Thermal behavior and structural properites of plant-derived eugenyl acetate

Santos, Amilton dos; Chierice, Gilberto Orivaldo; Riga, Alan T.; Alexander, Kenneth S.; Matthews, Ellen

doi:10.1007/s10973-008-9753-0

Cited by 5 publications

(6 citation statements)

References 12 publications

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“…One of possible ways to overcome these limits is to use a dedicated drug delivery system, for example polymeric nanoparticles, to solubilize hydrophobic agent and increase its efficiency [21]. Another way is to use eugenol in the acetate form which leads to improved physical and chemical stability, by adding acetate functional groups in its structure increasing the therapeutic efficacy [22]. Eugenol acetate has excellent anti-tumoral properties and, furthermore, is a natural product with low systemic toxicity [23].…”

Section: Introductionmentioning

confidence: 99%

Spongious Fillers Based on Collagen – Hydroxyapatite – Eugenol Acetate With Therapeutic Potential in Bone Cancer

et al. 2020

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The aim of this study was to develop and characterize composite materials based on collagen, hydroxyapatite and eugenol acetate as new filler biomaterial for the reconstruction of the tissue damage arising after the resection in case of bone cancer. Composite gels consisting of collagen and hydroxyapatite in different proportions (Coll:HAp -100:0; 70:30; 40:60 -w/w) and 0.5% eugenol acetate were lyophilized and spongious fillers were obtained. The fillers were characterized by water absorption, enzymatic degradation and examined by optical and scanning electron microscopy, EDS, FT-IR spectroscopy while eugenol acetate release from the compositions was also studied. The results showed that the filler with optimal composition (Coll-HAp -40:60 w/w) completely degrade over about 48 hours, the release capacity being longer during the 144 hours. The complex results obtained from physicalchemical, morphological and eugenol acetate release profile evaluation for the designed composite materials based on collagen and hydroxyapatite testify these formulations as drug delivery systems with potential applications as fillers in orthopaedic field in bone cancer. RezumatStudiul a avut ca obiectiv dezvoltarea și caracterizarea unor materiale compozite pe bază de colagen, hidroxiapatită și acetat de eugenol ca biomateriale de umplere în reconstrucția tisulară după rezecția în cancerul osos. Geluri compozite care conțin colagen și hidroxiapatită în diferite proporții (Coll:HAp -100:0; 70:30; 40:60 -g/g) și 0,5% acetat de eugenol au fost liofilizate și s-au obținut materiale spongioase pentru umplere. Aceste materiale au fost caracterizate din punct de vedere a capacității de absorbție a apei și a degradării enzimatice, examinate prin microscopie optică și electronică, EDS, spectroscopie FT-IR și a fost investigată cedarea acetatului de eugenol din compozite. Rezultatele obținute au demonstrat că materialele de umplere cu compoziție optimă (Coll-HAp -40:60 g/g) se degradează complet după 48 de ore, iar capacitatea de eliberare depășește 144 de ore. Rezultatele complexe obținute în urma evaluărilor morfologice, fizico-chimice și a profilului de cedare al acetatului de eugenol privind materialele compozite pe bază de colagen și hidroxiapatită susțin potențialul acestor formulări ca sisteme de cedare de umplere în ortopedia cancerului osos.

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Section: Introductionmentioning

confidence: 99%

Spongious Fillers Based on Collagen – Hydroxyapatite – Eugenol Acetate With Therapeutic Potential in Bone Cancer

et al. 2020

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“…Furthermore, it has shown antimicrobial, antifungal, antioxidant, anti‐inflammatory, antispasmodic, antidepressant, antigenotoxic, and anticarcinogenic properties . The efficiency of this compound in therapeutic treatments is limited by its poor water solubility, however . Nevertheless, in virtue of its easy access and polyfunctional structure, it is considered as a useful starting material to produce valuable derivatives through chemical synthesis and biotransformation .…”

Section: Introductionmentioning

confidence: 99%

“…1 The efficiency of this compound in therapeutic treatments is limited by its poor water solubility, however. 2 Nevertheless, in virtue of its easy access and polyfunctional structure, it is considered as a useful starting material to produce valuable derivatives through chemical synthesis and biotransformation. 1,3,4 Biotechnological approaches based on the use of hydrolytic enzymes as biocatalysts have been proven efficient for the preparation of many attractive esters; 5 despite this, applications of hydrolases on an industrial scale remain limited.…”

Section: Introductionmentioning

confidence: 99%

Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Giovannini

Catani

Massi

et al. 2019

Flavour & Fragrance J

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The enzymatic synthesis of biologically active compounds is receiving increasing interest from academic and industrial researchers. Herein, we report on the continuous‐flow enzymatic production of eugenol esters with packed‐bed microreactors prepared with the Novozym 435 and Lipozyme RM IM lipases. After optimization of the independent process variables, namely temperature (68 °C), flow rate (8 μL min−1), and eugenol/isobutyric anhydride molar ratio (1 : 5) by means of experimental design methodologies, the unprecedented continuous‐flow production of eugenyl isobutyrate has been achieved with steady‐state conversions of 77 and 70%, using packed‐bed microreactors prepared with Novozym 435 and Lipozyme RM IM, respectively. With acetic anhydride as the acylating agent, the same reactors, under the same conditions, afforded eugenyl acetate with steady‐state conversions of 82% (Novozym 435) and 90% (Lipozyme RM IM). The two ester products have been tested against phytopathogenic and dermatophytic fungi, demonstrating interesting action against dermatophytic fungi. The reported results demonstrated the suitability of the enzymatic packed‐bed microreactors as a sustainable and scalable technology for the solvent‐free continuous‐flow production of biologically active esters of eugenol.

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“…It is used as an antiseptic, analgesic, fungicide, bactericide, insecticide, anticarcinogenic, antiallergic, antioxidant, antiinflammatory, and so forth [15][16][17]. As derivative, the eugenyl acetate was characterized and its structural properties have investigated by Dos Santos et al [18,19].…”

Section: Introductionmentioning

confidence: 99%

Structural Conformational Study of Eugenol Derivatives Using Semiempirical Methods

Mahboub

2014

Advances in Chemistry

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We investigated the conformational structure of eugenol and eugenyl acetate under torsional angle effect by performing semiempirical calculations using AM1 and PM3 methods. From these calculations, we have evaluated the strain energy of conformational interconversion. To provide a better estimate of stable conformations, we have plotted the strain energy versus dihedral angle. So, we have determined five geometries of eugenol (three energy minima and two transition states) and three geometries of eugenyl acetate (two energy minima and one transition state). From the molecular orbital calculations, we deduce that the optimized trans form by AM1 method is more reactive than under PM3 method. We can conclude that both methods are efficient. The AM1 method allows us to determine the reactivity and PM3 method to verify the stability.

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Thermal behavior and structural properites of plant-derived eugenyl acetate

Cited by 5 publications

References 12 publications

Spongious Fillers Based on Collagen – Hydroxyapatite – Eugenol Acetate With Therapeutic Potential in Bone Cancer

Spongious Fillers Based on Collagen – Hydroxyapatite – Eugenol Acetate With Therapeutic Potential in Bone Cancer

Continuous production of eugenol esters using enzymatic packed‐bed microreactors and an evaluation of the products as antifungal agents

Structural Conformational Study of Eugenol Derivatives Using Semiempirical Methods

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