Oxidation kinetics of linoleic acid in the presence of saturated acyl <scp>l</scp>‐ascorbate

Watanabe, Yoshihisa; Ishido, Eiichiro; Xu, Fang; Adachi, Shuji; Matsuno, Ryuichi

doi:10.1007/s11746-005-1082-5

Cited by 31 publications

(23 citation statements)

References 20 publications

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“…In addition, when a comparison was done between the antioxidative abilities of ascorbic acid and stearoyl ascorbate in the matrix of wheat starch, they were not much different because their k and Y 0 values were close to each other. The result was in accordance with previous reports about the antioxidative ability of the stearoyl ascorbate in prevention of the oxidation of linoleic acid 4,6 .…”

Section: Resultssupporting

confidence: 93%

Antioxidative Properties of Stearoyl Ascorbate in a Food Matrix System

et al. 2016

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Section: Resultssupporting

confidence: 93%

Antioxidative Properties of Stearoyl Ascorbate in a Food Matrix System

et al. 2016

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“…The oxidation processes of linoleic acid with ascorbic acid or saturated acyl ascorbate in bulk system were analyzed by applying a kinetic equation of the autocatalytic type in order to evaluate the antioxidative property of acyl ascorbate (Watanabe et al, 2005). …”

Section: Suppressive Effect Of Acyl Ascorbate On Lipid Oxidation Inmentioning

confidence: 99%

“…(Fig. 1), and examined their properties as an antioxidant and emulsifier (Kuwabara et al, 2003a(Kuwabara et al, , 2003b(Kuwabara et al, , 2003c(Kuwabara et al, , 2005Watanabe et al, 1999Watanabe et al, , 2000aWatanabe et al, , 2001aWatanabe et al, , 2001bWatanabe et al, , 2002Watanabe et al, , 2003Watanabe et al, , 2004Watanabe et al, , 2005Watanabe et al, , 2008aWatanabe et al, , 2008bWatanabe et al, , 2009aWatanabe et al, , 2009bWatanabe et al, , 2010aWatanabe et al, , 2010bWatanabe et al, , 2012. In this context, first, the optimal conditions for enzymatic synthesis of acyl ascorbate using an immobilized lipase in a batch reaction system are found.…”

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confidence: 99%

Antioxidative Properties of Acyl Ascorbates on Lipid Oxidation in Bulk, Disperse and Microcapsule Systems

Watanabe¹

2015

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Acyl ascorbates were synthesized through the condensation of L-ascorbic acid with various fatty acids using an immobilized lipase in water-miscible organic solvent, and their antioxidative properties on lipid oxidation in bulk, disperse and microcapsule systems were examined. The optimal conditions for enzymatic synthesis in a batch reaction were determined and the continuous production of acyl ascorbate was conducted using a continuous stirred tank reactor and a plug flow reactor. The oxidative stability of lipid with saturated acyl ascorbate in bulk system increased with increasing acyl chain length, whereas that in the oil-in-water emulsion and microcapsule system depended on the acyl chain length and the concentration of the ascorbate.Keywords: acyl ascorbate, antioxidative emulsifier, continuous production, immobilized lipase, lipid oxidation IntroductionLipid, which is one of the main components in food, is susceptible to oxidation, resulting in the generation of undesirable flavors and toxic products such as hydroperoxides. Therefore, lipid oxidation has received much attention due to its involvement in food deterioration and the relevance of lipid peroxidation in vivo to membrane damage, cancer, heart disease and aging (Cosgrove et al., 1987). Lipid oxidation is a complicated process consisting of three steps: initiation, propagation and termination, and the reaction mechanism has been elucidated in detail (Endo, 1998;Frankel, 1991;Porter, 1986). The addition of an antioxidant is one way to suppress oxidation, as the antioxidant may lengthen the oxidation induction period at very low concentrations (Gwo et al., 1985).These are usually phenolic compounds such as tocopherols, butylated hydroxyanisole, butylated hydroxytoluene and propyl gallate, and are used to inhibit the chain reaction by scavenging free radicals generated from lipid molecules. l-Ascorbic acid is a water-soluble compound also known as vitamin C. It is used widely as an additive in foods and cosmetics owing to its strong reducing ability. Its lipophilic derivatives are acylated with a long-chain fatty acid, such as palmitic acid, and used in lipid-rich foods (Enomoto et al., 1991). These are mainly synthesized by a chemical procedure (Tanaka and Yamamoto, 1966), and are edible surfactants because each substrate is eaten daily. The antitumor activity and metastasis-inhibitory effects of 6-O-palmitoyl ascorbate have been reported (Miwa and Yamazaki, 1986;Nagao et al., 1996). In addition, the 6-O-and 2-O-monoesters of ascorbic acid with phosphate or fatty acid are known to have physiological activity equivalent to unmodified ascorbic acid (Inagaki and Kawaguchi, 1966). Acyl ascorbate consists of an ascorbyl moiety as the hydrophilic group and an acyl residue as the hydrophobic group, and therefore is a promising emulsifier with both reductivity and surface activity. However, palmitoyl and stearoyl ascorbates, which are commercially available, are highly water insoluble, preventing their use as an emulsifier in oil-in-water emulsions. (Fig...

