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

China 254 Europe 3 Germany 3 India 4 Japan 1 Russia 1 Switzerland 1 United Kingdom 11 United States 36 Global 314

chemcube

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

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

Hebei Weibang Biotechnology Co., Ltd

Product: 2',3',5'-Tri-O-acetyluridine 4105-38-8
Price: US $10.00/KG
Min. Order: 100KG
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-22

Wuhan Nutra Biotechnology Co.,Ltd

Product: TAU;2',3',5'-Tri-O-acetyluridine 4105-38-8
Price: US $0.00-0.00/g
Min. Order: 100g
Purity: 98%+
Supply Ability: 100kgs
Release date: 2021-05-21

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

2',3',5'-TRI-O-ACETYLURIDINE

2',3',5'-TRIACETYLURIDINE

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

Mouse Anti-Tau antibody

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

2',3',5'-Triacetyluridine

4105-38-8

4105-38-3

C15H18N2O9

Biochemicals and Reagents

BioChemical

Nucleoside Analogs

Nucleosides, Nucleotides, Oligonucleotides