Title: Ilimaquinone
CAS Registry Number: 71678-03-0
CAS Name: 3-[[(1R,2S,4aS,8aS)-Decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione
Additional Names: IQ
Molecular Formula: C22H30O4
Molecular Weight: 358.47
Percent Composition: C 73.71%, H 8.44%, O 17.85%
Literature References: Sesquiterpenoid quinone isolated from the marine sponge, Hippiospongia metachromia; naturally occurring as (-)-form. Inhibits cellular secretions by selective breakdown of the Golgi apparatus. Isoln and structure determn: R. T. Luibrand et al., Tetrahedron 35, 609 (1979). Revised stereochemistry: R. J. Capon, J. K. MacLeod, J. Org. Chem. 52, 5059 (1987). Total stereosynthesis: S. D. Bruner et al., ibid. 60, 1114 (1995); increased yield: S. Poigny et al., ibid. 63, 5890 (1998). Photoaffinity study on cellular targets: H. S. Radeke, M. N. L. Snapper, Bioorg. Med. Chem. 6, 1227 (1998). Mechanism of action studies: P. A. Takizawa et al., Cell 73, 1079 (1993); H. S. Radeke et al., Chem. Biol. 6, 639 (1999). Use as inhibitor of protein secretion: P. A. Feldman et al., J. Membr. Biol. 155, 275 (1997).
Properties: Orange needles from hexane, mp 113-114°. [a]D23 -23.2° (c = 1.12 in CHCl3).
Melting point: mp 113-114°
Optical Rotation: [a]D23 -23.2° (c = 1.12 in CHCl3)
Use: Biological probe for intracellular communications and vesicle-mediated transport. |