Conjugated Linoleic Acid Production by Alkali Isomerization of Linoleic Acid from Idesia polycarpa Maxim. var. vestita Diels Oil

Wang, Hongtao; Li, X.; Du, K.F.; Yao, S.; Song, H.

doi:10.14233/ajchem.2013.13740

Cited by 9 publications

(12 citation statements)

References 18 publications

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“…The reaction mixture consisted with m(KOH): m(LNA): V(EG) = 1:4.8:7.7. The microwave process and ultrasound process remarkably improved the over consumption of KOH and the solvent, comparing to the optium condition for current process: a ratio of 1.0:0.4:5.2 (w/w/w) of linoleic acid/KOH/ethylene glycol, 188.3 C and 4.4 hours (Wang et al, 2013).…”

Section: Introductionmentioning

confidence: 82%

“…Except the CLA yield, the selectivity, that is, the content of desirable CLA isomers (cis-9, trans11 and trans-10, cis-12) was also the target. The current major applied processes include alkali isomerization (Berdeaux et al, 1998;Da Porto et al, 2012;Goli et al, 2008;Kim et al, 2000;Liu et al, 2019;Ma et al, 1999;Nagao et al, 2003;Wang et al, 2013;Yang and Liu, 2004), which is the current most applied industrial process, and catalytic conjugation catalyzed by VIII Group metals (Bauer et al, 2009;Bernas and Murzin, 2003;Kreich and Supporting information Additional supporting information may be found online in the Supporting Information section at the end of the article. Claus, 2005;Larock et al, 2001) (Liu et al, 2019), as well as enzymatic conversion of LNA (Lin, 2000;Zhang et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

“…Among them, alkali isomerization of LNA is the most popular commercial process because its green, simple and economic characters, and its high yield (Alasalvar et al, 2019). The current alkali isomerization of LNA is a one-pot process catalyzed with KOH or NaOH in polyols as like ethylene glycol (EG) (Blasi et al, 2008;Nagao et al, 2003;Wang et al, 2013), which contains isomerization (i) as the target reaction, along with saponification (s) and esterification (e) as side reactions:…”

Section: Introductionmentioning

confidence: 99%

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A Soap‐Free Strategy for One‐Pot Synthesizing Conjugated Linoleic Acid: Alkali Isomerization of Linoleic Acid through Preferential Esterification Pathway

San

Fan

Fang

et al. 2020

J Americ Oil Chem Soc

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Conjugated linoleic acid (CLA) exhibits beneficial biological activities but possesses poor natural abundance, which is usually obtained by alkali isomerization of linoleic acid (LNA). The one‐pot alkali isomerization consists two reactions, firstly saponifying LNA and then isomerizing linoleate. This current process has been limited by two drawbacks, the overconsumption of both alkali and solvent, as well as the weak mass/heat transfer of the viscous paste of reaction mixture that limits the synthesis scale. The present study alternated the reaction pathway with a soap‐free preferential esterification pathway, that is, firstly employing slight NaOH to induce the esterification of LNA and diol (the reaction solvent), then conducting alkali isomerization of the intermediate alkyl linoleate instead of sodium linoleate. In this developed one‐pot procedure, a CLA yield of 90% and the selectivity of the desired isomers (“c9, t11” and “t10, c12” CLA) of 82.4% were obtained; and it reduced the consumption of NaOH and the solvent by 60% and 25% comparing to the current soap pathway, respectively; Yet the result is comparative to that obtained with assistant of microwave/ultrasound in even longer reaction time. In this way, the two drawbacks can be overcome and the green characteristics of the current process was well kept.

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Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Soap‐Free Strategy for One‐Pot Synthesizing Conjugated Linoleic Acid: Alkali Isomerization of Linoleic Acid through Preferential Esterification Pathway

San

Fan

Fang

et al. 2020

J Americ Oil Chem Soc

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“…In the traditional alkali isomerization process, the main bases used include inorganic bases NaOH and KOH, and organic bases sodium ethoxide, sodium methoxide, tetraethyl ammonium hydroxide, etc. [28][29][30]. The essence of alkali isomerization involves the process of a carbon anion, and its reaction mechanism features the base grabbing the protons of the allylic hydrogen of LA and its ester to generate a carbon anion, followed by the carbon anion rearranging to form a stable conjugated structure, thereby achieving a conjugated product [31,32].…”

