Production of benzyl cinnamate by a low-cost immobilized lipase and evaluation of its antioxidant activity and toxicity

Piazza, Suelen P.; Puton, Bruna Maria Saorin; Dallago, Rogério Marcos; Oliveira, Débora de; Cansian, Rogério Luís; Mignoni, Marcelo Luís; Paroul, Natália

doi:10.1016/j.btre.2021.e00586

Cited by 4 publications

(4 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A latest publication reported that benzyl cinnamate was successfully synthesized using immobilized lipase NS88011 as biocatalyst and the highest yield of 97.6% was achieved at 59°C after 32 hours of reaction. 7 Although the yield of benzyl cinnamate in this study was slightly lower (1-3%) than those of previous studies, 10,21,22 low price of solid acid and short reaction time suggested solid acid HND-26 as an effective catalyst for the synthesis of benzyl cinnamate.…”

Section: Optimization Of Hnd-26-catalysed Synthesis Of Benzyl Cinnama...contrasting

confidence: 60%

“…A yield of 95.1% was achieved under the optimal conditions for the synthesis of benzyl cinnamate (reaction temperature 58°C, reaction time 25 hours and catalyst loading 13.8%), which was close to predicted value (94.8%), indicating that adequacy of the model is satisfactory. A latest publication reported that benzyl cinnamate was successfully synthesized using immobilized lipase NS88011 as biocatalyst and the highest yield of 97.6% was achieved at 59°C after 32 hours of reaction 7 . Although the yield of benzyl cinnamate in this study was slightly lower (1–3%) than those of previous studies, 10,21,22 low price of solid acid and short reaction time suggested solid acid HND‐26 as an effective catalyst for the synthesis of benzyl cinnamate.…”

Section: Resultsmentioning

confidence: 53%

“…[3][4][5] Among the cinnamic acid ester derivatives, benzyl cinnamate has been approved as a flavour agent by the US Food and Drug Administration 6 and have many applications in cosmetic and pharmaceutical industry because of its lower melting point (34.5°C) and lipophilicity. 3,7 Therefore, the low-cost and high-efficiency synthesis of benzyl cinnamate have been attracting increasing attention.…”

Section: Introductionmentioning

confidence: 99%

“…Ester modifications in the cinnamic acid molecule can endow it more potent biological activities such as antimicrobial and antitumor activity on melanoma and colon cancer 3–5 . Among the cinnamic acid ester derivatives, benzyl cinnamate has been approved as a flavour agent by the US Food and Drug Administration 6 and have many applications in cosmetic and pharmaceutical industry because of its lower melting point (34.5°C) and lipophilicity 3,7 . Therefore, the low‐cost and high‐efficiency synthesis of benzyl cinnamate have been attracting increasing attention.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Solid acid HND‐26 as a novel catalyst: Green and sustainable alternatives towards synthesis of benzyl cinnamate

Qian

Zhang

Tian

et al. 2022

Flavour & Fragrance J

View full text Add to dashboard Cite

High melting point and hydrophilicity of phenolic acids limit their application in lipophilic environments such as fat‐containing cosmetics and foods. The esterification of the carboxyl group with fatty and aromatic alcohols has been considered as an effective way to enhance the lipophilicity of phenolic acids and thus enable better location of the antioxidant moiety into membranes and interface of emulsion systems where oxidation is expected to occur. Therefore, this study aims to evaluate the catalytic properties of six solid acids (HND‐34, HND‐6, HND‐580, HND‐2, HND‐8 and HND‐26) for the synthesis of benzyl cinnamate. Results show that HND‐26 was the most effective solid acid to catalyse the esterification reaction of cinnamic acid with benzyl alcohol. By using response surface methodology, the influence of key experimental factors on the yield of benzyl cinnamate was investigated and the maximum yield (95.1%) was obtained under the optimized conditions (58°C, cinnamic acid/benzyl alcohol 1:20 (mol/mol), HND‐26 loading 13.8% and 25 hours). The activation energy of cinnamic acid conversion with benzyl alcohol was 30.3 kJ/mol. Obtained results provide a cost‐effective way of green synthesis of benzyl cinnamate and highlights the potential applications of HND‐26 as an efficient catalyst for the production of phenolic acid esters with broad usage in cosmetic industry.

show abstract