Title: Iridomyrmecin
CAS Registry Number: 485-43-8
CAS Name: [4S-(4a,4ab,7b,7ab)]-Hexahydro-4,7-dimethylcyclopenta[c]pyran-3(1H)-one
Additional Names: 2-(hydroxymethyl)-a,3-dimethylcyclopentaneacetic acid d-lactone; iridomyrmexin
Molecular Formula: C10H16O2
Molecular Weight: 168.23
Percent Composition: C 71.39%, H 9.59%, O 19.02%
Literature References: Iridolactone isolated from the Argentine ant Iridomyrmex humilis Mayr., Dolichoderinae. Exhibits antibacterial and insect antifeedant activity. Isoln: Pavan, Ric. Sci. 19, 1011 (1949); Chim. Ind. (Milan) 37, 625 (1955); Fusco et al., ibid. 251, 958; Cavill et al., Aust. J. Chem. 9, 288 (1956); 10, 352 (1957). Synthesis: Korte et al., Tetrahedron 6, 201 (1959); Sisido et al., J. Org. Chem. 29, 3361 (1964); R. S. Matthews, J. K. Whitesell, ibid. 40, 3312 (1975); Y. Yamada et al., Chem. Lett. 1978, 1405; P. Callant et al., Tetrahedron 37, 2085 (1981). Stereochemistry: Korte et al., Ber. 94, 1952 (1961); McConnell et al., Tetrahedron Lett. 1962, 445; Büchi, Manning, Tetrahedron 18, 1049 (1962). Activity as bactericide and insecticide: M. Pavan, Z. Hyg. Infektionskrankh. 134, 136 (1952), C.A. 46, 9796f (1952).
Properties: Prisms from petr ether. Aromatic odor, resembling catnip. Salty taste. mp 60-61°. Sublimes0.01 50-55°. bp1.5 104-108°. [a]D20 +210° (c = 4 in ethanol); [a]D17 +205° (c = 0.223 in carbon tetrachloride). nD65 1.4607. Sparingly sol in water: 0.2 g/100 ml H2O (25°). Sol in fats and fat solvents. Freely sol in ether.
Melting point: mp 60-61°
Boiling point: bp1.5 104-108°
Optical Rotation: [a]D20 +210° (c = 4 in ethanol); [a]D17 +205° (c = 0.223 in carbon tetrachloride)
Index of refraction: nD65 1.4607 |