LWT-FOOD SCIENCE AND TECHNOLOGY
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2021
·
IF 4.952
Zhe Dong,Yu Zhao,Jinliang Chen,Ming Chang,Xiaosan Wang,Qingzhe Jin,Xingguo Wang
Borneol esters have attracted increasing interest due to their potential application in the food industry. In this study, the extraction of d -borneol from Cinnamomum camphora chvar. borneol seed was carried out via steam distillation to gain highly purified d -borneol (99.66%). The lipase-catalyzed lipophilization of extracted d -borneol with oleic acid was performed in a solvent-free system. The influences of lipase type, substrate molar ratio, lipase loading, reaction temperature and reaction time on d -bornyl oleate yield were evaluated. Among four kinds of commercial lipases screened for their esterification efficiency, CRL (lipase from Candida rugose ) displayed the highest catalytic activity in the synthesis of d -bornyl oleate. The yield of more than 95% was obtained under the optimal conditions: substrate molar ratio 1:2 ( d -borneol/oleic acid), lipase loading 8%, reaction temperature 45 °C, reaction time 48 h. The structural identification of d -borneol and product d -bornyl oleate was performed by gas chromatography mass spectrometry (GC-MS) and proton nuclear magnetic resonance spectroscopy ( 1 H NMR). The results showed that the product was confirmed to be d -bornyl oleate and the purity of which was 97.51%. This study will pave the way for d -borneol and its esters application in food industry.
研究领域:
食品科学
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生物化学
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产品关联
DOI
高影响因子
BioDesign Research
·
2025
·
IF 4.7
Qian Li,Mingpeng Li,Ling Wang,Xiaojuan Yu,Yuling Zhou,Chenghua Gao,Aitao Li
Clascoterone (cortexolone 17α-propionate), a novel therapeutic agent for acne, provides enhanced safety and efficacy over conventional therapies. However, the traditional synthesis of clascoterone, especially the final step, suffers from the use of hazardous and excessive organic solvents, along with suboptimal yields due to side reactions and incomplete conversion, which poses environmental and economic challenges. In this study, we developed a regioselective solvent-free alcoholysis method with the commercially available immobilized lipase Novozyme 435 as a catalyst and isopropanol (IPA) as an alcohol donor, achieving a conversion rate of over 98.0% with 20 g/L substrate. Furthermore, we implemented a continuous flow microreactor process that increased the conversion rate to 100% with 4 g/L substrate, demonstrating scalability for industrial manufacturing.
研究领域:
有机合成
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生物催化
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药物化学
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化学工程
✓ 已验证
DOI
PubMed
高影响因子
Catalysts
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2025
·Vol. 15
·期 5
·482
·
IF 4
Yongqi Zeng,Yong Tang,Minglu Xu,Dantong Wang,Zhi Wang,Yin Gao,Lei Wang
Tetrasubstituted furans and their derivatives represent a versatile class of important heterocyclic frameworks widely distributed in natural products. These scaffolds also demonstrate significant potential in pharmaceutical chemistry, materials science, and organic synthesis methodologies. In this study, we successfully established a synergistic catalytic system utilizing benzoylacetonitriles, aldehydes, and benzoyl chlorides as substrates, facilitated by tributylphosphine and immobilized lipase (Novozym 435), to achieve efficient synthesis of cyano-containing tetrasubstituted furans. Under optimized conditions, we obtained a series of target products exhibiting exceptional substrate tolerance with good to excellent isolated yields ranging from 80% to 94%. Additionally, we proposed a reasonable reaction mechanism and verified it through controlled experiments. This methodology not only expands the synthetic utility of lipase in non-natural transformations but also establishes a paradigm of green chemistry for the construction of tetrasubstituted furans.
