378. Amarolide

Nomenclature

CAS number: 29913-86-8
(2α,11α)-2,11-Dihydroxypicrasane-1,12,16-trione.
C20H28O6; mol wt 364.43.
C 65.91%, H 7.74%, O 26.34%.

Description and references

Isoln from Ailanthus altissima (Mill.) Swingle (A. glandulosa Desf.), Simaroubaceae, and proposed structure: Casinovi et al., Tetrahedron Lett. 1965, 2273. Isoln from Castela nicholsoni Hook, Simaroubaceae, and revised structure: Stcklin et al., ibid. 1970, 2399.

Chemical structure

Properties

mp 253-255°. Practically insol in weak alkaline solns. Slightly sol in sodium carbonate, easily dissolved by sodium hydroxide.

Derivative

Monoacetate.
C22H30O7; mol wt 406.47.
C 65.01%, H 7.44%, O 27.55%.

Properties

mp 264-265° for 11-acetate; mp 225° for 2-acetate.

Derivative

Diacetate.
C24H32O8; mol wt 448.51.
C 64.27%, H 7.19%, O 28.54%.

Properties

mp 269-270° (from alcohol). Also reported as mp 260-262°.