7544. Pododacric Acid

Nomenclature

CAS number: 32630-75-4
[1S-(1α,4aα,10aβ)]-1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-7-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,4a-dimethyl-1-phenanthrenecarboxylic acid; 12-hydroxy-13-[2-hydroxy-1-(hydroxymethyl)ethyl]podocarpa-8,11,13-trien-16-oic acid.
C20H28O5; mol wt 348.43.
C 68.94%, H 8.10%, O 22.96%.

Description and references

From heartwood of Podocarpus dacrydioides; P. totara: Briggs et al., Tetrahedron 7, 270 (1959); Cambie, Mander, ibid. 18, 465 (1962). Structure: Cambie, Mathai, Chem. Commun. 1971, 154.

Chemical structure

Properties

Colorless needles from 30% methanol, mp 213-214°. [α]D25 +118° (c = 0.9 in 5:1 chloroform-methanol). uv max: 225, 284 nm (ε 5500, 3100). pK 8.44 (in methyl cellosolve system).