Ascaridole

Title: Ascaridole
CAS Registry Number: 512-85-6
CAS Name: 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
Additional Names: 1,4-peroxido-p-menthene-2
Molecular Formula: C10H16O2
Molecular Weight: 168.23
Percent Composition: C 71.39%, H 9.59%, O 19.02%
Literature References: An organic peroxide which constitutes 60-80% of oil of chenopodium. Synthesis from a-terpinene by treatment with oxygen, chlorophyll, and light: Schenck, Ziegler, Naturwissenschaften 1944, 157. Purification: Beckett et al., J. Pharm. Pharmacol. 7, 55 (1955). Isoln from Chenopodium ambrosioides L.: E. Okuyama et al., Chem. Pharm. Bull. 41, 1309 (1993). Review of use as anthelmintic: M. M. Kliks, Soc. Sci. Med. 21, 879-886 (1985).
Properties: Liquid; unstable; prone to explode when heated or when treated with organic acids. d420 1.0103; d2020 1.0113. mp 3.3°. bp0.2 39-40°. Sol in hexane, pentane, ethanol, toluene, benzene, castor oil.
Melting point: mp 3.3°
Boiling point: bp0.2 39-40°
Density: d420 1.0103; d2020 1.0113
Therap-Cat: Has been used as anthelmintic (Nematodes).
Therap-Cat-Vet: Anthelmintic.
Keywords: Anthelmintic (Nematodes).
Asclepias Ascorbic Acid Ascorbigen Asiaticoside Asoprisnil

Ascaridole
Skeletal formula Ascaridole-3D-balls.png
Identifiers
CAS number 512-85-6 N
PubChem 10545
ChemSpider 10105 YesY
ChEBI CHEBI:2866 YesY
ChEMBL CHEMBL467614 YesY
Jmol-3D images Image 1
Properties[1]
Molecular formula C10H16O2
Molar mass 168.23 g/mol
Density 1.010 g/cm3
Melting point 3.3 °C
Boiling point 40 °C at 0.2 mmHg
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 a colorless liquid with a pungent smell and taste 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. Ascaridole determines the specific flavor of the Chilean tree boldo and is a major constituent of the oil of Mexican Tea (wormseed). It is a component of natural medicine, tonic drinks and food flavoring in Latin American cuisine. As part of the oil, ascaridole is used as an anthelmintic drug that expels parasitic worms from plants, domestic animals and the human body.