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.
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| - 1,2,4-Trioxane (en)
- 1,2,4-Trioxane (fr)
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| - 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. (en)
- Le 1,2,4-trioxane est un des deux isomères du trioxane. Il a pour formule brute C3H6O3 et consiste en un cycle à 6 atomes composé de trois groupes méthylène et de trois atomes d'oxygène. Les deux atomes d'oxygène consécutifs forment le groupe fonctionnel peroxyde et le méthylène encadré de deux éthers forme un acétal, l'un des deux atomes d'oxygène appartenant au groupe peroxyde. (fr)
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| - 1,2,4-Trioxane
- 1,2,4-Trioxane
- 1,2,4-Trioxane
- 1,2,4-Trioxane
- 1,2,4-Trioxane
- 1,2,4-Trioxane
- 1,2,4-Trioxane
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| - 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. (en)
- Le 1,2,4-trioxane est un des deux isomères du trioxane. Il a pour formule brute C3H6O3 et consiste en un cycle à 6 atomes composé de trois groupes méthylène et de trois atomes d'oxygène. Les deux atomes d'oxygène consécutifs forment le groupe fonctionnel peroxyde et le méthylène encadré de deux éthers forme un acétal, l'un des deux atomes d'oxygène appartenant au groupe peroxyde. Le 1,2,4-trioxane lui-même n'a pas encore été isolé ou caractérisé mais seulement étudié théoriquement. Cépendant, il constitue un élément structurel important de certains composés organiques plus complexes. Par exemple, l'artémisinine, un produit naturel isolé de l'armoise annuelle (Artemisia annua) et certains de ses dérivés semi-synthétiques sont des anti-paludéens importants. Des analogues complètement synthétiques, contenant aussi un cycle 1,2,4-trioxane présentent de possibles améliorations importantes par rapport aux artémisinines naturelles. Le groupe peroxyde du cœur 1,2,4-trioxane de l'artimisinine est clivé en présence du parasite de la malaria produisant un dérivé réactif de l'oxygène radicalaire qui endommage le parasite. (fr)
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