Complanine
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| Names | |
|---|---|
| IUPAC name
4-{[(2R,5Z,8Z)-2-Hydroxy-5,8-undecadien-1-yl]amino}-N,N,N-trimethyl-4-oxo-1-butanaminium | |
| Other names
(−)-Complanine,(R)-(−)-Complanine | |
| Identifiers | |
1042688-43-6  | |
| ChemSpider | 25047857  |
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| Jmol-3D images | Image |
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| Properties | |
| Molecular formula |
C11H22NO |
| Molar mass | 184.30 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Eurythoe complanata
Complanine is an organic amide and quaternary ammonium compound isolated from the marine fireworm Eurythoe complanata. It causes an inflammatory effect upon contact with the skin or mucous membranes.
Occurrence
It was previously known that handling the fireworm caused it to release a chemical that induces inflammation of the skin of marine predators and mammals (including humans). Complanine was the first compound isolated from the fireworm which causes these effects. The chemical structure of Complanine was determined by spectroscopical methods[1] and the absolute configuration was confirmed with a total synthesis.[2]
It is presumed that this compound's function is to deter predators of the fireworm.
References
- ↑ Kazuhiko Nakamura, Yu Tachikawa, Makoto Kitamura, Osamu Ohno, Masami Suganuma and Daisuke Uemura (2008). "Complanine, an inflammation-inducing substance isolated from the marine fireworm Eurythoe complanata". Org. Biomol. Chem. 6 (12): 2058–2060. doi:10.1039/b803107j. PMID 18528565.
- ↑ Nakamura, Kazuhiko; Tachikawa, Yu; Uemura, Daisuke (2009). "(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study". Beilstein Journal of Organic Chemistry 5. doi:10.3762/bjoc.5.12.