efficiency of the BBBA plus TAU combination in rescuing from FUra host toxicities is attributed to the exceptional effectiveness of this combination in raising and maintaining higher plasma uridine concentrations than those achieved by TAU alone or by equimolar doses of uridine. The present results suggest that the BBBA plus TAU combination can provide a better substitute for the massive doses of uridine required to achieve the high levels of uridine necessary to rescue or protect from FUra host toxicities without the toxic side-effects associated with such doses of uridine[2].

References

[1] E.D. Gudio, M.L. Ferreira, L.E. Iglesias . “A rational approach to the regioselective deacetylation of 2′,3′,5′-tri-O-acetyluridine by Novozym 435 catalysed alcoholysis.” Biochimica et biophysica acta. Proteins and proteomics 1824 4 (2012): Pages 627-636.
[2] Osama M Ashour . “Modulation of 5-fluorouracil host toxicity by 5-(benzyloxybenzyl)barbituric acid acyclonucleoside, a uridine phosphorylase inhibitor, and 2′,3′,5′-tri-O-acetyluridine, a prodrug of uridine.” Biochemical pharmacology 60 3 (2000): Pages 427-431.

2',3',5'-Tri-O-acetyluridine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2',3',5'-Tri-O-acetyluridine manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
2',3',5'-Tri-O-acetyluridine 4105-38-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-06-26
WUHAN FORTUNA CHEMICAL CO., LTD
Product
2',3',5'-Tri-O-acetyluridine 4105-38-8
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min HPLC
Supply Ability
100kg
Release date
2021-08-06
Guangzhou Tengyue Chemical Co., Ltd.
Product
2',3',5'-Tri-O-acetyluridine; Uridine Triacetate 4105-38-8
Price
US $830.00-590.00/kg
Min. Order
1kg
Purity
99% Purity (What/sapp: +86 18145728414)
Supply Ability
1000 Tons/Month
Release date
2023-06-30

4105-38-8, 2',3',5'-Tri-O-acetyluridineRelated Search:

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

  • 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
  • ANTI-TAU(C-TERMINAL) antibody produced in rabbit
  • MAPTL
  • Microtubule-associated protein tau
  • MTBT1
  • ANTI-TAU (MAPT) (S720) antibody produced in rabbit
  • [4-acetoxy-2-(acetoxymethyl)-5-(2,4-dioxopyrimidin-1-yl)tetrahydrofuran-3-yl] acetate
  • [4-acetyloxy-2-(acetyloxymethyl)-5-(
  • [4-acetyloxy-2-(acetyloxymethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  • 2-(acetoxymethyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  • 2-[(acetyloxy)methyl]-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  • acetic acid [4-acetoxy-2-(acetoxymethyl)-5-(2,4-diketopyrimidin-1-yl)tetrahydrofuran-3-yl] ester
  • acetic acid [4-acetoxy-2-(acetoxymethyl)-5-(2,4-dioxo-1-pyrimidinyl)-3-tetrahydrofuranyl] ester
  • 1-((2R,3R,4R,5R)-3,4-Diacetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)tetrahydrofuran-2-yl)pyri
  • (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4
  • 2',3',5'-tri-O-Acetyluridine≥ 98% (HPLC)
  • TAU
  • URIDINE 2',3',5'-TRIACETATE
  • 1-(2-O,3-O,5-O-Triacetyl-β-D-ribofuranosyl)-4-hydroxypyrimidine-2(1H)-one
  • [(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
  • [(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] ethanoate
  • acetic acid [(2R,3R,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-(2,4-diketopyrimidin-1-yl)tetrahydrofuran-3-yl] ester
  • 2',3',5'-Tri-O-acety
  • [(2S,3R,4S,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyriMidin-1-yl)oxolan-2-yl]Methyl acetate
  • 2',3',5'-Tri0acetyluridine
  • 2`,3`,5`-Tracetyluridine
  • 2',3',5'-Tri-O-acetyl-D-uridine
  • 2'', 3'', 5''-TRIACETYLURIDINE (2'', 3'', 5''-TRI-O-ACETYLURIDINE)
  • (Ser232) BioAssay&trade
  • Phospho-14-3-3 &theta
  • phosphorylated (S232)
  • 2',3',5'-TriacetyL
  • 2',3',5'-Tri-O-acetyluridine USP/EP/BP
  • 2',3',5'-Tri-O-acetyluridine
  • 2',3',5'-Triacetyluridine
  • Mouse Anti-Tau antibody
  • Uridine triacetate, 10 mM in DMSO
  • 4105-38-8
  • 4105-38-3
  • C15H18N2O9
  • Biochemicals and Reagents
  • BioChemical
  • Nucleoside Analogs
  • Nucleosides, Nucleotides, Oligonucleotides