Uridine

Base Information

• Chemical Name: Uridine
• CAS No.: 3083-77-0
• Deprecated CAS: 12693-39-9,68184-15-6
• Molecular Formula: C9H12N2O6
• Molecular Weight: 244.204
• Hs Code.: 29349990
• European Community (EC) Number: 221-386-9,200-407-5
• UNII: WHI7HQ7H85
• DSSTox Substance ID: DTXSID40891555
• Nikkaji Number: J4.593D
• Wikipedia: Uridine
• Wikidata: Q422573
• NCI Thesaurus Code: C922
• RXCUI: 11017
• Metabolomics Workbench ID: 37190
• ChEMBL ID: CHEMBL100259
• Mol file: 3083-77-0.mol

Synonyms:Allo Uridine;Allo-Uridine;Allouridine;Uridine

Chemical Property of Uridine

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: 220-222 °C
• Refractive Index: 1.643
• PKA: pK1:9.30 (25°C)
• PSA: 124.78000
• Density: 1.674 g/cm³
• LogP: -2.85190
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 244.06953611
• Heavy Atom Count: 17
• Complexity: 371

Purity/Quality:

99% ^*data from raw suppliers

Uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Recent ClinicalTrials: Clinical and Imaging Trial of Uridine for Veterans With Suicidal Ideation
• Description: 1-β-D-Arabinofuranosyluracil (ara-U) is an inactive metabolite of cytarabine . Ara-U is formed when cytarabine undergoes deamination by cytidine deaminase.
• Uses: Antiviral agent.1-β-D-Arabinofuranosyluracil is used for the treatment of severe acute respiratory syndrome (SARS).

Technology Process of Uridine

There total 57 articles about Uridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,2'-Anhydrouridine (3736-77-4) → araU (3083-77-0)

Guidance literature:

With hydrogenchloride; In methanol; water; at 50 ℃; for 24h; under 760.051 Torr;

Reference yield: 99.0%

arabinosyl cytosine (147-94-4) → araU (3083-77-0)

Guidance literature:

With cytidine deaminase enzyme; In aq. phosphate buffer; at 37 ℃; for 0.0833333h; pH=7; Enzymatic reaction;

Reference yield: 96.0%

(2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one (31501-46-9) → 1-(β-L-arabinofuranosyl)-uracil (58-96-8,3083-77-0,3258-07-9,3565-16-0,4348-60-1,4348-61-2,4348-71-4,4401-72-3,4433-38-9,16535-78-7,20289-55-8,20289-61-6,24259-58-3,26287-69-4,26524-61-8,36684-86-3,40093-89-8,41545-81-7,41545-82-8)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(94)00997-9

upstream raw materials:

2,2'-Anhydrouridine

diiminosuccinonitrile

uridine-5'-monophosphate sodium

5-iodouridine

Downstream raw materials:

5'-O-monomethoxytrityl-3'-O-tert-butyldimethylsilylarabinouridine

1-{(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione

1-(2,3,5-tri-O-p-toluyl-β-D-arabinofuranosyl)uracil

uracil

Refernces

• 1、 FOX,WEMPEN. "NUCLEOSIDES. XXVI. A FACILE SYNTHESIS OF 2,2' -ANHYDRO-ARABINO". . p. 643 - 646. Retrieved 1965.
• 2、 Ozaki, Hiroaki,Nakajima, Kiyohiro,Tatsui, Kaoru,Izumi, Chieko,Kuwahara, Masayasu,Sawai, Hiroaki. "Convenient synthesis of oligodeoxyribonucleotides bearing arabinofuranosyl pyrimidine derivatives and its duplex formation with complementary DNA". . p. 2441 - 2443. Retrieved 2003.
• 3、 Smirnov,Zav'yalov,Eremin. "A comparative study of the kinetics of cytarabine hydrolytic deamination in aqueous solutions". . p. 451 - 454. Retrieved 2000.
• 4、 -. "MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF". Page/Page column 83; 86. . Retrieved 2021/02/19.
• 5、 Adluri, Bharanishashank,Britton, Robert,Campeau, Louis-Charles,Cohen, Ryan,Lehmann, Johannes,Meanwell, Michael,Silverman, Steven M.,Wang, Yang. "A short de novo synthesis of nucleoside analogs". . p. 725 - 730. Retrieved 2020/09/02.