Ascaridole
1-methyl- 4-(1 -methylethyl ) -2,3 - dioxabicyclo [2.2.2 ] oct -5-ene
Slightly greenish yellow liquid
Liquid
1.01 g · cm -3
3 ° C
113-114 ° C ( 2.6 kPa), explosive decomposition > 130 ° C
Sparingly soluble in water
1.4769 (20 ° C)
Template: Infobox chemical / molecular formula search available
Ascaridol is a herbal natural products, and thus a chemical compound. It is a monocyclic monoterpene peroxide with not clearly enlightened absolute configuration. 1943 could be synthesized by Günther Otto Schenck and Karl Ziegler for the first time. It is synthesized from pinene and oxygen in the presence of chlorophyll. It was formerly used as an anthelmintic.
Occurrence
Ascaridol be found in the so-called Fragrant goosefoot ( artemisia ) and in the oil of Boldo leaves. Ascaridol is unstable due to the peroxide group.
Historical
Ascaridol was the first discovered in naturally occurring organic peroxide. It was isolated from plants of the genus goose feet ( Chenopodium ). Hüthig recognized in 1908 the explosive character of ascaridol and determined the molecular formula C10H16O2 with. In the reaction of sulfuric acid with ascaridol or in the reduction to p-cymene with Zink-Pulver/Essigsäure forms. These results were confirmed in 1911 by EK, Nelson. Nelson clearly showed that ascaridol neither a hydroxyl nor contains a carbonyl group. An almost correct structure proposal by Nelson in 1912 corrected by Otto Wallach.
The first laboratory synthesis was achieved in 1944 Günther Schenck and Karl Ziegler. The starting material α -terpinene reacts with oxygen in the presence of chlorophyll and light. Under these reaction conditions the singlet is photochemically generated first, which reacts in a hetero-Diels -Alder reaction with the diene system in terpinene. Back in 1945 this reaction in Germany was industrially developed into a commercial process for the production of large quantities ascaridol. Ascaridol was used as a cost-effective drug against worms.
Physiological effects
Ascaridol allergenic. As a breakdown product of monoterpenes, among others the tea tree oil is responsible for the allergenicity of certain essential oils.