| Identification | More | [Name]
5-Hydroxymethyluracil | [CAS]
4433-40-3 | [Synonyms]
2,4-DIHYDROXY-5-HYDROXYMETHYLPYRIMIDINE
5-(HYDROXYMETHYL)-2,4(1H,3H)PYRIMIDINEDIONE
5-HYDROXYMETHYLURACIL
5-(HYDROXYMETHYL)URACIL HYDRATE
5-HYDROXYMETHYLURACYL
AURORA KA-547
HYDROXYMETHYL URACIL
RARECHEM AH CK 0115
TIMTEC-BB SBB000084
3h)-pyrimidinedione,5-(hydroxymethyl)-4(1h
5-(hydroxymethyl)-uraci
2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-(9CI)
5-(Hydroxymethyl)uracil,98%
5-(hydroxymethyl)pyrimidine-2,4-dione
uracil-5-methanol
5-(Hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione | [EINECS(EC#)]
224-636-5 | [Molecular Formula]
C5H6N2O3 | [MDL Number]
MFCD00056024 | [Molecular Weight]
142.11 | [MOL File]
4433-40-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [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. | [Detection Methods]
HPLC | [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]
4433-40-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P305+P351+P338 | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
YR0513000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids |
| Raw materials And Preparation Products | Back Directory | [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)- |
| Hazard Information | Back Directory | [Description]
Hydroxymethyl uracil is a product of oxidative damage to DNA, predominantly by hydroxyl radical via the Fenton reaction.1,2,3 | [Chemical Properties]
White Powder | [Uses]
5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis. | [Definition]
ChEBI: A primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. | [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. | [References]
[1] Patent: US2004/38995, 2004, A1. Location in patent: Page/Page column 4-6
[2] Synlett, 2002, # 12, p. 2043 - 2044
[3] Patent: US2016/75720, 2016, A1. Location in patent: Paragraph 0321
[4] Canadian Journal of Chemistry, 2007, vol. 85, # 4, p. 302 - 312
[5] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740 |
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