Strophanthidin
Title: Strophanthidin
CAS Registry Number: 66-28-4
CAS Name: (3b,5b)-3,5,14-Trihydroxy-19-oxocard-20(22)-enolide
Additional Names: apocynamarin; convallatoxigenin; corchorin; cymarigenin; cynotoxin; corchorgenin; corchsularin
Molecular Formula: C23H32O6
Molecular Weight: 404.50
Percent Composition: C 68.29%, H 7.97%, O 23.73%
Literature References: By acid or enzymic hydrolysis of glycosides present in several species of Strophanthus, Apocynaceae. Isoln: Jacobs, Heidelberger, J. Biol. Chem. 54, 253 (1922). Structure: Kon, Chem. Ind. (London) 53, 593, 956 (1934); Jacobs, Elderfield, Science 80, 533 (1934). Identity with corchorin, corchorgenin and corchsularin: Sen et al., Helv. Chim. Acta 40, 588 (1957). Synthesis from pregnenolone acetate, q.v.: E. Yoshii et al., J. Org. Chem. 43, 3946 (1978). Toxicity study: Graebner, Geisel, Arzneim.-Forsch. 22, 1854 (1972). Reviews: Elderfield, Chem. Rev. 17, 187 (1935); Tschesche, Ergeb. Physiol. 38, 31 (1936); Stoll, The Cardiac Glycosides (Pharmaceutical Press, London, 1937); Strain in Organic Chemistry vol. II, Gilman, Ed. (New York, 2nd ed., 1943); Fieser, Fieser, Steroids (Reinhold, New York, 1959) pp 729-730, 736-750.
Properties: Orthorhombic tablets from 5 parts methanol and 10 parts water. Very poisonous! Contains ½ mol H2O which is given up at 110° over P2O5 at 20 mm Hg. mp 171-175° with effervescence. Occasionally a few isolated crystals are found which melt at ~230°. [a]D25 +43.1° (c = 2.8 in methanol). Sol in alcohol, acetone, chloroform, benzene, and glacial acetic acid. Practically insol in water, ether, petr ether. Color reaction with H2SO4 and Ac2O like cholesterol. LD100 i.v. in cats: 0.337 mg/kg (Graebner, Geisel).
Melting point: mp 171-175° with effervescence; Occasionally a few isolated crystals are found which melt at ~230°
Optical Rotation: [a]D25 +43.1° (c = 2.8 in methanol)
Toxicity data: LD100 i.v. in cats: 0.337 mg/kg (Graebner, Geisel)
 
Derivative Type: 3-Benzoylstrophanthidin
Molecular Formula: C30H36O7
Molecular Weight: 508.60
Percent Composition: C 70.85%, H 7.13%, O 22.02%
Properties: mp 230°. [a]D26 +47.8° (c = 1.07 in acetone).
Melting point: mp 230°
Optical Rotation: [a]D26 +47.8° (c = 1.07 in acetone)
 
Derivative Type: 3-(p-Bromobenzoyl)strophanthidin
Molecular Formula: C30H35BrO7
Molecular Weight: 587.50
Percent Composition: C 61.33%, H 6.00%, Br 13.60%, O 19.06%
Properties: mp 222-224°. [a]D20 +42.0° (c = 1.094 in acetone).
Melting point: mp 222-224°
Optical Rotation: [a]D20 +42.0° (c = 1.094 in acetone)
 
Derivative Type: Dihydrostrophanthidin
Molecular Formula: C23H34O6
Molecular Weight: 406.51
Percent Composition: C 67.96%, H 8.43%, O 23.61%
Properties: mp 100-103°, resolidifies and again melts at 190-195°. [a]D23 +34.9° (methanol).
Melting point: mp 100-103°
Optical Rotation: [a]D23 +34.9° (methanol)
 
Derivative Type: 16-Hydroxystrophanthidin
Additional Names: Strophadogenin
Molecular Formula: C23H32O7
Molecular Weight: 420.50
Percent Composition: C 65.69%, H 7.67%, O 26.63%
Properties: Long prisms from ethanol, dec 238-241°. [a]D23 +52.9° (c = 1.24 in 96% alc). uv max: 219 nm (log e 4.3).
Optical Rotation: [a]D23 +52.9° (c = 1.24 in 96% alc)
Absorption maximum: uv max: 219 nm (log e 4.3)

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