Octadecanolide: Difference between revisions
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{{Short description|Organic chemical compound}} |
{{Short description|Organic chemical compound}} |
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{{Draft topics|chemistry|biology}} |
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{{AfC topic|stem}} |
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{{AfC submission|||ts=20241031215926|u=Aalleddem|ns=118}} |
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{{AfC submission|t||ts=20241031201014|u=Aalleddem|ns=118|demo=}}<!-- Important, do not remove this line before article has been created. --> |
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{{Chembox |
{{Chembox |
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| OtherNames = {{ubl|1-oxacyclononadecan-2-one|18-Octadecanolide}} |
| OtherNames = {{ubl|1-oxacyclononadecan-2-one|18-Octadecanolide}} |
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| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
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| CASNo = 4444-85-3 |
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| CASNo_Ref = {{Cascite|changed|EPA}} |
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| ChEBI = 191925 |
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| ChemSpiderID = 10633281 |
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| PubChem = 12628864 |
| PubChem = 12628864 |
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| StdInChI=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 |
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| StdInChIKey = PGRBVLPTXLOMNB-UHFFFAOYSA-N |
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| SMILES = C1CCCCCCCCC(=O)OCCCCCCCC1 |
| SMILES = C1CCCCCCCCC(=O)OCCCCCCCC1 |
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| Section2 = {{Chembox Properties |
| Section2 = {{Chembox Properties |
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| C=18|H=34|O=2 |
| C=18|H=34|O=2 |
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'''Octadecanolide''' is an [[organic compound]] with the [[chemical formula]] {{chem2|C18H34O2}}. It is a cyclic ester or [[lactone]], more specifically a [[macrolide]]. |
'''Octadecanolide''' is an [[organic compound]] with the [[chemical formula]] {{chem2|C18H34O2}}. It is a cyclic [[ester]] or [[lactone]], more specifically a [[macrolide]]. |
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==Occurrence== |
==Occurrence== |
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Several species of [[bee]]s (such as some of genera [[Colletes]], [[Halictus]], [[Lasioglossum]] |
Several species of [[bee]]s (such as some of genera ''[[Colletes]], [[Halictus]], [[Lasioglossum]]'') and [[butterflies]] (such as some of genus ''[[Heliconius]]'') use octadecanolide as a [[pheromone]].<ref name="pheromone">[https://pherobase.com/database/compound/compounds-detail-18-octadecanolide.php octadecanolide] in Pherobase</ref> 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, [[larva]]l food and chemical communication.<ref name="macrolide1">{{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}}</ref><ref name="macrolide2">{{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}}</ref><ref name=glandfunction>{{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 }}</ref> |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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[[Category:Lactones]] |
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[[Category:Heterocyclic compounds with 1 ring]] |
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[[Category:Pheromones]] |
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{{Organic-compound-stub}} |
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Latest revision as of 20:43, 2 November 2024
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| Names | |
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| IUPAC name
oxacyclononadecan-2-one
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| 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).
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Octadecanolide is an organic compound with the chemical formula C18H34O2. It is a cyclic ester or lactone, more specifically a macrolide.
Occurrence
[edit]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]
References
[edit]- ^ 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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