Title: Polygodial
CAS Registry Number: 6754-20-7
CAS Name: (1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde
Additional Names: tadeonal
Molecular Formula: C15H22O2
Molecular Weight: 234.33
Percent Composition: C 76.88%, H 9.46%, O 13.66%
Literature References: Widely distributed drimane sesquiterpene with insect antifeedant properties; naturally occurring as the (-)-form. Isoln from Polygonum hydropiper L., Polygonaceae (Australia) and structure: C. S. Barnes, J. W. Loder, Aust. J. Chem. 15, 322 (1962); from the bark of Warburgia stuhlmanni Engl. or W. ugandensis, Canellacceae (E. Africa): I. Kubo et al., Chem. Commun. 1976, 1013; from nudibranch Dendrodons limbata (Mediterranean): G. Cimino et al., Science 219, 1237 (1983); from nudibranchs D. nigra, D. tuberculosa (Hawaii) and D. krebsii (Mexico): R. K. Okuda et al., J. Org. Chem. 48, 1866 (1983). Relationship between structure and antifeedant-activity: K. Nakanishi, I. Kubo, Isr. J. Chem. 16, 28 (1977); M. D'Ischia et al., Tetrahedron Lett. 1982, 3295. Synthesis of racemate: T. Kato et al., Tetrahedron Lett. 1971, 1961; S. C. Howell et al., Chem. Commun. 1981, 507. Synthesis of (-)-form: I. Razmilic et al., Synth. Commun. 17, 95 (1987).
Properties: Colorless needles from petroleum (40-60°), mp 57° (Barnes, Loder). [a]D24 -131° (c = 0.96 in ethanol). uv max (ethanol): 231, 295 nm (e 11800, 76).
Melting point: mp 57° (Barnes, Loder)
Optical Rotation: [a]D24 -131° (c = 0.96 in ethanol)
Absorption maximum: uv max (ethanol): 231, 295 nm (e 11800, 76)
Derivative Type: (±)-Form
Properties: mp 93-94° (Tanis, Nakanishi).
Melting point: mp 93-94° (Tanis, Nakanishi)
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