Solid-catalyzed synthesis of isomers–free terpinen–4–ol

Garnes-Portolés, Francisco; López-Cruz, Carlos; Sánchez‐Quesada, Jorge; Espinós-Ferri, Estela; Leyva‐Pérez, Antonio

doi:10.1016/j.mcat.2022.112785

Cited by 3 publications

(3 citation statements)

References 39 publications

(64 reference statements)

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“…Taken together, we propose the formation mechanism of 1,4-dihydroxy- p -menth-2-ene from terpinen-4-ol via epoxide and diol intermediates ( Fig. S9 ) as described previously [ 49 , 64 ]. We suggest that the mono-hydroxylated product is produced through intermediate epoxidation and that engineered CYP102A1 can be applied to biotechnology industries as a biocatalyst for the production of terpene derivatives.…”

Section: Discussionsupporting

confidence: 81%

“…In particular, various oxidized compounds were detected from reaction products of limonene derivatives catalyzed by engineered CYP102A1 [ 35 , 36 , 45 , 46 ], and terpinen-4-ol has been produced from limonene by Aspergillus niger [ 47 , 48 ]. Chemical synthesis of terpinen-4-ol from limonene has also been reported [ 49 , 50 ]. Interestingly, human CYP1A2, CYP2A6, and CYP3A4 catalyze the oxidation of (+)-terpinen-4-ol.…”

Section: Introductionmentioning

confidence: 99%

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Production of Mono-Hydroxylated Derivatives of Terpinen-4-ol by Bacterial CYP102A1 Enzymes

Kim,

Park,

Jeong

et al. 2023

J. Microbiol. Biotechnol.

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CYP102A1 from Bacillus megaterium is an important enzyme in biotechnology, because engineered CYP102A1 enzymes can react with diverse substrates and produce human cytochrome P450-like metabolites. Therefore, CYP102A1 can be applied to drug metabolite production. Terpinen-4-ol is a cyclic monoterpene and the primary component of essential tea tree oil. Terpinen-4-ol was known for therapeutic effects, including antibacterial, antifungal, antiviral, and anti-inflammatory. Because terpenes are natural compounds, examining novel terpenes and investigating the therapeutic effects of terpenes represent responses to social demands for eco-friendly compounds. In this study, we investigated the catalytic activity of engineered CYP102A1 on terpinen-4-ol. Among CYP102A1 mutants tested here, the R47L/F81I/F87V/E143G/L188Q/N213S/E267V mutant showed the highest activity to terpinen-4-ol. Two major metabolites of terpinen-4-ol were generated by engineered CYP102A1. Characterization of major metabolites was confirmed by liquid chromatography-mass spectrometry (LC-MS), gas chromatography-MS, and nuclear magnetic resonance spectroscopy (NMR). Based on the LC-MS results, the difference in mass-to-charge ratio of an ion (m/z) between terpinen-4-ol and its major metabolites was 16. One major metabolite was defined as 1,4-dihydroxy- p -menth-2-ene by NMR. Given these results, we speculate that another major metabolite is also a mono-hydroxylated product. Taken together, we suggest that CYP102A1 can be applied to make novel terpene derivatives.

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Section: Discussionsupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Production of Mono-Hydroxylated Derivatives of Terpinen-4-ol by Bacterial CYP102A1 Enzymes

Kim,

Park,

Jeong

et al. 2023

J. Microbiol. Biotechnol.

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“…Leyva-Peréz et al introduced an indomuscone-based sterically encumbered phosphine ligand L4 for the Pd-catalyzed SM reaction. 27 The use of Pd(OAc) 2 (2.5 mol%) and L4 (5 mol%) provided biaryl derivatives in up to 80% yield. In 2021, Schaub et al reported a Pd(OAc) 2 (50 ppm)-catalyzed SM coupling of aryl chlorides and arylboronic acids in water.…”

Section: Scheme 8 Activation Of a Pd Species For Base-free Lewis Acid...mentioning

confidence: 99%

Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions

Yamada,

Sen

2024

Synthesis

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Palladium- and nickel-catalyzed cross-couplings are powerful methods for constructing C-C and C-N bonds, particularly through Suzuki-Miyaura and Buchwald-Hartwig reactions. Although aryl iodides, bromides, and triflates are the most commonly used substrates, aryl chlorides are less frequently utilized due to their lower reactivity. However, they are appealing because they are readily available and inexpensive. This short review highlights recent developments in Suzuki-Miyaura and Buchwald-Hartwig cross-couplings of aryl chlorides, using both homogeneous and heterogeneous catalysis with palladium and nickel.

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Determination of Volatilome Profile in Carbonated Beverages Using n-Hexane as an Extractant by GC-MS

Mu,

Meng,

Luo

et al. 2024

Separations

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A liquid–liquid extraction pretreatment method using n-hexane as the extractant was developed for the analysis of volatile aroma substances in three flavors (six cola samples, six lemon samples, and six orange samples) of carbonated beverages by gas chromatography–mass spectrometry (GC-MS). Quantitative analysis was conducted using the external standard method. The spiked recovery rate of α-terpineol was used as the evaluation criterion. Single-factor and response surface experiments were conducted to investigate the effects of extraction temperature, extraction time, and solvent-to-sample ratio. The results indicated that the maximum spiked recovery rate of α-terpineol, 81.00%, was achieved at an extraction temperature of 45 °C, extraction time of 30 min, and a solvent-to-sample ratio of 1 mL:15 mL. Thirty-four components were identified by GC-MS on the pretreated samples via the internal standard method. 1,4-Cineole, fenchyl alcohol, borneol, and α-terpineol are covered aroma substances in cola beverages. Two aromatic substances, D-limonene and α-terpineol, were detected in orange juices. α-Terpineol was detected in each lemon-flavor carbonated beverage sample. Going a step further, α-terpineol was detected in all 18 carbonated beverage samples and had high response values. The principal component analysis by functional group classification led to the conclusion that acids, phenols, hydrocarbons, alcohols, and ethers played a major contribution to the aroma of these 18 beverages. Increased separation of target compounds was found using the new pre-treatment methods, resulting in improved analytical resolution and selectivity.

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Solid-catalyzed synthesis of isomers–free terpinen–4–ol

Cited by 3 publications

References 39 publications

Production of Mono-Hydroxylated Derivatives of Terpinen-4-ol by Bacterial CYP102A1 Enzymes

Production of Mono-Hydroxylated Derivatives of Terpinen-4-ol by Bacterial CYP102A1 Enzymes

Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions

Determination of Volatilome Profile in Carbonated Beverages Using n-Hexane as an Extractant by GC-MS

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