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1,2,4-Trioxane

Names

Preferred IUPAC name

1,2,4-Trioxane

Identifiers

CAS Number

7049-17-4^Y

3D model (JSmol)

ChemSpider

10629025^Y

PubChem CID

21584057

UNII

X5CWB98J7S^Y

CompTox Dashboard (EPA)

DTXSID30616113

InChI

InChI=1S/C3H6O3/c1-2-5-6-3-4-1/h1-3H2^Y
Key: FQERLIOIVXPZKH-UHFFFAOYSA-N^Y
InChI=1/C3H6O3/c1-2-5-6-3-4-1/h1-3H2
Key: FQERLIOIVXPZKH-UHFFFAOYAX

SMILES

C1COCOO1
C1OCCOO1

Properties

Chemical formula

C₃H₆O₃

Molar mass

90.078 g·mol⁻¹

Related compounds

1,3,5-trioxane
artemisinin

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox 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 like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by 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 some semi-synthetic derivatives are important antimalarial drugs containing the 1,2,4-trioxane ring. Completely synthetic analogs containing the 1,2,4-trioxane ring are important potential improvements over the naturally derived artemisinins.^[1] 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.^[2]

References

^ Gary H. Posner; Michael H. Parker; John Northrop; Jeffrey S. Elias; Poonsakdi Ploypradith; Suji Xie; Theresa A. Shapiro (1999). "Orally Active, Hydrolytically Stable, Semisynthetic, Antimalarial Trioxanes in the Artemisinin Family". J. Med. Chem. 42 (2): 300–304. doi:10.1021/jm980529v. PMID 9925735.
^ Cumming, Jared N.; Ploypradith, Poonsakdi; Gary H. Posner (1997). Antimalarial Activity of Artemisinin (Qinghaosu) and Related Trioxanes: Mechanism (S) of Action. Advances in Pharmacology. Vol. 37. pp. 253–297. doi:10.1016/s1054-3589(08)60952-7. ISBN 9780120329380. PMID 8891104.

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