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“…Thus, acyl ascorbate is expected to be a useful food additive. We also synthesized acyl ascorbates using an immobilized lipase in a batch or continuous reactor (Watanabe et al, 1999;, estimated their surfactant property (Watanabe et al, 2001, and demonstrated their antioxidative ability against an unsaturated fatty acid (Watanabe et al, 2005). Furthermore, we prepared microcapsules of linoleic acid with various saturated acyl ascorbates by spray-drying, and showed its antioxidative ability against encapsulated linoleic acid ( Watanabe et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

Suppressive Effect of Decanoyl Ascorbate on the Oxidation of Fish Oil Encapsulated with a Polysaccharide

Watanabe¹,

Xu²,

Adachi³

2009

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6-O-Decanoyl l-ascorbate, which was synthesized by the immobilized lipase-catalyzed condensation of decanoic and l-ascorbic acids in acetone, was used for the microencapsulation of fish oil with maltodextrin (MD), gum arabic (GA), or soluble soybean polysaccharide (SSPS). The oxidation processes at 65℃ and 12% relative humidity of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in the encapsulated fish oil were measured, and kinetically evaluated using the Weibull model. The oxidative stabilities of EPA and DHA in the microencapsulated fish oil were high, in the order of SSPS > GA > MD. Decanoyl ascorbate suppressed the oxidation of EPA and DHA in each system. It was indicated that the contribution of high concentrations of decanoyl ascorbate to the oxidative stability of the encapsulated fish oil is attributable to its antioxidative ability, which was due to the ascorbyl moiety in the decanoyl ascorbate molecule, but not to its emulsifying ability. In addition, it was found that the antioxidative effect of decanoyl ascorbate on the acids in the system sensitive to oxidation, such as in bulk and microencapsulated with MD, was high. Therefore, when using wall materials with a low suppressive ability for oxidation of the encapsulated oil, the application of decanoyl ascorbate would be effective.Keywords: decanoyl ascorbate, oxidation, fish oil, microencapsulation, polysaccharide *To whom correspondence should be addressed. E-mail: adachi@kais.kyoto-u.ac.jp IntroductionMicroencapsulation of lipids, as a core material, with a wall can improve the storage stability of lipids (especially oxidative stability), handling of the core material, and can provide the core material with additional functions (Matsuno and Adachi, 1993;Gibbs et al., 1999). Microencapsulation includes two steps: the first is the emulsification of the core material, such as a lipid, with a dense solution of a wall material, and the second is the drying of the emulsions. Saccharides with low and high molecular masses, proteins and other polymers have been used as wall materials. Spray-drying is the general technique for preparing microcapsules.l-Ascorbic acid is a water-soluble vitamin known as vitamin C. It is widely used as an additive in foods and cosmetics due to its strong reducing ability. The lipase-catalyzed synthesis of 6-O-monoacyl ascorbate, through the condensation of ascorbic acid and a fatty acid in an organic solvent, has been reported (Humeau et al., 1995;Yan et al., 1999). The enzymatic synthesis of acyl ascorbates would be more advantageous than a chemical method because of the simplicity of its reaction process and its high regioselectivity. Acyl ascorbate, which consists of ascorbic acid and a fatty acid as the hydrophilic antioxidant and lipophilic group, respectively, is an amphilic antioxidant. It has been reported that 6-Opalmitoyl ascorbate has antitumor activity and metastasisinhibitory effects (Miwa and Yamazaki, 1986;Nagao et al., 1996). Thus, acyl ascorbate is expected to be a useful food additive. We also syn...

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Oxidation kinetics of linoleic acid in the presence of saturated acyl l‐ascorbate

Cited by 31 publications

References 20 publications

Antioxidative Properties of Stearoyl Ascorbate in a Food Matrix System

Antioxidative Properties of Stearoyl Ascorbate in a Food Matrix System

Antioxidative Properties of Acyl Ascorbates on Lipid Oxidation in Bulk, Disperse and Microcapsule Systems

Suppressive Effect of Decanoyl Ascorbate on the Oxidation of Fish Oil Encapsulated with a Polysaccharide

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