Macluraxanthone

Macluraxanthone

Names
Preferred IUPAC name 5,9,10-Trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6-one
Identifiers
CAS Number	5848-14-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6623
ChEMBL	ChEMBL478960
ChemSpider	4444965
KEGG	C10076
PubChem CID	5281646
CompTox Dashboard (EPA)	DTXSID40207172
InChI InChI=1S/C23H22O6/c1-6-22(2,3)15-19-12(9-10-23(4,5)29-19)17(26)14-16(25)11-7-8-13(24)18(27)20(11)28-21(14)15/h6-10,24,26-27H,1H2,2-5H3 Key: XRVLGJCHUWXTDX-UHFFFAOYSA-N
SMILES CC1(C=CC2=C(C3=C(C(=C2O1)C(C)(C)C=C)OC4=C(C3=O)C=CC(=C4O)O)O)C
Properties
Chemical formula	C23H22O6
Molar mass	394.423 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Macluraxanthone is a naturally occurring organic compound with the formula C₂₃H₂₂O₆.^[1] Belonging to the xanthone family,^[2] it is a trihydroxylated xanthone characterized by the presence of a pyran ring and a prenyl chain.^[3]

Its structure features a catechol moiety,^[2] a xanthene core, and a chromene ring.^[4] Acetylation of macluraxanthone yields a triacetate derivative with the formula C₂₉H₂₈O₉. X-ray crystallography of a synthesized derivative (Di-p-bromobenzenesulfonyl-macluraxanthone) reveals a planar xanthene ring system and a screw boat conformation in the chromene ring.^[4] Macluraxanthone has demonstrated antimalarial and larvicidal activity,^[2] including effects against Plasmodium falciparum and vector mosquito larvae.^[5] Additional studies have reported antibacterial activity against Enterococcus faecalis.^[4]