76. Acetoxolone
Nomenclature
CAS number: 6277-14-1
(3β,20β)-3-(Acetyloxy)-11-oxoolean-12-en-29-oic acid; 3β-hydroxy-11-oxoolean-12-en-30-oic acid acetate; 3-O-acetyl-18β-glycyrrhetic acid; acetylglycyrrhetinic acid; glycyrrhetic acid acetate. C32H48O5; mol wt 512.72.
C 74.96%, H 9.44%, O 15.60%.
Description and references
Deriv of enoxolone, q.v.; homolog of carbenoxolone, q.v. Prepn: J. M. Beaton, F. S. Spring, J. Chem. Soc. 1955, 3126. Prepn of the aluminum salt: A. Bonati, ZA 7006901; idem, US 3764618 (1971, 1973 both to Dott. Inverni & Della Beffa). NMR study of the acetate: M. Mousseron-Canet et al., Bull. Soc. Chim. Fr. 12, 4668 (1967). Pharmacology of the aluminum salt: C. Capra, Fitoterapia 40, 8 (1969), C.A. 73, 64754 (1970). Absorption in rats: B. D. Cameron et al., Arzneim.-Forsch. 26, 1680 (1976). Analysis of gastric protective effect: P. Altmayer et al., ibid. 31, 853 (1981).
Properties
Crystals, mp 322-325°. [α]D20 +141°.Derivative
Aluminum salt.Nomenclature
CAS number: 29728-34-5
Almacet (Celtia). C96H141AlO15; mol wt 1562.12.
C 73.81%, H 9.10%, Al 1.73%, O 15.36%.
Properties
White powder, mp 286-290°. [α]D20 +126±2° (c = 1 in chloroform). Insol in water. Sol in most organic solvents. LD50 in male rats (mg/kg): >3300 orally, and i.p. (Bonati).Therapeutic Category
Antiulcerative.
Keywords
Antiulcerative; Cytoprotectant (Gastric)