6998. Palustric Acid

Nomenclature

CAS number: 1945-53-5
[1R-(1α,4aβ,10aα)]-1,2,3,4,4a,5,6,9,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid; 13-isopropylpodocarpa-8,13-dien-15-oic acid.
C20H30O2; mol wt 302.45.
C 79.42%, H 10.00%, O 10.58%.

Description and references

Isoln from gum rosin: Loeblich et al., J. Am. Chem. Soc. 77, 2823 (1955); Joye et al., J. Org. Chem. 30, 654 (1965). Structure: Shuller et al., J. Am. Chem. Soc. 82, 1734 (1960). Prepn of the 4-epi-form: Tabacik, Poisson, Bull. Soc. Chim. Fr. 1969, 3264.

Chemical structure

Properties

Crystals from methanol, mp 162-167°. [α]D +71.6°. uv max (0.01N NaOH): 265-266 nm.

Derivative

Methyl ester.
C21H32O2; mol wt 316.48.
C 79.70%, H 10.19%, O 10.11%.

Properties

Crystals from methanol, mp 25-27°. [α]D +67.7°. uv max: 265-266 nm.