Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Christopoulou, C. N.; Perkins, E. G.

doi:10.1007/bf03022760

Cited by 8 publications

(4 citation statements)

References 14 publications

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“…GE-IS is a derivative of isostearic acid, which is the by-product in acidcatalyzed dimerization of unsaturated fatty acids. The chemical structures of the dimer acids are now being studied, but have not been fully determined and characterized yet (48)(49)(50). However, both the preparation and applications of dimer acid derivatives have attracted much attention.…”

Section: Methodsmentioning

confidence: 99%

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Urata

Takaishi

1996

J Americ Oil Chem Soc

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Lipids from natural sources consist mainly of saponifiable substances, such as glycerides, along with some unsaponifiable lipids, some of which are ether lipids. Typical ether lipids are monoalkyl ethers of glycerin, also called alkyl/alkenyl glyceryl ethers. Alkyl/alkenyl glyceryl ethers have also been reported in marine organisms and in human feces. Several chemical syntheses of such ether [ipids have been reported. Typical examples are alkyl glyceryl ether formation by the addition reaction of alkyl glycidyl ether and the telomerization reaction of butadiene with glycerin and a transition metal catalyst. Characteristic chemical structures, such as terpene alkyl glyceryl ethers, archaebacterial macrocyclic ether lipids, and glyceryl ethers of condensed cyclic planar molecules, have been obtained as well. Over the past few decades, industry has shown much interest in the chemistry and application of highly branched fatty acids. For example, isostearyl glyceryl ether (GE-IS) with methyl branching in the middle chain was already known, but it is now prepared at an industrial scale by proprietary alkyl glycidyl ether methods. The characteristic behavior of GE-IS toward water, such as formation of water-in-oil emulsions containing large amounts of water and of liquid crystals, has made it applicable for use in hair and skin care cosmetics. Based on these studies and considerations, glycery[ ether lipids, which are rarely investigated, may become one of the most important and useful lipids in the industry. JAOCS 73, 819-830 (1996). KEY WORDS:Ether lipids, GE-IS, glyceryl ether, glycidyl ether, isostearic acid, isostearyl glyceryl ether, liquid crystal, W/O emulsion.Saponification of lipids from tissues and organs of many marine animals results in water-soluble soaps that have high levels of some unsaponifiable substances, which chiefly include hydrocarbons, such as squalene, sterols, and long-chain alcohols with one or more hydroxyl groups (1,2). Typical longchain alcohols that contain one or more hydroxyl groups are particularly present as monoalkyl ethers of glycerin:RO-CH2-CH-CH 2 cyl glycerol, and batyl alcohol as the major constituents in a mixture of free alkyl glyceryl ethers isolated from the sponge Desmapsamma anchorata, harvested in the Gulf of Mexico, and minor components consisted of Cls, Cl9, C20, and Czl alkyl glyceryl ethers (12). They also found that sponges such

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Section: Methodsmentioning

confidence: 99%

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Urata

Takaishi

1996

J Americ Oil Chem Soc

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“…The low molecular weight components responsible for flavors and odors in many deep fried food products are formed via decomposition of lipid hydroperoxides by various mechanisms (7). For instance, hexanal, a very common aldehyde flavoring component, is formed by the destruction of a 13-hydroperoxide fatty acid derivative.…”

Section: Determination Of Volatile and Nonvolatile Oxidation Productsmentioning

confidence: 99%

“…In this phase peroxides are stabilized which, after a time period, begin to decompose. During this period volatile flavor and odor components and nonvolatile higher molecular weight products are formed as a result of oxidation (7). This process occurs at different rates depending upon the total unsaturation of the fat and many other associated factors ( Figure 2).…”

mentioning

confidence: 97%

Effect of Lipid Oxidation on Oil and Food Quality in Deep Frying

Perkins

1992

ACS Symposium Series

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Deep frying is a popular method for food preparation, especially in fast food restaurants. However, lipid oxidation easily occurs at relatively high temperatures in the presence of air and produces a multiplicity of compounds and exerts both desirable and undesirable effects on food flavor and quality. A low level of oxidation actually improves the desirability of a food but higher levels decrease food quality. The presence of low molecular weight materials such as aldehydes, lactones and pyrazines influence the flavor of deep fried foods such as potatoes; while the presence of high molecular weight materials contribute to the overall quality deterioration of both the frying fat and the fried product. The application of GC-MS to the determination of flavor components in french fries and corresponding frying oil yielded information indicating a relationship between the presence of these materials and french fry quality. A larger scale study in which the amounts of high molecular weight products were determined showed the time course of oil deterioration and a relationship between total polar material formed and food quality.Deep frying is a popular method for food preparation, especially in fast food restaurants. Although used primarily as a heat exchange medium to cook food, the oil used for deep frying contributes to the quality of the fried food. Lipid oxidation at higher temperatures in the presence of oxygen and steam, as in deep fat frying, produces a multiplicity of compounds which exert both desirable and undesirable effects on food flavor and quality. For instance (Figure 1), oxidative and chemical changes in frying fats during use are characterized by a decrease in the total unsaturation of the fat with increases in free fatty acid content, foaming, color, viscosity, polar materials, and polymeric material. All of these increase with time, at the expense of the original triglyceride via lipid oxidation through free radical mechanisms. Most of the free fatty acids found are from hydrolysis of the frying oil by steam generated from the food product.Fats at any temperature appear to go through a free radical initiation period during oxidation. They then move into a free radical propagation or peroxide formation phase. The rate of formation then slows and a free radical termination

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“…Characterization of polymer products formed in the thermal oxidative treatment of fats and oils has been of great interest over the last thirty years. Most recently, Christopoulou and Perkins synthesized several dimer standards for characterization by chromatography and mass spectrometry (4)(5)(6). They later used these techniques to thoroughly characterize the dimers formed in heated soybean oil (7,8).…”

mentioning

confidence: 99%

Isolation and characterization of polymers in heated olestra and an olestra/triglyceride blend

Gardner

Sanders

1990

J Americ Oil Chem Soc

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High molecular weight components in thermally oxidized olestra (formerly called sucrose polyesters) and a mixture of olestra and soybean oil were characterized. The high molecular weight components of these oils were separated by preparative size exclusion chromatography and analyzed intact by mass spectrometry, infrared, and nuclear magnetic resonance spectroscopy. The materials isolated from the heated olestra were identified as olestra polymers. Materials isolated from the heated mixed oil (olestra and soybean oil) were identified as polymers of olestra and copolymers of olestra and triglycerides. Polymer linkages identified were identical to those resulting from thermal oxidation of natural vegetable oils of similar fatty acid composition.

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Dimer acids: Synthesis and mass spectrometry of the tetrahydroxy, dihydroxy, and diketo dinners of methyl stearate

Cited by 8 publications

References 14 publications

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Ether lipids based on the glyceryl ether skeleton: Present state, future potential

Effect of Lipid Oxidation on Oil and Food Quality in Deep Frying

Isolation and characterization of polymers in heated olestra and an olestra/triglyceride blend

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