N4-Acetylcytidine

Base Information

• Chemical Name: N4-Acetylcytidine
• CAS No.: 3768-18-1
• Molecular Formula: C11H15N3O6
• Molecular Weight: 285.257
• Hs Code.: 29335990
• European Community (EC) Number: 223-195-6
• DSSTox Substance ID: DTXSID40958718
• Nikkaji Number: J130.843B
• Wikidata: Q20890503
• Metabolomics Workbench ID: 38788
• Mol file: 3768-18-1.mol

Synonyms:Acetamide,N-(1,2-dihydro-2-oxo-1-b-D-ribofuranosyl-4-pyrimidinyl)- (8CI);4-Acetylcytidine;N-Acetylcytidine;

Chemical Property of N4-Acetylcytidine

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Melting Point: 199 °C (dec.)(lit.)
• Refractive Index: 1.698
• PKA: 10.21±0.20(Predicted)
• PSA: 133.91000
• Density: 1.72 g/cm³
• LogP: -2.11380
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 285.09608521
• Heavy Atom Count: 20
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

N4-Acetylcytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-36/37/39-26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: CC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
• Description: N4-Acetylcytidine is a modified nucleoside and endogenous urinary nucleoside product of the degradation of tRNA. N4-Acetylcytidine is a biological marker for various cancers with elevated concentrations present in urine. tRNA has been shown to be excreted in abnormal amounts in the urine of cancer patients. tRNA from neoplastic tissue had a much more rapid turnover rate than the tRNA from the corresponding normal tissue. Evidence indicates that methylation of tRNA occurs only after synthesis of the intact macromolecule. Because there are no specific enzyme systems to incorporate the modified nucleosides into the macromolecular nucleic acid, these nucleosides once released in the process of tRNA turnover cannot be reutilized, nor are they further degraded, but are excreted in urine.N4-Acetylcytidine is also a partially protected cytidine and therefore can be used as a synthetic building block to prepare further derivatized nucleosides such as 2’,3’-dideoxycytidine.
• Uses: N4-Acetylcytidine (cas# 3768-18-1) is a nucleotide-derived metabolite used as biomarkers for diagnosis of inflammation-related diseases.

Technology Process of N4-Acetylcytidine

There total 8 articles about N4-Acetylcytidine 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%

CYTIDINE (65-46-3) → N-acetylcytidine (3768-18-1)

Guidance literature:

With tiolacetic acid; In pyridine; at 50 ℃; for 4h;

DOI:10.1016/0040-4039(91)85095-M

Reference yield: 96.0%

acetic anhydride (108-24-7) + CYTIDINE (65-46-3) → N-acetylcytidine (3768-18-1)

Guidance literature:

In N,N-dimethyl-formamide; for 0.0111111h; Irradiation;

DOI:10.1016/S0040-4039(97)01684-5

Reference yield: 93.0%

acetic acid (64-19-7,77671-22-8) + CYTIDINE (65-46-3) → N-acetylcytidine (3768-18-1)

Guidance literature:

acetic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In dichloromethane; at 20 ℃;

CYTIDINE; In dichloromethane; N,N-dimethyl-formamide; at 20 - 50 ℃;

DOI:10.5012/bkcs.2010.31.7.2061

upstream raw materials:

acetyl chloride

O^2'_,O3'_,O5'-tris-trimethylsilanyl-cytidine

acetic anhydride

CYTIDINE

Downstream raw materials:

4-N-2',3',5'-O-tetraacetylcytidine

5'-O-DMTr-2'-O-TBDMS-N4-acetylcytidine

2-Acetoxy-benzoic acid (2S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

2'-Deoxycytidine

Refernces

• 1、 Ohashi et al.. "-". . p. 209,211, 212. Retrieved 1972.
• 2、 Kuboki, Atsuhito,Ishihara, Takashi,Kobayashi, Eiko,Ohta, Hiromichi,Ishii, Takeshi,Inoue, Ayumu,Mitsuda, Satoshi,Miyazaki, Tatsuo,Kajihara, Yasuhiro,Sugai, Takeshi. "Synthesis of regioselectively protected forms of cytidine based on enzyme-catalyzed deacetylation as the key step". . p. 363 - 368. Retrieved 2000.
• 3、 -. "Preparation method of 3'-deoxyuridine". Paragraph 0033; 0034; 0035; 0036. . Retrieved 2017/09/02.
• 4、 Rode, Ambadas B.,Son, Sang Jun,Hong, In Seok. "An efficient one-pot N-acylation of deoxy- and ribo-cytidine using carboxylic acids activated in situ with 2-chloro-4,6-dimethoxy-1,3,5-triazine". experimental part. p. 2061 - 2064. Retrieved 2010/11/19.