Microbial production of 4-hydroxybenzylidene acetone, the direct precursor of raspberry ketone


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Abstract

AimsTo investigate the enzymatic aldol reaction between acetone as a donor and 4-hydroxybenzaldehyde as a receptor to generate 4-(4-hydroxyphenyl)-but-3-ene-2-one or 4-hydroxybenzylidene acetone, the direct precursor of 4-(4-hydroxyphenyl)-butan-2-one or raspberry ketone, using different species of filamentous fungi and bacteria.Methods and ResultsDifferent classes of micro-organisms were tested in a medium containing mainly acetone and 4-hydoxybenzaldehyde. Of the micro-organisms tested, only bacteria were able to synthesize significant amounts of 4-hydroxybenzylidene acetone, ranging from 15 to 160 mg l−1 after 21 h of bioconversion, as a function of the bacteria tested.ConclusionsThe biological production of 4-hydroxybenzylidene acetone has been described with bacteria possessing 2-deoxyribose-5-phosphate aldolase (DERA, EC 4·1·2·4). This result suggests that DERA is involved in the catalytic aldolization of precursors for the production of 4-hydroxybenzylidene acetone.Significance and Impact of the StudyRaspberry ketone or frambinone represents a total market value of between €6 million and €10 million. The possibility of producing its direct precursor through a simple process using bacteria is of considerable interest to the flavour market and the food industry as a whole. This paper broadens the spectrum for the use of aldolase to achieve the biological synthesis of compounds of interest.

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