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C3506

Cytosine

Name: Cytosine
Brand: SIGMA

≥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

Assay:

≥99%

Biological source:

synthetic (organic)

Form:

powder

Solubility:

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

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Product Name

Cytosine, ≥99%

biological source

synthetic (organic)

Quality Level

200

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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Related Categories

Biochemicals

Nucleosides and Nucleotides

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 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).

Cytosine (C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA).

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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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)

A pooling-based approach to mapping genetic variants associated with DNA methylation.

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

Binding of metal ions by pyrimidine base pairs in DNA duplexes.

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

TET enzymes, TDG and the dynamics of DNA demethylation.

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

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Global Trade Item Number

SKU	GTIN
C3506-1G	04061833485910
C3506-10G	04061833485903
C3506-5G	04061833485934
C3506-25G	04061833485927
C3506-100G	04061833485897

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