5-Hydroxymethyluracil

Names

[ Name ]:
5-Hydroxymethyluracil

[Synonym ]:
5-(hydroxymethyl)-1H-pyrimidine-2,4-dione
EINECS 224-636-5
2,4-Pyrimidinediol, 5-(hydroxymethyl)-
5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione
5-hydroxymethyluracil
MFCD00056024
2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-
5-(hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione
5-(Hydroxymethyl)uracil
5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedione

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]:

Natural Products >> Others

Research Areas >> Others

[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.

[Related Small Molecules]

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

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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...