Uzarin
Title: Uzarin
CAS Registry Number: 20231-81-6
CAS Name: (3b,5a)-3-[(2-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Molecular Formula: C35H54O14
Molecular Weight: 698.79
Percent Composition: C 60.16%, H 7.79%, O 32.05%
Literature References: Isoln from the dried root of a Gomphocarpus sp, Asclepiadaceae: Windaus, Haack, Ber. 63, 1377 (1930); Tschesche, Brathge, ibid. 85, 1042 (1952); Schmid et al., Helv. Chim. Acta 42, 72 (1959). Yields uzarigenin by enzymic cleavage. Structure: Tschesche, Bohle, Ber. 68, 2252 (1935). Structure of uzarigenin: Rangaswami, Reichstein, Helv. Chim. Acta 32, 939 (1949); Russel et al., ibid. 44, 1320 (1961). Unlike all other known cardiac glycosides, has the A/B-trans configuration: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 762-763. Review: Heusser, Fortschr. Chem. Org. Naturst. 7, 101 (1950).
Properties: Prisms from pyridine + water, mp 266-270°; stout needles from methanol + ether, mp 206-208°. [a]D20 -27° (c = 1.075 in pyridine); [a]D19 -1.4° (c = 0.85 in methanol). uv max: 217 nm (log e 4.23). Sol in pyridine, hot methyl Cellosolve; sparingly sol in water. Practically insol in ether, chloroform, acetone.
Melting point: mp 266-270°; mp 206-208°
Optical Rotation: [a]D20 -27° (c = 1.075 in pyridine); [a]D19 -1.4° (c = 0.85 in methanol)
Absorption maximum: uv max: 217 nm (log e 4.23)
 
Derivative Type: Uzarigenin
CAS Registry Number: 466-09-1
CAS Name: (3b,5a)-3,14-Dihydroxycard-20(22)-enolide
Additional Names: odorigenin
Molecular Formula: C23H34O4
Molecular Weight: 374.51
Percent Composition: C 73.76%, H 9.15%, O 17.09%
Literature References: Synthesis: Stache et al., Ann. 726, 136 (1969); Kamano et al., J. Org. Chem. 39, 2319 (1974); eidem, J. Chem. Soc. Perkin Trans. 1 1975, 1972.
Properties: Crystals from methanol, mp 240-256°. [a]D20 +10.5° (c = 1.056 in alc).
Melting point: mp 240-256°
Optical Rotation: [a]D20 +10.5° (c = 1.056 in alc)
 
Derivative Type: 3-O-Acetyluzarigenin
Molecular Formula: C25H36O5
Molecular Weight: 416.55
Percent Composition: C 72.08%, H 8.71%, O 19.20%
Properties: Hexagonal plates from methanol, mp 262-266°. [a]D22 +4.6° (c = 1.09 in chloroform).
Melting point: mp 262-266°
Optical Rotation: [a]D22 +4.6° (c = 1.09 in chloroform)
 
Therap-Cat: Antidiarrheal.
Keywords: Antidiarrheal.

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