2281. Cimigenol

Nomenclature

CAS number: 3779-59-7
(3β,15α,16α,23R,24S)-16,23:16,24-Diepoxy-9,19-cyclolanostane-3,15,25-triol; cimicifugol.
C30H48O5; mol wt 488.70.
C 73.73%, H 9.90%, O 16.37%.

Description and references

From the resin of Cimicifuga racemosa Nutt. (Actaea racemosa L.), Ranunculaceae: Corsano, Spano, Atti Accad. Naz. Lincei Cl. Sci. Fis. Mat. Nat. Rend. 32, 674 (1962), C.A. 58, 11408e (1963). Structure: Corsano et al., Chem. Commun. 1965, 185; Corsano, Piancatelli, Ric. Sci. 37, 366 (1967); eidem, Gazz. Chim. Ital. 99, 1140 (1969). Identity with cimicifugol: J. Pharm. Soc. Jpn. 87, 1569 (1967).

Chemical structure

Properties

Needles from methanol, mp 227.5-228.5°. [α]D +38° (c = 0.86 in chloroform).

Derivative

Diacetate.
C34H52O7; mol wt 572.77.
C 71.30%, H 9.15%, O 19.55%.

Properties

Needles from hexane, mp 202-204°. [α]D +46.3° (c = 1.07 in chloroform).

Derivative

Triacetate.
C36H54O8; mol wt 614.81.
C 70.33%, H 8.85%, O 20.82%.

Properties

Needles from hexane, mp 149.5-150.5°. [α]D +25.4° (chloroform).