Ascaridole

Chembox new
Name = Ascaridole
ImageFile = Ascaridol.svg
ImageSize = 60px
ImageName = Ascaridole
IUPACName = 1-methyl-4-(1-methylethyl)-2,3-
dioxabicyclo [2.2.2] oct-5-ene
Section1 = Chembox Identifiers
CASNo = 512-85-6
SMILES =
Section2 = Chembox Properties
Formula = C₁₀H₁₆O₂
MolarMass = 168.23 g/mol
Density = 1.0103 g/cm³
MeltingPt = 3.3 °C
BoilingPt = 39-40 °C at 0.2 mmHg

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").cite journal
title = Chenopodium oil. Part III. Ascaridole
author = Humphrey Paget
journal = J. Chem. Soc.
volume = 392
issue = 1
year = 1938
pages = 829–833
doi = 10.1039/JR9380000829]

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.cite journal
title = Zur Kenntnis der Terpene und der ätherischen Öle
author = O. Wallach
journal = Justus Liebig's Annalen der Chemie
volume = 392
issue = 1
year = 1912
pages = 49–75
doi = 10.1002/jlac.19123920104]

Ascaridole has been used as an anthelmintic for controlling nematodes.

History

Ascaridole was the first and for a long time only discovered peroxide. The structure was resolved by Otto Wallach in 1912, but the first synthesis was done by Karl Ziegler in 1944. [cite journal
title = Die Synthese des Ascaridols
author = Günther, O. Schenck and K. Ziegler
journal = Naturwissenschaften
volume = 32
issue = 14-26
year = 1944
pages = 157
doi = 10.1007/BF01467891 ] 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