9,12,15‐octadecatrien‐6‐ynoic acid, new acetylenic acid from mosses
- 1 August 1974
- Vol. 9 (8) , 506-511
- https://doi.org/10.1007/bf02532496
Abstract
Lipids of the moss,Ceratodon purpureus, yield up to 25% of an acetylenic acid which was identified as allcis‐9,12,15‐octadecatrien‐6‐ynoic acid. The methyl ester of this acid was isolated in 95% purity by gas liquid chromatography. Mass spectroscopy provided the mol wt and confirmed methyl stearate as product of hydrogenation. Ozonization indicated a triple bond in position 6 and a double bond in position 15. UV and IR spectra showedcis‐double bonds, no conjugation, and notrans‐double bonds. The Raman spectrum provided direct evidence for the triple bond and confirmed the presence of double bonds and the absence of conjugation. The ratio of intensities indicated 1 triple bond/3 double bonds. 9,12,15‐Octadecatrien‐6‐ynoic acid has not previously been isolated from biological materials. It was found only in the triglycerides ofCeratodon purpureus and several other mosses. In contrast to arachidonic and eicosapentaenoic acids, the acetylenic acid seems to be restricted to few moss genera.Keywords
This publication has 27 references indexed in Scilit:
- Synthesis of 2trans‐alkene‐mono‐and ‐poly‐ynoic acids with a triple bond in the 5‐position and their hydrogenation. A new synthesis of arachidonic acidRecueil des Travaux Chimiques des Pays-Bas, 1973
- Highly Unsaturated Lipids of Mnium, Polytrichum, Marchantia, and MatteucciaThe Bryologist, 1972
- Fettsäuren im Pflanzen‐ und Tierreich (eine Übersicht) II: Trans‐ungesättigte, Alkin‐, Hydroxy‐, Epoxy‐, Oxo‐, Cyclopropan‐ und Cyclopropen‐FettsäurenFette, Seifen, Anstrichmittel, 1972
- Infrared and Raman studies of some monounsaturated olefinic and acetylenic fatty acids and their derivativesJournal of the Chemical Society, Perkin Transactions 2, 1972
- Biosynthesis of wax esters in fish. Metabolism of dietary alcoholsBiochemistry, 1971
- Occurrence of unusual fatty acids in plantsProgress in the Chemistry of Fats and other Lipids, 1971
- Pyrrolidide als Derivate für die Strukturaufklärung aliphatischer und alicyclischer Carbonsäuren mittels MassenspektrometrieHelvetica Chimica Acta, 1971
- Rapid micromethod for location of ene-yne and .alpha.-hydroxy conjugated diene systems in straigth-chain compoundsAnalytical Chemistry, 1969
- The mass spectrometry of large molecules I. The triglycerides of straight chain fatty acids.Tetrahedron Letters, 1964
- A portable semimicro ozonizerJournal of Chemical Education, 1953