Title: Deguelin
CAS Registry Number: 522-17-8
CAS Name: (7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6¢,5¢-e]pyran-7(7aH)-one
Molecular Formula: C23H22O6
Molecular Weight: 394.42
Percent Composition: C 70.04%, H 5.62%, O 24.34%
Literature References: From roots of Tephrosia toxicaria Pers., leaves of Tephrosia vogelii Hook f., Leguminosae, and from derris and cubé roots: H. L. Haller, F. B. LaForge, J. Am. Chem. Soc. 56, 2415 (1934); E. Brierly, H. J. Smith, J. Pharm. Pharmacol. 20, 840 (1968). Structure: Clark, J. Am. Chem. Soc. 54, 3000 (1932). Stereoselective synthesis: P. B. Anzeveno, J. Org. Chem. 44,2578 (1979). Total synthesis of racemate: Fukami et al., Agric. Biol. Chem. 25, 252 (1961); Omokawa, Yamashita, ibid. 38, 1731 (1974). Stereochemical studies: Djerassi et al., J. Chem. Soc. 1961, 1448.
Properties: Yellow oil, [a]D27 -97.2° (c = 0.2 in benzene).
Optical Rotation: [a]D27 -97.2° (c = 0.2 in benzene)
Derivative Type: (±)-Form
Properties: Pale green crystals, mp 171°. Practically insol in water. Sol in alc.
Melting point: mp 171°
CAUTION: Irritates skin. Inhalation may cause fatal pulmonary damage.
Use: Insecticide. |