Pimaric Acid
Title: Pimaric Acid
CAS Registry Number: 127-27-5
CAS Name: [1R-(1a,4ab,4ba,7b,10aa)]-7-Ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenecarboxylic acid
Additional Names: 13a-methyl-13-vinylpodocarp-8(14)-ene-15-oic acid; dextropimaric acid; d-pimaric acid; a-pimaric acid
Molecular Formula: C20H30O2
Molecular Weight: 302.45
Percent Composition: C 79.42%, H 10.00%, O 10.58%
Literature 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°; [a]D18 +74.7° (c = 0.4 in chloroform); [a]D20 +87.3° (in chloroform).
Melting point: mp 217-219°
Boiling point: bp18 282°
Optical Rotation: [a]D18 +74.7° (c = 0.4 in chloroform); [a]D20 +87.3° (in chloroform)
 
Derivative Type: Hydrochloride
Molecular Formula: C20H31O2Cl
Molecular Weight: 338.91
Percent Composition: C 70.88%, H 9.22%, O 9.44%, Cl 10.46%
Properties: Dec 184°. [a]D20 +13.6° (c = 0.5 in alcohol). Can be reconverted by heating with quinoline at 250°.
Optical Rotation: [a]D20 +13.6° (c = 0.5 in alcohol)
 
Derivative Type: Quinidine salt
Molecular Formula: C40H54N2O4
Molecular Weight: 626.87
Percent Composition: C 76.64%, H 8.68%, N 4.47%, O 10.21%
Properties: mp 90°.
Melting point: mp 90°
 
Derivative Type: Methyl ester
Molecular Formula: C21H32O2
Molecular Weight: 316.48
Percent Composition: C 79.70%, H 10.19%, O 10.11%
Properties: mp 69°.
Melting point: mp 69°

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