Levopimaric Acid
Title: Levopimaric Acid
CAS Registry Number: 79-54-9
CAS Name: [1R-(1a,4ab,4ba,10aa)]-1,2,3,4,4a,4b,5,9,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid
Additional Names: 13-isopropylpodocarpa-8(14),12-dien-15-oic acid; D6,8(14)-abietadienoic acid; l-pimaric acid; b-pimaric acid; l-sapietic acid
Molecular Formula: C20H30O2
Molecular Weight: 302.45
Percent Composition: C 79.42%, H 10.00%, O 10.58%
Literature References: Isolation from American pine oleoresin: Palkin, Harris, J. Am. Chem. Soc. 55, 3677 (1933); from French galipot, from Pinus maritima: Ruzicka, Bacon, Helv. Chim. Acta 20, 1542 (1937); from Pinus palustris: Harris, Sanderson, J. Am. Chem. Soc. 70, 334, 3671 (1948). Structure: Ruzicka, Kaufmann, Helv. Chim. Acta 23, 1346 (1940): cf. Arbuzov, Chem. Zentralbl. 1942, II, 893. Stereochemistry: Schuller, Lawrence, J. Am. Chem. Soc. 83, 2563 (1961); Burgstahler et al., ibid. 83, 4660 (1961); Weiss et al., Chem. Ind. (London) 1962, 1286; Dauben, Coates, J. Org. Chem. 28, 1698 (1963). Conformation: Burgstahler et al., Chem. Commun. 1971, 121; Weiss et al., ibid. 1972, 17.
Properties: Orthorhombic crystals, mp 150°; [a]D20 -280.4° (c = 0.7 in alcohol); [a]D14 -266.6° (c = 0.4 in chloroform). Absorption max 273 nm: Kraft, Ann. 520, 133 (1935). Practically insol in water, sol in most organic solvents. Forms a crystalline ammonium salt.
Melting point: mp 150°
Optical Rotation: [a]D20 -280.4° (c = 0.7 in alcohol); [a]D14 -266.6° (c = 0.4 in chloroform)
Absorption maximum: Absorption max 273 nm: Kraft, Ann. 520, 133 (1935)
 
Derivative Type: Methyl ester
Molecular Formula: C21H32O2
Molecular Weight: 316.48
Percent Composition: C 79.70%, H 10.19%, O 10.11%
Properties: Crystals from methanol, mp 64°. [a]D20 -268° (c = 1 in ether).
Melting point: mp 64°
Optical Rotation: [a]D20 -268° (c = 1 in ether)
 
Derivative Type: Molecular compd with quinone
Molecular Formula: C26H34O4
Molecular Weight: 410.55
Percent Composition: C 76.06%, H 8.35%, O 15.59%
Properties: Yellow prisms from methanol, mp 214°. [a]D20 -148° (c = 0.7 in chloroform).
Melting point: mp 214°
Optical Rotation: [a]D20 -148° (c = 0.7 in chloroform)

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