LC-MS identification of derivatized free fatty acids from adipocere in soil samples. 2010

Manuel Algarra, and José E Rodríguez-Borges, and Joaquim C G Esteves da Silva
Centro de Geologia do Porto, Faculdade de Ciências da Universidade do Porto, Porto, Portugal.

Free fatty acids were derivatized as amides (DFFA) by reaction with (R)-(+)-1-phenylethylamine, using a simple, fast and robust reaction scheme. A HPLC method with diode array and ESI MS detection was developed for the analysis of the derivatized substances. Six fatty acids were used in the method development: myristic, linoleic, palmitic, oleic, margaric and stearic acids. Under these conditions the elution of the DFFA are well resolved with retention times raging from 6.9 to 16.0 min. Fatty acids were extracted from cemetery soil and from adipocere formation experimental soils using a Soxhlet extraction, using as solvent ether/dichloromethane (1:1). Each DFFA is characterized by three m/z peaks: molecular weight of the substance; molecular weight of a dimer of the substance; the molecular weight of the dimer plus the atomic mass of sodium. The analysis of soil samples detected the six fatty acids used in the method developed plus palmitoleic and pentadecanoic. Beside this set of eight fatty acids other 13 fatty acids were detected in trace quantities or only in some soils and some were tentatively assigned as: 10-hydroxystearic, myristoleic, heptadecenoic and arachidic acids.

UI MeSH Term Description Entries
D010627 Phenethylamines A group of compounds that are derivatives of beta- aminoethylbenzene which is structurally and pharmacologically related to amphetamine. (From Merck Index, 11th ed) Phenylethylamines
D011180 Postmortem Changes Physiological changes that occur in bodies after death. Adipocere,Algor Mortis,Cruor,Livor Mortis,Change, Postmortem,Changes, Postmortem,Postmortem Change
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D005227 Fatty Acids Organic, monobasic acids derived from hydrocarbons by the equivalent of oxidation of a methyl group to an alcohol, aldehyde, and then acid. Fatty acids are saturated and unsaturated (FATTY ACIDS, UNSATURATED). (Grant & Hackh's Chemical Dictionary, 5th ed) Aliphatic Acid,Esterified Fatty Acid,Fatty Acid,Fatty Acids, Esterified,Fatty Acids, Saturated,Saturated Fatty Acid,Aliphatic Acids,Acid, Aliphatic,Acid, Esterified Fatty,Acid, Saturated Fatty,Esterified Fatty Acids,Fatty Acid, Esterified,Fatty Acid, Saturated,Saturated Fatty Acids
D005230 Fatty Acids, Nonesterified FATTY ACIDS found in the plasma that are complexed with SERUM ALBUMIN for transport. These fatty acids are not in glycerol ester form. Fatty Acids, Free,Free Fatty Acid,Free Fatty Acids,NEFA,Acid, Free Fatty,Acids, Free Fatty,Acids, Nonesterified Fatty,Fatty Acid, Free,Nonesterified Fatty Acids
D005231 Fatty Acids, Unsaturated FATTY ACIDS in which the carbon chain contains one or more double or triple carbon-carbon bonds. Fatty Acids, Polyunsaturated,Polyunsaturated Fatty Acid,Unsaturated Fatty Acid,Polyunsaturated Fatty Acids,Acid, Polyunsaturated Fatty,Acid, Unsaturated Fatty,Acids, Polyunsaturated Fatty,Acids, Unsaturated Fatty,Fatty Acid, Polyunsaturated,Fatty Acid, Unsaturated,Unsaturated Fatty Acids
D005554 Forensic Medicine The application of medical knowledge to questions of law. Legal Medicine,Medicine, Forensic,Medicine, Legal
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D012987 Soil The unconsolidated mineral or organic matter on the surface of the earth that serves as a natural medium for the growth of land plants. Peat,Humus,Soils

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