beta-Peltatin

Title: b-Peltatin
CAS Registry Number: 518-29-6
CAS Name: [5R-(5a,5ab,8aa)]-5,8,8a,9-Tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)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-(3¢,4¢,5¢-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylic acid lactone; b-peltatin A
Molecular Formula: C22H22O8
Molecular Weight: 414.41
Percent Composition: C 63.76%, H 5.35%, O 30.89%
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. 70, 2833 (1948); 72, 246 (1950); from Hyptis verticillata Jacq., Labiatae: German, J. Pharm. Sci. 60, 649 (1971).
Properties: Prisms from abs ethanol. Dec 238-241° (slight sintering begins at 234°). [a]D20 -122.9° (c = 0.578 in chloroform). Somewhat less sol than a-peltatin. Soly in water at 23°: 13 mg/liter. Fairly sol in chloroform, hot ethanol, acetic acid, acetone, dil caustic; less sol in benzene, ether, carbon tetrachloride, propylene glycol. Practically insol in petr ether.
Optical Rotation: [a]D20 -122.9° (c = 0.578 in chloroform)
Derivative Type: b-Peltatin-b-D-glucoside
Molecular Formula: C28H32O13
Molecular Weight: 576.55
Percent Composition: C 58.33%, H 5.59%, O 36.08%
Properties: White amorph powder from acetone + ether, dec 156-159°. [a]D20 -122.7° (c = 0.587 in methanol); [a]D20 -169.2° (c = 0.556 in pyridine).
Optical Rotation: [a]D20 -122.7° (c = 0.587 in methanol); [a]D20 -169.2° (c = 0.556 in pyridine)
CAUTION: Irritates the skin.
beta-Phellandrene beta-Picoline beta-Pinene beta-Propiolactone beta-Resorcylaldehyde