Cytosine-5-carboxylic acid

Base Information

• Chemical Name: Cytosine-5-carboxylic acid
• CAS No.: 3650-93-9
• Molecular Formula: C5H5 N3 O3
• Molecular Weight: 155.113
• Hs Code.: 2933599090
• European Community (EC) Number: 222-890-1
• NSC Number: 9309
• UNII: 760CU98B9K
• DSSTox Substance ID: DTXSID70190003
• Nikkaji Number: J205.569D
• Wikidata: Q27146335
• Mol file: 3650-93-9.mol

Synonyms:5-carboxycytosine;5caC nucleoside

Chemical Property of Cytosine-5-carboxylic acid

Chemical Property:

• Melting Point: 256-257 °C
• Boiling Point: °Cat760mmHg
• PKA: -3.50±0.20(Predicted)
• Flash Point: °C
• PSA: 109.33000
• Density: 1.88g/cm³
• LogP: 0.04380
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Aqueous Base (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 155.03309103
• Heavy Atom Count: 11
• Complexity: 279

Purity/Quality:

97% ^*data from raw suppliers

5-Carboxycytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=O)NC(=C1C(=O)O)N
• Uses: Cytosine derivatives, such as 5-Carboxylcytosine, are involved with a wide variety of biological functions including cytosine methylation, gene expression, genome stability, and chromatin modification. In addition, 5-Carboxylcytosine interacts with the RNA polymerase II elongation complex that can influence the pluripotent states during early embryonic development.

Technology Process of Cytosine-5-carboxylic acid

There total 17 articles about Cytosine-5-carboxylic acid 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: 96.8%

ethyl cytosine-5-carboxylate (20187-46-6) → 5-carboxylcytosine (3650-93-9)

Guidance literature:

With sodium hydroxide; at 70 ℃; for 0.5h; Reagent/catalyst; Temperature;

Reference yield: 62.0%

5-carboxyl-2′-deoxy-(N1,N3-N)cytidine → 5-carboxylcytosine (3650-93-9)

Guidance literature:

5-carboxyl-2′-deoxy-(N¹,N³-N)cytidine; With hydrogenchloride; water; at 20 ℃; for 48h; Inert atmosphere;

at 45 ℃; for 15h; Inert atmosphere;

DOI:10.1002/anie.202107277

Reference yield:

5-carboxylmethyl-3',5'-(tert-butyldimethylsilyl)-2'-deoxycytidine (1361013-63-9) → 5-carboxylcytosine (3650-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine hydrogenfluoride / ethyl acetate / 14 h / 21 °C / Inert atmosphere

1.2: 18 h / 20 °C / Inert atmosphere

2.1: water; hydrogenchloride / 48 h / 20 °C / Inert atmosphere

2.2: 15 h / 45 °C / Inert atmosphere

With hydrogenchloride; water; pyridine hydrogenfluoride; In ethyl acetate;

DOI:10.1002/anie.202107277

upstream raw materials:

ethyl 4-amino-2-thioxo-1H-pyrimidine-5-carboxylate

ethyl 4-amino-2-(ethylthio)pyrimidine-5-carboxylate

ethyl cytosine-5-carboxylate

5-methylcytosin

Downstream raw materials:

uracil

2,4-dihydroxypyrimidine-5-carboxylic acid

Cytosine