12-08598. Senegenin [Archived]
Nomenclature
CAS number: 2469-34-3
(2β,3β,4α,12α)-12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic
acid. C30H45ClO6; mol wt 537.13.
C 67.08%, H 8.44%, Cl 6.60%, O 17.87%.
Description and references
From root of Polygala senega Linn., Polygalaceae: Jacobs, Isler, J. Biol. Chem. 119, 155 (1937). Structure studies: Shamma, Reiff, Chem. Ind. (London) 1960, 1272; Dugan et al., Can. J. Chem. 42, 491 (1964). Structure: Dugan et al., Proc. Chem. Soc. London 1964, 264. Formation from presenegenin: Pelletier et al., Chem. Commun. 1966, 727.
Properties
Needles from dil alc, mp 281-283°. [α]D +19° (c = 0.70 in ethanol). uv max: 205 nm (ε 6950). Sol in alcohol, acetone, acetic acid; practically insol in chloroform, benzene.Derivative
Monoacetate.C32H47ClO7; mol wt 579.16.
C 66.36%, H 8.18%, Cl 6.12%, O 19.34%.
Properties
Crystals from methanol + chloroform, mp 209-211°. [α]D +23° (c = 1.32). uv max (methanol): 205 nm (ε 6400).Derivative
Diacetate.C34H49ClO8; mol wt 621.20.
C 65.74%, H 7.95%, Cl 5.71%, O 20.60%.
Properties
Dec 257-263°. [α]D +29° (c = 1.09 in methanol).Status
This monograph has been retired and is no longer subject to revision or update.