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Merck

C3506

Cytosine

≥99%, synthetic (organic), powder

Synonym(s):

4-Amino-2-hydroxypyrimidine, 4-Aminopyrimidin-2-(1H)-one

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About This Item

Empirical Formula (Hill Notation):
C4H5N3O
CAS Number:
71-30-7
Molecular Weight:
111.10
NACRES:
NA.51
PubChem Substance ID:
24892620
UNSPSC Code:
41106305
EC Number:
200-749-5
MDL number:
MFCD00006034
Beilstein/REAXYS Number:
2637

Product Name

Cytosine, ≥99%

InChI

1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)

InChI key

OPTASPLRGRRNAP-UHFFFAOYSA-N

SMILES string

NC1=NC(=O)NC=C1

biological source

synthetic (organic)

assay

≥99%

form

powder

mp

>300 °C (lit.)

solubility

0.5 M HCl: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

Quality Level

200

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Application

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 rate
  • for nucleoside 5′-triphosphate (NTP) synthesis
  • purification

Biochem/physiol Actions

Cytosine (C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA).
Cytosine is a pyrimidine, which forms three hydrogen bonds to base pair with guanine. It forms a nucleotide cytidine, that is phosphorylated to cytidine 5′ monophosphate (CMP), cytidine 5′ diphosphate (CDP) and cytidine 5′ triphosphate (CTP).

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9464
MKCZ6210
MKCZ2775
0000474161
0000474164

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Deuterated nucleotides as chemical probes of RNA structure: a detailed protocol for the enzymatic synthesis of a complete set of nucleotides specifically deuterated at ribose carbons
Azad R, et al.
ScienceOpen Research (2015)
Encyclopedia of Genetics (2001)
Nucleobase sensing using highly-sensitive surface-enhanced Raman spectroscopy templates comprising organic semiconductor peptide nanotubes and metal nanoparticles
Almohammed S, et al.
Sensing and Bio-Sensing Research, 24, 100287-100287 (2019)
Akira Ono et al.
Chemical Society reviews, 40(12), 5855-5866 (2011-08-10)
Pyrimidine base pairs in DNA duplexes selectively capture metal ions to form metal ion-mediated base pairs, which can be evaluated by thermal denaturation, isothermal titration calorimetry, and nuclear magnetic resonance spectroscopy. In this critical review, we discuss the metal ion
Irene M Kaplow et al.
Genome research, 25(6), 907-917 (2015-04-26)
DNA methylation is an epigenetic modification that plays a key role in gene regulation. Previous studies have investigated its genetic basis by mapping genetic variants that are associated with DNA methylation at specific sites, but these have been limited to
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