References of 13-(chloromethyl)-2,3-dihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,
8,9,10,12,12a,13,14,14a-tetradecahydro-1H-picene-4,8a-dicarboxylic acid
Title: Senegenin
CAS Registry Number: 2469-34-3
CAS Name: (2b,3b,4a,12a)-12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid
Molecular Formula: C30H45ClO6
Molecular Weight: 537.13
Percent Composition: C 67.08%, H 8.44%, Cl 6.60%, O 17.87%
Literature 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°. [a]D +19° (c = 0.70 in ethanol). uv max: 205 nm (e 6950). Sol in alcohol, acetone, acetic acid; practically insol in chloroform, benzene.
Melting point: mp 281-283°
Optical Rotation: [a]D +19° (c = 0.70 in ethanol)
Absorption maximum: uv max: 205 nm (e 6950)
Derivative Type: Monoacetate
Molecular Formula: C32H47ClO7
Molecular Weight: 579.16
Percent Composition: C 66.36%, H 8.18%, Cl 6.12%, O 19.34%
Properties: Crystals from methanol + chloroform, mp 209-211°. [a]D +23° (c = 1.32). uv max (methanol): 205 nm (e 6400).
Melting point: mp 209-211°
Optical Rotation: [a]D +23° (c = 1.32)
Absorption maximum: uv max (methanol): 205 nm (e 6400)
Derivative Type: Diacetate
Molecular Formula: C34H49ClO8
Molecular Weight: 621.20
Percent Composition: C 65.74%, H 7.95%, Cl 5.71%, O 20.60%
Properties: Dec 257-263°. [a]D +29° (c = 1.09 in methanol).
Optical Rotation: [a]D +29° (c = 1.09 in methanol)
Status: This monograph has been retired and is no longer subject to revision or update.
