9-Oxodecenoic acid (9-oxo-2(E)-decenoic acid, also called 9-ODA) is an unsaturated ketocarboxylic or fatty acid and a
pheromone secreted by the
queen bee of the honeybee species Apis mellifera.[1][2] It functions as a sex attractant that stimulates the
olfactory receptors of
male drones.[3] Additionally, this acid plays a crucial role in regulating the colony's social structure; it inhibits the development of
ovaries in
worker bees, which are sterile females.[3] However, its inhibitory effect on the worker bees' ovaries is only fully effective when combined with another pheromone,
9-hydroxydecenoic acid.[4] When the queen bee is removed from the hive, the worker bees initiate the construction of new queen cells and the previously inhibited drones develop functional ovaries. The exact biological mechanisms through which 9-oxodecenoic acid and related substances influence these processes are not fully understood, but they are thought to affect the
nervous system in some way.[5]
Synthesis
9-Oxodecenoic acid can be synthesized starting from
azelaic acid.[6]