Surf Wiki
Save to docs
general/alkene-derivatives

From Surf Wiki (app.surf) — the open knowledge base

Ectocarpene

Ectocarpene

Dictyopterene D

Ectocarpene is the rearrangement product of pre-ectocarpene, the sexual attractant, or pheromone, found with several species of brown algae (Phaeophyceae). Ectocarpene 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's precursor to attract the male gametes.

All the double bonds are cis and the absolute configuration of the stereocenter is (S).

History

Ectocarpene was isolated from algae Ectocarpus (order Ectocarpales) by Müller and col. in 1971. It has been mistook to be the active substance for gamete attraction until 1995, and pre-ectocarpene was discovered to be active. This confusion arises from the sigmatropic rearrangement (and thus deactivation) of pre-ectocarpene in minutes at room temperature:

Mechanism of ectocarpene formation from precursor

This is as to only have the phermon active in the proximity of the female gametes.

The presence of ectocarpene in Capsicum fruit was reported in 2010. Studies concluded that its "sweet and green" aroma surfaced through identification tests as well as sensory tests. Its relatively low but influential presence helps develop the Capsicum fruit’s profile.

References

References

  1. Wilhelm Boland. (1995). "The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones". Proceedings of the National Academy of Sciences of the United States of America.
  2. (1971). "Sex attractant in a brown alga: chemical structure". Science.
  3. (2012). "Organic chemistry". Oxford University Press.
  4. (2010-04-14). "HS-SPME Comparative Analysis of Genotypic Diversity in the Volatile Fraction and Aroma-Contributing Compounds of Capsicum Fruits from the annuum − chinense − frutescens Complex". Journal of Agricultural and Food Chemistry.
  5. (2018-03-23). "Chemical Constituents of Bryophytes: Structures and Biological Activity". Journal of Natural Products.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alkene-derivatives hydrocarbons pheromones ectocarpales cycloalkenes
Want to explore this topic further?

Ask Mako anything about Ectocarpene — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report