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.
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| Names | |
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| 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)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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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All the double bonds are cis and the absolute configuration of the stereocenter is (S).[1]
History
editEctocarpene was isolated from algae Ectocarpus (order Ectocarpales) by Müller and col. in 1971.[2] It has been mistakened 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]
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]
Related Compounds
edit(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
editReferences
edit- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.