Surface-Active Properties of Lipophilic Antioxidants Tyrosol and Hydroxytyrosol Fatty Acid Esters: A Potential Explanation for the Nonlinear Hypothesis of the Antioxidant Activity in Oil-in-Water Emulsions

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 13; pp. 8021 - 8026
• Main Authors: Lucas, Ricardo, Comelles, Francisco, Alcántara, David, Maldonado, Olivia S, Curcuroze, Melanie, Parra, Jose L, Morales, Juan C
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 14-07-2010
• Subjects: antioxidant activity; antioxidants; Antioxidants - chemistry; Biological and medical sciences; emulsions; Emulsions - chemistry; Esters - chemistry; fatty acid esters; fish oils; Food Chemistry/Biochemistry; Food industries; Fundamental and applied biological sciences. Psychology; hydrophobicity; hydroxytyrosol; oil-water interface; Oils - chemistry; Phenylethyl Alcohol - analogs & derivatives; Phenylethyl Alcohol - chemistry; surface active properties; Surface Properties; Surface-Active Agents - chemistry; surfactants; tyrosol; surfactants; antioxidants; emulsions; surface activity; hydroxytyrosol; Tyrosol; lipophilic; Water oil emulsion; Oil water emulsion; Fatty ester; Lipids; Surfactant; Antioxidant; Fatty acids; Surface properties; Surface activity
• DOI: 10.1021/jf1009928
• EISSN: 1520-5118
• ISSN: 0021-8561

Our group has recently observed a nonlinear tendency in antioxidant capacity of different hydroxytyrosol fatty acid esters in fish oil-in-water emulsions, where a maximum of antioxidant efficiency appeared for hydroxytyrosol octanoate. These results appear to disagree with the antioxidant polar paradox. Because the physical location of the antioxidants in an oil−water interface has been postulated as an important factor in explaining this behavior, we have prepared a series of tyrosol and hydroxytyrosol fatty acid esters with different chain length and studied their surface-active properties in water, because these physicochemical parameters could be directly related to the preferential placement at the interface. We have found that tyrosol and hydroxytyrosol fatty acid esters are relevant surfactants when the right hydrophilic−lipophilic balance (HLB) is attained and, in some cases, as efficient as emulsifiers commonly used in industry, such as Brij 30 or Tween 20. Moreover, a nonlinear dependency of surfactant effectiveness is observed with the increase in chain length of the lipophilic antioxidants. This tendency seems to fit quite well with the reported antioxidant activity in emulsions, and the best antioxidant of the series (hydroxytyrosol octanoate) is also a very effective surfactant. This potential explanation of the nonlinear hypothesis will help in the rational design of antioxidants used in oil-in-water emulsions.