Ectocarpene

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IUPACName = (5S)-5- [(1E)-but-1-en-1-yl] cyclohepta-1,3-diene
OtherNames = (6R)-6- [(E)-but-1-enyl] cyclohepta-1,4-diene, 6- [Z-butenyl] -1,4-cycloheptadiene, 1-(1-butenyl)-2,5-cycloheptadiene, (+)-(6S)-6-(1Z-butenyl)cyclohepta-1,4-diene
Section1 = Chembox Identifiers
CASNo = 33156-93-3
PubChem = 6440990
SMILES = CCC=C [C@H] 1CC=CCC=C1
InChI = 1/C11H16/c1-2-3-8-11-9-6-4-5-7-10-11 /h3-4,6-8,10-11H,2,5,9H2,1H3/b8-3+/t11-/m0/s1
Section2 = Chembox Properties
Formula = C₁₁H₁₆
MolarMass = 148.24 g/mol
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Section3 = Chembox Hazards
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Ectocarpene is a sexual attractant, or pheromone, found with several species of brown algae (Phaeophyceae). The substance has a fruity scent and can be sensed by humans when millions of algae gametes swarm the seawater and the females start emitting the substance to attract the male gametes.

Ectocarpene was the first isolated algal pheromone. It was isolated from algae "Ectocarpus" (ordo "Ectocarpales") by Müller and col. in 1971 [ [http://www.ice.mpg.de/bol/research/ectocarpus/ectocarpene.htm?mp=83 Ectocarpene] ] . More recent studies have shown that a pre-ectocarpene compound may be responsible for actual attraction of the male gametes [ [http://www.jstor.org/pss/2366495 Pre-ectocarpene compound] ] .

All the double bonds are cis & the absolute configuration of the stereocentre is S.

References

External links

* [http://aslo.org/lo/toc/vol_29/issue_6/1322.pdf Evidence of ectocarpene and dictyopterenes A and C’ in the water of a freshwater lake’]