Structural Homogeneity in Unsaturated Fatty Acids of Marine Lipids. A Review

1964 ◽  
Vol 21 (2) ◽  
pp. 247-254 ◽  
Author(s):  
R. G. Ackman
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Chain Length ◽  
Unsaturated Fatty Acids ◽  
Analytical Data ◽  
Double Bonds ◽  
Marine Origin ◽  
Methyl Group ◽  
Marine Lipids

Consideration of recent analytical data supports the conclusion that the longer-chain polyunsaturated fatty acids of marine origin are all structurally homogeneous in that the double bonds are cis, the double bonds methylene interrupted, and that, with the exception of the C16 chain length, the ultimate double bond will normally be three, six or nine carbon atoms removed from the terminal methyl group.

scholarly journals β-oxidation of polyunsaturated fatty acids with conjugated double bonds. Mitochondrial metabolism of octa-2,4,6-trienoic acid

1989 ◽  
Vol 264 (1) ◽  
pp. 47-52 ◽  
Author(s):  
H Y Wang ◽  
H Schulz
Keyword(s):  
Fatty Acids ◽  
Polyunsaturated Fatty Acids ◽  
Unsaturated Fatty Acids ◽  
Liver Mitochondria ◽  
Trienoic Acid ◽  
Rat Liver Mitochondria ◽  
Double Bonds ◽  
Beta Oxidation ◽  
Rat Heart Mitochondria ◽  
Coa Reductase

The mitochondrial beta-oxidation of octa-2,4,6-trienoic acid was studied with the aim of elucidating the degradation of unsaturated fatty acids with conjugated double bonds. Octa-2,4,6-trienoic acid was found to be a respiratory substrate of coupled rat liver mitochondria, but not of rat heart mitochondria. Octa-2,4,6-trienoyl-CoA, the product of the inner-mitochondrial activation of the acid, was chemically synthesized and its degradation by purified enzymes of beta-oxidation was studied spectrophotometrically and by use of h.p.l.c. This compound is a substrate of NADPH-dependent 2,4-dienoyl-CoA reductase or 4-enoyl-CoA reductase (EC 1.3.1.34), which facilitates its further beta-oxidation. The product obtained after the NADPH-dependent reduction of octa-2,4,6-trienoyl-CoA and one round of beta-oxidation was hex-4-enoyl-CoA, which can be completely degraded via beta-oxidation. It is concluded that polyunsaturated fatty acids with two conjugated double bonds extending from even-numbered carbon atoms can be completely degraded via beta-oxidation because their presumed 2,4,6-trienoyl-CoA intermediates are substrates of 2,4-dienoyl-CoA reductase.

scholarly journals Gas Chromatographic Determination of Fatty Acids in Oils with Regard to the Assessment of Fire Hazard

2017 ◽  
Vol 25 (40) ◽  
pp. 73-81 ◽  
Author(s):  
Alica Bartošová ◽  
Tomáš Štefko
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Spontaneous Combustion ◽  
Unsaturated Fatty Acids ◽  
Fire Hazard ◽  
Accurate Determination ◽  
Coconut Oil ◽  
Double Bonds ◽  
Self Heating

Abstract The aim of the paper was to study and research the application of processing gas chromatographic method for the rapid and accurate determination of the composition of different types of oils, such as substances with the possibility of an adverse event spontaneous combustion or self-heating. Tendency to spontaneous combustion is chemically characterized mainly by the amount of unsaturated fatty acids, which have one or more double bonds in their molecule. Vegetable oils essentially consist of the following fatty acids: palmitic, stearic, oleic, linoleic, and linoleic. For the needs of assessment, the fire hazard must be known, in which the double bond is present, as well as their number in a molecule. As an analytical method, GCMS was used for determination of oils content. Three types of oil were used - rapeseed, sunflower, and coconut oil. Owing to the occurrence of linoleic acid C18:2 (49.8 wt.%) and oleic acid C18:1 (43.3 wt.%) with double bonds, sunflower oil is the most prone to self-heating. The coconut and rapeseed oils contain double bond FAME in lesser amount, and their propensity to self-heating is relatively low.

scholarly journals Phenolation of vegetable oils

2011 ◽  
Vol 76 (4) ◽  
pp. 591-606 ◽  
Author(s):  
Mihail Ionescu ◽  
Zoran Petrovic
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Double Bond ◽  
Vegetable Oils ◽  
Raw Materials ◽  
Complex Mixture ◽  
Double Bonds ◽  
Triflic Acid ◽  
Model Compounds ◽  
Phenol Alkylation

Novel bio-based compounds containing phenols suitable for the synthesis of polyurethanes were prepared. The direct alkylation of phenols with different vegetable oils in the presence of superacids (HBF4, triflic acid) as catalysts was studied. The reaction kinetics was followed by monitoring the decrease of the double bond content (iodine value) with time. In order to understand the mechanism of the reaction, phenol was alkylated with model compounds. The model compounds containing one internal double bond were 9-octadecene and methyl oleate and those with three double bonds were triolein and high oleic safflower oil (82% oleic acid). It was shown that the best structures for phenol alkylation are fatty acids with only one double bond (oleic acid). Fatty acids with two double bonds (linoleic acid) and three double bonds (linolenic acid) lead to polymerized oils by a Diels Alder reaction, and to a lesser extent to phenol alkylated products. The reaction product of direct alkylation of phenol with vegetable oils is a complex mixture of phenol alkylated with polymerized oil (30-60%), phenyl esters formed by transesterification of phenol with triglyceride ester bonds (<10 %) and unreacted oil (30%). The phenolated vegetable oils are new aromatic-aliphatic bio-based raw materials suitable for the preparation of polyols (by propoxylation, ethoxylation, Mannich reactions) for the preparation of polyurethanes, as intermediates for phenolic resins or as bio-based antioxidants.

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