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Abstract
Low-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary supplements and stabilizers of foods and cosmetics in non-aqueous media are limited for the hydrophilic character. With the aim to overcome this limitation, the paper describes a simple and low-cost procedure for the synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. The reactions were carried out under mild and green chemistry conditions, at room temperature, solubilizing the phenolic compounds in dimethyl carbonate, an eco-friendly solvent, and adding a little excess of the appropriate C2–C18 acyl chloride. The final products were isolated in good yields. Finally, according to the “circular economy” strategy, the procedure was applied to hydroxytyrosol-enriched extracts obtained by Olea europaea by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required.
Highlights
Tyrosol 1 (4-hydroxyphenethyl alcohol), homovanillyl alcohol 2 (3-hydroxy-4-methoxyphenethyl alcohol) and hydroxytyrosol 3 (3,4-dihydroxyphenethyl alcohol) are low-molecular weight phenols (Figure 1) found mainly in olive mill wastewater, the by-products of the olive oil production [1,2], from which they can be extracted using environmentally and economically sustainable technologies [3,4]and reused according to the circular economy strategy [5].They are valuable compounds, displaying a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity [6,7]
This study has demonstrated that lipophilic tyrosol esters were well absorbed by the intestinal lumen, confirming the relevant role of the alkyl chain [43]
The procedure was applied to hydroxytyrosol-enriched extracts obtained by Olea europaea by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required
Summary
Tyrosol 1 (4-hydroxyphenethyl alcohol), homovanillyl alcohol 2 (3-hydroxy-4-methoxyphenethyl alcohol) and hydroxytyrosol 3 (3,4-dihydroxyphenethyl alcohol) are low-molecular weight phenols (Figure 1) found mainly in olive mill wastewater, the by-products of the olive oil production [1,2], from which they can be extracted using environmentally and economically sustainable technologies [3,4]and reused according to the circular economy strategy [5].They are valuable compounds, displaying a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity [6,7]. Tyrosol 1 suppresses allergic inflammatory disorders [8], and prevents apoptosis in irradiated keratinocytes [9] It is Antioxidants 2019, 8, 174; doi:10.3390/antiox8060174 www.mdpi.com/journal/antioxidants. In accordance with the theoretical predictions on ortho-diphenols [14], hydroxytyrosol 3 is the most powerful antioxidant found in olive oil by-products. It increases high-density lipoprotein (HDL)-cholesterol, inhibits inflammation, improves endothelial function, decreases tumor growth and metastasis, and protects the central nervous system [15,16,17,18].
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