Eicosanolide is an organic compound with the chemical formula C20H38O2. It is a cyclic ester or lactone, more specifically a macrolide.

Eicosanolide
Names
IUPAC name
oxacyclohenicosan-2-one
Other names
20-Eicosanolide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C20H38O2/c21-20-18-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-17-19-22-20/h1-19H2
    Key: XNVIXRMFBUDCLP-UHFFFAOYSA-N
  • C1CCCCCCCCCC(=O)OCCCCCCCCC1
Properties
C20H38O2
Molar mass 310.522 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Occurrence

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Eicosanolide is used by several species of bees (such as some of genera Colletes, Lasioglossum, Halictus) and butterflies (such as some of genus Heliconius) as a pheromone.[1] The Dufour's gland of bees in the Halictinae subfamily, contains eicosanolide 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]

References

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  1. ^ eicosanolide in pherobase
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.