1,2,4-Trioxane

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1,2,4-Trioxane
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IUPAC name 1,2,4-Trioxane
Identifiers
CAS number 7049-17-4
SMILES C1COCOO1
Properties
Molecular formula C3H6O3
Molar mass 90.08 g/mol
Related Compounds
Related compounds 1,3,5-trioxane
artemisinin
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is a cyclic acetal with one of the oxygen atoms in the acetal group being in a peroxide group.

1,2,4-Trioxane itself has not been isolated or characterized, but rather only studied computationally. However, it constitutes an important structural element of some more complex organic compounds. The natural compound artemisinin, isolated from the sweet wormwood plant (Artemisia annua), and its synthetic derivatives are important antimalarial drugs. The peroxide group in the 1,2,4-trioxane core of artemisinin is cleaved in the presence of the malaria parasite leading to reactive oxygen radicals that are damaging to the parasite.

References


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