Octadecanolide

Octadecanolide
Names
	IUPAC name oxacyclononadecan-2-one
	Other names 1-oxacyclononadecan-2-one; 18-Octadecanolide;
Identifiers
CAS Number	4444-85-3 [EPA];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:191925;
ChemSpider	10633281;
PubChem CID	12628864;
CompTox Dashboard (EPA)	DTXSID00504917 ;
	InChI InChI=1S/C18H34O2/c19-18-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-17-20-18/h1-17H2 Key: PGRBVLPTXLOMNB-UHFFFAOYSA-N;
	SMILES C1CCCCCCCCC(=O)OCCCCCCCC1;
Properties
Chemical formula	C18H34O2
Molar mass	282.468 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

Octadecanolide is an organic compound with the chemical formula C₁₈H₃₄O₂. It is a cyclic ester or lactone, more specifically a macrolide.

Occurrence

Several species of bees (such as some of genera Colletes, Halictus, Lasioglossum) and butterflies (such as some of genus Heliconius) use octadecanolide as a pheromone.^[1] The Dufour's gland of bees in the Halictinae subfamily, contains octadecanolide along with other macrocyclic lactones, which could be used for a range of different applications like nest building, larval food and chemical communication.^[2]^[3]^[4]

^ octadecanolide in Pherobase
^ Hefetz, Abraham; Blum, Murray; Eickwort, George; Wheeler, James (1978). "Chemistry of the dufour's gland secretion of halictine bees". Comparative Biochemistry and Physiology B. 61 (1): 129–132. doi:10.1016/0305-0491(78)90229-8.
^ Johansson, Ingela (1982). "Systematic relationship of halictinae bees based on the pattern of macrocyclic lactones in the Dufour gland secretion". Insect Biochemistry. 12 (2): 161–170. doi:10.1016/0020-1790(82)90004-X.
^ Mitra, Aniruddha (2013). "Function of the Dufour's gland in solitary and social Hymenoptera". Journal of Hymenoptera Research. 35: 33–58. doi:10.3897/JHR.35.4783.

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