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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Encyclopedia of Genetics (2001)
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)
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
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)
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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