Photocatalytic Production and Processing of Conjugated Linoleic Acid-Rich Soy Oil

Jain, Vishal; Proctor, Andrew

doi:10.1021/jf060513a

Cited by 32 publications

(58 citation statements)

References 12 publications

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“…As seen in Figure 8, the level of headspace oxygen decreased by CLA was faster than that of PCLA. Consistent with these results, CLA in the FFA form was extremely unstable (similar to DHA) 4 and had an oxidation rate considerably greater than LA and ACA. 4,5 Also, Yurawecz and others reported that CLA rapidly decomposed to form furan fatty acids when it was oxidized in air.…”

Section: Resultssupporting

confidence: 80%

“…Consistent with these results, CLA in the FFA form was extremely unstable (similar to DHA) 4 and had an oxidation rate considerably greater than LA and ACA. 4,5 Also, Yurawecz and others reported that CLA rapidly decomposed to form furan fatty acids when it was oxidized in air. 23 By contrast, PCLA had increased oxidative stability when compared with CLA.…”

Section: Resultssupporting

confidence: 80%

“…2 Application of the CLA as a functional food ingredient has been limited due to the high cost of purification and its insolubility in water 3 although the CLA is widely found in ruminant meats, pasteurized cheese, and dairy products as a natural part of the diet. 4 Also, CLA in the free fatty acid (FFA) form is extremely unstable under air atmosphere and rapidly decomposes by oxidation to form furan fatty acids. 5 The CLA was reported to be similar with docosahexanenoic acid (DHA) in its unstability and it had an oxidation rate considerably greater than that of linoleic acid (LA) and arachidonic acid (ACA).…”

Section: Introductionmentioning

confidence: 99%

“…5 The CLA was reported to be similar with docosahexanenoic acid (DHA) in its unstability and it had an oxidation rate considerably greater than that of linoleic acid (LA) and arachidonic acid (ACA). 4 Therefore, the CLA must be protected from oxidation if it is to be used in food systems as fortifiers or additives.…”

Section: Introductionmentioning

confidence: 99%

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Oxidative stabilization of conjugated linoleic acid by one-pot PEGylation

et al. 2011

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This study describes a novel and one-step procedure for the PEGylation of conjugated linoleic acid (CLA) in the melting state without solvents or catalysts for oxidative stabilization of CLA. The double bonds of CLA in PEGylated CLA (PCLA) were clearly detected by 1 H NMR (nuclear magnetic resonance) spectroscopy, indicating the successful PEGylation of CLA without oxidation during PEGylation, even at high temperatures. The level of headspace oxygen depletion by PCLA was lower than CLA, indicating that the oxidation of CLA was protected by PEGylation. This easy and simple one-pot PEGylation of CLA is an effective way of preparing fatty acids with increased stability to oxidation, which would be quite useful for nutritional and pharmaceutical studies.

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Section: Resultssupporting

confidence: 80%

Section: Resultssupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Oxidative stabilization of conjugated linoleic acid by one-pot PEGylation

et al. 2011

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“…Under irradiation, the I 2 possesses radical forming potential (GANGIDI & PROCTOR, 2004). By optimization of the process and performing the reaction in stirred batch photoreactor (JAIN & PROCTOR, 2006), a production of 240 mg CLA/g substrate was obtained.…”

Section: Obtaining Clas By Photochemical Methodsmentioning

confidence: 99%

Synthetic methods to obtain conjugated linoleic acids (CLAs) by catalysis – A review

