4829. Hydroxylupanine

Nomenclature

CAS number: 15358-48-2
[2S-(2α,7β,7aβ,14β,14aα)]-Dodecahydro-2-hydroxy-7,14-methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one; octalupine; oxylupanine; 13-hydroxylupanine.
C15H24N2O2; mol wt 264.36.
C 68.15%, H 9.15%, N 10.60%, O 12.10%.

Description and references

From seed of Lupinus perennis L., L. angustifolius L. and L. polyphyllus Lindl., Leguminosae: Rink, Schfer, Arch. Pharm. 287, 290 (1954); Winterfeld, Pies, ibid. 290, 537 (1957); Bohlmann, Winterfeldt, Ber. 93, 1956 (1960). Structure: Galinovsky et al., Monatsh. Chem. 81, 77 (1950). Biosynthesis: Schuette et al., Arch. Pharm. 296, 438 (1963).

Chemical structure

Properties

Crystals from dry acetone, mp 169-170°. [α]D20 +45.6° (c = 1.49 in ethanol); [α]D20 +65.1° (c = 1.09 in water). Sol in water, alc, chloroform; slightly sol in benzene, ether.

Derivative

Methiodide.
C15H24N2O2.CH3I; mol wt 406.30.
C 47.30%, H 6.70%, N 6.89%, O 7.88%, I 31.23%.

Properties

Needles from methanol + ether, mp 254-255°.