Ascaridole
From Wikipedia, the free encyclopedia
| Ascaridole | |
|---|---|
 |
|
| IUPAC name | 1-methyl-4-(1-methylethyl)-2,3- dioxabicyclo[2.2.2]oct-5-ene |
| Identifiers | |
| CAS number | [512-85-6] |
| Properties | |
| Molecular formula | C10H16O2 |
| Molar mass | 168.23 g/mol |
| Density | 1.0103 g/cm3 |
| Melting point |
3.3 °C |
| Boiling point |
39-40 °C at 0.2 mmHg |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Ascaridole is a natural organic compound classified as a bicyclic monoterpene that has an unusual bridging peroxide functional group. It is the primary constituent of the oil of chenopodium or Mexican Tea (Chenopodium ambrosioides).[1]
It is a colorless liquid that is soluble in most organic solvents. Like other low molecular weight organic peroxides, it is unstable and prone to explosion when heated or treated with organic acids.[2]
Ascaridole has been used as an anthelmintic for controlling nematodes.
[edit] History
Ascaridole was the first and for a long time only discovered peroxide. The structure was resolved by Otto Wallach in 1912,[2] but the first synthesis was done by Karl Ziegler in 1944.[3] The synthesis started from α-Terpinene which reacts with oxygen under the influence of chlorophyll and light. Under these conditions singlet oxygen is generated which is reacting in a Diels-Alder reaction with the dien system in the Terpinene.
[edit] References
- ^ Humphrey Paget (1938). "Chenopodium oil. Part III. Ascaridole". J. Chem. Soc. 392 (1): 829–833. doi:.
- ^ a b O. Wallach (1912). "Zur Kenntnis der Terpene und der ätherischen Öle". Justus Liebig's Annalen der Chemie 392 (1): 49–75. doi:.
- ^ Günther, O. Schenck and K. Ziegler (1944). "Die Synthese des Ascaridols". Naturwissenschaften 32 (14-26): 157. doi:.
