1,2,4-Trioxane (original) (raw)
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.
| Property | Value |
|---|---|
| dbo:abstract | 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) |
| dbo:iupacName | 1,2,4-Trioxane (en) |
| dbo:thumbnail | wiki-commons:Special:FilePath/1,2,4-Trioxane.png?width=300 |
| dbo:wikiPageID | 3056987 (xsd:integer) |
| dbo:wikiPageLength | 3739 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1105946572 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Carbon dbr:1,3,5-Trioxane dbc:Hypothetical_chemical_compounds dbc:Organic_peroxides dbc:Trioxanes dbr:Organic_compound dbr:Molecular_formula dbr:Malaria dbr:Acetal dbr:Oxygen dbr:Isomer dbr:Artemisinin dbr:Artemisia_annua dbr:Bond_cleavage dbr:Organic_peroxide dbr:Radical_(chemistry) dbr:Reactive_oxygen_species dbr:Ether dbr:Trioxane dbr:Parasitic_disease dbr:Antimalarial_drug dbr:Semi-synthetic |
| dbp:imagealtr | Trioxane molecule (en) |
| dbp:imagefilel | 124 (xsd:integer) |
| dbp:imagefiler | 124 (xsd:integer) |
| dbp:imagenamel | 124 (xsd:integer) |
| dbp:imagesizer | 140 (xsd:integer) |
| dbp:name | 124 (xsd:integer) |
| dbp:pin | 124 (xsd:integer) |
| dbp:verifiedfields | changed (en) |
| dbp:verifiedrevid | 477202901 (xsd:integer) |
| dbp:watchedfields | changed (en) |
| dbp:wikiPageUsesTemplate | dbt:Chembox dbt:Chembox_Hazards dbt:Chembox_Identifiers dbt:Chembox_Properties dbt:Reflist dbt:Sub dbt:Cascite dbt:Chembox_Related dbt:Chemspidercite dbt:Fdacite dbt:Stdinchicite |
| dcterms:subject | dbc:Hypothetical_chemical_compounds dbc:Organic_peroxides dbc:Trioxanes |
| gold:hypernym | dbr:Isomers |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q11173 yago:Abstraction100002137 yago:Acetal114710805 yago:Chemical114806838 yago:Compound114818238 yago:Material114580897 yago:Matter100020827 yago:OrganicCompound114727670 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 yago:WikicatHypotheticalChemicalCompounds dbo:ChemicalCompound yago:Substance100019613 yago:WikicatAcetals umbel-rc:ChemicalSubstanceType |
| rdfs:comment | 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) |
| rdfs:label | 1,2,4-Trioxane (en) 1,2,4-Trioxane (fr) |
| owl:sameAs | freebase:1,2,4-Trioxane yago-res:1,2,4-Trioxane wikidata:1,2,4-Trioxane dbpedia-fr:1,2,4-Trioxane dbpedia-sh:1,2,4-Trioxane dbpedia-sr:1,2,4-Trioxane https://global.dbpedia.org/id/2cLHk |
| prov:wasDerivedFrom | wikipedia-en:1,2,4-Trioxane?oldid=1105946572&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/1,2,4-Trioxane-3D-balls.png wiki-commons:Special:FilePath/1,2,4-Trioxane.png |
| foaf:isPrimaryTopicOf | wikipedia-en:1,2,4-Trioxane |
| foaf:name | 1,2,4-Trioxane (en) |
| is dbo:wikiPageRedirects of | dbr:1,2,4-trioxane |
| is dbo:wikiPageWikiLink of | dbr:C3H6O3 dbr:1,2,4-trioxane dbr:1,3,5-Trioxane |
| is foaf:primaryTopic of | wikipedia-en:1,2,4-Trioxane |
