5-Hydroxymethylcytosine is a DNA pyrimidine nitrogen base. It is formed from the DNA base cytosine by adding a methyl group and then a hydroxy group. It is important in epigenetics, because the hydroxymethyl group on the cytosine can possibly switch a gene on and off. It was first seen in bacteriophages in 1952. However, in 2009 it was found to be abundant in human and mouse brains, as well as in embryonic stem cells. In mammals, it can be generated by oxidation of 5-methylcytosine, a reaction mediated by the Tet family of enzymes. 5-Hydroxymethylcytidine is a product in DNA hydroxymethylation. The concentrations of 5-Hydroxymethylcytidine in the brain were used to study Alzheimer’s disease.

Synonyms:
5-hydroxymethyl-1-(β-D-ribofuranosyl)cytosine; 4-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(hydroxymethyl)pyrimidin-2(1H)-one

CAS No:
19235-17-7

Molecular Formula:
C₁₀H₁₅N₃O₆

Molecular Weight:
273.24

Purity:
≥95% (HPLC)

Appearance:
White to off-white powder

Identity (1H NMR):
Conforms to structure

Melting Point:
>210°C (dec.) (lit)

Density:
1.92±0.1g/cm3 (20ºC 760Torr) (lit)

Storage and Stability:
Store at 4ºC. Stable for 12 months after receipt.