Ectocarpene: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 421040671

| ImageFile = Ectocarpene, Structure.svg

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| ImageSize1 = 200px

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| ImageSize2 = 200px

| PIN = (6''S'')-6-[(1''Z'')-But-1-en-1-yl]cyclohepta-1,4-diene

| OtherNames = (''S'',''Z'')-6-(But-1-en-1-yl)cyclohepta-1,4-diene<br />Dictyopterene D

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5LT5CQ3SYJ

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 28290131

| PubChem = 6440990

| SMILES = CC/C=C\[C@H]1CC=CCC=C1

| 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

| InChIKey = KIFXGGYCNMHCSX-DZHRUPLWBJ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KIFXGGYCNMHCSX-DZHRUPLWSA-N

| Section2 = {{Chembox Properties

| C=11 | H=16

| Appearance =

| Density = 0.908 g/mL

| MeltingPt =

| BoilingPt =

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| Section3 = {{Chembox Hazards

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'''Ectocarpene''' is the rearrangement product of pre-ectocarpene,<ref name="Wilhelm Boland2">{{cite journal |author=Wilhelm Boland |year=1995 |title=The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=92 |issue=1 |pages=37–43 |bibcode=1995PNAS...92...37B |doi=10.1073/pnas.92.1.37 |jstor=2366495 |pmc=42813 |pmid=7816845 |doi-access=free}}</ref> 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-trans isomerism|''cis'']] and the absolute configuration of the [[stereocenter]] is (''S'').<ref name="Wilhelm Boland">{{cite journal |author=Wilhelm Boland |year=1995 |title=The Chemistry of Gamete Attraction: Chemical Structures, Biosynthesis, and (a)biotic Degradation of Algal Pheromones |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=92 |issue=1 |pages=37–43 |bibcode=1995PNAS...92...37B |doi=10.1073/pnas.92.1.37 |jstor=2366495 |pmc=42813 |pmid=7816845 |doi-access=free}}</ref>

==History==

Ectocarpene was isolated from algae ''Ectocarpus'' (order ''[[Ectocarpales]]'') by Müller and col. in 1971.<ref>{{cite journal |author1=Mueller, D. G. |author2=Jaenickel, L. |author3=Donike, M. |author4=Akintobi, T. | title = Sex attractant in a brown alga: chemical structure | journal = Science | year = 1971 | volume = 171 | issue = 3973 | pages = 815–817 | doi = 10.1126/science.171.3973.815 | pmid = 17812027|bibcode=1971Sci...171..815M |s2cid=41629286 }}</ref> 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 reaction|sigmatropic rearrangement]] (and thus deactivation) of pre-ectocarpene in minutes at room temperature:<ref>{{Cite book |last1=Clayden |first1=Jonathan |title=Organic chemistry |last2=Greeves |first2=Nick |last3=Warren |first3=Stuart G. |date=2012 |publisher=Oxford University Press |isbn=978-0-19-927029-3 |edition=2nd |location=Oxford ; New YorK |pages=915}}</ref>

[[File:Ectocarpene_formation.png|thumb|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.<ref>{{Cite journal|last1=Rodríguez-Burruezo|first1=Adrián|last2=Kollmannsberger|first2=Hubert|last3=González-Mas|first3=M. Carmen|last4=Nitz|first4=Siegfried|last5=Fernando|first5=Nuez|date=2010-04-14|title=HS-SPME Comparative Analysis of Genotypic Diversity in the Volatile Fraction and Aroma-Contributing Compounds of Capsicum Fruits from the annuum − chinense − frutescens Complex|url=https://pubs.acs.org/doi/10.1021/jf903931t|journal=Journal of Agricultural and Food Chemistry|language=en|volume=58|issue=7|pages=4388–4400|doi=10.1021/jf903931t|pmid=20199081|issn=0021-8561}}</ref>

==Related Compounds==

(''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.<ref>{{Cite journal|last1=Asakawa|first1=Yoshinori|last2=Ludwiczuk|first2=Agnieszka|date=2018-03-23|title=Chemical Constituents of Bryophytes: Structures and Biological Activity|url=https://pubs.acs.org/doi/10.1021/acs.jnatprod.6b01046|journal=Journal of Natural Products|language=en|volume=81|issue=3|pages=641–660|doi=10.1021/acs.jnatprod.6b01046|pmid=29019405|issn=0163-3864}}</ref>

* [https://web.archive.org/web/20070930190637/http://aslo.org/lo/toc/vol_29/issue_6/1322.pdf Evidence of ectocarpene and dictyopterenes A and C’ in the water of a freshwater lake’]

[[Category:Alkene derivatives]]

[[Category:Hydrocarbons]]

[[Category:Ectocarpales]]

[[Category:Cycloalkenes]]