7428. Pimaric Acid
Nomenclature
CAS number: 127-27-5
[1R-(1α,4aβ,4bα,7β,10aα)]-7-Ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenecarboxylic
acid; 13α-methyl-13-vinylpodocarp-8(14)-ene-15-oic acid; dextropimaric acid; d-pimaric acid; α-pimaric acid. C20H30O2; mol wt 302.45.
C 79.42%, H 10.00%, O 10.58%.
Description and references
Isoln from American rosin: Rimbach, Ber. Dtsch. Pharm. Ges. 6, 61 (1896); from French galipot from Pinus maritima Mill, Pinaceae: Ruzicka, Balas, Helv. Chim. Acta 6, 677 (1923); Ruzicka et al., ibid. 15, 915 (1932). Structure: Ruzicka, Sternbach, ibid. 23, 124 (1940); Fleck, J. Am. Chem. Soc. 62, 2044 (1940); Harris, Sanderson, ibid. 70, 2081 (1948). Stereochemistry: Wenkert, Chamberlin, ibid. 81, 688 (1959).
Properties
Orthorhombic, bisphenoidal crystals from acetone or acetic acid, mp 217-219°; bp18 282°; [α]D18 +74.7° (c = 0.4 in chloroform); [α]D20 +87.3° (in chloroform).Derivative
Hydrochloride.C20H31O2Cl; mol wt 338.91.
C 70.88%, H 9.22%, O 9.44%, Cl 10.46%.
Properties
Dec 184°. [α]D20 +13.6° (c = 0.5 in alcohol). Can be reconverted by heating with quinoline at 250°.Derivative
Quinidine salt.C40H54N2O4; mol wt 626.87.
C 76.64%, H 8.68%, N 4.47%, O 10.21%.
Properties
mp 90°.Derivative
Methyl ester.C21H32O2; mol wt 316.48.
C 79.70%, H 10.19%, O 10.11%.