Ascaridole
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| Names | |
|---|---|
| IUPAC names
1-methyl-4-(1-methylethyl)-2,3-
dioxabicyclo[2.2.2]oct-5-ene | |
| Identifiers | |
| ECHA InfoCard | 100.007.408 |
| Properties | |
| 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Mexican Tea (Dysphania ambrosioides, formerly 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.
History
Ascaridole was the first and for a long time only discovered organic 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.
References
- ^ Humphrey Paget (1938). "Chenopodium oil. Part III. Ascaridole". J. Chem. Soc. 392 (1): 829–833. doi:10.1039/JR9380000829.
- ^ a b O. Wallach (1912). "Zur Kenntnis der Terpene und der ätherischen Öle". Justus Liebig's Annalen der Chemie. 392 (1): 49–75. doi:10.1002/jlac.19123920104.
- ^ Günther, O. Schenck and K. Ziegler (1944). "Die Synthese des Ascaridols". Naturwissenschaften. 32 (14–26): 157. doi:10.1007/BF01467891.