Title: Queen Substance
CAS Registry Number: 334-20-3
CAS Name: (E)-9-Oxo-2-decenoic acid
Molecular Formula: C10H16O3
Molecular Weight: 184.23
Percent Composition: C 65.19%, H 8.75%, O 26.05%
Literature References: Secreted in the mandibular gland of queen honey bees (Apis mellifera, A. florea, A. cerana, A. dorsata); inhibits the development of ovaries in worker bees, prevents queen cell formation and attracts male bees (drones) to virgin queens for the purpose of mating: Butler, Experientia 13, 256 (1957); Sannasi, Rajulu, Life Sci. 10, part 2, 195 (1971). Similarity with the ovary inhibiting hormone of prawns (Leander serratus): Carlisle, Butler, Nature 177, 276 (1956). Extraction and purification: Carlisle, Butler, loc. cit.; Butler et al., Nature 184, 1871 (1959). Synthesis: Barbier et al., Compt. Rend. 251, 1133 (1960); Jaeger, Robinson, Tetrahedron 14, 320 (1961); Y. Naoshima et al., Agric. Biol. Chem. 48, 2151 (1984); U. P. Dhokte, A. S. Rao, Synth. Commun. 17, 355 (1987).
Properties: Transparent elongated plates from ether + petr ether or aq methanol, mp 54.5-55.5°. Stable to heat, acids, less stable to alkalies. Sol in acetone, alcohol. IR spectrum: Butler et al., loc. cit.
Melting point: mp 54.5-55.5° |