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).
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Ectocarpene is the rearrangement product of pre-ectocarpene, [1] 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.

Contents

All the double bonds are cis and the absolute configuration of the stereocenter is (S). [1]

History

Ectocarpene was isolated from algae Ectocarpus (order Ectocarpales ) by Müller and col. in 1971. [2] 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: [3]

Mechanism of ectocarpene formation from precursor Ectocarpene formation.png
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. [4]

(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. [5]

See also

References

  1. 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.
  2. ↑ 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.
  3. ↑ Clayden, Jonathan; Greeves, Nick; Warren, Stuart G. (2012). Organic chemistry (2nd ed.). Oxford; New YorK: Oxford University Press. p. 915. ISBN   978-0-19-927029-3.
  4. ↑ 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. hdl: 20.500.11939/4429 . ISSN   0021-8561. PMID   20199081.
  5. ↑ 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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