eicosanolide
{{Short description|Organic chemical compound}}
{{Chembox
| Name = Eicosanolide
| ImageFile = Eicosanolid.svg
| IUPACName = oxacyclohenicosan-2-one
| OtherNames = 20-Eicosanolide
| Section1 = {{Chembox Identifiers
| CASNo = 31844-01-6
| CASNo_Ref = {{Cascite|changed|???}}
| ChEBI = 180271
| ChemSpiderID = 9089195
| PubChem = 10913938
| StdInChI=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
| StdInChIKey = XNVIXRMFBUDCLP-UHFFFAOYSA-N
| SMILES = C1CCCCCCCCCC(=O)OCCCCCCCCC1
}}
| Section2 = {{Chembox Properties
| C=20|H=38|O=2
}}
}}
Eicosanolide is an organic compound with the chemical formula {{Chem2 | C20H38O2}}. It is a cyclic ester or lactone, more specifically a macrolide.
Occurrence
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.[https://pherobase.com/database/compound/compounds-detail-20-eicosanolide.php eicosanolide] in pherobase 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.{{Cite journal|title=Chemistry of the dufour's gland secretion of halictine bees|last1=Hefetz|first1=Abraham|date=1978|journal=Comparative Biochemistry and Physiology B|doi=10.1016/0305-0491(78)90229-8|last2=Blum|first2=Murray|last3=Eickwort|first3=George|last4=Wheeler|first4=James|issue=1|volume=61|pages=129–132}}{{cite journal|title=Systematic relationship of halictinae bees based on the pattern of macrocyclic lactones in the Dufour gland secretion|doi=10.1016/0020-1790(82)90004-X|volume=12|issue=2|pages=161–170|journal=Insect Biochemistry|year=1982 | last1=Johansson | first1=Ingela}}{{cite journal |author=Mitra, Aniruddha |year=2013 |title=Function of the Dufour's gland in solitary and social Hymenoptera |journal=Journal of Hymenoptera Research |volume=35 |pages=33–58 |doi=10.3897/JHR.35.4783 |doi-access=free }}