Ectocarpene

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Ectocarpene
Ectocarpene, Structure.svg
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
PubChem CID
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 X mark.svgN
    Key: KIFXGGYCNMHCSX-DZHRUPLWSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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]

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. [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

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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. 1 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.