Title: Ambrosin
CAS Registry Number: 509-93-3
CAS Name: 3,3a,4,5,6,6a,9a,9b-Octahydro-6,9a-dimethyl-3-methyleneazuleno[4,5-b]furan-2,9-dione
Additional Names: 6b-hydroxy-4-oxo-10aH-ambrosa-2,11(13)-dien-12-oic acid g-lactone
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: From herb of Ambrosia maritima L., Compositae: Abu-Shady, Soine, J. Am. Pharm. Assoc. 42, 387 (1953); 43, 365 (1954). Structure: Bernardi, Büchi, Experientia 13, 466 (1957); Sorm et al., Collect. Czech. Chem. Commun. 24, 1548 (1959); Nerz et al., J. Am. Chem. Soc. 84, 2601 (1962). Absolute configuration: Emerson et al., Tetrahedron Lett. 1966, 6151. Stereospecific total synthesis of (±)-form: P. A. Grieco et al., J. Am. Chem. Soc. 99, 7393 (1977).
Properties: Crystals from alc, mp 146°. [a]D22 -154.50° (c = 2 in alcohol). uv max (95% ethanol): 217, 324 nm (e 13465; 36). Very sol in chloroform; sol in alc, benzene, sparingly sol in ether, petr ether. Practically insol in water, cold dil NaOH, dil acids.
Melting point: mp 146°
Optical Rotation: [a]D22 -154.50° (c = 2 in alcohol)
Absorption maximum: uv max (95% ethanol): 217, 324 nm (e 13465; 36)
Derivative Type: (±)-Form
Properties: mp 188-190°.
Melting point: mp 188-190°
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