9-Oxodecenoic acid

9-oxodecenoic acid
Names
	Other names 9-oxo-2(E)-decenoic acid ; 9-ODA; Queen substance
Identifiers
CAS Number	334-20-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:165439;
ChemSpider	1362276;
PubChem CID	1713086;
UNII	618LR3X900;
	InChI InChI=1S/C10H16O3/c1-9(11)7-5-3-2-4-6-8-10(12)13/h6,8H,2-5,7H2,1H3,(H,12,13)/b8-6+ Key: INJRDZMWIAYEMM-SOFGYWHQSA-N;
	SMILES CC(=O)CCCCC/C=C/C(=O)O;
Properties
Chemical formula	C10H16O3
Molar mass	184,23 g·mol−1
Appearance	transparent flakes
Melting point	54.5–55.5 °C (130.1–131.9 °F; 327.6–328.6 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. It functions as a sex attractant that stimulates the olfactory receptors of male drones. 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. However, its inhibitory effect on the worker bees' ovaries is only fully effective when combined with another pheromone, 9-hydroxydecenoic acid. 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.