Ectocarpene

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
Names
Preferred IUPAC name
(6S)-6-[(1Z)-But-1-en-1-yl]cyclohepta-1,4-diene
Other names
(S,Z)-6-(But-1-en-1-yl)cyclohepta-1,4-diene
Dictyopterene D
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/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 ☒N
    Key: KIFXGGYCNMHCSX-DZHRUPLWSA-N ☒N
  • 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
    Key: KIFXGGYCNMHCSX-DZHRUPLWBJ
  • CC/C=C\[C@H]1CC=CCC=C1
Properties
C11H16
Molar mass 148.249 g·mol−1
Density 0.908 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ectocarpene was the first isolated algal pheromone. It was isolated from algae Ectocarpus (order Ectocarpales) by Müller and col. in 1971.[1] More recent studies have shown that a pre-ectocarpene compound may be responsible for actual attraction of the male gametes.[2]

Moreover, Ectocarpene’s presence, in 2010, has been identified within the Capsicum fruit for the first time. 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.[3]

(E)-Ectocarpene is a product associated to a group referred to as Bryophytes, a family of liverworts, algae, and other species with medicinal and nutritional properties. It is suggested that (E)-Ectocarpene may have an evolutionary relationship between families of liverworts and algae as its concentration of formation varies based on the species’ environmental conditions.[4]

All the double bonds are cis and the absolute configuration of the stereocenter is (S).[2]

See also

References
  1. Mueller, D. G.; Jaenickel, L.; Donike, M.; Akintobi, T. (1971). "Sex attractant in a brown alga: chemical structure". Science. 171 (3973): 815–817. Bibcode:1971Sci...171..815M. doi:10.1126/science.171.3973.815. PMID 17812027. S2CID 41629286.
  2. 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. 92 (1): 37–43. Bibcode:1995PNAS...92...37B. doi:10.1073/pnas.92.1.37. JSTOR 2366495. PMC 42813. PMID 7816845.
  3. Rodríguez-Burruezo, Adrián; Kollmannsberger, Hubert; González-Mas, M. Carmen; Nitz, Siegfried; Fernando, Nuez (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. 58 (7): 4388–4400. doi:10.1021/jf903931t. ISSN 0021-8561. PMID 20199081.
  4. Asakawa, Yoshinori; Ludwiczuk, Agnieszka (2018-03-23). "Chemical Constituents of Bryophytes: Structures and Biological Activity". Journal of Natural Products. 81 (3): 641–660. doi:10.1021/acs.jnatprod.6b01046. ISSN 0163-3864. PMID 29019405.


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