研究领域:
有机化学
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生物催化
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药物化学
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DOI
高影响因子
RSC Advances
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2017
·Vol. 7
·期 3
·1504-1512
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IF 3.108
Guiying Wu,Xin He,Yunjun Yan
Polyols are one of the dominant reactants in polyurethane (PU) synthesis. However, polyols from Sapium sebiferum oil prepared by epoxidation–hydroxylation have an inferiority of secondary alcohol groups and large non-functional branches. Their lower reactivity, which in turn limits the properties of the generated PU. In this study, the optimal reaction conditions for the synthesis of polyols with primary alcohol groups by lipase hydrolysis have been investigated by single factorial experiments and response surface methodology. The optimized conditions for lipase hydrolysis were identified as a molar ratio of 2.2 : 1, a reaction time of 11.2 h, and a temperature of 47.2 °C. The highest hydroxyl value of the obtained polyol with primary alcohol groups reached 211 mg KOH per g. Furthermore, a novel PU was successfully synthesized from the synthetic polyol and isophorone diisocyanate by an in situ polymerization method. The generated PU showed a glass transition temperature of 60.6 °C, an initial decomposition temperature of 307.2 °C, a tensile strength of 12.5 MPa, and a Young's modulus of 22.3 MPa. These good thermal and mechanical properties of the PU prepared from the modified polyol by lipase hydrolysis can be attributed to its greater number of chemical interactions and cross-linked networks.
研究领域:
生物化学
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材料科学
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产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Shuo Zou,Zhen Zhang,Yee-Ying Lee,Hongzeng Ai,Yufei Zhang,Yong Wang
Acylglycerols are widely used in the food industry due to their antimicrobial, emulsifying and nutritional properties. This study investigated the key reaction parameters, mass transfer mechanisms, and kinetic features of lipase-catalyzed esterification in a solvent-free system. Taguchi method was further employed to explore the relationship between “reaction parameter - yield composition”. The results revealed that the maximum selectivity were achieved fror MAG (57.72 %), DAG (82.67 %) and TAG (79.29 %) under different enzymatic conditions. Fatty acid-to-glycerol molar ratio had the greatest impact on DAG selectivity, contributing 38.08 % of total impact level. Mass transfer analysis showed that external mass transfer limitation could be effectively overcome at stirring speeds above 600 rpm. Kinetic analysis confirmed that the reaction followed the Ping-Pong Bi Bi mechanism with alcohol and acid inhibition (SSE = 0.000643). This work provided a theoretical basis for developing more efficient and selective catalytic processes, aiding in quality control, reactor design, and industrial scale-up.
研究领域:
食品科学
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生物化学
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酶工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Journal of Oleo Science
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2021
·
IF 1.601
Hongli Yang,Xu Han,Ahmed S. M. Saleh,Chen Shao,Yumin Duan,Zhi-gang Xiao
In this study, Novozym 435-catalyzed interesterification of ethyl ferulate (EF) with phosphatidylcholine (PC) in a two-phase system consisting of an ionic liquid (IL) and toluene was optimized to prepare feruloylated lysophospholipids (FLPs). Optimum conditions for the interesterification process were found to be [Bmim][Tf2N]/toluene ratio of 1:1 (v/v), solvent volume of 4 mL, molecular sieves (4 Å) concentration of 80 mg/mL, reaction temperature of 55°C, substrate molar ratio of 5:1 (PC/EF), Novozym 435 concentration of 50 mg/mL. Under these conditions, two FLPs products (1-FLP and 2-FLP) with total conversion rate of 50.79% were obtained. Because the formation of 1-FLP was significantly higher than 2-FLP, 1-FLP was purified and characterized by LC-MS and NMR. In addition, 1-FLP showed DPPH scavenging activity comparable with those of EF and BHT. Therefore, this study provides a good method for transformation of ferulic acid to improve its solubility and promote its application as functional ingredient in the food and pharmaceutical industries.
研究领域:
食品科学
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生物化学
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制药工程
✓ 已验证
DOI
PubMed
高影响因子
MOLECULES
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2025
·Vol. 30
·期 11
·2429
·
IF 4.6
Wei Wang,Xiangyao Chen,Wen-Can Huang,Simiao Di,Jie Luo
This study presents a multilayer magnetic Janus sub-micrometric particle (MMJSP) as a nanoreactor for lipase catalysis. The core of the nanoparticle is constructed from a core-shell Fe3O4@SiO2framework, which serves as a precursor for the sequential amino and aldehyde modifications using 3-aminopropyltriethoxysilane and benzaldehyde. Following localized etching and subsequent modification with N,N-dimethyldodecylamine, a Janus nanoparticle with distinct hydrophilic and hydrophobic domains is synthesized. The resulting MMJSP demonstrates a stable attachment to the reaction interface and significantly enhances lipase performance, exhibiting 1.4-fold and 1.6-fold enhancements in activity after immobilization during 1 h hydrolysis and 24 h esterification reactions, respectively. Additionally, the storage stability of the immobilized lipase is improved by 100% over a period of 30 days. Reusability assessments reveal that the immobilized enzyme retains 80.7% activity after 10 cycles of esterification and 80.6% after 50 cycles of hydrolysis, with the magnetic properties allowing for rapid separation and recovery of the immobilized enzyme.
