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

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

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;MTBT1;MAPTL;RG 2133;Vistonuridine;2',3',5'-TriacetyL;Tri-O-acetyl uridine;2',3',5'-Tri-O-acety

CBNumber:: CB0687805

Molecular Formula:: C15H18N2O9

Molecular Weight:: 370.31

MDL Number:: MFCD00023795

MOL File:: 4105-38-8.mol

Last updated:2024-08-21 22:41:43

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2',3',5'-Tri-O-acetyluridine 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)
EWG's Food Scores	1
NCI Dictionary of Cancer Terms	uridine triacetate
FDA UNII	2WP61F175M
NCI Drug Dictionary	uridine triacetate
ATC code	A16AX13

SAFETY

Risk and Safety Statements

Safety Statements	24/25
WGK Germany	3
HS Code	29349990

2',3',5'-Tri-O-acetyluridine price More Price(38)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	SAB1306711	ANTI-TAU(C-TERMINAL) antibody produced in rabbit IgG fraction of antiserum, buffered aqueous solution	4105-38-8	400μL	$481	2024-03-01	Buy
Sigma-Aldrich	SAB1306682	ANTI-TAU (MAPT) (S720) antibody produced in rabbit affinity isolated antibody, buffered aqueous solution	4105-38-8	400μL	$481	2024-03-01	Buy
Sigma-Aldrich	S451738	2'',3'',5''-TRIACETYLURIDINE AldrichCPR	4105-38-8	250MG	$179	2024-03-01	Buy
TCI Chemical	T2549	2',3',5'-Tri-O-acetyluridine >98.0%(HPLC)(T)	4105-38-8	5g	$28	2024-03-01	Buy
TCI Chemical	T2549	2',3',5'-Tri-O-acetyluridine >98.0%(HPLC)(T)	4105-38-8	25g	$90	2024-03-01	Buy

Product number	Packaging	Price	Buy
SAB1306711	400μL	$481	Buy
SAB1306682	400μL	$481	Buy
S451738	250MG	$179	Buy
T2549	5g	$28	Buy
T2549	25g	$90	Buy

2',3',5'-Tri-O-acetyluridine Chemical Properties,Uses,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.
Synthesis_4105-38-8

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 synthesis

Synthesis of 2',3',5'-Tri-O-acetyluridine from 1-Acetylimidazole and Uridine

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

Raw materials

1-beta-D-Arabinofuranosyluracil Acetic anhydride

Preparation Products

5-Bromouridine 3-METHYL URIDINE

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

Global( 312)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Wuhu Nuowei chemistry Co., Ltd.	+86-0553-2911116-802 +undefined17756524438	sales1@nuowei-chem.com	China	1640	58
Hangzhou Measure Life Technology Co., LTD	+8613343730176	2924244016@qq.com	China	83	58
Chongqing Chemdad Co., Ltd	+86-023-6139-8061 +86-86-13650506873	sales@chemdad.com	China	39916	58
Hebei Mojin Biotechnology Co., Ltd	+86 13288715578 +8613288715578	sales@hbmojin.com	China	12446	58
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	sales1@chuanghaibio.com	China	5882	58
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29798	60
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	18628	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21667	55
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29888	58
Accela ChemBio Inc.	+1-858-6993322	info@accelachem.com	United States	19536	58

Supplier	Advantage
Wuhu Nuowei chemistry Co., Ltd.	58
Hangzhou Measure Life Technology Co., LTD	58
Chongqing Chemdad Co., Ltd	58
Hebei Mojin Biotechnology Co., Ltd	58
Hebei Chuanghai Biotechnology Co,.LTD	58
Capot Chemical Co.,Ltd.	60
Shanghai Daken Advanced Materials Co.,Ltd	58
Henan Tianfu Chemical Co.,Ltd.	55
career henan chemical co	58
Accela ChemBio Inc.	58

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-09-19	2',3',5'-Tri-O-acetyluridine 4105-38-8	US $10.50-10.50 / KG	1KG	99%	10 ton	Hebei Chuanghai Biotechnology Co,.LTD
2024-09-18	2',3',5'-Tri-O-acetyluridine 4105-38-8	US $0.00 / Kg/Drum	1KG	98%min HPLC	100kg	WUHAN FORTUNA CHEMICAL CO., LTD
2024-04-23	uridine triacetate 4105-38-8	US $1.00 / KG	1KG	99.91%	200000	Ouhuang Engineering Materials (Hubei) Co., Ltd

2',3',5'-Tri-O-acetyluridine
4105-38-8
US $10.50-10.50 / KG
99%
Hebei Chuanghai Biotechnology Co,.LTD

2',3',5'-Tri-O-acetyluridine
4105-38-8
US $0.00 / Kg/Drum
98%min HPLC
WUHAN FORTUNA CHEMICAL CO., LTD

uridine triacetate
4105-38-8
US $1.00 / KG
99.91%
Ouhuang Engineering Materials (Hubei) Co., Ltd

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

2',3',5'-Tri-O-acetyluridine(4105-38-8)¹HNMR 2',3',5'-Tri-O-acetyluridine(4105-38-8)IR

4105-38-8(2',3',5'-Tri-O-acetyluridine)Related Search:

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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

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2'', 3'', 5''-TRIACETYLURIDINE (2'', 3'', 5''-TRI-O-ACETYLURIDINE) RG 2133 Tri-O-acetyl uridine 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 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) 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 (Ser232) BioAssay&trade Phospho-14-3-3 &theta phosphorylated (S232) 2',3',5'-TriacetyL 2',3',5'-Tri-O-acetyluridine USP/EP/BP Uridine triacetate (2R,3R,4R,5R)-2-(AcetoxyMethyl)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate TAU 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