On the occurrence and structural identification of long chain unsaturated ketones and hydrocarbons in sediments

Leeuw, J.W. de; Meer, F.W. van de; Rijpstra, W. Irene C.; Schenck, P.A.

doi:10.1016/0079-1946(79)90105-8

Cited by 110 publications

(91 citation statements)

References 5 publications

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“…First attempts of double bond location of these C 37 -C 40 alkenones were assayed with direct epoxidation by reaction with dimethyldioxirane [20] or formation of oximes [13,14] but none of these methods provided useful structural information, e.g., oxime derivatives provide information on the position of the carbonyl group but not on the location of the double bonds.…”

Section: Double Bond Derivatizationmentioning

confidence: 99%

“…The first research on the structural characterization of the alkenones addressed the location of double bonds by mass spectral interpretation of the trimethylsilyl ethers (TMSiE) after hydroxylation with osmium tetrox-ide (OsO 4 ) [13]. The structures of 15,22-heptatriacontadien-2-one, 16,23-octatriacontadien-2-one, and 9,16,23-octatriacontatrien-2-one were determined with this method.…”

mentioning

confidence: 99%

“…The position of the carbonyl group was recognized by McLafferty type rearrangements m/z (M-58 and M-72). The EI mass spectra of the O-methyl and O-ethyl oximes and the TMSiE of the alkenols obtained by NaBH 4 alkenone reduction allowed further differentiation between the ethyl and methyl ketones [13,14]. This derivatization approach was also used for double bond location in a novel series of monounsaturated ketones (C 35 -C 38 ) [15].…”

mentioning

confidence: 99%

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Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

López

Grimalt

2004

J. Am. Soc. Mass Spectrom.

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A method for the identification of double bond locations in polyunsaturated long chain alkenones adapted to nanogram amounts as currently analyzed by gas chromatography coupled to mass spectrometry (GC-MS) has been developed. The method is based on interpretation of the electron impact mass spectra of the imino derivatives of the carbonyl groups using either cyclopentyl or phenyl substitutents. Other complementary derivatization methods such as elaidization and hydrogenation have also been used for structural characterization of these compounds. This application has led to the identification of a novel homologous series of di-, tri-, and tetraunsaturated ketones with carbon number chain lengths between 37 and 40 in coastal hypersaline sediments. The novel series identified shows a distribution in which the double bond position between different homologs is established by reference to the distance from the carbonyl group whereas the previously known alkenones were constituted by unsaturated homologs with double bonds located at defined distances of the terminal methyl. This difference points out to a dissimilar, but still unknown, biogenic precursor of these novel alkenones. (J Am Soc Mass Spectrom 2004, 15, 1161-1172

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Section: Double Bond Derivatizationmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

López

Grimalt

2004

J. Am. Soc. Mass Spectrom.

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“…However, the tentatively identified long-chain alken-2-ols (VI) and alken-3-ols (VII) show great similarity in carbon chain length distribution and number of double bonds (Figs. 8A and 8B) with the long-chain alkenones (de Leeuw et al, 1980). A common origin (i.e., haptophyte algae) therefore seems likely.…”

Section: Polar Lipidsmentioning

confidence: 99%

Molecular paleontology of eastern Mediterranean sapropels: evidence for photic zone euxinia

Bosch¹,

Damsté²,

Leeuw³

1998

Proceedings of the Ocean Drilling Program, 160 Scientific Results

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Organic geochemical data are presented for two Pliocene sapropels recovered during Ocean Drilling Program (ODP) Leg 160 in the Eastern Mediterranean Basin. One sapropel from Site 969 is exceptionally rich in organic carbon (TOC up to 30%) and the other one, from Site 967, has a more typical organic carbon content (TOC up to 8%). The majority of the solvent extractable organic matter of these sapropels can be ascribed to autochthonous sources. Higher plant-derived organic compounds are present in only minor amounts. Pyrolysis gas chromatography-mass spectrometry (GC-MS) analyses of the bulk organic matter also indicates that the contribution of terrestrial organic matter to these sapropels is insignificant. The presence of biomarkers derived from green sulfur bacteria, which are indicative of anoxygenic photosynthesis, show that during sapropel formation anoxia was not merely confined to the lower parts of the water column but, in fact, extended into the photic zone, resulting in an almost completely euxinic water column, a setting similar to the present-day Black Sea. Furthermore, it is proposed that these paleoenvironmental conditions have been a major controlling factor in the accumulation of organic matter in these sapropels.

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“…Alkenones are a class of mono-, di-, tri-, tetra-and penta-unsaturated C 35 -C 40 methyl and ethyl ketones (Boon et al, 1978;Volkman et al, 1980;de Leeuw et al, 1980;Marlowe et al, 1984;Prahl et al, 2006;Jaraula et al, 2010), which are produced by certain marine haptophytes. Emiliania huxleyi and Gephyrocapsa oceanica are the major sources of alkenones in the open ocean (Volkman et al, 1980;Conte et al, 1994).…”

Section: Alkenonesmentioning

confidence: 99%

Photo- and Free Radical-Mediated Oxidation of Lipid Components During the Senescence of Phototrophic Organisms

Rontani¹

2012

Senescence

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On the occurrence and structural identification of long chain unsaturated ketones and hydrocarbons in sediments

Cited by 110 publications

References 5 publications

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Molecular paleontology of eastern Mediterranean sapropels: evidence for photic zone euxinia

Photo- and Free Radical-Mediated Oxidation of Lipid Components During the Senescence of Phototrophic Organisms

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On the occurrence and structural identification of long chain unsaturated ketones and hydrocarbons in sediments

Cited by 110 publications

References 5 publications

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C37-C40 alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C37-C40 alkenones by GC-MS

Molecular paleontology of eastern Mediterranean sapropels: evidence for photic zone euxinia

Photo- and Free Radical-Mediated Oxidation of Lipid Components During the Senescence of Phototrophic Organisms

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Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS