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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

Key Documents

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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)
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
Transition from somatic embryo to friable embryogenic callus in cassava: dynamic changes in cellular structure, physiological status, and gene expression profiles
Ma Q, et al.
Frontiers in Plant Science, 6, 824-824 (2015)
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