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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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Sylke Schneider et al.
Journal of the American College of Surgeons, 200(3), 336-344 (2005-03-02)
To find out if neoadjuvant therapy could alter tumor response determinants that might affect tumor sensitivity to the treatment, we investigated intratumoral expressions of genes associated with chemosensitivity, radiosensitivity, or both before and after radiochemotherapy. Twenty-four patients with locally advanced
The mechanism of photochemical addition of cysteine to uracil and formation of dihydrouracil.
Jellinek T and Johns RB.
Photochemistry and Photobiology, 11(5), 349-359 (1970)
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