5-Hydroxymethyluracil

Modify Date: 2025-08-20 17:16:36

5-Hydroxymethyluracil Structure
5-Hydroxymethyluracil structure
Common Name 5-Hydroxymethyluracil
CAS Number 4433-40-3 Molecular Weight 142.113
Density 1.4±0.1 g/cm3 Boiling Point 530.4ºC at 760mmHg
Molecular Formula C5H6N2O3 Melting Point >300 °C(lit.)
MSDS Chinese USA Flash Point 274.6ºC

 Use of 5-Hydroxymethyluracil


5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.

 Names

Name 5-hydroxymethyluracil
Synonym More Synonyms

 5-Hydroxymethyluracil Biological Activity

Description 5-Hydroxymethyluracil is a product of oxidative DNA damage. 5-Hydroxymethyluracil can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.
Related Catalog
Target

Human Endogenous Metabolite

References

[1]. Djuric Z, et al. Quantitation of 5-(hydroxymethyl)uracil in DNA by gas chromatography with mass spectral detection. Chem Res Toxicol. 1991 Nov-Dec;4(6):687-91.

[2]. Janoušková M, et al. 5-(Hydroxymethyl)uracil and -cytosine as potential epigenetic marks enhancing or inhibiting transcription with bacterial RNA polymerase. Chem Commun (Camb). 2017 Dec 12;53(99):13253-13255.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 530.4ºC at 760mmHg
Melting Point >300 °C(lit.)
Molecular Formula C5H6N2O3
Molecular Weight 142.113
Flash Point 274.6ºC
Exact Mass 142.037842
PSA 86.47000
LogP -0.50
Index of Refraction 1.528
InChIKey JDBGXEHEIRGOBU-UHFFFAOYSA-N
SMILES O=c1[nH]cc(CO)c(=O)[nH]1
Storage condition Refrigerator

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YR0513000
CHEMICAL NAME :
Uracil, 5-(hydroxymethyl)-
CAS REGISTRY NUMBER :
4433-40-3
LAST UPDATED :
199701
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C5-H6-N2-O3
MOLECULAR WEIGHT :
142.13

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
400 nmol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 48,5466,1988

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi: Irritant;
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS YR0513000
HS Code 2933599090

 Synthetic Route

 Customs

HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles29

More Articles
Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct.

Toxicol. Lett. 155(3) , 403-10, (2005)

5-Hydroxymethyluracil (5-HMU) is derived from radiation in addition to endogenous oxidative DNA damage and it is one of the most abundant DNA adducts. Human 5-HMU-DNA-glycosylase has been shown to rep...

Mutational analysis of the damage-recognition and catalytic mechanism of human SMUG1 DNA glycosylase.

Nucleic Acids Res. 32(17) , 5291-302, (2004)

Single-strand selective monofunctional uracil-DNA glycosylase (SMUG1), previously thought to be a backup enzyme for uracil-DNA glycosylase, has recently been shown to excise 5-hydroxyuracil (hoU), 5-h...

Qualitative and quantitative analyses of the decomposition products that arise from the exposure of thymine to monochromatic ultrasoft X rays and 60Co gamma rays in the solid state.

Radiat. Res. 161(4) , 442-50, (2004)

HPLC analyses of condensed thymine irradiated with monochromatic synchrotron ultrasoft X rays in the energy region around nitrogen and oxygen K-shell edges were performed. Cobalt-60 gamma rays were us...

 5-HydroxymethyluracilBioassay

View more

Name: Discovery of Small Molecules to Inhibit Human Cytomegalovirus Nuclear Egress
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: HCMV UL50
External Id: HMS1262
Name: Chemical Probes of Kaposi's Sarcoma Herpes Virus Latent Infection
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: ORF 73 [Human herpesvirus 8 type M]
External Id: HMS791
Name: Competitive inhibition of human erythrocytes CA1 using 4-nitrophenylacetate as substr...
Source: ChEMBL
Target: Carbonic anhydrase 1
External Id: CHEMBL3602571
Name: Inhibition of human erythrocytes CA1 using 4-nitrophenylacetate as substrate by ester...
Source: ChEMBL
Target: Carbonic anhydrase 1
External Id: CHEMBL3602569
Name: A screen for compounds that inhibit the activity of LtaS in Staphylococcus aureus
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
External Id: HMS979
Name: Inhibition of human erythrocytes CA2 using 4-nitrophenylacetate as substrate by ester...
Source: ChEMBL
Target: Carbonic anhydrase 2
External Id: CHEMBL3602570
Name: Cell-based high throughput primary assay to identify activators of GPR151
Source: The Scripps Research Institute Molecular Screening Center
Target: RecName: Full=G-protein coupled receptor 151; AltName: Full=G-protein coupled receptor PGR7; AltName: Full=GPCR-2037; AltName: Full=Galanin receptor 4; AltName: Full=Galanin-receptor-like protein; Short=GalRL
External Id: GPR151_PHUNTER_AG_LUMI_1536_1X%ACT
Name: Stabilization of p53 in human papillomavirus-positive cells
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: Cellular tumor antigen p53
External Id: HMS1485
Name: A screen for compounds that inhibit viral RNA polymerase binding and polymerization a...
Source: ICCB-Longwood/NSRB Screening Facility, Harvard Medical School
Target: Chain A, Poliovirus Polymerase With Gtp
External Id: HMS750
Name: Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)
Source: NCGC
External Id: APP-Toga-CHIKV-nsp2-p
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 Synonyms

5-(hydroxymethyl)-1H-pyrimidine-2,4-dione
EINECS 224-636-5
5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
5-hydroxymethyluracil
MFCD00056024
5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione
5-(Hydroxymethyl)uracil
5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedione
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