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C3506

Sigma-Aldrich

Cytosine

≥99%

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
Beilstein:
2637
EC Number:
200-749-5
MDL number:
MFCD00006034
UNSPSC Code:
41106305
PubChem Substance ID:
24892620
NACRES:
NA.51

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

SMILES string

NC1=NC(=O)NC=C1

InChI

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

InChI key

OPTASPLRGRRNAP-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
Rahul M Kohli et al.
Nature, 502(7472), 472-479 (2013-10-25)
DNA methylation has a profound impact on genome stability, transcription and development. Although enzymes that catalyse DNA methylation have been well characterized, those that are involved in methyl group removal have remained elusive, until recently. The transformative discovery that ten-eleven
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)
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