Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
2000-10-02
2004-04-06
Wong, Leslie (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
C426S534000, C426S650000
Reexamination Certificate
active
06716468
ABSTRACT:
The present invention relates to flavoured foodstuffs and flavouring compositions. More in particular the present invention relates to foodstuffs having a savoury flavour and to flavouring compositions suitable for imparting such a flavour. Under a savoury flavour is here to be understood a flavour associated with meat, sausage, poultry, cheese etc. The term foodstuff as used herein includes both solid and liquid ingestible materials which may or may not have nutritional value.
Flavoured foodstuffs having a savoury flavour and flavouring compositions for imparting to and/or enhancing in a foodstuffs a savoury flavour have been known for a long time, but so far these compositions were not been quite satisfactory. Therefore the present invention aims to improve the organoleptic properties.
Many compounds have been used to impart a savoury flavour to foodstuffs and therefore most of the compositions used for a savoury flavour contain a multitude of compounds. One group of particular useful compounds for savoury flavours are certain (hydrogenated) furan thiols and derivatives thereof like thio-acetates are e.g. disclosed and/or claimed in GB-A-1 283 912 (Unilever). GB-A-1 256 462 (International Plavours and Fragrances) also discloses certain furan thiols such as 2-methylfuran-3-thiol and it derivatives such as its disulphide and other sulphides as meat flavours. Especially 2-methylfuran-3-thiol and its precursors are powerful flavouring compounds capable of imparting a pleasant roast meat flavour to foodstuffs [cf e.g. “Volatile compounds in foods en beverages” methyl-3-furyldithioby H. Maarse (ED) Marcel Dekker, New York (1991)]. Its powerful roast or fried beef note is, however, not always appreciated. Therefore attempts have been made to obtain products with a powerful, somewhat milder, more rounded off meat flavour more reminiscent of the flavour of boiled beef and beef broth.
The present invention solves the problem of obtaining a powerful mild beef flavour reminiscent of beef broth, and boiled beef which is especially needed for soups, sausages, pastry etc. Also varying the relative amounts of the key components the present invention enables the flavourist to prepare flavouring compositions varying from a mild roast beef flavour to a mild beef broth flavour.
In a first embodiment the present invention therefore provides a flavoured foodstuff comprising an effective amount of at least one compound with a (hydrogenated) 2-methyl-3-furyl-thio moiety and a hydrogen atom, an —S—CH
3
group, an —CO—CH, group or a 2-methyl-3-furyl-thio moiety and an effective amount of at least one compound having the structure
U—CH
2
—S—T
in which C, H and S have the conventional meanings of carbon, hydrogen and sulphur atoms respectively, U represents a thiol group, a lower thioacyl group, a lower thioalkylgroup, a hydroxyl group or a 2-methyl-3-furyldithio group and T represents a hydrogen atom, a lower acyl group or a 2-methyl-3-furyl-thio group or a —S—CR
2
—U group as defined above.
Suitable compounds in the practice of the present invention having a (hydrogenated) 2-methyl-3-furyl-thio moiety and a hydrogen atom, an —S—CH
3
group, an —CO—CH
3
group or a 2-methyl-3-furyl-thio moiety are e.g. 2-methylfuran-3-thiol, 2-methyl-4,5-dihydrofuran-3-thiol, cis/trans 2-methyltetra-hydrofuran-3-thiol, 2-methyl-3-thiomethoxyfuran, methyl-2-methyl-3-furyldisulphide, 2-methylfuran-3-thioacetate, 2-methylfuran-3-thiopropionate and the disulphide of 2-methylfuran-3-thiol. The use of non-hydrogenated furan derivatives is preferred. Several of these compounds are available from Oxford Chemicals, Hartlepool, U.K. It is observed that 2-methylfuran-3-thiol like many other thiols is liable to oxidise partially under the influence of oxygen in the atmosphere to its disulphide and consequently quite often commercially available 2-methylfuran-3-thiol preparations contain certain amounts of its disulphide. Thioesters like 2-methyl-3-furan-3-thioacetate and e.g. 2-methyl-3-furan-3-thiopropionate may hydrolyze partially to form 2-methyl-3-furan-3-thiol under certain food processing conditions. This may apply e.g. under the conventional sterilising conditions after canning.
