D7628
Dihydrouracil
powder
Synonym(s):
5,6-Dihydro-2,4-dihydroxypyrimidine
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About This Item
Empirical Formula (Hill Notation):
C4H6N2O2
CAS Number:
Molecular Weight:
114.10
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352005
EC Number:
207-982-1
MDL number:
Form:
powder
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Ryota Hidese et al.
Journal of bacteriology, 193(4), 989-993 (2010-12-21)
The reductive pyrimidine catabolic pathway is absent in Escherichia coli. However, the bacterium contains an enzyme homologous to mammalian dihydropyrimidine dehydrogenase. Here, we show that E. coli dihydropyrimidine dehydrogenase is the first member of a novel NADH-dependent subclass of iron-sulfur
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)