5-(Hydroxymethyl)uracil

HCID 78168

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

5-Hydroxymethyluracil4433-40-35-(Hydroxymethyl)uracil2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-Uracil, 5-(hydroxymethyl)-5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedionehydroxymethyluracil5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione590TQ3GL34NSC-20901DTXSID9063455CHEBI:16964
Show more names
NSC 20901AURORA KA-5475-methyloluracilα-HydroxythyMinea-Hydroxythymineuracil-5-methanolTIMTEC-BB SBB000084RARECHEM AH CK 0115HYDROXYMETHYL URACIL
RefChem:536253DTXCID8040307224-636-55-(HYDROXYMETHYL)PYRIMIDINE-2,4(1H,3H)-DIONE5-(Hydroxymethyl)pyrimidine-2,4-diol5-Oxymethyluracil5-Hydroxymethyl uracil5-(hydroxymethyl)-1H-pyrimidine-2,4-dione

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

Experimental & physicochemical properties

LogP-1.94
Solubility44 mg/mL
Physical DescriptionSolid
Collision Cross Section · 3 items

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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

Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
YR0513000
hs_code
29335990
Signal word
Warning

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing Information2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-: INACTIVE

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.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

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

20 records

Compound notes

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