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852589

Sigma-Aldrich

5-(Hydroxymethyl)uracil

97%

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Empirical Formula (Hill Notation):
C5H6N2O3
CAS Number:
Molecular Weight:
142.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

powder

mp

>300 °C (lit.)

SMILES string

[H]O[H].OCC1=CNC(=O)NC1=O

InChI

1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)

InChI key

JDBGXEHEIRGOBU-UHFFFAOYSA-N

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H41803556793752975
5-(Hydroxymethyl)uracil 97%

852589

5-(Hydroxymethyl)uracil

N-(Hydroxymethyl)phthalimide 97%

H41803

N-(Hydroxymethyl)phthalimide

Ethyl 2-(hydroxymethyl)acrylate 97%

752975

Ethyl 2-(hydroxymethyl)acrylate

mp

>300 °C (lit.)

mp

147-149 °C (lit.)

mp

147-151 °C (lit.)

mp

-

form

powder

form

-

form

solid

form

liquid

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Hideharu Hashimoto et al.
Nucleic acids research, 40(11), 4841-4849 (2012-03-01)
Cytosine residues in mammalian DNA occur in at least three forms, cytosine (C), 5-methylcytosine (M; 5mC) and 5-hydroxymethylcytosine (H; 5hmC). During semi-conservative DNA replication, hemi-methylated (M/C) and hemi-hydroxymethylated (H/C) CpG dinucleotides are transiently generated, where only the parental strand is
Masaki Hori et al.
Nucleic acids research, 31(4), 1191-1196 (2003-02-13)
The oxidation and deamination of 5-methylcytosine (5mC) in DNA generates a base-pair between 5-hydroxymethyluracil (5hmU) and guanine. 5hmU normally forms a base-pair with adenine. Therefore, the conversion of 5mC to 5hmU is a potential pathway for the generation of 5mC
Rafal Rozalski et al.
Free radical research, 38(11), 1201-1205 (2004-12-29)
In order to eliminate the possibility that diet may influence urinary oxidative DNA lesion levels, in our experiments we used a recently developed technique involving HPLC pre-purification followed by gas chromatography with isotope dilution mass spectrometric detection. This methodology was
R J Boorstein et al.
The Journal of biological chemistry, 276(45), 41991-41997 (2001-08-30)
Purification from calf thymus of a DNA N-glycosylase activity (HMUDG) that released 5-hydroxymethyluracil (5hmUra) from the DNA of Bacillus subtilis phage SPO1 was undertaken. Analysis of the most purified fraction by SDS-polyacrylamide gel electrophoresis revealed a multiplicity of protein species
Hideharu Hashimoto et al.
Nucleic acids research, 40(17), 8276-8284 (2012-06-29)
The mammalian DNA glycosylase--methyl-CpG binding domain protein 4 (MBD4)--is involved in active DNA demethylation via the base excision repair pathway. MBD4 contains an N-terminal MBD and a C-terminal DNA glycosylase domain. MBD4 can excise the mismatched base paired with a

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