研究领域:
生物化学
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材料科学
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酶工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
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2014
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IF 2.745
Long-Hua Zhou,Na Wang,Guan-Nan Chen,Qi Yang,Sheng-Yong Yang,Wei Zhang,Yang Zhang,Xiao-Qi Yu
Lipase-catalyzed direct vinylogous Michael addition reactions of electron-deficient vinyl malononitriles to nitroalkenes are reported for the first time. A series of nitroalkenes reacting with vinyl malononitriles generate the corresponding products with moderate to high yields in the presence of Lipozyme ® (immobilized lipase from Mucor miehei ) with excellent diastereoselectivities in all reactions under optimized conditions. Docking studies were performed to further elucidate the differences between the various enzymes and substrates. Furthermore, we demonstrated the synthetic potential of the multi-functional products by performing reactions that employed the electron-deficient alkylidene double bond.
研究领域:
有机化学
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生物催化
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合成化学
✓ 已验证
产品关联
DOI
高影响因子
Molecular Catalysis
·
2024
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IF 3.9
Xiaoyuan Zhang,Yunjian Ma,Bo Ouyang,Yonghua Wang,Fanghua Wang
Ceramide III (CER III) series compounds are essential constituents in cosmetic formulations and dermatological applications. As the cosmetics industry trends toward more sustainable practices, the development of an eco-friendly synthesis method for these vital compounds is increasingly critical. This research introduces a sustainable technique for producing CER III series compounds, using lipase-catalyzed amidation of phytosphingosine with various fatty acid esters or natural oils in an eco-compatible solvent. Through an extensive examination of various lipases and eco-friendly solvents, we first identified Novozym 435 as the most efficient biocatalyst and cyclopentyl methyl ether (CPME) as the preferred solvent. This combination established a high-efficiency reaction system for CER III series compounds synthesis. We further optimized the enzymatic conditions - a substrate molar ratio of 1:1, lipase loading at 30 wt%, at 65 °C, which presented an impressive yield of 94 % for ceramide IIIB (CER IIIB). We also investigated the reusability of enzymes in this synthetic system and further extended the scope of acyl donors using natural oils, results indicating the method excellent potentiality in industrial settings. In summary, this study provides a green and efficient pathway for synthesizing CER III series compounds, aligning with the growing eco-conscious trends in cosmetic science and technology.
研究领域:
生物化学
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化妆品科学
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绿色化学
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产品关联
DOI
高影响因子
MOLECULES
·
2017
·Vol. 22
·期 10
·1598
·
IF 2.861
Jing Chen,Yuchao Chen,Yi Cheng,Youheng Gao
Mannose-diester lauric diacid-cholesterol (Man-DLD-Chol), as a liposomal target ligand, was synthesized by lipase catalyzed in a non-aqueous medium. Its chemical structure was confirmed by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. Glycyrrhetinic acid (GA) liposomes containing Man-DLD-Chol (Man-DLD-Chol-GA-Lp) were prepared by the film-dispersion method. We evaluated the characterizations of liposomes, drug-release in vitro, the hemolytic test, cellular uptake, pharmacokinetics, and the tissue distributions. The cellular uptake in vitro suggested that the uptake of Man-DLD-Chol-modified liposomes was significantly higher than that of unmodified liposomes in HepG2 cells. Pharmacokinetic parameters indicated that Man-DLD-Chol-GA-Lp was eliminated more rapidly than GA-Lp. In tissue distributions, the targeting efficiency (Te) of Man-DLD-Chol-GA-Lp on liver was 54.67%, relative targeting efficiency (RTe) was 3.39, relative uptake rate (Re) was 4.78, and peak concentration ratio (Ce) was 3.46. All these results supported the hypothesis that Man-DLD-Chol would be an efficient liposomal carrier, and demonstrated that Man-DLD-Chol-GA-Lp has potential as a drug delivery for liver-targeting therapy.Keywords:lipase-catalytic acylation;mannose-diester lauric diacid-cholesterol;glycyrrhetinic acid liposomes;mannose receptor;liver-targeting
研究领域:
药剂学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）