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I2127

Sigma-Aldrich

Isocytosine

≥99%

Synonym(s):

2-Amino-4-hydroxypyrimidine, 2-Aminouracil

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About This Item

Empirical Formula (Hill Notation):
C4H5N3O
CAS Number:
108-53-2
Molecular Weight:
111.10
EC Number:
203-592-0
MDL number:
MFCD00057557
UNSPSC Code:
41106305
PubChem Substance ID:
24895959

biological source

synthetic (organic)

Assay

≥99%

form

powder

solubility

acetic acid: 50 mg/mL, clear, colorless

SMILES string

NC1=NC=CC(=O)N1

InChI

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

InChI key

XQCZBXHVTFVIFE-UHFFFAOYSA-N

Application

Isocytosine (2-aminouracil) is an isomer of cytosine used in physical chemical studies involving metal complex binding, hydrogen-bonding, and tautomerism and proton transfer effects in nucleobases.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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Vitaliy Feyer et al.
The journal of physical chemistry. A, 115(26), 7722-7733 (2011-05-20)
Core-level X-ray photoemission and near-edge X-ray absorption fine structure spectra of 5-methylcytosine, 5-fluorocytosine, and isocytosine are presented and discussed with the aid of high-level ab initio calculations. The effects of the methylation, halogenation, and isomerization on the relative stabilities of
Vassil B Delchev et al.
Journal of molecular modeling, 13(1), 19-28 (2006-05-20)
Eight H-bonded complexes between isocytosine (isoC) tautomeric forms and R/S-lactic acid (LA) have been studied at the B3LYP and HF levels of theory using 6-31+G(d) basis set. The energy barriers of the intermolecular proton transfers were also estimated as the
C Roberts et al.
Chemistry & biology, 4(12), 899-908 (1998-03-07)
iso-Guanine (iso-G) is the purine component of an isomeric Watson-Crick base pair that may have existed prebiotically. By comparing the abiotic molecular recognition properties of iso-G and its complement, iso-cytosine (iso-C), with those of genomic nucleotide bases, it may be
X L Yang et al.
Biophysical journal, 75(3), 1163-1171 (1998-09-03)
Isoguanine (2-hydroxyladenine) is a product of oxidative damage to DNA and has been shown to cause mutation. It is also a potent inducer of parallel-stranded DNA duplex structure. The structure of the parallel-stranded DNA duplex (PS-duplex) 5'-d(TiGiCAiCiGiGAiCT) + 5'-d(ACGTGCCTGA), containing
K J LaChance-Galang et al.
Inorganic chemistry, 40(3), 485-492 (2001-02-24)
Pentaammineruthenium moves on ambidentate nitrogen heterocycles by both rotation and linkage isomerization, which may affect the biological activity of potential ruthenium metallopharmaceuticals. The rapid rotation rates of [(NH3)5RuIII] coordinated to the exocyclic nitrogens of isocytosine (ICyt) and 6-methylisocytosine (6MeICyt) have
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