Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Reaction flavor per se – or containing reaction flavor...
Patent
1997-09-11
2000-04-11
Sayala, Chhaya D.
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Reaction flavor per se, or containing reaction flavor...
A23L 122, A23L 256
Patent
active
060485604
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of international application PCT/EP96/00156, filed Jan. 9, 1996 which was designated the U.S.
The invention concerns a process for the preparation of a flavouring component through oxidative degradation of certain substituted p-hydroxystyrene-type compounds.
The enzymatic oxidation of various p-hydroxystyrene-type compounds, leading to the corresponding benzaldehydes, is described in EP 542 348. The enzyme used in this process is lipoxydase. Thus, coniferyl alcohol, coniferyl benzoate and isoeugenol are converted into vanillin.
In U.S. Pat. Nos. 4,927,805 and 4,810,824 the hydrolytic degradation of curcumin at high temperature (>200.degree. C.) and high pressure is described. The reaction mixture is rich in vanillin and/or guaiacol and vinylguaiacol, depending on the pH of the aqueous reaction mixture. Furthermore, the hydrolysis of curcumin, demethoxycurcumin and bisdemethoxycurcumin in a wide pH range has been studied by H. H. Tonnesen et al, Z. Lebensm. Unters. Forsch (1985) 180: 132-134 and 402-404. These compounds are the main constituents of the essential oil from the rhizomes of turmeric (Curcuma longa L).
However, there is a continuous need for novel flavouring components with rich and complex flavour notes, which nay be produced under moderate conditions and without the need for excessively high temperatures.
It has now been found that valuable flavouring components may be obtained through non-enzymatic oxidative degradation at moderate temperatures of certain substituted p-hydroxystyrene-type compounds according to the general formula given below: ##STR2## wherein R1 is hydrogen or a hydroxy or alkoxy group and R2 is an alkyl group or an organic functional group such as an aldehyde or keto group, a carboxylic acid or ester group, or a carbinol, carbinol ester or an ether group. Preferably R1 is hydrogen, hydroxy or methoxy, particularly hydrogen or methoxy.
Thus, the invention provides a process for preparing flavouring components through non-enzymatic oxidative degradation of the substituted p-hydroxystyrene-type starting materials.
The invention also provides novel flavouring components obtained by the process according to the invention.
Furthermore, the invention provides novel flavourings containing the flavouring components according to the invention.
Finally, the invention provides flavoured foodstuffs containing the flavouring components of the invention added either as such or as part of a flavouring according to the invention.
Suitable p-hydroxystyrene-type starting materials for the non-enzymatic oxidative degradation are e.g.: CO--CH.sub.2 --CO--X with X being the structural element indicated as such in the general formula above in which either both of R1 are methoxy, one of R1 is methoxy and the other is hydrogen, or both of R1 are hydrogen; with R3 being derived from e.g. a lower aliphatic alcohol or a sterol; many examples may be found in vegetable products; CH.sub.2 OH or CH.sub.2 OOCR, with R being an aliphatic or aromatic group.
The oxidative degradation reaction is advantageously carried out in a solvent, particularly an organic solvent, such as a lower aliphatic (i.e. C1-C4) mono- or polyhydric alcohol. Although the solvent may be separated completely from the reaction product after the degradation is completed, preferably a solvent is chosen which is undisputed from a toxicological point of view. Such a solvent is e.g. ethanol. Other solvents, particularly those generally used for flavourings, may be used as well.
The oxidative degradation reaction is carried out at elevated but moderate temperatures, preferably between 80.degree. and 250.degree. C., more preferably between 120.degree. and 200.degree. C. Particularly good results are generally obtained at temperatures above 140.degree. C. For satisfactory conversion at least an equimolar amount of oxygen calculated on the amount of p-hydroxystyrene-type starting material is used, but preferably at least a bimolar excess of oxygen. optimal results are obtained with at least a 5-fold exc
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Kopain et al., Khin. Drev. vol. 2, pp. 68-72, 1975.
Ljunggier, Nord. Pulp Pap. Res. J., vol. 5(1), pp. 38-43, 1990.
Patent Abstracts of Japan, vol. 005, No. 079, (C-056), May 23, 1981, & JP,A,56 026829 (Mar. 16, 1981), see abstract.
Patent Abstracts of Japan, vol. 004, No. 069 (C-011), May 22, 1980, see abstract.
de Heij Johannes Theodorus
van Dort Johannes Marinus
Quest International B.V.
Sayala Chhaya D.
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