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Merck
CN

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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Product Name

Isobarbituric acid, analytical standard

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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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
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.
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
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
William R Markesbery et al.
Antioxidants & redox signaling, 8(11-12), 2039-2045 (2006-10-13)
Oxidative damage to DNA may play an important role in aging and neurodegenerative diseases such as Alzheimer's disease (AD). Attack on DNA by reactive oxygen species, particularly hydroxyl radicals, can lead to strand breaks, DNA-DNA and DNA-protein cross-linking, sister chromatid
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