Podophyllic Acids
Title: Podophyllic Acids
Molecular Formula: C22H24O9
Molecular Weight: 432.42
Percent Composition: C 61.11%, H 5.59%, O 33.30%
Literature References: Since the prepn of a "podophyllic acid", mp 145-150° (crude), 163-165° (pure), by Borsche, Niemann, Ann. 494, 126 (1932), studies have been made of two isomers: the 2,3-trans-hydroxy acid and the 2,3-cis-hydroxy acid. Prepn of the trans-acid: Kuhn, Wartburg, Experientia 19, 391 (1963); NL 6405480 (1964 to Sandoz), C.A. 62, 9083c (1965); and cis-acid: Renz et al., Ann. 681, 207 (1965). Prepn of a DL-stereoisomer: Gensler et al., J. Am. Chem. Soc. 76, 315 (1954). Configuration and nomenclature: Rutschmann, Renz, Helv. Chim. Acta 42, 890 (1959).
 
Derivative Type: 2,3-trans-Hydroxy acid
CAS Registry Number: 1853-37-8
Additional Names: Podophyllinic acid
Properties: Crystals from acetone + ether, mp 164-168°. [a]D20 -199.9° (c = 0.463 in ethanol), -292.6° (c = 0.671 in pyridine).
Melting point: mp 164-168°
Optical Rotation: [a]D20 -199.9° (c = 0.463 in ethanol), -292.6° (c = 0.671 in pyridine)
 
Derivative Type: 2,3-cis-Hydroxy acid
CAS Registry Number: 477-67-8
Additional Names: Picropodophyllic acid
Properties: Needles from methanol + ether, double mp 150-155° and 200-232°. [a]D21 -100.4° (c = 0.615 in ethanol), -185° (c = 0.746 in pyridine).
Melting point: mp 150-155° and 200-232°
Optical Rotation: [a]D21 -100.4° (c = 0.615 in ethanol), -185° (c = 0.746 in pyridine)
 
Derivative Type: 2,3-trans-Hydroxy acid hydrazide
CAS Registry Number: 78178-41-3
Additional Names: Podophyllinic acid hydrazide
Literature References: Prepn and properties: Rutschmann, US 2977359 (1961 to Sandoz).
Properties: Prisms from methanol, mp 198-199°. [a]D -202° (c = 0.4 in ethanol).
Melting point: mp 198-199°
Optical Rotation: [a]D -202° (c = 0.4 in ethanol)
 
Derivative Type: trans-2-Ethylhydrazide
CAS Registry Number: 1508-45-8
Additional Names: Podophyllinic acid 2-ethylhydrazide
Manufacturers' Codes: SP-I
Literature References: Prepn: Rutschmann, US 3054802 (1962 to Sandoz).
Properties: Amorphous powder, pptd from chloroform + petr ether. [a]D -154° (c = 0.5 in chloroform).
Optical Rotation: [a]D -154° (c = 0.5 in chloroform)

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