36995-92-3

Basic information

• Product Name: 6-uracil
• Synonyms: 6-uracil
• CAS NO: 36995-92-3
• Molecular Weight: 365.386
• Mol File: 36995-92-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6-uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 6-uracil(36995-92-3)
• EPA Substance Registry System: 6-uracil(36995-92-3)

Safety Data

• Hazardous Substances Data: 36995-92-3(Hazardous Substances Data)

Upstream product

• 111619-05-7 3,4-xylidino-D-ribofuranoside 
• 95-64-7 4-amino-o-xylene 
• 36468-53-8 β-D-ribofuranose 
• 50-69-1 D-ribose 
• 4270-27-3 6-chlorouracil 
• 3051-94-3 3,4-dimethyl-N-ribitylaniline 

Downstream Products

• 57818-88-9 5-deazaflavin adenine dinucleotide 
• 19342-73-5 5-deazariboflavin 
• 59389-71-8 6-uracil 

Relevant articles and documents

Dibenzothiophene Catabolism Proceeds via a Flavin-N5-oxide Intermediate

The dibenzothiophene catabolic pathway converts dibenzothiophene to 2-hydroxybiphenyl and sulfite. The third step of the pathway, involving the conversion of dibenzothiophene sulfone to 2-(2-hydroxyphenyl)-benzenesulfinic acid, is catalyzed by a unique flavoenzyme DszA. Mechanistic studies on this reaction suggest that the C2 hydroperoxide of dibenzothiophene sulfone reacts with flavin to form a flavin-N5-oxide. The intermediacy of the flavin-N5-oxide was confirmed by LC-MS analysis, a co-elution experiment with chemically synthesized FMN-N5-oxide and 18O2 labeling studies.

Improved Chemical Syntheses of 1- and 5-Deazariboflavin

The cofactor flavin adenine dinucleotide (FAD) is required for the catalytic activity of a large class of enzymes known as flavoenzymes. Because flavin cofactors participate in catalysis via a number of different mechanisms, isoalloxazine analogues are valuable for mechanistic studies. We report improved chemical syntheses for the preparation of the two key analogues, 5-deazariboflavin and 1-deazariboflavin.

Preparation of 5-deazariboflavins

This invention relates generally to a novel process for preparing 5-deazariboflavins by the cyclization of the corresponding 6-(N-substituted arylamino)uracils with trialkylorthoformate in the presence of a strong acid catalyst. An improved process for preparing the uracil intermediate is also disclosed. More particularly, it is concerned with the process for preparing 5-deazariboflavin by cyclizing 6-[3,4-dimethyl-N-(D-ribityl)anilino[uracil with trialkylorthoformate in the presence of a strong acid catalyst and hydrolyzing the resulting alkoxymethylene derivative. The corresponding uracil intermediate is prepared by reacting 6-chlorouracil with N-D-ribityl-3,4-xylidine. 5-Deazariboflavins having the general Formula (I) herein below: STR1 wherein R7 is hydrogen or methyl, R8 is methyl, hydroxy or acyloxy and R10 is a ribityl group and the corresponding acyl and alkoxymethylene derivatives are useful as riboflavin antagonists with particular utility for the chemotherapy of coccidiosis in chickens or as intermediates for the preparation of said antagonists. The bis(alkoxymethylene) derivatives described herein are useful as prodrug forms of 5-deazariboflavins. When used for the treatment of coccidiosis, such compounds are administered to the animals by way of the feed and are effective in preventing coccidiosis when administered at levels of from about 0.0005% to about 0.05% by weight of the total feed consumed, the amount required for optimum prevention or control of the disease varying with the particular compound employed.