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| | 5-Hydroxymethyluracil Basic information |
| | 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) |
| Hazard Codes | Xi | | Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | YR0513000 | | TSCA | Yes | | HazardClass | IRRITANT | | HS Code | 29335990 |
| | 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 Preparation Products And Raw materials |
| Raw materials | Hydrochloric acid-->Potassium hydroxide-->Formaldehyde-->Uracil-->4(3H)-Pyrimidinone, 2-(ethylthio)-5-(isocyanatomethyl)--->2,4(1H,3H)-Pyrimidinedione, dihydro-5,6-dihydroxy--->Propanamide, N-[(formylamino)carbonyl]-2-oxo--->5-(2-Hydroxy-ethoxymethyl)-1H-pyrimidine-2,4-dione-->2,4(1H,3H)-Pyrimidinedione, 5-(aminomethyl)- (9CI)-->2,4(1H,3H)-Pyrimidinedione, 5-(isocyanatomethyl)--->5-hydroperoxymethyl-2'-deoxyuridine-->Thymidine, α-(phenylseleno)--->5-(CHLOROMETHYL)URACIL-->2,4,5-TRIHYDROXYPYRIMIDINE-->2(1H)-Pyrimidinone, 4-amino-5-hydroxy- (9CI)-->DIHYDROTHYMINE | | Preparation Products | 2,4-Dihydroxypyrimidine-5-carboxylic acid-->BenzaMide, N-[3-[1,4-dihydro-1-Methyl-7-[(6-Methyl-3-pyridinyl)aMino]-2-oxopyriMido[4,5-d]pyriMidin-3(2H)-yl]-4-Methylphenyl]-3-(trifluoroMethyl)- |
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