Steganacin

Steganacin
	; (−)-Steganacin
Names
	Preferred IUPAC name (3aS,14S,14aS)-6,7,8-Trimethoxy-3-oxo-1,3,3a,4,14,14a-hexahydro-11H-benzo[3,4]furo[3′,4′:6,7]cycloocta[1,2-f][1,3]benzodioxol-14-yl acetate
Identifiers
CAS Number	(−): 41451-68-7 [ChemSpider];
3D model (JSmol)	(+): Interactive image; (−): Interactive image;
ChEBI	(−): CHEBI:9259;
ChEMBL	(−): ChEMBL154064;
ChemSpider	(+): 264758; (−): 391322;
KEGG	(−): C10886;
PubChem CID	(+): 299674; (−): 443021;
	InChI InChI=1S/C24H24O9/c1-11(25)33-21-14-8-18-17(31-10-32-18)7-13(14)20-12(5-15-16(21)9-30-24(15)26)6-19(27-2)22(28-3)23(20)29-4/h6-8,15-16,21H,5,9-10H2,1-4H3/t15-,16+,21+/m0/s1 Key: XJTXBUKLGQCZHC-GCKMJXCFSA-N; (−): InChI=1S/C24H24O9/c1-11(25)33-21-14-8-18-17(31-10-32-18)7-13(14)20-12(5-15-16(21)9-30-24(15)26)6-19(27-2)22(28-3)23(20)29-4/h6-8,15-16,21H,5,9-10H2,1-4H3/t15-,16+,21+/m1/s1 Key: XJTXBUKLGQCZHC-XFQAVAEZSA-N;
	SMILES (+): CC(=O)O[C@H]1[C@@H]2COC(=O)[C@H]2CC3=CC(=C(C(=C3C4=CC5=C(C=C14)OCO5)OC)OC)OC; (−): CC(=O)O[C@H]1c2cc3c(cc2-c4c(cc(c(c4OC)OC)OC)C[C@@H]5[C@@H]1COC5=O)OCO3;
Properties
Chemical formula	C24H24O9
Molar mass	456.447 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

Steganacin is an dibenzocyclooctadiene lactone, an unusual type of lignan.^[1] It exhibits some antileukemic properties in vitro.^[2] It has been isolated from Steganotaenia araliacea.^[2] (−)-Steganacin is the natural form.^[3]

Notes

^ Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews. 2 (3): 371–390. Bibcode:2003PChRv...2..371U. doi:10.1023/B:PHYT.0000045487.02836.32. S2CID 6276953.
^ ^a ^b Kupchan, SM; Britton, RW; Ziegler, MF; Gilmore, CJ; Restivo, RJ; Bryan, RF (21 February 1973). "Steganacin and steganangin, novel antileukemic lignan lactones from Steganotaenia araliacea". Journal of the American Chemical Society. 95 (4): 1335–6. doi:10.1021/ja00785a054. PMID 4687687.
^ Augros, David; Yalcouye, Boubacar; Choppin, Sabine; Chessé, Matthieu; Panossian, Armen; Leroux, Frédéric R. (18 January 2017). "Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin: Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin" (PDF). European Journal of Organic Chemistry. 2017 (3): 497–503. doi:10.1002/ejoc.201601239. S2CID 100375916.