4624. Hederagenin

Nomenclature

CAS number: 465-99-6
(3β,4α)-3,23-Dihydroxyolean-12-en-28-oic acid; caulosapogenin; melanthigenin.
C30H48O4; mol wt 472.70.
C 76.23%, H 10.24%, O 13.54%.

Description and references

Occurs as glycoside in many saponins, see α-Hederin. Isoln and structure: van der Haar, Arch. Pharm. 250, 424 (1912); Ruzicka et al., Helv. Chim. Acta 28, 380 (1945); Haynes et al., J. Chem. Soc. 1963, 744. Identity with melanthigenin: Mustafa, Soliman, ibid. 1943, 70. Identity with caulosapogenin: McShefferty, Stenlake, ibid. 1956, 2314. Molecular and crystal structure: R. Roques et al., Acta Crystallogr. B34, 1634 (1978). See also α- and β-Amyrin and Oleanolic Acid.

Chemical structure

Properties

Crystals from alc, mp 332-334°. [α]D20 +81° (c = 0.7 in pyridine). Freely sol in pyridine; sol in chloroform-alcohol mixtures; slowly sol in alcohol; practically insol in water; sol in dil alcoholic NaOH, but not in water solns of alkalies.

Derivative

Diacetate.

Properties

mp 172-174°. [α]D20 +64° (CHCl3).

Derivative

Methyl ester.

Properties

mp 240°. [α]D23 +76° (c = 0.8 in CHCl3).