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Merck
CN

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:
504-07-4
Molecular Weight:
114.10
NACRES:
NA.21
PubChem Substance ID:
24894143
UNSPSC Code:
12352005
EC Number:
207-982-1
MDL number:
MFCD00006029

Key Documents

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Product Name

Dihydrouracil, powder

InChI

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

InChI key

OIVLITBTBDPEFK-UHFFFAOYSA-N

SMILES string

O=C1CCNC(=O)N1

form

powder

mp

279-281 °C (lit.)

Quality Level

100

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Application

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

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ1052
MKCL7634
MKBW1788V
MKBT1601V
MKBQ1521V

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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
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)
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
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
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
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