Structural Formula Vector Image
Title: Warburganal
CAS Registry Number: 62994-47-2
CAS Name: (1S,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-1-hydroxy-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde
Molecular Formula: C15H22O3
Molecular Weight: 250.33
Percent Composition: C 71.97%, H 8.86%, O 19.17%
Literature References: Drimane sesquiterpene with antifeedant activity against the African army worm. Biological activity includes plant growth regulation, cytotoxic, antimicrobial and molluscicidal properties. Isoln from Warburgia ugandensis, Canellaceae and structure: I. Kubo et al., Chem. Commun. 1976, 1013. Relationship between structure and antifeedant activity: K. Nakanishi, I. Kubo, Isr. J. Chem. 16, 28 (1977). Synthesis of (±)-warburganal: S. P. Tanis, K. Nakanishi, J. Am. Chem. Soc. 101, 4398 (1979); T. Nakata et al., ibid. 4400; A. S. Kende, T. J. Blacklock, Tetrahedron Lett. 1980, 3119; P. A. Wender, S. L. Eck, ibid. 1982, 1871; D. M. Hollinshead et al., J. Chem. Soc. Perkin Trans. 1 1983, 1579. See also: JP Kokai 80 136238, and JP 80 136240 (both 1980 to Inst. Phys. Chem. Res.); JP Kokai 81 43236 (1981 to Suntory Ltd.); JP Kokai 83 38232 (1983 to Teikoku Zoki). Synthesis of (-)-warburganal: H. Okawara et al., Tetrahedron Lett. 1982, 1087.
Properties: mp 98-99°. uv max (methanol): 224 nm (e 6300). [a]D21 -260° (c = 0.350 in CHCl3).
Melting point: mp 98-99°
Optical Rotation: [a]D21 -260° (c = 0.350 in CHCl3)
Absorption maximum: uv max (methanol): 224 nm (e 6300)

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