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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:
Molecular Weight:
111.10
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:

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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
Deepali Gupta et al.
Inorganic chemistry, 43(11), 3386-3393 (2004-05-25)
Isocytosine (ICH) exists in solution as two major tautomers, the keto form with N1 carrying a proton (1a) and the keto form with N3 being protonated (1b). In water, 1a and 1b exist in equilibrium with almost equal amounts of
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
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
Chandrika B-Rao et al.
Bioorganic & medicinal chemistry, 20(9), 2930-2939 (2012-04-10)
In recent years, xanthine oxidase has emerged as an important target not only for gout but also for cardiovascular and metabolic disorders involving hyperuricemia. Contrary to popular belief, recent clinical trials with uricosurics have demonstrated that enhanced excretion of uric

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