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Ascaridole

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]

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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 disovered 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 chlorophyl 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.