5-Hydroxymethyluracil

CAS NO.：4433-40-3
Empirical Formula: C5H6N2O3
Molecular Weight: 142.11
MDL number: MFCD00056024
EINECS: 224-636-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:08:57

What is 5-Hydroxymethyluracil?

Description

5-Hydroxymethyluracil is a product of oxidative damage to DNA, predominantly by hydroxyl radical via the Fenton reaction. It can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.

Chemical properties

White Powder

The Uses of 5-Hydroxymethyluracil

5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.

What are the applications of Application

Hydroxymethyl uracil is a stable major oxidative modification of thymine formed through the action of ionizing radiation

Definition

ChEBI: 5-hydroxymethyluracil is a primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. It has a role as a human metabolite. It is a primary alcohol and a pyrimidone. It derives from a uracil.

Biosynthesis

5-Hydroxymethyluracil is produced by the enzyme thymine dioxygenase (EC 1.14.11.6) which catalyzes the chemical reaction thymine + 2-oxoglutarate + O2 <-> 5-hydroxymethyluracil + succinate + CO2.
The 3 substrates of this enzyme are thymine, 2-oxoglutarate, and O2, whereas its 3 products are 5-hydroxymethyluracil, succinate, and CO2. The 5hmU base can also be generated by oxidation/hydroxylation of thymine by the Ten-Eleven-Translocation (TET) proteins or result from deamination of 5hmC. DNA containing 5hmU has been reported to be more flexible and hydrophilic.

Biotechnological Production

5-Hydroxymethyluracil (5hmU) is a thymine base modification found in the genomic DNA of diverse organisms ranging from bacteriophages to mammals.

Properties of 5-Hydroxymethyluracil

Melting point:	>300 °C(lit.)
Density	1.401±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)
form	Solid
pka	8.46±0.10(Predicted)
color	White
Water Solubility	Soluble in water. (50 g/L ) at 20°C, DMSO, dimethyl formamide or 100% ethanol.
BRN	125482
InChI	InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)
CAS DataBase Reference	4433-40-3(CAS DataBase Reference)
EPA Substance Registry System	2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)- (4433-40-3)

Safety information for 5-Hydroxymethyluracil

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.