Basic information
- CAS
4433-40-3- Standard SMILES
O=c1[nH]cc(CO)c(=O)[nH]1- InChIKey
JDBGXEHEIRGOBU-UHFFFAOYSA-N- Molecular formula
- C5H6N2O3
- Average molar mass
- 142.11 g/mol
- Monoisotopic mass
- 142.03784205
Overview
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 is functionally related to a uracil.
Names & identifiers
- Preferred name
- 5-(Hydroxymethyl)uracil
- IUPAC
- 5-(hydroxymethyl)-1H-pyrimidine-2,4-dione
- English name
- 5-Hydroxymethyluracil
- Molecular formula
- C5H6N2O3
- Molecular weight
- 142.11
Names & synonyms
Show more names
Database identifiers
- CAS
4433-40-3- PubChem CID
- 78168
- DTXSID
DTXSID9063455- ChEMBL
CHEMBL1233360- ChEBI
CHEBI:16964- UNII
- 590TQ3GL34
- EC Number
- 224-636-5
- Nikkaji
- J58.058I
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 78.4 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 209
Experimental & physicochemical properties
Collision Cross Section
119.21 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
124.5 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
124.1 Ų [M-H]-
Physicochemical properties
- Melting point
- 300 °C · >300 °C(lit.)
- Density
- 1.401 · 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 · 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 · 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 · 4433-40-3(CAS DataBase Reference)
- FDA UNII
- 590 TQ3GL34 · 590TQ3GL34
- EPA Substance Registry System
- 2 · 2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)- (4433-40-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 513000 · YR0513000
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YR0513000
- hs_code
- 29335990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Uses & manufacturing
Applications
Description5-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.
Uses5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: 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.
Related reactions
Compound notes
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