5-Hydroxycytidine

Base Information

• Chemical Name: 5-Hydroxycytidine
• CAS No.: 39638-73-8
• Molecular Formula: C₉H₁₃N₃O₆
• Molecular Weight: 259.219
• DSSTox Substance ID: DTXSID80960259
• Nikkaji Number: J2.148.949B
• Wikidata: Q82941385
• ChEMBL ID: CHEMBL217770
• Mol file: 39638-73-8.mol

Synonyms:5-Hydroxycytidine;Cytidine, 5-hydroxy-;39638-73-8;CCRIS 8241;CHEMBL217770;SCHEMBL1138717;DTXSID80960259;LS-59074;4-Imino-1-pentofuranosyl-1,4-dihydropyrimidine-2,5-diol

Chemical Property of 5-Hydroxycytidine

Chemical Property:

• Vapor Pressure: 4.51E-16mmHg at 25°C
• Boiling Point: 584°Cat760mmHg
• Flash Point: 307°C
• PSA: 151.06000
• Density: 2.06g/cm³
• LogP: -2.27620
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 259.08043514
• Heavy Atom Count: 18
• Complexity: 423

Purity/Quality:

97% ^*data from raw suppliers

5-HYDROXYCYTIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=O)N1C2C(C(C(O2)CO)O)O)N)O
• Isomeric SMILES: C1=C(C(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)O

Technology Process of 5-Hydroxycytidine

There total 6 articles about 5-Hydroxycytidine 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: 64.0%

CYTIDINE (65-46-3) → 5-hydroxycytidine (58461-29-3,39638-73-8)

Guidance literature:

CYTIDINE; With water; bromine; at 0 ℃;

With 2,4,6-trimethyl-pyridine; at 40 ℃; for 2h;

DOI:10.1093/nar/gkr673

Reference yield:

5-bromocytidine (3066-86-2,17676-66-3) → 5-bromouridine (957-75-5) + 5-hydroxycytidine (58461-29-3,39638-73-8)

Guidance literature:

With sodium hydroxide; at 90.1 ℃; Rate constant; Mechanism; various reagent concentration;

Reference yield:

5-hydroxyuridine-5'-triphosphate → 5-hydroxycytidine (58461-29-3,39638-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: adenylate kinase; CTP synthetase; dATP; kanamycin; creatine phosphate; DL-dithiothreitol; ampicillin; ammonium chloride; 2'-deoxyadenosine-5'-monophosphoric acid; creatine phosphokinase / water / 24 h / pH 8.5 / Enzymatic reaction

2: calf intestinal alkaline phosphatase; zinc acetate dehydrate; magnesium chloride / water / 24 h / pH 9.5 / Enzymatic reaction

With calf intestinal alkaline phosphatase; adenylate kinase; DL-dithiothreitol; zinc acetate dehydrate; CTP synthetase; creatine phosphate; dATP; kanamycin; ampicillin; ammonium chloride; 2'-deoxyadenosine-5'-monophosphoric acid; magnesium chloride; creatine phosphokinase; In water;

DOI:10.1007/s13361-011-0126-8

upstream raw materials:

5-bromocytidine

CYTIDINE

5-hydroxycytidine-5'-triphosphate

α-arabinofuranose

Downstream raw materials:

C₃₇H₃₆N₄O₁₀

C₄₀H₄₁N₅O₁₀

C₄₆H₅₅N₅O₁₀Si

C₄₆H₅₅N₅O₁₀Si

Refernces

• 1、 -. "SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS". . . Retrieved 2019/01/15.
• 2、 K?ppi,L?nnberg. "Reactions of 5-bromo substituted pyrimidine nucleosides with aqueous alkalies: kinetics and mechanisms.". . p. 768 - 775. Retrieved 2007/10/02.