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1,2,4-Trioxane

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1,2,4-Trioxane
1,2,4-Trioxane
1,2,4-Trioxane
Trioxane molecule
Names
Preferred IUPAC name 1,2,4-Trioxane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6O3/c1-2-5-6-3-4-1/h1-3H2Key: FQERLIOIVXPZKH-UHFFFAOYSA-N
  • InChI=1/C3H6O3/c1-2-5-6-3-4-1/h1-3H2Key: FQERLIOIVXPZKH-UHFFFAOYAX
SMILES
  • C1COCOO1
  • C1OCCOO1
Properties
Chemical formula C3H6O3
Molar mass 90.078 g·mol
Related compounds
Related compounds 1,3,5-trioxane
artemisinin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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

  1. 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.
  2. 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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