Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds

Panten, Johannes; Surburg, Horst

doi:10.1002/14356007.t11_t02

Cited by 13 publications

(15 citation statements)

References 16 publications

(10 reference statements)

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“…Aromatic aldehydes are widely found in nature as secondary metabolites, e.g., in plants [1,2]. Commercially, aromatic aldehydes such as vanillin, anisaldehyde or cinnamaldehyde are popular flavour and fragrance ingredients [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

Li²,

Zhang³

et al. 2023

Catalysts

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Aromatic aldehydes are important aromatic compounds for the flavour and fragrance industry. In this study, a parallel cascade combining aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) and unspecific peroxygenase from the basidiomycete Agrocybe aegerita (AaeUPO) to convert aromatic primary alcohols into high-value aromatic aldehydes is proposed. Key influencing factors in the process of enzyme cascade catalysis, such as enzyme dosage, pH and temperature, were investigated. The universality of PeAAOx coupled with AaeUPO cascade catalysis for the synthesis of aromatic aldehyde flavour compounds from aromatic primary alcohols was evaluated. In a partially optimised system (comprising 30 μM PeAAOx, 2 μM AaeUPO at pH 7 and 40 °C) up to 84% conversion of 50 mM veratryl alcohol into veratryl aldehyde was achieved in a self-sufficient aerobic reaction. Promising turnover numbers of 2800 and 21,000 for PeAAOx and AaeUPO, respectively, point towards practical applicability.

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Section: Introductionmentioning

confidence: 99%

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

Li²,

Zhang³

et al. 2023

Catalysts

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“…3 Conceptually, olefin transpositions are key strategies to obviate these issues by converging a mixture of stereo/regioisomers to a single product, leading to higher yielding reactions and simplified purifications. As such, developing methodologies to selectively manipulate pre-existing C=C bonds has found broad application in many industrial processes including pharmaceutical synthesis, 3 cosmetics and fragrance development, 4 and the valorization of fundamental resources within the petroleum industry. 5 Typically, these transformations are mediated by transition metal hydride intermediates, which undergo a rapid 1,2-migratory insertion of the substrate, followed by -H elimination to furnish the transposed olefin.…”

Section: Introduction Figure 1 Prior Art and This Workmentioning

confidence: 99%

Catalytic Olefin Transpositions Facilitated by Ruthenium N,N,N-Pincer Complexes

Davies

Greene

Allen

et al. 2022

Preprint

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Previous reports with our N,N,N-pincer Ru hydride catalysts have shown their synthetic versatility in the ability to perform various transfer dehydrogenation reactions, deuterations, and (semi)-hydrogenations. In this report, we expand the reactivity of these complexes to encompass olefin transposition/isomerization via a chain-walking mechanism. Furthermore, we report several one-pot cascade reaction sequences derived from the products of the transposition reactions. The protocol occurs at room temperature achieving excellent yields, regioselectivity, and diastereoselectivity in short reaction times

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“…In this work, a combined experimental and computational study of thermodynamic properties of two selected monoterpenoids, (þ)-carvone ((5S)-5-isopropenyl-2-methyl-2cyclohexen-1-one) and eugenol (2-methoxy-4-prop-2enylphenol), is presented. Eugenol is the major component of several essential oils such as cinnamon leaf oil and clove leaf oil, and, due to its high availability in natural sources, it is preferably isolated from clove oil [5]. (þ)-Carvone is the main component of caraway oil and dill oil, being mainly prepared by synthetic methods [6].…”

Section: Introductionmentioning

confidence: 99%

Vapor pressure and thermophysical properties of eugenol and (+)-carvone

Vilas-Boas

Pokorný

Štejfa

et al. 2019

Fluid Phase Equilibria

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In this work, vapor pressures, liquid-phase heat capacities, and phase behavior of two monoterpenoids, (þ)-carvone and eugenol were studied. The vapor pressure experiments were performed using a static method over an environmentally relevant range of temperatures, from 258 K to 308 K. Liquid-phase heat capacities were measured by Tian-Calvet calorimetry between 265 K and 355 K. The phase behavior was investigated by heat-flux differential scanning calorimetry from 183 K. Experimental data were supplemented by ideal-gas thermodynamic properties obtained by combining quantum chemical and statistical thermodynamic calculations. Vapor pressures and heat capacities obtained in this work along with selected literature values were treated simultaneously by multi-property correlation in order to obtain a consistent description of thermodynamically linked properties. To our knowledge, liquid-phase heat capacities and phase behavior of eugenol are reported for the first time in this work.

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Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds

Cited by 13 publications

References 16 publications

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

Bienzymatic Cascade Combining a Peroxygenase with an Oxidase for the Synthesis of Aromatic Aldehydes from Benzyl Alcohols

Catalytic Olefin Transpositions Facilitated by Ruthenium N,N,N-Pincer Complexes

Vapor pressure and thermophysical properties of eugenol and (+)-carvone

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