Section: The Role Of Iodine In Diels-alder Reactionmentioning

confidence: 99%

The Role of Iodine Catalyst in the Synthesis of 22-Carbon Tricarboxylic Acid and Its Ester: A Case Study

et al. 2019

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Here, 22-carbon tricarboxylic acid (C22TA) and its ester (C22TAE) were prepared via the Diels–Alder reaction of polyunsaturated fatty acids (PUFAs) and their esters (PUFAEs) as dienes with fumaric acid (FA) and dimethyl fumarate (DF) as dienophiles, respectively. The role of an iodine catalyst for the synthesis of C22TA and C22TAE in the Diels–Alder type reaction was investigated using a spectroscopic approach. The chemical structures of the products were characterized using proton nuclear magnetic resonance (1H-NMR) and electrospray ionization mass spectrometry (ESI-MS) analysis. Results showed that nonconjugated dienes can react with dienophiles through a Diels–Alder reaction with an iodine catalyst, and that iodine transformed the nonconjugated double bonds of dienes into conjugated double bonds via a radical process. DF was more favorable for the Diels–Alder reaction than FA. This was mainly because the dienophile DF contained an electron-withdrawing substituent, which reduced the highest and lowest occupied molecular orbital (HOMO–LUMO) energy gap and accelerated the Diels–Alder reaction. By transforming nonconjugated double bonds into conjugated double bonds, iodine as a Lewis acid increased the electron-withdrawing effect of the carbonyl group on the carbon–carbon double bond and reduced the energy difference between the HOMO of diene and the LUMO of dienophile, thus facilitating the Diels–Alder reaction.

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“…vestita Diels) is widely distributed in south China, and it is known for its high-quality edible oil, which has a high content of conjugated linoleic acid (CLA). Moreover, the application of Idesia polycarpa oil in biodiesel production has been demonstrated (1, 2). There have been several studies on Idesia polycarpa fruit, including functional research on Idesia polycarpa fruit extraction and studies on the improvement of the extraction process.…”

Section: Introductionmentioning

confidence: 99%

Effects of Fermented Idesia Polycarpa Residues supplementation on laying performance of Laying Quails

Liu

Shu

et al. 2018

Preprint

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L. Tang). Tel: (028) 8541 7281 Abbreviated Title：A new feeding raw material applying on laying quails.ABSTRACT: Idesia polycarpa Maxim. var. vestita Diels (Idesia polycarpa), which is 1 widely distributed in south China, is still underexplored. This study applied Idesia 2 polycarpa defatted fruit (IPF) and Candida utilis to the feed of laying quails using 3 solid-state fermentation. In comparison to the standard diet group, birds fed with 4 mixture of IPF and candida utilis (MIC) showed better production capacity, and the 5 ML group (1% MIC added) achieved the greatest egg mass (9.77 on average; P<0.01) 6 and laying rate (87.7% on average; P<0.01). Compared to the standard diet group, the 7 cholesterol content was lower in both the ML (1% MIC addition groups) and IL (1% 8 IPF addition groups), and 5% MIC added group had higher n-3 polyunsaturated fatty 9 acid content. Furthermore, birds given the MIC dietary supplement showed a thicker 10 jejunum wall than the standard diet group. In addition, the related mRNA expression 11 of SRBEP-1, SREBP-2, ATGL, APOVLDL-II which are involved in the fatty acid and 12 cholesterol biosynthesis suggested that the addition of candida utilis could effectively 13 improve the production capacity of laying quails while decrease the negative effects 14 of IPF. This work also demonstrates how MIC can be applied to improve the 15 production of laying quails. 16 IntroductionIdesia polycarpa (Idesia polycarpa Maxim. var. vestita Diels) is widely 19 distributed in south China, and it is known for its high-quality edible oil, which has a 20 high content of conjugated linoleic acid (CLA). Moreover, the application of Idesia 21 polycarpa oil in biodiesel production has been demonstrated (1, 2). There have been 22 several studies on Idesia polycarpa fruit, including functional research on Idesia 23 polycarpa fruit extraction and studies on the improvement of the extraction process. 24The remarkable antioxidant qualities, anti-skin-aging ability (3) and anti-adipogenic 25 ability (4) of Idesia polycarpa extracts have been demonstrated, and an optimized 26 extraction method has also been established (5). However, reports on the application 27 of Idesia polycarpa fruit for the other purposes are still limited. In this study, we are 28 tried to apply Idesia polycarpa defatted fruit (IPF) in laying quail's breeding, and for 29 purpose of effective use, solid-fermentation was selected. 30From a historical perspective, phytogenic materials fermented with specific 31 microbe are recognized to benefit farm animals and are described as far back as the 32 beginning of the last century (6, 7). Even now, fermentation is still gaining interest 33 because of its important role in the production of quality feed and the utilization of 34 unexploited feed materials (8, 9). Moreover, based on existing studies, the addition of 35 probiotic could effectively decrease anti-nutritive factors and allergenic proteins (10, 36 11). Furthermore, fermented feed represents a plausible alternative to traditional 37 anti...

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Conjugated Linoleic Acid Production by Alkali Isomerization of Linoleic Acid from Idesia polycarpa Maxim. var. vestita Diels Oil

Cited by 9 publications

References 18 publications

A Soap‐Free Strategy for One‐Pot Synthesizing Conjugated Linoleic Acid: Alkali Isomerization of Linoleic Acid through Preferential Esterification Pathway

A Soap‐Free Strategy for One‐Pot Synthesizing Conjugated Linoleic Acid: Alkali Isomerization of Linoleic Acid through Preferential Esterification Pathway

The Role of Iodine Catalyst in the Synthesis of 22-Carbon Tricarboxylic Acid and Its Ester: A Case Study

Effects of Fermented Idesia Polycarpa Residues supplementation on laying performance of Laying Quails

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