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Gas‐phase Reagents for Carbon–Carbon Double Bond Location: New Applications. Part I‐Nitric Oxide Chemical Ionization Mass Spectrometry of 1‐ O ‐Alkenylglycerols from the Deep‐sea Shark Centrophorus Squamosus Liver Oil
Author(s) -
Sellier Nicole,
Bordier Catherine,
Kerhoas Lucien,
Einhorn Jacques
Publication year - 1997
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199707)32:7<723::aid-jms524>3.0.co;2-0
Subject(s) - chemistry , double bond , mass spectrometry , chemical ionization , bifunctional , carbon fibers , nitric acid , ion , medicinal chemistry , organic chemistry , ionization , chromatography , catalysis , materials science , composite number , composite material
Nitric oxide chemical ionization (CI) mass spectrometry (MS) has proved to be a very efficient tool for locating the carbon–carbon double bond in monoalkenylglycerols of the HOCH 2 CHOHCH 2 O(CH 2 ) n CH = CH(CH 2 ) m CH 3 type. Such compounds, e.g. containing a ω‐7 C 16 :1, ω‐8 C 17 :1 (minor) and ω‐9 C 18 :1 alkenyl chain, were extracted from the liver oil of the deep‐sea shark Centrophorus squamosus and found among the most characteristic substances of the species. Double bond location was unambiguously deduced from the abundant CH 3 (CH 2 ) m CO + acylium ion being produced when examining the permethylated compounds under gas chromato‐graphic (GC) nitric oxide CIMS conditions. This ion probably results, as suggested by GC/MS/MS studies, from mechanisms similar to those previously reported for mono‐ or bifunctional alkenes. © 1997 by John Wiley & Sons, Ltd.