Ectocarpene

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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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.

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

  1. ^ 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.