Cytosine

Base Information

• Chemical Name: Cytosine
• CAS No.: 71-30-7
• Deprecated CAS: 118511-36-7,14987-28-1,26661-23-4,504-05-2,66322-75-6,66460-16-0,918399-36-7,1268833-99-3,149297-78-9,66398-98-9,66460-17-1,80275-67-8,88733-25-9,1268833-99-3,149297-78-9,14987-28-1,26661-23-4,504-05-2,66322-75-6,66398-98-9,66460-17-1,80275-67-8,88733-25-9,918399-36-7
• Molecular Formula: C4H5N3O
• Molecular Weight: 111.103
• Hs Code.: 2933.59
• European Community (EC) Number: 200-749-5
• NSC Number: 27787
• UNII: 8J337D1HZY
• DSSTox Substance ID: DTXSID4044456
• Nikkaji Number: J9.343B
• Wikipedia: Cytosine
• Wikidata: Q178425
• NCI Thesaurus Code: C410
• Metabolomics Workbench ID: 37339
• ChEMBL ID: CHEMBL15913
• Mol file: 71-30-7.mol

Synonyms:Cytosine

Chemical Property of Cytosine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.46E-08mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.688
• Boiling Point: 445.8 °C at 760 mmHg
• PKA: 4.60, 12.16(at 25℃)
• Flash Point: 223.4 °C
• PSA: 71.77000
• Density: 1.55 g/cm³
• LogP: -0.06670
• Storage Temp.: Store at RT.
• Solubility.: Clear to very slightly hazy colorless to faint yellow solution a
• Water Solubility.: soluble
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 111.043261792
• Heavy Atom Count: 8
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Cytosine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=C(NC(=O)N=C1)N
• Recent NIPH Clinical Trials: Japanese Pediatric Leukemia/Lymphoma Study Group (JPLSG) AML-R11: Multi-center Phase II Study of the efficacy and the safety in the induction chemotherapy containing fludarabine for children with the first bone marrow relapse and induction failure of acute myeloid leukemia.
• Description: Cytosine is pyrimidine; along with adenine and guanine they account for the fi ve nucleic acid bases. Pyrimidines are heterocyclic single-ringed compounds based on the structure of pyrimidine. Cytosinelike adenine and guanine, form nucleosides and nucleotides in RNA and DNA. When the bases combine with ribose, a ribonucleoside forms; and when it attaches to deoxyribose, a deoxyribosenucleoside is formed. Names of the nucleoside are summarized in Table 29.1.these in turn combine with phosphoryl groups, in a process called phosphorylation, to form their respective nucleotides that form nucleic acids.the nucleotides can be tri, di, and mono phosphate nucleotides similar to the way in which adenine forms ATP, ADP, and AMP.
• Uses: Cytosine is a nucleoside used for proteomics research. It is also used as an enzyme substrate or precursor of effector molecules such as cytosine sugars. Cytosine has been used: for the preparation of nucleobase solutions as a standard for high-performance liquid chromatography (HPLC)for the estimation of global methylation ratefor nucleoside 5′-triphosphate (NTP) synthesis purification

Technology Process of Cytosine

There total 112 articles about Cytosine 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: 93.0%

2-thiocytosine (333-49-3) → Cytosine (71-30-7)

Guidance literature:

With dihydrogen peroxide; at 80 ℃; for 20h; Temperature;

Reference yield: 91.5%

3-hydroxylacrylic nitrile (25078-62-0) + urea (57-13-6) → Cytosine (71-30-7)

Guidance literature:

3-hydroxylacrylic nitrile; With sodium t-butanolate; In tert-butyl alcohol;

urea; In tert-butyl alcohol; at 50 ℃; for 8h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 91.5%

urea, monosodium salt (29878-39-5) + 3-hydroxylacrylic nitrile (25078-62-0) → Cytosine (71-30-7)

Guidance literature:

3-hydroxylacrylic nitrile; With sodium methylate; In methanol;

urea, monosodium salt; In methanol; at 40 ℃; for 6h;

upstream raw materials:

2-chloropyrimidin-4-amine

4-amino-2-methoxypyrimidine

4-ethoxypyrimidin-2-one

2-ethylsulfanyl-pyrimidin-4-ylamine

Downstream raw materials:

C₃₀H₂₅N₃O₈

3-methylcytosine

3-methyluracil

1-MeCyt

Refernces

• 1、 Roy, Béatrice,Lefebvre, Isabelle,Puy, Jean-Yves,Périgaud, Christian. "A facile and effective synthesis of lamivudine 5′-diphosphate". . p. 1250 - 1252. Retrieved 2011.
• 2、 Azuma, Atsushi,Hanaoka, kenji,Kurihara, Atsushi,Kobayashi, Tomowo,Miyauchi, Seiji,et al.. "Nucleosides and Nucleotides. 141. Chemical Stability of a new Antitumor Nucleoside, 2'-C-Cyano-2'-deoxy-1-β-D-arabino-pentofuranosylcytosine in Alkaline Medium: Formation of 2'-C-Cyano-2;-deoxy-1-β-D-ribo-pentofuranosylcytosine and Its Antitumor Activity.". . p. 3391 - 3397. Retrieved 1995.
• 3、 Duff,De Vroom,Geluk,Hecht,Van Der Marel,Van Boom. "Evidence for C-1' hydrogen abstraction from modified oligonucleotides by Fe-bleomycin". . p. 3350 - 3351. Retrieved 1993.
• 4、 Jonasson, Niko S. W.,Jan?en, Rachel,Menke, Annika,Zott, Fabian L.,Zipse, Hendrik,Daumann, Lena J.. "TET-Like Oxidation in 5-Methylcytosine and Derivatives: A Computational and Experimental Study". . p. 3333 - 3340. Retrieved 2021/09/25.
• 5、 Balucani, Nadia,Bonino, Francesca,Martra, Gianmario,Pantaleone, Stefano,Signorile, Matteo,Ugliengo, Piero. "Monitoring the reactivity of formamide on amorphous SiO2 by in-situ UV-Raman spectroscopy and DFT modeling". . . Retrieved 2020/05/28.