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D7628

Sigma-Aldrich

Dihydrouracil

powder

Synonyme(s) :

5,6-Dihydro-2,4-dihydroxypyrimidine

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About This Item

Formule empirique (notation de Hill):
C4H6N2O2
Numéro CAS:
504-07-4
Poids moléculaire :
114.10
Numéro CE :
207-982-1
Numéro MDL:
MFCD00006029
Code UNSPSC :
12352005
ID de substance PubChem :
24894143
Nomenclature NACRES :
NA.21

Niveau de qualité

100

Forme

powder

Pf

279-281 °C (lit.)

Chaîne SMILES 

O=C1CCNC(=O)N1

InChI

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

Clé InChI

OIVLITBTBDPEFK-UHFFFAOYSA-N

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Description générale

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).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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L-Dihydroorotic acid ≥99%

Sigma-Aldrich

D7128

L-Dihydroorotic acid

Thymine ≥99%

Sigma-Aldrich

T0376

Thymine

N-Acetyl-L-aspartic acid ≥99.0% (T)

Sigma-Aldrich

00920

N-Acetyl-L-aspartic acid

Purine 98%

Sigma-Aldrich

P55805

Purine

Futao Yu et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(49), 19593-19598 (2011-11-30)
Dihydrouridine (D) is a highly conserved modified base found in tRNAs from all domains of life. Dihydrouridine synthase (Dus) catalyzes the D formation of tRNA through reduction of uracil base with flavin mononucleotide (FMN) as a cofactor. Here, we report
Yvonne Wettergren et al.
Cancer, 118(11), 2935-2943 (2011-10-25)
In Nordic countries, the standard treatment of colorectal cancer (CRC) in the adjuvant setting is bolus 5-fluorouracil (5-FU) plus leucovorin alone or in combination with oxaliplatin. 5-FU competes with the natural occurring pyrimidine uracil (Ura) as a substrate for dihydropyrimidine
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)
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
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
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