Community hub
Recent from talks
Knowledge base stats:
Talk channels stats:
Members stats:
Alloxan
Alloxan, sometimes referred to as alloxan monohydrate, is an organic compound with the formula OC(NHCO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative OC(NHCO)2CO is also known, as well as a dimeric derivative. These are some of the earliest known organic compounds. They exhibit a variety of biological activities.
The compound was discovered by Justus von Liebig and Friedrich Wöhler. It is one of the oldest named organic compounds. It was originally prepared in 1818 by Luigi Valentino Brugnatelli (1761-1818) and was named in 1838 by Wöhler and Liebig. The name "Alloxan" emerged from an amalgamation of the words "Allantoïn" and "Oxalsäure" (oxalic acid). The alloxan model of diabetes was first described in rabbits by Dunn, Sheehan and McLetchie in 1943. The name is derived from allantoin, a product of uric acid excreted by the fetus into the allantois, and oxaluric acid derived from oxalic acid and urea, found in urine.
Alloxan was used in the production of the purple dye murexide, discovered by Carl Wilhelm Scheele in 1776. Murexide is the product of the complex in-situ multistep reaction of alloxantin and gaseous ammonia.[citation needed] Murexide results from the condensation of the unisolated intermediate uramil with alloxan liberated during the course of the reaction.
Scheele sourced uric acid from human calculi (such as kidney stones) and called the compound lithic acid. William Prout investigated the compound in 1818 and he used boa constrictor excrement with up to 90% ammonium acid urate.
In the chapter "Nitrogen" of his memoir The Periodic Table, Primo Levi tells of his futile attempt to make alloxan for a cosmetics manufacturer who has read that it can cause permanent reddening of the lips. Levi considers the droppings of pythons as a source for uric acid for making alloxan, but he is turned down by the director of the Turin zoo because the zoo already has lucrative contracts with pharmaceutical companies, so he is obliged to use chickens as his source of uric acid. The synthesis fails, however, "and the alloxan and its resonant name remained a resonant name."
It was originally obtained by oxidation of uric acid by nitric acid. It is prepared by oxidation of barbituric acid by chromium trioxide.
Alloxan is highly unstable in aqueous solution, undergoing hydrolysis to alloxanic acid. Under physiological conditions, alloxan has an estimated half-life of 1.5 minutes.
Alloxan may be reduced to dialuric acid, which has a reductone structure, similar to ascorbic acid (Vitamin C). However, unlike ascorbic acid, alloxan and dialuric acid have strong pro-oxidant physiological effects.
Hub AI
Alloxan AI simulator
(@Alloxan_simulator)
Alloxan
Alloxan, sometimes referred to as alloxan monohydrate, is an organic compound with the formula OC(NHCO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative OC(NHCO)2CO is also known, as well as a dimeric derivative. These are some of the earliest known organic compounds. They exhibit a variety of biological activities.
The compound was discovered by Justus von Liebig and Friedrich Wöhler. It is one of the oldest named organic compounds. It was originally prepared in 1818 by Luigi Valentino Brugnatelli (1761-1818) and was named in 1838 by Wöhler and Liebig. The name "Alloxan" emerged from an amalgamation of the words "Allantoïn" and "Oxalsäure" (oxalic acid). The alloxan model of diabetes was first described in rabbits by Dunn, Sheehan and McLetchie in 1943. The name is derived from allantoin, a product of uric acid excreted by the fetus into the allantois, and oxaluric acid derived from oxalic acid and urea, found in urine.
Alloxan was used in the production of the purple dye murexide, discovered by Carl Wilhelm Scheele in 1776. Murexide is the product of the complex in-situ multistep reaction of alloxantin and gaseous ammonia.[citation needed] Murexide results from the condensation of the unisolated intermediate uramil with alloxan liberated during the course of the reaction.
Scheele sourced uric acid from human calculi (such as kidney stones) and called the compound lithic acid. William Prout investigated the compound in 1818 and he used boa constrictor excrement with up to 90% ammonium acid urate.
In the chapter "Nitrogen" of his memoir The Periodic Table, Primo Levi tells of his futile attempt to make alloxan for a cosmetics manufacturer who has read that it can cause permanent reddening of the lips. Levi considers the droppings of pythons as a source for uric acid for making alloxan, but he is turned down by the director of the Turin zoo because the zoo already has lucrative contracts with pharmaceutical companies, so he is obliged to use chickens as his source of uric acid. The synthesis fails, however, "and the alloxan and its resonant name remained a resonant name."
It was originally obtained by oxidation of uric acid by nitric acid. It is prepared by oxidation of barbituric acid by chromium trioxide.
Alloxan is highly unstable in aqueous solution, undergoing hydrolysis to alloxanic acid. Under physiological conditions, alloxan has an estimated half-life of 1.5 minutes.
Alloxan may be reduced to dialuric acid, which has a reductone structure, similar to ascorbic acid (Vitamin C). However, unlike ascorbic acid, alloxan and dialuric acid have strong pro-oxidant physiological effects.