Iridomyrmecin

Iridomyrmecin
Names
	Preferred IUPAC name (4S,4aS,7S,7aR)-4,7-Dimethylhexahydrocyclopenta[c]pyran-3(1H)-one
	Other names Iridomyrmexin
Identifiers
CAS Number	485-43-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	390867;
PubChem CID	442427;
UNII	9736R92EPU ;
CompTox Dashboard (EPA)	DTXSID40876125 ;
	InChI InChI=1S/C10H16O2/c1-6-3-4-8-7(2)10(11)12-5-9(6)8/h6-9H,3-5H2,1-2H3/t6-,7-,8+,9+/m0/s1;
	SMILES O=C1OC[C@@H]2[C@H](CC[C@@H]2[C@@H]1C)C;
Properties
Chemical formula	C10H16O2
Molar mass	168.236 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Iridomyrmecin is a defensive chemical, classified as an iridoid, isolated from ants of the genus Iridomyrmex.^[1] It has also evolved into a sex pheromone in wasps such as Leptopilina,^[2] with host species using the smell of iridomyrmecin as a way of detecting the presence of the parasitoid wasps.^[3] Iridomyrmecin is also found in a variety of plants including Actinidia polygama.^[4]

References

^ Cavill GW, Ford DL, Locksley HD (1956). "The chemistry of ants. I. Terpenoid constituents of some Australian Iridomyrmex species". Australian Journal of Chemistry. 9 (2): 288–293. doi:10.1071/CH9560288.
^ Weiss I, Rössler T, Hofferberth J, Brummer M, Ruther J, Stökl J (2013-11-15). "A nonspecific defensive compound evolves into a competition avoidance cue and a female sex pheromone". Nature Communications. 4 (1): 2767. Bibcode:2013NatCo...4.2767W. doi:10.1038/ncomms3767. PMC 3868268. PMID 24231727.
^ Ebrahim SA, Dweck HK, Stökl J, Hofferberth JE, Trona F, Weniger K, et al. (December 2015). "Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit". PLOS Biology. 13 (12): e1002318. doi:10.1371/journal.pbio.1002318. PMC 4687525. PMID 26674493.
^ Sakan T, Isoe S, Hyeon SB, Katsumura R, Maeda T, Wolinsky J, et al. (1965). "Exact nature of matatabilactone and the terpenes of Nepeta cataria". Tetrahedron Letters. 6 (46): 4097–4102. doi:10.1016/s0040-4039(01)99572-3.

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[1] Cavill GW, Ford DL, Locksley HD (1956). "The chemistry of ants. I. Terpenoid constituents of some Australian Iridomyrmex species". Australian Journal of Chemistry. 9 (2): 288–293. doi:10.1071/CH9560288.

[2] Weiss I, Rössler T, Hofferberth J, Brummer M, Ruther J, Stökl J (2013-11-15). "A nonspecific defensive compound evolves into a competition avoidance cue and a female sex pheromone". Nature Communications. 4 (1): 2767. Bibcode:2013NatCo...4.2767W. doi:10.1038/ncomms3767. PMC 3868268. PMID 24231727.

[3] Ebrahim SA, Dweck HK, Stökl J, Hofferberth JE, Trona F, Weniger K, et al. (December 2015). "Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit". PLOS Biology. 13 (12): e1002318. doi:10.1371/journal.pbio.1002318. PMC 4687525. PMID 26674493.

[4] Sakan T, Isoe S, Hyeon SB, Katsumura R, Maeda T, Wolinsky J, et al. (1965). "Exact nature of matatabilactone and the terpenes of Nepeta cataria". Tetrahedron Letters. 6 (46): 4097–4102. doi:10.1016/s0040-4039(01)99572-3.

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See also

References