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414174

Sigma-Aldrich

5-Formyluracil

98%

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About This Item

Empirical Formula (Hill Notation):
C5H4N2O3
CAS Number:
1195-08-0
Molecular Weight:
140.10
MDL number:
MFCD00192185
UNSPSC Code:
12352100
PubChem Substance ID:
24865898
NACRES:
NA.22

Assay

98%

form

powder

mp

>300 °C (dec.) (lit.)

SMILES string

O=CC1=CNC(=O)NC1=O

InChI

1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10)

InChI key

OHAMXGZMZZWRCA-UHFFFAOYSA-N

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Application

5-Formyluracil may be used for the preparation of covalently linked base with 5-aminocytosine pair via Schiff base formation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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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
Gustavo Portalone et al.
Acta crystallographica. Section C, Crystal structure communications, 63(Pt 11), o650-o654 (2007-11-09)
The asymmetric unit of the amino-oxo tautomer of 5-formyluracil (systematic name: 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde), C(5)H(4)N(2)O(3), comprises one planar amino-oxo tautomer, as every atom in the structure lies on a crystallographic mirror plane. At variance with all the previously reported small-molecule crystal structures
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