Cytidine

Base Information

• Chemical Name: Cytidine
• CAS No.: 65-46-3
• Deprecated CAS: 4395-95-3,494210-74-1,873077-03-3
• Molecular Formula: C9H13N3O5
• Molecular Weight: 243.219
• Hs Code.: 2933.59
• European Community (EC) Number: 200-610-9
• UNII: 5CSZ8459RP
• DSSTox Substance ID: DTXSID60891552
• Nikkaji Number: J4.837B
• Wikipedia: Cytidine
• Wikidata: Q422538
• NCI Thesaurus Code: C409
• Metabolomics Workbench ID: 37069
• ChEMBL ID: CHEMBL95606
• Mol file: 65-46-3.mol

Synonyms:Cytidine;Cytosine Ribonucleoside;Cytosine Riboside;Ribonucleoside, Cytosine;Riboside, Cytosine

Chemical Property of Cytidine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 3.5E-14mmHg at 25°C
• Melting Point: 210-217 °C
• Refractive Index: 34 ° (C=0.7, H2O)
• Boiling Point: 545.7 °C at 760 mmHg
• PKA: 4.22, 12.5(at 25℃)
• Flash Point: 283.8 °C
• PSA: 130.83000
• Density: 1.89 g/cm³
• LogP: -1.98180
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: SOLUBLE
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.08552052
• Heavy Atom Count: 17
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

Cytidine 99+% ^*data from reagent suppliers

Safty Information:

• Statements: 68
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Recent ClinicalTrials: Cytidine- and Creatine-Containing Drug in Treating Bipolar Depression
• Recent NIPH Clinical Trials: A study of pharmacokinetic analysis of capecitabine and cytidine deaminase activity
• Description: Cytidine is a pyrimidine nucleoside that is composed of the pyrimidine base cytosine attached to the sugar ribose. As a constituent of RNA, cytidine pairs with guanine, and it is a precursor of uridine. Cytidine can incur several modifications in mRNA, including methylation and acetylation, that function to regulate translation. Cytidine can also be formylated to 5-formylcytidine in mitochondrial methionine transfer RNA (tRNAMet).
• Uses: Cytidine is a nucleoside molecule that is formed when cytosine is attached to a ribose ring, cytidine is a component of RNA. It was isolated from yeast nucleic acid. It can increases cell membrane phospholipids. Cytidine is used to synthesize enzyme inhibitors, antiviral agents, and anticancer agents. And also used as constituent of nucleic acids.

Technology Process of Cytidine

There total 179 articles about Cytidine 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:

highly polymerized dsDNA from salmon testes → protoanemonin (108-28-1) + furfural (98-01-1) + Malondialdehyde (542-78-9) + N-oxycarbonylmethyl-5-methylene-Δ3-pyrrolin-2-one + G (118-00-3) + CYTIDINE (65-46-3) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + adenosine (58-61-7)

Guidance literature:

With carbonatopentamminecobalt(III) nitrate hemihydrate; In aq. phosphate buffer; at 20 ℃; for 0.133333h; pH=6.9; UV-irradiation;

DOI:10.3109/10715762.2015.1081187

Reference yield:

5'-CGGCUXUUAACCGA-3', X=2-deoxouridine → G (118-00-3) + 1-(β-D-ribofuranosyl)-4-pyrimidinone (21052-20-0) + uridine (58-96-8) + CYTIDINE (65-46-3) + adenosine (58-61-7)

Guidance literature:

5'-CGGCUXUUAACCGA-3', X=2-deoxouridine; With 1U P₁ nuclease; In aq. buffer; at 37 ℃; for 16h; pH=7; Enzymatic reaction;

With 2U alkaline phosphatase; In aq. buffer; at 37 ℃; for 1h; Enzymatic reaction;

DOI:10.1016/j.bmcl.2015.06.019

Reference yield:

sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate → C17H24F2N8O5 + G (118-00-3) + uridine (58-96-8) + CYTIDINE (65-46-3) + adenosine (58-61-7)

Guidance literature:

sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate; Oceanobacillus iheyensis group II intron RNA; pH=6.5;

With tert.-butylhydroperoxide; In water; at 22 ℃; for 24h; Cooling with ice;

Enzymatic reaction;

upstream raw materials:

N⁴-acetyl-O^2'_,O3'_,O5'-tribenzoyl-cytidine

1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-4-thiouracil

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

N⁴-octanoylcytosine

Downstream raw materials:

Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester

(3aS)-3c-benzoyloxy-2t-hydroxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine

(3aS)-3c-[11-(toluene-4-sulfonylamino)-undecanoyloxy]-2t-[11-(toluene-4-sulfonylamino)-undecanoyloxymethyl]-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine

(3aS)-3c-[N-(toluene-4-sulfonyl)-β-alanyloxy]-2t-[N-(toluene-4-sulfonyl)-β-alanyloxymethyl]-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine

Refernces

• 1、 Wright et al.. "-". . p. 1898. Retrieved 1951.
• 2、 Bamann,Trapmann. "-". . p. 237,239. Retrieved 1954.
• 3、 Ahmed, Ajaz,Ahmed, Qazi Naveed,Mukherjee, Debaraj. "Conversion of: N- acyl amidines to amidoximes: A convenient synthetic approach to molnupiravir (EIDD-2801) from ribose". . p. 36143 - 36147. Retrieved 2021/12/04.
• 4、 Xie, Li-Jun,Yang, Xiao-Ti,Wang, Rui-Li,Cheng, Hou-Ping,Li, Zhi-Yan,Liu, Li,Mao, Lanqun,Wang, Ming,Cheng, Liang. "Identification of Flavin Mononucleotide as a Cell-Active Artificial N6-Methyladenosine RNA Demethylase". supporting information. p. 5028 - 5032. Retrieved 2019/03/17.