Orotic acid
Colorless and odorless powder
Fixed
348-350 ° C
- 2.4
- 8.13
- 9.45
- Almost insoluble in water and ethanol
- Soluble in wässrg. alkalis
Attention
2000 mg · kg -1 ( LD50, mouse, oral)
Template: Infobox chemical / molecular formula search available
Orotic acid is a pyrimidine derivative, and intermediate in the biosynthesis of Uridinmonophosphats (UMP). It occurs, among others, as part of the nucleoside orotidine. The salts of orotic acid are called " Orotate ".
History
Orotic acid was first isolated in 1904 by the Italian researchers Biscaro and Belloni from Kuhmolke. They described the acidic substance as orotic acid, derived from the Greek " Orós " whey. Since you previously assumed that orotic acid is essential to life, it was also known as vitamin B13.
Occurrence
Orotic acid is found in dairy products, yeast and molds of the genus Neurospora as Neurospora crassa.
Properties
Orotic acid is a white, odorless, sweet -tasting crystalline powder that almost does not dissolve in water or ethanol. The tribasic, medium strong acid dissolves better in aqueous alkali metal hydroxide solution. During the slow crystallizing colorless prism- shaped crystals form. In solid, crystalline form orotic acid is almost unlimited.
Reactions
Orotic acid is an intermediate in the biosynthesis of Uridinmonophosphats. In organisms orotic acid is formed by the oxidation of dihydroorotate. It is this reaction at the fourth step of the pyrimidine de novo synthesis is catalyzed by the dihydroorotate dehydrogenase.
By transmitting a Phosphoribosylrestes by orotate phosphoribosyltransferase Orotsäue reacted in the subsequent step continues to orotidine monophosphate ( OMP), which decarboxylation leads to the formation of uridine. This in turn is the starting product for the biosynthesis of the pyrimidines cytosine, thymidine and uracil.
Biological Significance
In a disturbed running the urea cycle is anstauende carbamyl phosphate leads to an increased synthesis of orotic acid. Accumulation of orotic acid in the serum and tissue also occurs due to a hereditary defect in orotidine -5-phosphate pyrophosphorylase. A concomitant increased excretion in the urine is called Orotacidurie.
Although orotic acid is synthesized in small quantities in the body itself, it must be taken for a daily supply through food.
Orotic acid has many functions in the body.
So orotic acid can prevent ATP levels completely emptied in the heart. Orotic acid to thereby increase the amount of pyrimidine nucleotides in the liver, which then results in an increased production of ATP in the myocardial region to the sequence.
Furthermore, orotic acid and derivatives may improve memory and learning performance ( nootropic). In animal experiments, improved adaptive performance, such as improved education of long-term memory could be detected. The nootropic effect recorded orotic acid is attributed to the filling of the cerebral pyrimidine nucleotide pools, as the de novo synthesis of orotic acid in the brain is a limiting factor for their availability.