Biocatalytic oxidation of fatty alcohols into aldehydes for the flavors and fragrances industry

Ribeaucourt, David; Bissaro, Bastien; Lambert, Fanny; Lafond, Mickaël; Berrin, Jean‐Guy

doi:10.1016/j.biotechadv.2021.107787

Cited by 55 publications

(32 citation statements)

References 235 publications

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“…The enzymatic activity, which led to the formation of colored product, was measured at 515 nm for 60 s and expressed as U/mL per mg protein. Initial rates of reaction at the various substrate concentrations were determined at three different pH values (6,7,8), and the kinetic parameters were calculated by non-linear regression fitting of the data to the Michaelis-Menten equation V = Vmax(S)/(Km + (S)). All curve fitting was carried out using Kaleidagraph software (Synergy Software, Reading, PA, USA).…”

Section: Lcao Acitivitymentioning

confidence: 99%

“…The high reactivity of the carbonyl group of aldehydes makes them versatile feedstocks for the synthesis of resins, dyes, pharmaceutical intermediates through carboligation, condensation, hydrocyanation, transamination, and α-alkylation [1][2][3][4][5]. They can also be used as flavors and fragrances in the cosmetic and food industry [6][7][8]. Many aldehydes, especially those used by the perfume industry, are extracted from natural sources.…”

Section: Introductionmentioning

confidence: 99%

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Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase

et al. 2021

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Aldehydes are a class of carbonyl compounds widely used as intermediates in the pharmaceutical, cosmetic and food industries. To date, there are few fully enzymatic methods for synthesizing these highly reactive chemicals. In the present work, we explore the biocatalytic potential of an amino oxidase extracted from the etiolated shoots of Lathyrus cicera for the synthesis of value-added aldehydes, starting from the corresponding primary amines. In this frame, we have developed a completely chromatography-free purification protocol based on crossflow ultrafiltration, which makes the production of this enzyme easily scalable. Furthermore, we determined the kinetic parameters of the amine oxidase toward 20 differently substituted aliphatic and aromatic primary amines, and we developed a biocatalytic process for their conversion into the corresponding aldehydes. The reaction occurs in aqueous media at neutral pH in the presence of catalase, which removes the hydrogen peroxide produced during the reaction itself, contributing to the recycling of oxygen. A high conversion (>95%) was achieved within 3 h for all the tested compounds.

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Section: Lcao Acitivitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase

et al. 2021

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“…One advantage of CROs is that the oxidation usually stops at the aldehyde and oxidation to the acid is rarely observed. Aldehydes constitute an important class of molecule in flavours and fragrances (F&F), as described in a recent review [ 13 ]. The biotechnological production of aldehydes, such as fatty aldehydes, is becoming more common.…”

Section: Discussionmentioning

confidence: 99%

Oxidase enzymes as sustainable oxidation catalysts

et al. 2022

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Oxidation is one of the most important processes used by the chemical industry. However, many of the methods that are used pose significant sustainability and environmental issues. Biocatalytic oxidation offers an alternative to these methods, with a now significant enzymatic oxidation toolbox on offer to chemists. Oxidases are one of these options, and as they only depend on molecular oxygen as a terminal oxidant offer perfect atom economy alongside the selectivity benefits afforded by enzymes. This review will focus on examples of oxidase biocatalysts that have been used for the sustainable production of important molecules and highlight some important processes that have been significantly improved through the use of oxidases. It will also consider emerging classes of oxidases, and how they might fit in a future biorefinery approach for the sustainable production of important chemicals.

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“…Flavors and fragrances are one of the main additives used in the food, medicine, personal care product, beverage, and pharmaceutical industries. − In recent years, their global demand has been expected to rise from 5% to more than US$23.5 billion per year . Isoamyl butyrate has a fruity banana flavor and can be synthesized by catalyzing the esterification of isoamyl alcohol and butyrate. − Reactive distillation (RD) is suitable for production of isoamyl butyrate .…”

Section: Introductionmentioning

confidence: 99%

Isobaric Vapor–Liquid Equilibrium of Isoamyl Alcohol, Cyclohexane, n-Hexane, and the n-Heptane + Isoamyl Butyrate Binary System at 101.3 kPa

et al. 2021

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Isoamyl butyrate is a common food additive. Water will be generated by esterification reaction in the process of its formation. Cyclohexane, n-hexane, and n-heptane are often selected as entrainers to remove water and promote the reaction. In this work, the vapor–liquid equilibrium data of the binary systems of isoamyl alcohol + isoamyl butyrate, cyclohexane + isoamyl butyrate, n-hexane + isoamyl butyrate, and n-heptane + isoamyl butyrate were determined by using a modified Rose vapor recirculating-type equilibrium still at 101.3 kPa. Fredenslund test and Van Ness point test methods are used to verify the thermodynamic consistency of the experimental vapor–liquid equilibrium data. In addition, three classical activity coefficient models, Wilson, NRTL, and UNIQUAC, were used to fit the isobaric vapor–liquid equilibrium data of four binary systems. The binary interaction parameters were obtained by regression of experimental data.

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Biocatalytic oxidation of fatty alcohols into aldehydes for the flavors and fragrances industry

Cited by 55 publications

References 235 publications

Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase

Biocatalytic Production of Aldehydes: Exploring the Potential of Lathyrus cicera Amine Oxidase

Oxidase enzymes as sustainable oxidation catalysts

Isobaric Vapor–Liquid Equilibrium of Isoamyl Alcohol, Cyclohexane, n-Hexane, and the n-Heptane + Isoamyl Butyrate Binary System at 101.3 kPa

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