Grindelic Acid

Title: Grindelic Acid
CAS Registry Number: 1438-57-9
CAS Name: (1¢R,4¢aS,5S,8¢aS)-4,4¢a,5,5¢,6¢,7¢,8¢,8¢a-Octahydro-2¢,5,5¢,5¢,8¢a-pentamethylspiro[furan-2(3H),1¢(4¢H)-naphthalene]-5-acetic acid
Additional Names: 9,13-epoxylabd-7-en-15-oic acid
Molecular Formula: C20H32O3
Molecular Weight: 320.47
Percent Composition: C 74.96%, H 10.06%, O 14.98%
Literature References: Major grindelane diterpenoid isolated from the resin of Grindelia robusta Nutt., Compositae. Isoln and structure: L. Panizzi et al., Gazz. Chim. Ital. 92, 522 (1962). Stereochemical studies: L. Mangoni, M. Belardini, ibid. 92, 1379 (1962); 93, 455, 465 (1963). Synthesis: M. Adinolfi et al., ibid. 106, 625 (1976). Absolute configuration: M. Adinolfi et al., Phytochemistry 27, 1878 (1988); L. A. Paquette, H.-L. Wang, J. Org. Chem. 61, 5352 (1996).
Properties: Crystals from acetic acid, mp 100-101°. [a]D -102.2°.
Melting point: mp 100-101°
Optical Rotation: [a]D -102.2°
Derivative Type: Methyl ester
Molecular Formula: C21H34O3
Molecular Weight: 334.49
Percent Composition: C 75.41%, H 10.25%, O 14.35%
Properties: Crystals from methanol, mp 70-70.5°. [a]D -134.1° (c = 1.46 in methanol).
Melting point: mp 70-70.5°
Optical Rotation: [a]D -134.1° (c = 1.46 in methanol)
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