7075. α-Peltatin

Nomenclature

CAS number: 568-53-6
[5R-(5α,5aβ,8aα)]-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; 8-hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(4′-hydroxy-3′,5′-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylic acid lactone.
C21H20O8; mol wt 400.38.
C 63.00%, H 5.03%, O 31.97%.

Description and 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).

Chemical structure

Properties

Prismatic leaflets from abs ethanol. Begins to sinter at 236°. Dec 242-246°. [α]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.

Derivative

α-Peltatin-β-d-glucoside.
C27H30O13; mol wt 562.52.
C 57.65%, H 5.38%, O 36.98%.

Properties

Prismatic needles from acetone, mp 168-171°. [α]D20 -128.9° (c = 0.590 in methanol); [α]D20 -174.4° (c = 0.579 in pyridine).

Caution

Irritates the skin.