Premium
Mass fragmentation and structure of siphonaxanthin, siphonein and derivatives
Author(s) -
Strain H. H.,
Svec W. A.,
Aitzetmüller K.,
Cope B. T.,
Harkness A. L.,
Katz J. J.
Publication year - 1971
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210050508
Subject(s) - fragmentation (computing) , chemistry , formaldehyde , carbon monoxide , ether , photochemistry , mass spectrometry , pigment , carbon dioxide , organic chemistry , medicinal chemistry , chromatography , catalysis , computer science , operating system
High resolution mass spectrometry has been employed to establish the structural formulae of the unique carotenoid pigment siphonaxanthin, its natural ester, siphonein and several derivatives. Siphonaxanthin exhibits a fragmentation reaction that is unusual among carotenoid pigments, namely, the elimination of carbon dioxide, observed as [M ‐ CO 2 ] and [M ‐ (CO 2 + H 2 O)]. This reaction involves the migration of an oxygen atom. Siphonaxanthol, a partially hydrogenated siphonaxanthin, exhibits a similar reaction involving the elimination of carbon monoxide and formaldehyde. From the fragmentation of derivatives of siphonaxanthin, such as the triacetate, the dimethyl ether and siphonaxanthol, and also from the fragmentation of related pigments, such as loroxanthin and fucoxanthin, the unique structural units responsible for the elimination of the carbon dioxide and carbon monoxide have been identified.