Ectocarpene
Encyclopedia
Ectocarpene is a sexual attractant, or pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

, found with several species of brown algae
Brown algae
The Phaeophyceae or brown algae , is a large group of mostly marine multicellular algae, including many seaweeds of colder Northern Hemisphere waters. They play an important role in marine environments, both as food and for the habitats they form...

 (Phaeophyceae). The substance has a fruity scent and can be sensed by humans when millions of algae gametes swarm the seawater
Seawater
Seawater is water from a sea or ocean. On average, seawater in the world's oceans has a salinity of about 3.5% . This means that every kilogram of seawater has approximately of dissolved salts . The average density of seawater at the ocean surface is 1.025 g/ml...

 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 (order Ectocarpales
Ectocarpales
Ectocarpales is a very large order in the brown algae . The order includes families with pseudoparenchymatous or true parenchymatous tissue...

) by Müller and col. in 1971. More recent studies have shown that a pre-ectocarpene compound may be responsible for actual attraction of the male gametes.

All the double bonds are cis and the absolute configuration of the stereocenter
Stereocenter
A stereocenter or stereogenic center is an atom, bearing groups such that an interchanging of any two groups leads to a stereoisomer.A chirality center is a stereocenter consisting of an atom holding a set of ligands in a spatial arrangement which is not superposable on its mirror image...

is (S).

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