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Chemistry of Isoeugenol and Its Oxidation Products: Mechanism and Kinetics of Isoeugenol as a Skin Sensitizer

Chemical Research in Toxicology, 2023
Structurally similar phytochemical compounds may elicit markedly different skin sensitization responses. Eugenol and isoeugenol are natural phenylpropanoids found in various essential oils are frequently used as fragrance ingredients in consumer products due to their pleasing aromatic properties. Both compounds are also skin sensitizers with isoeugenol
Jongmin Ahn   +6 more
openaire   +2 more sources

Efficient Biosynthesis of Vanillin from Isoeugenol by Recombinant Isoeugenol Monooxygenase from Pseudomonas nitroreducens Jin1

Applied Biochemistry and Biotechnology, 2021
Currently, the biotechnological preparation of fragrances using natural materials attracted growing attention. Enzymatic synthesis of vanillin from isoeugenol by recombinant isoeugenol monooxygenase from Pseudomonas nitroreducens Jin1 was systematically investigated herein. With series of work on the construction of recombinant E.
Qian, Wang   +5 more
openaire   +2 more sources

Characterization of an Isoeugenol Monooxygenase (Iem) From Pseudomonas nitroreducens Jin1 That Transforms Isoeugenol to Vanillin

open access: yesBioscience, Biotechnology and Biochemistry, 2013
The isoeugenol monooxygenase (iem) gene from Pseudomonas nitroreducens Jin1, responsible for the conversion of isoeugenol to vanillin, was cloned and overexpressed in Escherichia coli. The purified Iem had a predicted molecular mass of 54 kDa. The V(max), K(M), and k(cat) values for it, using isoeugenol as substrate, were 4.2 µmol vanillin min(-1) mg ...
Hor-Gil Hur   +2 more
exaly   +3 more sources

Isomerization of eugenol to isoeugenol

Reaction Kinetics and Catalysis Letters, 1987
The isomerization of eugenol to isoeugenol was investigated by employing catalysis by KOH in amyl alcohol or glycerol, or by RhCl3. A number of factors which affect the reaction (solvent, temperature, molar ratios, presence of water) were examined.
L. Červený   +3 more
openaire   +1 more source

INFLUENCE OF VEHICLES ON PENETRATION THROUGH HUMAN EPIDERMIS OF BENZYL ALCOHOL, ISOEUGENOL AND METHYL ISOEUGENOL

The Journal of Dermatology, 1983
ABSTRACTThe influence of 5 liquid, 6 cosmetic and 2 ointment vehicles on the penetration of benzyl alcohol, isoeugenol and methyl isoeugenol through human epidermis was studied. Benzyl alcohol penetrated most rapidly from almost all vehicles. Among liquid vehicles, liquid paraffin provided the best penetration for the 3 compounds. As the ratio of water
Y, Jimbo   +4 more
openaire   +2 more sources

Studies on the Photodimerization of Isoeugenol

Journal of the Chinese Chemical Society, 1978
AbstractUnder the irradiation of the ultraviolet light, Isoeugenol (I) undergoes dimerization in acetone to give diisoeugenol (II) and dehydrodiisoeugenol (III). The structures are determined by the comparison of the mixed m. p., I. R. spectra and T. L. C. with synthesized authentic samples. Also the photoreaction mechanism is discussed in detail.
Hung‐Cheh Chiang, Shyh‐Yuan Li
openaire   +1 more source

Conversion of Isoeugenol into Vanillic Acid by Pseudomonas putida I58 Cells Exhibiting High Isoeugenol-Degrading Activity

Journal of Bioscience and Bioengineering, 2003
Pseudomonas putida I58 was isolated from soil by a conventional enrichment culture method using isoeugenol as a sole carbon source. The strain utilized isoeugenol, vanillin and vanillic acid as carbon sources. On the other hand, the intermediates of the eugenol-degrading pathway, such as eugenol, coniferyl alcohol, coniferyl aldehyde and ferulic acid ...
Hirotaka, Furukawa   +3 more
openaire   +2 more sources

Biotransformation of Isoeugenol into Vanillin Using Immobilized Recombinant Cells Containing Isoeugenol Monooxygenase Active Aggregates

Applied Biochemistry and Biotechnology, 2019
For efficiently enhancing the activity of isoeugenol monooxygenase, a whole cell overproducing active aggregate IEM720-18A was successfully fabricated via the fusion of amphiphilic short peptide 18A (EWLKAFYEKVLEKLKELF) and isoeugenol monooxygenase and then efficiently expressed in E. coli BL21 (DE3). Such resulting bacteria, E.
Liqing, Zhao   +6 more
openaire   +2 more sources

Ferric chloride oxidation of isoeugenol

Experientia, 1983
Ferric chloride oxidation of isoeugenol gave 5 products. The elucidation of the structures of those products and the mechanism of their formation are discussed.
Y. H. Kuo, S. T. Lin
openaire   +1 more source

Oxidation of isoeugenol by Nocardia iowensis

Enzyme and Microbial Technology, 2008
Abstract Isoeugenol is a starting material for both the synthetic and biotechnological production of vanillin and vanillic acid. Nocardia iowensis DSM 45197 (formerly Nocardia species NRRL 5646) resting cells catalyze the conversion of isoeugenol to vanillic acid, vanillin, vanillyl alcohol and guaiacol.
Ramya Seshadri   +3 more
openaire   +1 more source

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