Product distribution in the microbial biogeneration of raspberry ketone from 4-hydroxybenzalacetone

Recent advances in the synthesis and applications of raspberry ketone are reviewed in this paper. Different routes to this material including chemical and biotechnological synthetic methods and extraction from natural sources are compared, and the applications of the ketone in flavour and fragrance, pharmaceuticals and in food and tobacco processing are discussed. Synthesis from petrochemical raw materials has the advantages of ready availability of ingredients and well‐understood synthetic steps, but direct synthesis from petrochemicals will eventually be replaced because of low yields and hazardous results to environment. The ketone can be made from natural raw materials, and the methods are promising if their disadvantages such as limited availability and complex, multi‐step reactions and harsh reaction conditions can be overcome. Biotechnological preparation methods have the advantages of reaction specificity, mild reaction conditions, but are limited in applicability because of complications associated with their synthetic and purification procedures at present. With the development of biotechnology, biotechnological preparation methods of the ketone may be the most important route in the future. Direct extraction of the ketone from natural raw materials is possible, but the cost is very high. From the view of syntheses and applications, the research perspectives of raspberry ketone are outlined in the end of this paper, which are the development of green and effective synthetic methods for raspberry ketone from natural raw materials and the preparation and application of raspberry ketone by biotechnological preparation methods.

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“…Among the different micro‐organisms surveyed, Pichia etchellsii CBS 2011 was found to be the most suitable for the reaction 52 …”

Section: Synthesis Of Raspberry Ketonementioning

confidence: 99%

Advances in the synthesis and applications of raspberry ketone: A review

Guo

Chang

Jia

et al. 2021

Flavour & Fragrance J

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“…A preferência dos consumidores por produtos naturais, tem estimulado estudos com a finalidade de se obter abundantemente precursores extrativos naturais através de métodos enzimáticos Estes métodos tem capacidade de produzir grandes quantidades de substâncias aromáticas, que não seriam acessíveis por processos extrativos. Os produtos obtidos desta forma são de fato considerados naturais pela legislação 27,28 .…”

Section: Esquemaunclassified

“…Por exemplo, a bioconversão seletiva de cetonas insaturadas (19) que leva à formação de cetonas saturadas (20) (Esquema 5), não oferece vantagens sobre processos químicos existentes de hidrogenação catalítica. Entretanto, esta simples transformação levando a intermediários para a síntese de fragrâncias e aromatizantes, é bastante significativa se feita enzimaticamente 27 . …”

unclassified

Biocatálise: avanços recentes

Conti¹,

Rodrigues²,

Moran³

2001

Quím. Nova

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“…In addition, the enzymatic saturation of the double bond of 4-hydroxybenzylidenacetone is of practical importance for the natural synthesis of RK and has been studied in a variety of microorganisms. Baker’s yeast converts 4-hydroxybenzylidenacetone to saturate ketone, then reduced to carbinol, in which interested in the selective conversion of 4-hydroxybenzylidenacetone to RK . It has been reported that NADPH-dependent 2-alkenal reductase may catalyze the reduction of α,β-unsaturated double bonds of the enol moiety in the molecule .…”

Section: Introductionmentioning

confidence: 99%

Efficient Biosynthesis of Raspberry Ketone by Engineered Escherichia coli Coexpressing Zingerone Synthase and Glucose Dehydrogenase

Yang

Zheng

et al. 2021

J. Agric. Food Chem.

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Raspberry ketone (RK), the main aroma compound of raspberry fruit, has applications in cosmetics, food industry, and pharmaceutics. In this study, we biosynthesized RK via the catalytic reduction of 4-hydroxybenzylidenacetone using a whole-cell biocatalyst. Reductase RiRZS1 from Rubus idaeus and glucose dehydrogenase SyGDH from Thermoplasma acidophilum were expressed in Escherichia coli to regenerate NADPH for the whole-cell catalytic reaction. Following the optimization of balancing the coexpression of two enzymes in pRSFDuet-1, we obtained 9.89 g/L RK with a conversion rate of 98% and a space–time yield of 4.94 g/(L·h). The optimum conditions are 40 °C, pH 5.5, and a molar ratio of substrate to auxiliary substrate of 1:2.5. Our study findings provide a promising method of biosynthesizing RK.

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Product distribution in the microbial biogeneration of raspberry ketone from 4-hydroxybenzalacetone

Cited by 18 publications

References 12 publications

Advances in the synthesis and applications of raspberry ketone: A review

Advances in the synthesis and applications of raspberry ketone: A review

Biocatálise: avanços recentes

Efficient Biosynthesis of Raspberry Ketone by Engineered Escherichia coli Coexpressing Zingerone Synthase and Glucose Dehydrogenase

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