13-08466. Scabiolide [Archived]

Nomenclature

CAS number: 20055-57-6
2,3-Dihydroxy-2-methylpropanoic acid 6-[(acetyloxy)methyl]-2,3,3a,4,7,8,11,11a-octahydro-10-methyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester.
C21H28O8; mol wt 408.44.
C 61.75%, H 6.91%, O 31.34%.

Description and references

A sesquiterpenic lactone, the bitter principle of Centaurea scabiosa (L.) Presl., Compositae. Isolation: Suchy et al., Collect. Czech. Chem. Commun. 27, 1905 (1962). Structure: eidem, ibid. 27, 2398 (1962). Revised structure: eidem, ibid. 30, 3473 (1965). Further structural revisions: eidem, ibid. 33, 2238 (1968).

Chemical structure

Properties

Crystals, mp 120°. [α]D20 +101.0° (c = 3.67 in chloroform). Slightly sol in ether, diisopropyl ether, acetone; practically insol in petr ether.

Status

This monograph has been retired and is no longer subject to revision or update.