Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1997-07-14
1999-06-01
Weber, Jon P.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435189, 4352551, 568309, C12P 726, C12N 902, C12N 114, C07C 4500
Patent
active
059087706
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to an enzymatic process for preparing aromatic derivatives of butanone.
There is a confirmed general interest in producing rare natural products under physiological conditions, and in particular those which have intense organoleptic properties. These processes are all the more attractive when they can be carried out starting from easily available natural precursors. As products obtained in this way are considered natural, they can be used as ingredients for natural flavourings, which are preferred by consumers.
This category of substances includes arylated derivatives of butanone and in particular derivatives of phenylbutanone such as "raspberry ketone", "zingerone" and "Cassione.RTM." (registered trade mark of the company Firmenich).
Raspberry ketone or 4-(4-hydroxyphenyl)-butan-2-one, was described for the first time as a characteristic component of raspberry flavour by H. Schinz and C. F. Seidel, Helv. Chim. Acta, 1957, 40, 1839. However, this substance was already known in its natural state as a component, among others, of a polygonacaea: Rheum palmatum, both in the form of an aglycone and in the form of glucosides (T. Murakami et al., Tetrahedron Letters, 1972, 2965; Y. Kashiwada et al., Chem. Pharm. Bull., 1986, 34, 3237). A gallyglucoside of raspberry ketone was also identified in a crassulacaea: Aeonium lindleyi (A. G. Gonzalez et al., Phytochemistry, 1976, 15, 344). According to a recent study, the glucoside of raspberry ketone accompanies the aglycone in the raspberry (A. Pabst et al., Phytochemistry, 1990, 29, 3853).
"Cassione.RTM.", or 4-(3,4-methylenedioxyphenyl)-butan-2-one, had not been found in nature until recently. For this reason, outside perfumery, its use had only been authorised in artificial food flavourings. Its presence was recently established in the essential oil of the aerial part of the rue plant: Ruta angustifolia Pers., a plant which is self-sown and grows in Malaysia (D. Joulain et al., Journal of Essential Oil Research, 1991, 3, 355), and it is therefore possible to now use this substance in food flavourings labelled "natural".
Zingerone is a component of ginger and of raspberry flavouring, but its contribution to this flavour is clearly less significant than that of raspberry ketone. The proportion of raspberry ketone in the raspberry is thus only between 9 and 174 .mu.g per kilogram of fresh fruit, depending on to the variety (W. Borejsza-Wysocki et al., J.agric. Food Chem., 1992, 40, 1176).
The aromatic value of raspberry ketone is expressed by its olfactory detection threshold in water, comprised between 1 and 10 parts per billion (M. Larsen et al., Z. Lebensm. Unters. Forsch. 1990, 191, 129).
It will therefore be understood that raspberry ketone is an absolutely necessary substance, although insufficient to create a reconstituted raspberry flavouring.
Raspberry ketone is easily available on the market as a synthetic product at a very moderate cost, and it is therefore regularly used in flavouring compounds which are identical to nature or artificial.
However, there is no practical source of isolated natural raspberry ketone, which is vital to reconstitute a totally natural raspberry flavouring. The concentrations in which this substance exists in the raspberry fruit are indeed so low, even in the best of cases, that any attempt to extract it in order to isolate the substance would not be economically viable. A similar situation, although to a lesser extent, applies to Cassione.RTM., owing to the small quantity present in essential oil of ruta and the great difficulty in isolating it with sufficient purity.
Attempts to produce raspberry ketone by fermentation de novo using certain strains of Nidularia have only allowed production of concentrations of raspberry ketone of the same order of magnitude as those observed in the fruit (P. Tiefel and R. G. Berger in Progress in Flavour Precursor Studies, P. Schreier and P. Winterhalter, publishers, Allured Publishing Co., Carol Stream, III, 1993, P 439-450). When these same authors add a supposed p
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Fuganti Claudio
Joulain Daniel
Hanley Susan
Robertet S.A.
Weber Jon P.
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