414174
5-Formyluracil
98%
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About This Item
Empirical Formula (Hill Notation):
C5H4N2O3
CAS Number:
Molecular Weight:
140.10
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Form:
powder
InChI
1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10)
SMILES string
O=CC1=CNC(=O)NC1=O
InChI key
OHAMXGZMZZWRCA-UHFFFAOYSA-N
assay
98%
form
powder
mp
>300 °C (dec.) (lit.)
functional group
aldehyde
Quality Level
Application
5-Formyluracil may be used for the preparation of covalently linked base with 5-aminocytosine pair via Schiff base formation.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
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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Fernanda M Prado et al.
Free radical biology & medicine, 47(4), 401-409 (2009-05-12)
The decomposition of organic hydroperoxides into peroxyl radicals is a potential source of singlet molecular oxygen [O2 (1Deltag)] in biological systems. This study shows that 5-(hydroperoxymethyl)uracil (5-HPMU), a thymine hydroperoxide within DNA, reacts with metal ions or HOCl, generating O2
Katsuhito Kino et al.
Biochemistry, 43(10), 2682-2687 (2004-03-10)
5-Formyluracil (fU) is a major thymine lesion produced by reactive oxygen radicals and photosensitized oxidation. Although this residue is a potentially mutagenic lesion and is removed by several base excision repair enzymes, it is unknown whether fU is the substrate
Yinsheng Wang et al.
Journal of the American Society for Mass Spectrometry, 13(10), 1190-1194 (2002-10-22)
2-Aminoimidazolone and 5-formyluracil are major one-electron photooxidation products of guanine and thymine in oligodeoxynucleotides (ODNs). Herein we report the HPLC isolation and tandem mass spectrometric characterization of ODNs carrying those types of base modifications. Collision-activated dissociation (CAD) of the deprotonated
Q M Zhang
Journal of radiation research, 42(1), 11-19 (2001-06-08)
Ionizing radiation induces a wide variety of modifications to purine and pyrimidine residues. The exocyclic methyl group of thymine does not escape oxidative damage. Any 5-hydroperoxymethyluracil produced is spontaneously decomposed to form 5-formyluracil (5-foU) and 5-hydroxymethyluracil. The yield of 5-foU
Pingfang Liu et al.
DNA repair, 2(2), 199-210 (2003-01-18)
The oxidation of the thymine methyl group can generate 5-formyluracil (FoU). Template FoU residues are known to miscode, generating base substitution mutations. The repair of the FoU lesion is therefore important in minimizing mutations induced by DNA oxidation. We have
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