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D7628

Sigma-Aldrich

Dihydrouracil

powder

Synonym(s):

5,6-Dihydro-2,4-dihydroxypyrimidine

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About This Item

Empirical Formula (Hill Notation):
C4H6N2O2
CAS Number:
504-07-4
Molecular Weight:
114.10
EC Number:
207-982-1
MDL number:
MFCD00006029
UNSPSC Code:
12352005
PubChem Substance ID:
24894143
NACRES:
NA.21

form

powder

mp

279-281 °C (lit.)

SMILES string

O=C1CCNC(=O)N1

InChI

1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)

InChI key

OIVLITBTBDPEFK-UHFFFAOYSA-N

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General description

Dihydrouracil (DiHU) is a minor base found in transfer ribonucleic acid (tRNA). It is similar to uracil with the only exception that the C5-C6 bond is saturated. It crystallized in the monoclinic system with space group P21/C. Its crystalline structure has been analyzed. Its generation from L-cysteine and uracil via photochemical addition has been described.

Application

Dihydrouracil has been used as a standard for ureido group in the colorimentric assay of transfer ribonucleic acid (tRNA).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Teresa Di Desidero et al.
Investigational new drugs, 36(4), 709-714 (2018-03-01)
The aim of the present study was to assess the pharmacokinetics (PK) of metronomic capecitabine and its metabolites in a population of refractory metastatic colorectal cancer (mCRC) patients. Thirty-four patients (M/F, 22/12) with a diagnosis of mCRC received capecitabine 800 mg
Jihane Basbous et al.
Nucleic acids research, 48(4), 1886-1904 (2019-12-20)
Imbalance in the level of the pyrimidine degradation products dihydrouracil and dihydrothymine is associated with cellular transformation and cancer progression. Dihydropyrimidines are degraded by dihydropyrimidinase (DHP), a zinc metalloenzyme that is upregulated in solid tumors but not in the corresponding
Stereochemistry of nucleic acids and their constituents. VI. The crystal structure and conformation of dihydrouracil: a minor base of transfer-ribonucleic acid.
Rohrer DC and Sundaralingam M.
Acta Crystallographica Section B, Structural Science, 26(5), 546-553 (1970)
Cuiping Liu et al.
Methods in enzymology, 469, 69-93 (2009-01-01)
Transfer RNA (tRNA) molecules mediate translation of the nucleic acid genetic code into the amino acid building blocks of proteins, thus ensuring the survivability of cells. The dynamic properties of tRNA molecules are crucial to their functions in both activity
M Boisdron-Celle et al.
Cancer letters, 249(2), 271-282 (2006-10-27)
5-Fluorouracil (5-FU)-related early toxicity, due to a metabolic deficiency, is rare but is potentially severe and even lethal (0.1%). It is due to dihydropyrimidine dehydrogenase (DPYD) gene polymorphism or some epigenetic factors. The detection of metabolic change could prevent severe
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