Salamon¹,

Vargáné-Visi²,

András³

et al. 2015

Acta Alimentaria

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The addition of synthetic CLA is a possible way in order to compose foods enriched with conjugated linoleic acids (CLAs). The most environmental friendly methods for CLA synthesis are based on microbial biosynthesis. With homogeneous catalysis using organometallic catalysts (Ru and Rh complexes) high (approximately 80%) yields were obtained with high selectivity related to bioactive isomers. The heterogeneous catalysis has the advantage that at the end of the reaction there is no need for a supplementary separation operation or recycling of the catalyst. In heterogeneous process, the maximum yield may even be higher than 90% and the selectivity remains quite high as the reaction conditions are optimized. The substrates for obtaining CLAs are, in general, linoleic acid or alkyl linoleates and the catalysis is acidic. The yield and the selectivity depend on the strength and the type of acidic sites, as well as on the size distribution of the particles. Beside the existing catalytic methods, a photocatalytic process with UV and visible light irradiation with iodine promoter can be applied.Keywords: conjugated linoleic acid, CLA, homogeneous catalysis, heterogeneous catalysis, photocatalytic process Recently many new health-benefi t effects of the conjugated linoleic acids (CLAs) were discovered. They decrease the body fat quantity and increase muscle mass, possess antiinfl ammatory and cancer preventive effects, exert benefi cial effects on the skeletal system, act as immunostimulants, and decrease the probability of asthma occurrence (HA et al., 1989;PARIZA et al., 2001).Theoretically 56 isomers exist, however, few of them (cis(c)-9,trans(t)-11; t-10,c-12-and t-9,t-11 CLA) have been shown to have signifi cant biologic activity. The bioactivity of the c-9,t-11 CLA isomer (Fig. 1) was discovered two decades ago (HA et al., 1989) and this isomer is predominant in the natural products used as foods. The main foods rich in CLA are milk, dairy products, meat and fat of the ruminants, as this isomer is produced by the bacteria of the rumen microfl ora.Nowadays, CLAs are obtained for industrial purpose from vegetable oils that are processed at high temperature (PHILIPPAERTS et al., 2011). The basic method in the industrial approach is the isomerisation of linoleic acid (LA) with basic catalysis by which the amounts of the two formed isomers (c-9,t-11 and t-10,c-12 CLA) are almost equal, and the yield is quite high. This synthetic method cannot be applied for the direct transformation of vegetable oils into CLA-rich triacylglycerols, because ester bonds of triacylglycerols hydrolyze to free fatty acids (or salts) and glycerol.

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Catalytic Production of Conjugated Fatty Acids and Oils

et al. 2011

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The reactive double bonds in conjugated vegetable oils are of high interest in industry. Traditionally, conjugated vegetable oils are added to paints, varnishes, and inks to improve their drying properties, while recently there is an increased interest in their use in the production of bioplastics. Besides the industrial applications, also food manufactures are interested in conjugated vegetable oils due to their various positive health effects. While the isomer type is less important for their industrial purposes, the beneficial health effects are mainly associated with the c9,t11, t10,c12 and t9,t11 CLA isomers. The production of CLA-enriched oils as additives in functional foods thus requires a high CLA isomer selectivity. Currently, CLAs are produced by conjugation of oils high in linoleic acid, for example soybean and safflower oil, using homogeneous bases. Although high CLA productivities and very high isomer selectivities are obtained, this process faces many ecological drawbacks. Moreover, CLA-enriched oils can not be produced directly with the homogeneous bases. Literature reports describe many catalytic processes to conjugate linoleic acid, linoleic acid methyl ester, and vegetable oils rich in linoleic acid: biocatalysts, for example enzymes and cells; metal catalysts, for example homogeneous metal complexes and heterogeneous catalysts; and photocatalysts. This Review discusses state-of-the-art catalytic processes in comparison with some new catalytic production routes. For each category of catalytic process, the CLA productivities and the CLA isomer selectivity are compared. Heterogeneous catalysis seems the most attractive approach for CLA production due to its easy recovery process, provided that the competing hydrogenation reaction is limited and the CLA production rate competes with the current homogeneous base catalysis. The most important criteria to obtain high CLA productivity and isomer selectivity are (1) absence of a hydrogen donor, (2) absence of catalyst acidity, (3) high metal dispersion, and (4) highly accessible pore architecture.

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Photocatalytic Production and Processing of Conjugated Linoleic Acid-Rich Soy Oil

Cited by 32 publications

References 12 publications

Oxidative stabilization of conjugated linoleic acid by one-pot PEGylation

Oxidative stabilization of conjugated linoleic acid by one-pot PEGylation

Synthetic methods to obtain conjugated linoleic acids (CLAs) by catalysis – A review

Catalytic Production of Conjugated Fatty Acids and Oils

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