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Merck

I0627

Isobarbituric acid

analytical standard

Synonym(s):

2,4,5-Trihydroxypyrimidine, 5-Hydroxyuracil

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O3
CAS Number:
496-76-4
Molecular Weight:
128.09
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329815320
EC Number:
207-829-9
Beilstein/REAXYS Number:
127205
MDL number:
MFCD00082987

Key Documents

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InChI key

FQXOOGHQVPKHPG-UHFFFAOYSA-N

InChI

1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1H2,(H2,5,6,8,9)

SMILES string

O=C1CNC(=O)NC1=O

grade

analytical standard

assay

~98%

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

>300 °C (dec.) (lit.)

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class

11 - Combustible Solids

wgk

WGK 3

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
BCCM9048
STBK5580
STBJ8650
STBH7050
STBG9194

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Philippe Simon et al.
Nucleic acids research, 34(13), 3660-3669 (2006-08-04)
5-Hydroxyuracil is a major oxidized nucleobase that can be generated by the action of (*)OH radical and one-electron oxidants. The latter modified base that exhibits a low ionization potential is highly susceptible to further degradation upon exposure to various oxidants.
Nicolas Charlet-Berguerand et al.
The EMBO journal, 25(23), 5481-5491 (2006-11-18)
Oxidative lesions represent the most abundant DNA lesions within the cell. In the present study, we investigated the impact of the oxidative lesions 8-oxoguanine, thymine glycol and 5-hydroxyuracil on RNA polymerase II (RNA pol II) transcription using a well-defined in
Riccardo Amorati et al.
Organic letters, 12(18), 4130-4133 (2010-08-28)
Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form
Jason L Parsons et al.
Nucleic acids research, 35(4), 1054-1063 (2007-02-01)
Base excision repair (BER) is the major pathway for the repair of simple, non-bulky lesions in DNA that is initiated by a damage-specific DNA glycosylase. Several human DNA glycosylases exist that efficiently excise numerous types of lesions, although the close
Grégory Eot-Houllier et al.
Nucleic acids research, 33(1), 260-271 (2005-01-14)
Clustered DNA lesions, possibly induced by ionizing radiation, constitute a trial for repair processes. Indeed, recent studies suggest that repair of such lesions may be compromised, potentially leading to the formation of lethal double-strand breaks (DSBs). A complex multiply damaged
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