Accessing monomers, surfactants, and the queen bee substance by acrylate cross-metathesis of long-chain alkenones
O’Neil, Gregory W.
Williams, John R.
Craig, Alexander M.
Nelson, Robert K.
Gosselin, Kelsey M.
Reddy, Christopher M.
MetadataShow full item record
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.
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.
Suggested CitationPreprint: 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
Showing items related by title, author, creator and subject.
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 ...
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 ...
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 ...