5-(Hydroxymethyl)uracil

Bezeichnung:5-(Hydroxymethyl)uracil

Englisch Name:5-Hydroxymethyluracil

CBNumberCB7122987

SummenformelC5H6N2O3

Molgewicht142.11

Synonyma

5-(Hydroxymethyl)uracil

5-(Hydroxymethyl)uracil physikalisch-chemischer Eigenschaften

Schmelzpunkt	>300 °C(lit.)
Dichte	1.401±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly, Heated)
pka	8.46±0.10(Predicted)
Aggregatzustand	Solid
Farbe	White
Wasserlöslichkeit	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 Datenbank	4433-40-3(CAS DataBase Reference)
EPA chemische Informationen	2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)- (4433-40-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	YR0513000
TSCA	Yes
HazardClass	IRRITANT
HS Code	29335990

Gefahreninformationscode (GHS)

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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.
Chemische Eigenschaften
White Powder
Verwenden
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.
Biosynthese
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.
Biotechnologische Produktion
5-Hydroxymethyluracil (5hmU) is a thymine base modification found in the genomic DNA of diverse organisms ranging from bacteriophages to mammals.