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]
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| Other names
9-oxo-2(E)-decenoic acid
9-ODA Queen substance | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| 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).
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Synthesis
edit9-Oxodecenoic acid can be synthesized starting from azelaic acid.[6]
An efficient synthesis is possible starting from diethyl-3-oxoglutarate.[7] This is alkylated by 6-bromo-1-hexene[8] and magnesium ethanolate,[9] then decarboxylated. The double bond is oxidized to the aldehyde with osmium tetroxide and sodium periodate in aqueous tert-butanol. The acid group is introduced by condensation with malonic acid.[2]
References
edit- ^ "Hormone - Molting, Insects, Juveniles | Britannica". www.britannica.com. Retrieved 2024-04-13.
- ^ a b Naoshima, Yoshinobu; Ike, Hisashi; Ogawa, Tomiaki; Nakayama, Torn; Kondo, Hirokiyo (1984-08-01). "An Easy Synthesis of ( E )-9-Oxo-2-decenoic Acid, the Queen Substance of the Honey Bee, and ( Z )-6-Heneicosen-ll-one, the Sex Pheromone of the Douglas Fir Tussock Moth †". Agricultural and Biological Chemistry. 48 (8): 2151–2153. doi:10.1080/00021369.1984.10866466. ISSN 0002-1369.
- ^ a b Wanner, Kevin W.; Nichols, Andrew S.; Walden, Kimberly K. O.; Brockmann, Axel; Luetje, Charles W.; Robertson, Hugh M. (2007-09-04). "A honey bee odorant receptor for the queen substance 9-oxo-2-decenoic acid". Proceedings of the National Academy of Sciences. 104 (36): 14383–14388. Bibcode:2007PNAS..10414383W. doi:10.1073/pnas.0705459104. ISSN 0027-8424. PMC 1964862. PMID 17761794.
- ^ Brockmann, Axel; Dietz, Daniel; Spaethe, Johannes; Tautz, Jürgen (March 2006). "Beyond 9-ODA: SEX Pheromone Communication in the European Honey Bee Apis mellifera L." Journal of Chemical Ecology. 32 (3): 657–667. Bibcode:2006JCEco..32..657B. doi:10.1007/s10886-005-9027-2. ISSN 0098-0331. PMID 16586035.
- ^ Villar, Gabriel; Baker, Thomas C.; Patch, Harland M.; Grozinger, Christina M. (July 2015). "Neurophysiological mechanisms underlying sex- and maturation-related variation in pheromone responses in honey bees (Apis mellifera)". Journal of Comparative Physiology A. 201 (7): 731–739. doi:10.1007/s00359-015-1006-7. ISSN 0340-7594. PMID 25840687.
- ^ Butler, C. G.; Callow, R. K.; Johnston, Norah C. (1962-01-09). "The isolation and synthesis of queen substance, 9-oxodec- trans -2-enoic acid, a honeybee pheromone". Proceedings of the Royal Society of London. Series B. Biological Sciences. 155 (960): 417–432. Bibcode:1962RSPSB.155..417B. doi:10.1098/rspb.1962.0009. ISSN 0080-4649.
- ^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2024-04-13.
- ^ PubChem. "6-Bromo-1-hexene". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-04-13.
- ^ PubChem. "Magnesium ethanolate". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-04-13.