Structural Formula Vector Image
Title: a-Peltatin
CAS Registry Number: 568-53-6
CAS Name: [5R-(5a,5ab,8aa)]-5,8,8a,9-Tetrahydro-10-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3¢,4¢:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
Additional Names: 8-hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(4¢-hydroxy-3¢,5¢-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylic acid lactone
Molecular Formula: C21H20O8
Molecular Weight: 400.38
Percent Composition: C 63.00%, H 5.03%, O 31.97%
Literature References: Exists as a glucoside in the rhizomes of Podophyllum peltatum L., Berberidaceae: von Wartburg et al., Helv. Chim. Acta 40, 1331 (1957). Isoln from resin podophyllum: Hartwell, Detty, J. Am. Chem. Soc. 72, 246 (1950).
Properties: Prismatic leaflets from abs ethanol. Begins to sinter at 236°. Dec 242-246°. [a]D20 -124.8° (c = 0.5 in chloroform). Soly in water at 20°: ~30 mg/liter. Fairly sol in chloroform, hot ethanol, acetic acid, acetone, dilute caustic; less sol in benzene, ether, carbon tetrachloride, propylene glycol. Practically insol in petr ether.
Optical Rotation: [a]D20 -124.8° (c = 0.5 in chloroform)
Derivative Type: a-Peltatin-b-D-glucoside
Molecular Formula: C27H30O13
Molecular Weight: 562.52
Percent Composition: C 57.65%, H 5.38%, O 36.98%
Properties: Prismatic needles from acetone, mp 168-171°. [a]D20 -128.9° (c = 0.590 in methanol); [a]D20 -174.4° (c = 0.579 in pyridine).
Melting point: mp 168-171°
Optical Rotation: [a]D20 -128.9° (c = 0.590 in methanol); [a]D20 -174.4° (c = 0.579 in pyridine)
CAUTION: Irritates the skin.

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