5-Hydroxymethyluracil Chemical Properties

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)

pka

8.46±0.10(Predicted)

form 

Solid

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)

InChIKey

JDBGXEHEIRGOBU-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(CO)C(=O)N1

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

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

YR0513000

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Hydroxymethyluracil Usage And Synthesis

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

Uses

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

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.

5-Hydroxymethyluracil(4433-40-3)Related Product Information

• Silver sulfadiazine
• (Hydroxymethyl)urea
• Thymine
• Cytosine
• Sulfadiazine
• Uracil
• Fluorocytosine
• Pseudouridine
• 5-CARBETHOXYURACIL
• 5-HYDROXYMETHYL-2'-DEOXYURIDINE
• 2,4-Dihydroxypyrimidine-5-carboxylic acid
• 4-methyl-5-hydroxymethyluraci
• 2,4-DIMETHOXY-5-PYRIMIDINECARBOXYLIC ACID
• 5-Hydroxymethyluracil
• AURORA KA-4984
• AURORA KA-4986
• methyl 6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• AURORA KA-548