Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents

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Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents. / Yang, Zhiyong; Guo, Zheng; Xu, Xuebing.

I: Food Chemistry, Bind 132, Nr. 3, 2012, s. 1311-1315.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avisTidsskriftartikelForskningpeer review

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Yang, Zhiyong ; Guo, Zheng ; Xu, Xuebing. / Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents. I: Food Chemistry. 2012 ; Bind 132, Nr. 3. s. 1311-1315.

Bibtex

@article{fc0340d1912b4e71ad7b6179922c2b4e,
title = "Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents",
abstract = "In this study, we investigated and optimized the synthesis of lipophilized esters between selected phenolic acids and fatty alcohols in a binary solvent system, which is composed of hexane and butanone. The effect of different proportion of hexane and butanone was firstly studied by changing the volume ratio from 85:15 to 45:55. It was found that the conversion strongly depended on the proportion of hexane and butanone in the reaction system. Following the effect of carbons of fatty alcohol chains on estererification performance with dihydrocaffeic acid (DHCA) was evaluated by choosing different fatty alcohols from C4 to C18. The conversion of DHCA was significantly affected by the carbons of fatty alcohol chains. Roughly 95{\%} conversion was achieved within 3 days when DHCA was esterified with hexanol (C6), while only 56{\%} and 44{\%} conversion were achieved when esterified with 1-butanol and octadecenol respectively. However, the conversions of ferulic and caffeic acids under the same conditions were much lower than DHCA. The optimal mixture ratio of hexane to butanone was found to be 65:35. Using octanol and DHCA as model, the reaction parameters, such as temperature, enzyme load, reaction time and substrate molar ratio, were optimized with response surface modelling (RSM). The optimum conditions are finalized as: temperature 60 oC, reaction time 7 days, enzyme load 100 mg, and substrate molar ratio 4.34 (octanol/DHCA).",
keywords = "Phenolic acids • Fatty alcohols • Novozym 435 • RSM",
author = "Zhiyong Yang and Zheng Guo and Xuebing Xu",
year = "2012",
doi = "10.1016/j.foodchem.2011.11.110",
language = "English",
volume = "132",
pages = "1311--1315",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier BV",
number = "3",

}

RIS

TY - JOUR

T1 - Enzymatic Lipophilization of Phenolic Acids through Esterification with Fatty Alcohols in Organic Solvents

AU - Yang, Zhiyong

AU - Guo, Zheng

AU - Xu, Xuebing

PY - 2012

Y1 - 2012

N2 - In this study, we investigated and optimized the synthesis of lipophilized esters between selected phenolic acids and fatty alcohols in a binary solvent system, which is composed of hexane and butanone. The effect of different proportion of hexane and butanone was firstly studied by changing the volume ratio from 85:15 to 45:55. It was found that the conversion strongly depended on the proportion of hexane and butanone in the reaction system. Following the effect of carbons of fatty alcohol chains on estererification performance with dihydrocaffeic acid (DHCA) was evaluated by choosing different fatty alcohols from C4 to C18. The conversion of DHCA was significantly affected by the carbons of fatty alcohol chains. Roughly 95% conversion was achieved within 3 days when DHCA was esterified with hexanol (C6), while only 56% and 44% conversion were achieved when esterified with 1-butanol and octadecenol respectively. However, the conversions of ferulic and caffeic acids under the same conditions were much lower than DHCA. The optimal mixture ratio of hexane to butanone was found to be 65:35. Using octanol and DHCA as model, the reaction parameters, such as temperature, enzyme load, reaction time and substrate molar ratio, were optimized with response surface modelling (RSM). The optimum conditions are finalized as: temperature 60 oC, reaction time 7 days, enzyme load 100 mg, and substrate molar ratio 4.34 (octanol/DHCA).

AB - In this study, we investigated and optimized the synthesis of lipophilized esters between selected phenolic acids and fatty alcohols in a binary solvent system, which is composed of hexane and butanone. The effect of different proportion of hexane and butanone was firstly studied by changing the volume ratio from 85:15 to 45:55. It was found that the conversion strongly depended on the proportion of hexane and butanone in the reaction system. Following the effect of carbons of fatty alcohol chains on estererification performance with dihydrocaffeic acid (DHCA) was evaluated by choosing different fatty alcohols from C4 to C18. The conversion of DHCA was significantly affected by the carbons of fatty alcohol chains. Roughly 95% conversion was achieved within 3 days when DHCA was esterified with hexanol (C6), while only 56% and 44% conversion were achieved when esterified with 1-butanol and octadecenol respectively. However, the conversions of ferulic and caffeic acids under the same conditions were much lower than DHCA. The optimal mixture ratio of hexane to butanone was found to be 65:35. Using octanol and DHCA as model, the reaction parameters, such as temperature, enzyme load, reaction time and substrate molar ratio, were optimized with response surface modelling (RSM). The optimum conditions are finalized as: temperature 60 oC, reaction time 7 days, enzyme load 100 mg, and substrate molar ratio 4.34 (octanol/DHCA).

KW - Phenolic acids • Fatty alcohols • Novozym 435 • RSM

U2 - 10.1016/j.foodchem.2011.11.110

DO - 10.1016/j.foodchem.2011.11.110

M3 - Journal article

C2 - 29243616

VL - 132

SP - 1311

EP - 1315

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

IS - 3

ER -