10578-79-7

Basic information

• Product Name: N(4)-methylcytidine
• Synonyms: N(4)-methylcytidine;Nsc518744;Cytidine, N-Methyl-;4-Methylcytidine;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(methylamino)pyrimidin-2-one
• CAS NO: 10578-79-7
• Molecular Formula: C₁₀H₁₅N₃O₅
• Molecular Weight: 257.2432
• Mol File: 10578-79-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 202-203 °C(Solv: ethanol (64-17-5))
• Boiling Point: 504.2°Cat760mmHg
• Flash Point: 258.7°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 2.82E-12mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 13.48±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: N(4)-methylcytidine(CAS DataBase Reference)
• NIST Chemistry Reference: N(4)-methylcytidine(10578-79-7)
• EPA Substance Registry System: N(4)-methylcytidine(10578-79-7)

Safety Data

• Hazardous Substances Data: 10578-79-7(Hazardous Substances Data)

Usage

General Description

N(4)-methylcytidine (m4C) is a modified nucleoside that is found in RNAs, and is particularly abundant in transfer RNAs (tRNAs). It is a product of cytidine methylation, a chemical reaction that increases the stability and functionality of RNA molecules. The presence of m4C in RNA has been linked to various biological processes, including translation accuracy, gene expression, and the response to cellular stress. Additionally, methylation of cytidine is linked to several diseases, including cancer and neurological disorders. Its chemical structure is basically a cytidine molecule with a methyl group attached to the nitrogen atom at position 4 of the cytosine ring.

InChI:InChI=1/C10H15N3O5/c1-11-6-2-3-13(10(17)12-6)9-8(16)7(15)5(4-14)18-9/h2-3,5,7-9,14-16H,4H2,1H3,(H,11,12,17)

Upstream product

• 107-71-1 tert-butyl peroxyacetate 
• 65-46-3 CYTIDINE 
• 17331-14-5 N⁴-dimethylamino-methylenecytidine 
• 10457-16-6 2',3',5,-tris-O-(trimethylsilyl)uridine 
• 58-96-8 uridine 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 415903-48-9 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine 
• 111426-24-5 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-2-yloxy)-1H-pyrimidin-2-one 
• 111426-25-6 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-3-yloxy)-1H-pyrimidin-2-one 
• 111426-23-4 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(2-oxo-2H-pyridin-1-yl)-1H-pyrimidin-2-one 
• 111426-26-7 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-2-ylsulfanyl)-1H-pyrimidin-2-one 
• 108324-70-5 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 
• 108324-69-2 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-oxo-4-(pyridin-3-yloxy)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 
• 108782-91-8 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-3-yloxy)-1H-pyrimidin-2-one 

Downstream Products

• 65-46-3 CYTIDINE 

Relevant articles and documents

Synthesis and solution conformation studies of the modified nucleoside N4,2′-O-dimethylcytidine (m4Cm) and its analogues

The dimethylated ribosomal nucleoside m4Cm and its monomethylated analogues Cm and m4C were synthesized. The conformations (syn vs anti) of the three modified nucleosides and cytidine were determined by CD and 1D NOE difference spectroscopy. The ribose sugar puckers were determined by the use of proton coupling constants. The position of modification (e.g., O vs N methylation) was found to have an effect on the sugar pucker of cytidine.

Reductive monoalkylation of aromatic amines via amidine intermediates

The convenience and efficiency of using amidines as intermediates in the reductive monoalkylation of aromatic amines has been demonstrated. This monoalkylation can be performed as either a two-step synthesis or a one-pot procedure. Several examples are presented which clearly demonstrate the utility of this new method for the methylation or ethylation of aromatic amines, including unprotected nucleosides.

Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or formation of disulfides.