• Login
    About WHOAS
    View Item 
    •   WHOAS Home
    • Woods Hole Oceanographic Institution
    • Marine Chemistry and Geochemistry (MC&G)
    • View Item
    •   WHOAS Home
    • Woods Hole Oceanographic Institution
    • Marine Chemistry and Geochemistry (MC&G)
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of WHOASCommunities & CollectionsBy Issue DateAuthorsTitlesKeywordsThis CollectionBy Issue DateAuthorsTitlesKeywords

    My Account

    LoginRegister

    Statistics

    View Usage Statistics

    Accessing monomers, surfactants, and the queen bee substance by acrylate cross-metathesis of long-chain alkenones

    Thumbnail
    View/Open
    Author's manuscript (450.8Kb)
    Supplemental Material (1.758Mb)
    Date
    2017-05
    Author
    O’Neil, Gregory W.  Concept link
    Williams, John R.  Concept link
    Craig, Alexander M.  Concept link
    Nelson, Robert K.  Concept link
    Gosselin, Kelsey M.  Concept link
    Reddy, Christopher M.  Concept link
    Metadata
    Show full item record
    Citable URI
    https://hdl.handle.net/1912/9048
    As published
    https://doi.org/10.1007/s11746-017-2997-8
    Keyword
     Algae; Isochrysis; Alkenones; Metathesis; Surfactants; Polymers; Pheromones 
    Abstract
    Polyunsaturated long-chain alkenones are a unique class of lipids biosynthesized in significant quantities (up to 20% of cell carbon) by several algae including the industrially grown marine microalgae Isochrysis. Alkenone structures are characterized by a long linear carbon-chain (35-40 carbons) with one to four trans-double bonds and terminating in a methyl or ethyl ketone. Alkenones were extracted and isolated from commercially obtained Isochrysis biomass and then subjected to cross-metathesis (CM) with methyl acrylate or acrylic acid using the Hoveyda-Grubbs metathesis initiator. Within 1 h at room temperature alkenones were consumed, however complete fragmentation (i.e. conversion to the smallest subunits by double bond cleavage) required up to 16 h. Analysis of the reaction mixture by gas chromatography and comprehensive two-dimensional gas chromatography revealed a predictable product mixture consisting primarily of long-chain (mostly C17) acids (or methyl esters from CM with methyl acrylate) and diacids (or diesters), along with smaller amounts (~5%) of the honey bee “queen substance” (E)-9-oxo-decenoic acid. Together, these compounds comprise a diverse mixture of valuable chemicals that includes surfactants, monomers, and an agriculturally relevant bee pheromone.
    Description
    Author Posting. © The Author(s), 2017. This is the author's version of the work. It is posted here under a nonexclusive, irrevocable, paid-up, worldwide license granted to WHOI. It is made available for personal use, not for redistribution. The definitive version was published in Journal of the American Oil Chemists' Society 94 (2017): 831-840, doi: 10.1007/s11746-017-2997-8.
    Collections
    • Marine Chemistry and Geochemistry (MC&G)
    Suggested Citation
    Preprint: O’Neil, Gregory W., Williams, John R., Craig, Alexander M., Nelson, Robert K., Gosselin, Kelsey M., Reddy, Christopher M., "Accessing monomers, surfactants, and the queen bee substance by acrylate cross-metathesis of long-chain alkenones", 2017-05, https://doi.org/10.1007/s11746-017-2997-8, https://hdl.handle.net/1912/9048
     

    Related items

    Showing items related by title, author, creator and subject.

    • Thumbnail

      Ancient DNA derived from alkenone-biosynthesizing haptophytes and other algae in Holocene sediments from the Black Sea 

      Coolen, Marco J. L.; Boere, Arjan C.; Abbas, Ben; Baas, Marianne; Wakeham, Stuart G.; Sinninghe Damste, Jaap S. (American Geophysical Union, 2006-02-18)
      Holocene sea surface temperatures (SST) of the Black Sea have been reconstructed using sedimentary C37 unsaturated alkenones assumed to be derived from the coccolithophorid haptophyte Emiliania huxleyi, whose fossil ...
    • Thumbnail

      Global temperature calibration of the alkenone unsaturation index (UK′37) in surface waters and comparison with surface sediments 

      Conte, Maureen H.; Sicre, Marie-Alexandrine; Ruhlemann, Carsten; Weber, John C.; Schulte, Sonja; Schulz-Bull, Detlef; Blanz, Thomas (American Geophysical Union, 2006-02-07)
      In this paper, we compile the current surface seawater C37 alkenone unsaturation (UK′37) measurements (n=629, −1 to 30°C temperature range) to derive a global, field-based calibration of UK′37 with alkenone production ...
    • Thumbnail

      Reconstructing the thermal structure of the upper ocean : insights from planktic foraminifera shell chemistry and alkenones in modern sediments of the tropical eastern Indian Ocean 

      Mohtadi, Mahyar; Oppo, Delia W.; Luckge, Andreas; De Pol-Holz, Ricardo; Steinke, Stephan; Groeneveld, Jeroen; Hemme, Nils; Hebbeln, Dierk (American Geophysical Union, 2011-09-10)
      Shell chemistry of planktic foraminifera and the alkenone unsaturation index in 69 surface sediment samples in the tropical eastern Indian Ocean off West and South Indonesia were studied. Results were compared to modern ...
    All Items in WHOAS are protected by original copyright, with all rights reserved, unless otherwise indicated. WHOAS also supports the use of the Creative Commons licenses for original content.
    A service of the MBLWHOI Library | About WHOAS
    Contact Us | Send Feedback | Privacy Policy
    Core Trust Logo