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 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 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.

[edit] History

Ascaridole was the first and for a long time only discovered naturally occurring 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.

[edit] References