Periplogenin
Title: Periplogenin
CAS Registry Number: 514-39-6
CAS Name: (3b,5b)-3,5,14-Trihydroxycard-20(22)-enolide
Additional Names: desoxostrophanthidin
Molecular Formula: C23H34O5
Molecular Weight: 390.51
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Literature References: The aglycon of periplocin and periplocymarin; accompanies strophanthidin in Strophanthus eminii Asch. et Pax., Apocynaceae. Isoln: Lehmann, Arch. Pharm. 235, 157 (1897); Jacobs, Hoffmann, J. Biol. Chem. 79, 519 (1928); Stoll, Renz, Helv. Chim. Acta 22, 1193 (1939); Lardon, ibid. 33, 639 (1950). Structure: Speiser, Reichstein, Experientia 3, 323 (1947); eidem, Helv. Chim. Acta 30, 2143 (1947); 31, 622 (1948). Synthesis: Deghenghi, Gaudry, Tetrahedron Lett. 1963, 2045; Kamano et al., J. Org. Chem. 39, 2319 (1974).
Properties: Solvated prisms from methanol which contain an undetermined amount of methanol, sinter at 140°, mp 235°. [a]D27 +31.5° (c = 1.04 in alcohol). Sol in alcohol and chloroform; slightly sol in ether, water (1:2500); practically insol in benzene, petr ether. pH of aq solns ~7. Strong positive Legal test.
Melting point: mp 235°
Optical Rotation: [a]D27 +31.5° (c = 1.04 in alcohol)
 
Derivative Type: Monobenzoate
Molecular Formula: C30H38O6
Molecular Weight: 494.62
Percent Composition: C 72.85%, H 7.74%, O 19.41%
Properties: Stout glistening wedges from 95% alcohol, mp 235°.
Melting point: mp 235°
 
Derivative Type: Dihydroperiplogenin
Molecular Formula: C23H36O5
Molecular Weight: 392.53
Percent Composition: C 70.38%, H 9.24%, O 20.38%
Properties: Stout prisms from 25% alcohol, mp 204° (slight preliminary softening).
Melting point: mp 204° (slight preliminary softening)
 
Derivative Type: 3-O-Acetylperiplogenin
Molecular Formula: C25H36O6
Molecular Weight: 432.55
Percent Composition: C 69.42%, H 8.39%, O 22.19%
Properties: Crystals, mp 242-244°, [a]D22 +46.9° (c = 0.32 in chloroform).
Melting point: mp 242-244°
Optical Rotation: [a]D22 +46.9° (c = 0.32 in chloroform)

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