Synthesis of lipophilic antioxidant tyrosol laurate using imidazolium ionic liquid [Bmim]HSO 4 as a catalyst
Tyrosol is a natural phenolic compound with potent antioxidant properties in the field of food manufacturing. However, the low lipophilicity of tyrosol limited its application. Therefore, the construction of tyrosol laurate (Tyr-L) could effectively overcome the limitations of tyrosol. In this work,...
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Veröffentlicht in: | Food chemistry 2024-01, Vol.442, p.138418 |
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description | Tyrosol is a natural phenolic compound with potent antioxidant properties in the field of food manufacturing. However, the low lipophilicity of tyrosol limited its application. Therefore, the construction of tyrosol laurate (Tyr-L) could effectively overcome the limitations of tyrosol. In this work, four ionic liquids (ILs) were applied for TYr-L preparation. Among them, the 1-butyl-3-methylimidazolium hydrogen sulfate ([Bmim]HSO
) showed the best catalytic performance. The maximum TYr-L yield was achieved (94.24 ± 1.23 %) under the optimal conditions (reaction temperature 119 °C, substrate ratio 1:6.7, IL dosage 9.2 %, and reaction time 12 h). The kinetic and thermodynamic parameters were also evaluated and it was found that Ea, ΔH, ΔS, and ΔG were 80.81 kJ·mol
, 77.63 kJ·mol
, -82.08 J·(mol·K)
, and 109.89 kJ·mol
, respectively. The acidic [Bmim]HSO
demonstrated excellent reusability and stability, even after 6 cycles. Furthermore, TYr-L showed superior ABTS radical scavenging ability, which could be further applied in various industrial processes. |
doi_str_mv | 10.1016/j.foodchem.2024.138418 |
format | Article |
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) showed the best catalytic performance. The maximum TYr-L yield was achieved (94.24 ± 1.23 %) under the optimal conditions (reaction temperature 119 °C, substrate ratio 1:6.7, IL dosage 9.2 %, and reaction time 12 h). The kinetic and thermodynamic parameters were also evaluated and it was found that Ea, ΔH, ΔS, and ΔG were 80.81 kJ·mol
, 77.63 kJ·mol
, -82.08 J·(mol·K)
, and 109.89 kJ·mol
, respectively. The acidic [Bmim]HSO
demonstrated excellent reusability and stability, even after 6 cycles. Furthermore, TYr-L showed superior ABTS radical scavenging ability, which could be further applied in various industrial processes.</description><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2024.138418</identifier><identifier>PMID: 38237293</identifier><language>eng</language><publisher>England</publisher><ispartof>Food chemistry, 2024-01, Vol.442, p.138418</ispartof><rights>Copyright © 2024 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38237293$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Yimei</creatorcontrib><creatorcontrib>Zhang, Yaoyao</creatorcontrib><creatorcontrib>Qiao, Xing</creatorcontrib><creatorcontrib>Sun, Shangde</creatorcontrib><title>Synthesis of lipophilic antioxidant tyrosol laurate using imidazolium ionic liquid [Bmim]HSO 4 as a catalyst</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><description>Tyrosol is a natural phenolic compound with potent antioxidant properties in the field of food manufacturing. However, the low lipophilicity of tyrosol limited its application. Therefore, the construction of tyrosol laurate (Tyr-L) could effectively overcome the limitations of tyrosol. In this work, four ionic liquids (ILs) were applied for TYr-L preparation. Among them, the 1-butyl-3-methylimidazolium hydrogen sulfate ([Bmim]HSO
) showed the best catalytic performance. The maximum TYr-L yield was achieved (94.24 ± 1.23 %) under the optimal conditions (reaction temperature 119 °C, substrate ratio 1:6.7, IL dosage 9.2 %, and reaction time 12 h). The kinetic and thermodynamic parameters were also evaluated and it was found that Ea, ΔH, ΔS, and ΔG were 80.81 kJ·mol
, 77.63 kJ·mol
, -82.08 J·(mol·K)
, and 109.89 kJ·mol
, respectively. The acidic [Bmim]HSO
demonstrated excellent reusability and stability, even after 6 cycles. Furthermore, TYr-L showed superior ABTS radical scavenging ability, which could be further applied in various industrial processes.</description><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFjr1OwzAURq1KiBboK1T3BRr8ExGzgkDdGNqtqqpL4pBbXcchtiXC05MBZqYzfOeTjhAbJQsl1cP9pWhDaOrO-UJLXRbK2FLZhVgpW5ltJSu9FDcxXqSUWip7LZbGalPpR7MSvJ_61LlIEUILTEMYOmKqAftE4YuamZCmMcTAwJhHTA5ypP4DyM_rd2DKHij084fpM1MDxydP_rTbv0EJGAGhxoQ8xXQnrlrk6Na_vBWb15fD82475HfvmvMwksdxOv_lmX-FH64pTxk</recordid><startdate>20240113</startdate><enddate>20240113</enddate><creator>Wang, Yimei</creator><creator>Zhang, Yaoyao</creator><creator>Qiao, Xing</creator><creator>Sun, Shangde</creator><scope>NPM</scope></search><sort><creationdate>20240113</creationdate><title>Synthesis of lipophilic antioxidant tyrosol laurate using imidazolium ionic liquid [Bmim]HSO 4 as a catalyst</title><author>Wang, Yimei ; Zhang, Yaoyao ; Qiao, Xing ; Sun, Shangde</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmed_primary_382372933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Yimei</creatorcontrib><creatorcontrib>Zhang, Yaoyao</creatorcontrib><creatorcontrib>Qiao, Xing</creatorcontrib><creatorcontrib>Sun, Shangde</creatorcontrib><collection>PubMed</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Yimei</au><au>Zhang, Yaoyao</au><au>Qiao, Xing</au><au>Sun, Shangde</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of lipophilic antioxidant tyrosol laurate using imidazolium ionic liquid [Bmim]HSO 4 as a catalyst</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2024-01-13</date><risdate>2024</risdate><volume>442</volume><spage>138418</spage><pages>138418-</pages><eissn>1873-7072</eissn><abstract>Tyrosol is a natural phenolic compound with potent antioxidant properties in the field of food manufacturing. However, the low lipophilicity of tyrosol limited its application. Therefore, the construction of tyrosol laurate (Tyr-L) could effectively overcome the limitations of tyrosol. In this work, four ionic liquids (ILs) were applied for TYr-L preparation. Among them, the 1-butyl-3-methylimidazolium hydrogen sulfate ([Bmim]HSO
) showed the best catalytic performance. The maximum TYr-L yield was achieved (94.24 ± 1.23 %) under the optimal conditions (reaction temperature 119 °C, substrate ratio 1:6.7, IL dosage 9.2 %, and reaction time 12 h). The kinetic and thermodynamic parameters were also evaluated and it was found that Ea, ΔH, ΔS, and ΔG were 80.81 kJ·mol
, 77.63 kJ·mol
, -82.08 J·(mol·K)
, and 109.89 kJ·mol
, respectively. The acidic [Bmim]HSO
demonstrated excellent reusability and stability, even after 6 cycles. Furthermore, TYr-L showed superior ABTS radical scavenging ability, which could be further applied in various industrial processes.</abstract><cop>England</cop><pmid>38237293</pmid><doi>10.1016/j.foodchem.2024.138418</doi></addata></record> |
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title | Synthesis of lipophilic antioxidant tyrosol laurate using imidazolium ionic liquid [Bmim]HSO 4 as a catalyst |
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