ABC00204ZR

artemisinin Imp-B

Artemisinin Imp-B is a sesquiterpene endoperoxide derivative characterized by a 1,2,4-trioxane core and a modified side chain compared to artemisinin, featuring an additional hydroxyl group at C-10 and a methylene bridge substitution at C-12. This structural divergence disrupts the parent compound's antimalarial activity while preserving the peroxide pharmacophore. The compound arises as a synthetic byproduct during artemisinin semisynthesis from Qinghaosu, specifically during oxygenation steps. Serves as an HPLC reference standard for quantifying process-related impurities in artemisinin-based API manufacturing.

On Request
Molecular Formula C15H22O5
Molecular Weight 282.3300
CAS Number 113472-97-2 โš  Unverified
PubChem CID 821423 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Artemisinin
Lead Time On Request
IUPAC Name (1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

๐Ÿ“ Synonyms

9-epi-Artemisinin 9-Epiartemisinin 11-epi-Artemisinin (+)-9-Epiartemisinin 9-epi-Artemisinin [WHO-IP] 0474Z7MDH1 UNII-0474Z7MDH1 (1R,4S,5R,8S,9S,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one DTXSID70356309 (3R,5aS,6R,8aS,9S,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one

๐Ÿ”ฌ Chemical Identifiers

C[C@@H]1CC[C@H]2[C@@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C
InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9+,10+,11+,13-,14-,15-/m1/s1
BLUAFEHZUWYNDE-DWIPZSBTSA-N

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