Uridine

Base Information

• Chemical Name: Uridine
• CAS No.: 58-96-8
• Deprecated CAS: 12693-39-9,68184-15-6
• Molecular Formula: C9H12N2O6
• Molecular Weight: 244.204
• Hs Code.: 2933.59
• 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: 58-96-8.mol

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

Chemical Property of Uridine

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 163-167 °C(lit.)
• Refractive Index: 9 ° (C=2, H2O)
• Boiling Point: 387.12°C (rough estimate)
• PKA: 9.39±0.10(Predicted)
• PSA: 124.78000
• Density: 1.675 g/cm³
• LogP: -2.85190
• Storage Temp.: Keep Cold
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: Soluble in water, dimethylsulfoxide, and methanol.
• 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 99+% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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
• Sources: Derived from animals or plants. Naturally present in blood and cerebrospinal fluid.^[1]
• Chemical Composition and Structure: Uridine consists of uracil, a pyrimidine base, and ribose, a sugar molecule.^[2]
• Uses: Used as a component of nucleosides and nucleotides.; Essential for RNA synthesis, contributes to reduction of cytotoxicity, suppression of hepatic steatosis, and supports glycolysis in nutrient-limited conditions. Regulates inflammation, oxidative stress, and metabolic homeostasis.^[3][4]
• References: [1] Uridine Metabolism and Its Role in Glucose, Lipid, and Amino Acid Homeostasis>br/>DOI 10.1155/2020/7091718; [2] Uridine natural products: Challenging targets and inspiration for novel small molecule inhibitors; DOI 10.1016/j.bmc.2020.115661; [3] Salvage of ribose from uridine or RNA supports glycolysis in nutrient-limited conditions; DOI 10.1038/s42255-023-00774-2; [4] Intestinal aging is alleviated by uridine via regulating inflammation and oxidative stress in vivo and in vitro; DOI 10.1080/15384101.2022.2055252

Technology Process of Uridine

There total 298 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: 99.0%

CYTIDINE (65-46-3) → uridine (58-96-8)

Guidance literature:

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

Reference yield: 99.0%

2'-O-allyluridine (133766-24-2) → uridine (58-96-8)

Guidance literature:

With quinoline-2-carboxylic acid; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; In methanol; at 30 ℃;

DOI:10.1021/ol0493397

Reference yield: 98.0%

5'-O-trityluridine (6554-10-5) → uridine (58-96-8)

Guidance literature:

With ammonium cerium(IV) nitrate; silica gel; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1021/jo000024o

upstream raw materials:

C₁₈H₂₃N₅O₁₃P^(1-)

2',3',5'-tri-O-acetyl-uridine

[(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate

Tri-O-acetyluridine

Downstream raw materials:

Tri-O-acetyluridine

(R)-2',3'-O-benzylideneuridine

tribenzoyl uridine

3'-O-methyluridine

Refernces

• 1、 Oivanen, Mikko,Ora, Mikko,Almer, Helena,Stroemberg, Roger,Loennberg, Harri. "Hydrolytic Reactions of the Diastereomeric Phosphoromonothioate Analogs of Uridyl(3',5')uridine: Kinetics and Mechanisms for Desulfurization, Phosphoester Hydrolysis, and Transesterification to the 2',5'-Isomers". . p. 5620 - 5627. Retrieved 1995.
• 2、 Ora,Oivanen,Lonnberg. "Hydrolysis and desulfurization of the diastereomeric phosphoromonothioate analogs of uridine 2',3'-cyclic monophosphate". . p. 3951 - 3955. Retrieved 1996.
• 3、 Elzagheid, Mohamed,Oivanen, Mikko,Colin,Jones,Cosstick, Richard,Loennberg, Harri. "Hydrolytic reactions of an RNA dinucleotide containing a 3'-S- phosphorothiolate linkage". . p. 1265 - 1266. Retrieved 1999.
• 4、 Li, Yao,Ludford, Paul T.,Tor, Yitzhak,Yang, Shenghua. "Cytidine deaminase can deaminate fused pyrimidine ribonucleosides". . p. 6237 - 6243. Retrieved 2021.
• 5、 Jiao, Ping,Mudur, Sanjay V.,Gloer, James B.,Wicklow, Donald T.. "Kipukasins, nucleoside derivatives from Aspergillus versicolor". . p. 1308 - 1311. Retrieved 2007.
• 6、 Markiewicz, Wojciech T.,Nowakowska, Bozena,Adrych, Katarzyna. "TETRA-t-BUTOXYDISILOXANE-1,3-DIYL, A NEW TYPE OF BIFUNCTIONAL SILYL PROTECTIVE GROUP". . p. 1561 - 1564. Retrieved 1988.
• 7、 Birmingham, William R.,Burke, Ashleigh J.,Charnock, Simon J.,Crawshaw, Rebecca,Finnigan, James D.,Green, Anthony P.,Holgate, Gregory M.,Lovelock, Sarah L.,Muldowney, Mark P.,Rowles, Ian,Thorpe, Thomas W.,Turner, Nicholas J.,Young, Carl,Zhuo, Ying,Zucoloto Da Costa, Bruna. "An Engineered Cytidine Deaminase for Biocatalytic Production of a Key Intermediate of the Covid-19 Antiviral Molnupiravir". supporting information. p. 3761 - 3765. Retrieved 2022/03/15.
• 8、 Smiley-Moreno, Elizabeth,Smith, Douglas,Yu, Jieh-Juen,Cao, Phuong,Arulanandam, Bernard P.,Chambers, James P.. "Biochemical characterization of a recombinant acid phosphatase from Acinetobacter baumannii". . . Retrieved 2021/06/09.