Podocarpic Acid
Title: Podocarpic Acid
CAS Registry Number: 5947-49-9
CAS Name: [1S-(1a,4aa,10ab)]-1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid
Additional Names: 12-hydroxypodocarpa-8,11,13-trien-16-oic acid
Molecular Formula: C17H22O3
Molecular Weight: 274.35
Percent Composition: C 74.42%, H 8.08%, O 17.50%
Literature References: Chief acidic constituent of the resin of the Javanese Podocarpus cupressina (L'Hérit.) Pers., Coniferae, esp. in var. imbricata. Also in New Zealand kahikatea resin (from Podocarpus dacrydioides) and in rimu resin (Dacrydium cupressinum). A related component, nimbiol, q.v., occurs in the nim tree, Azadirachta indica Juss. (Melia azadirachta L.), Meliaceae. Isoln from Podocarpus cupressina: A. C. Oudemans, Ber. 6, 1122 (1873); from Dacrydium cupressinum: I. R. Sherwood, W. F. Short, J. Chem. Soc. 1938, 1008. Structure: Campbell, Todd, J. Am. Chem. Soc. 64, 928 (1942). Conversion to nimbiol as proof of structure: Bible, Tetrahedron 11, 22 (1960). Synthesis from desoxypodocarpic acid: Wenkert, Jackson, J. Am. Chem. Soc. 80, 217 (1958). Total synthesis of dl-form: Meyer, Maheshwari, Tetrahedron Lett. 1964, 2175; P. R. Kanjilal et al., Synth. Commun. 11, 795 (1981). Synthesis: Pelletier et al., Tetrahedron Lett. 1971, 4179.
Properties: Platelets from dil alcohol, mp 193.5°. [a]20546 +165° (c = 4 in abs ethanol). Sol in methanol, ethanol, ether, acetic acid. Practically insol in water, chloroform, benzene, carbon disulfide.
Melting point: mp 193.5°
Optical Rotation: [a]20546 +165° (c = 4 in abs ethanol)
 
Derivative Type: Methyl ester
Molecular Formula: C18H24O3
Molecular Weight: 288.38
Percent Composition: C 74.97%, H 8.39%, O 16.64%
Properties: Crystals from alcohol, mp 208°.
Melting point: mp 208°

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