Suitable compounds for the practice of the present invention having a (hydrogenated) 2-methyl-3-furyl-thio moiety and a hydrogen atom, an —S—CH
3
group, an —CO—CH
3
group or a 2-methyl-3-furyl-thio moiety and an effective amount of at least one compound having the structure
U—CH
2
—S—T
in which C, H and S have the conventional meanings of carbon, hydrogen and sulphur atoms respectively, U represents a thiol group, a lower thioacyl group, a lower thioalkylgroup, a hydroxyl group or a 2-methyl-3-furyldithio group and T represents a hydrogen atom, a lower acyl group or a 2-methyl-3-furyl-thio group or a —S—CH
2
—U group as defined above are methanedithiol, methanedithiol diacetate, methylthiomethanol, methylthiomethanethiol, methylthiomethanethiol acetate, methylthiomethanethiol propionate, methylthiomethanethiol 2-methylpropionate, methylthiomethanethiol 2-methylbutanoate, methylthiomethanethiol 2-methylbutanoate, 3-methylthiomethanethiol pentanoate, methylthiomethanethiol 4-methylpentanoate and methylthiomethanethiolhexanoate. Some of these compounds are to be regarded as precursors of the corresponding free thiols, whereas others have organoleptic properties resembling methanedithiol or methylthiomethanol etc. with slightly different flavour notes. Here also the possibility arises that free thiols are partially converted to corresponding disulphides under oxidising conditions and also thioesters may hydrolyse to form free thiols under certain food processing conditions.
The present invention not only covers foodstuffs flavoured by incorporating the above identified compounds per se, but also foodstuffs incorporating precursors of the above identified compounds.
2-Methyl-3-furanthiol and some of its derivatives discussed above can be obtained or synthesized as such, but it may also be convenient to prepare a meat/beef flavour composition containing one or more of these compounds (a reaction flavour composition) which comprises at least one of these compounds in a suitable quantity and incorporate in such a composition a suitable amount of a compound having the structure U—CH
2
—S—T. Suitable reaction flavour compositions can be prepared by reacting a hexose or pentose with a source of hydrogen sulphide such as cysteine in water as a solvent. Instead of a hexose or pentose a suitable degradation product of a sugar can be used such as e.g. 4-hydroxy-5-methyl-2,3-hydrofuran-3-one and ascorbic acid may also be used. It is also quite possible to prepare suitable reaction flavours containing 2-methyl-3-furanthiol by thermal degradation of thiamine. Several possibilities and reaction mechanisms of reaction flavours are discussed by Hoffmann & Schieberle in J. Agric. Food Chemistry, 46, 235-241 (1998) which is hereby incorporated by reference.
The flavouring compositions according to the present invention are especially incorporated in foodstuffs such as sausage, meat, reformed communicated meat, meat replacers such as texturized vegetable protein, and pastry products in an effective amount, i.e. in an amount sufficient to impart or reinforce the desired flavour. As a general guide flavouring amounts of 0.01 to 1000, preferably 0.5 to 100 ppb (parts per billion=1:10
9
) are incorporated in foodstuffs which proportions are expressed as one a weight basis calculated on the foodstuff. The flavouring amounts actually incorporated depend on the individual palate and on the nature of the foodstuff. In flavouring compositions the amounts present may easily be a factor 10 to 10,000 higher than in the actual flavoured foodstuff.
Preferably the present invention provides a flavoured foodstuff as defined above, in which lower thioacyl- and lower acyl group means that these groups comprise from 2 to 6, preferably 2 or 3 carbon atoms.
Preferably the present invention provides a flavoured foodstuff as defined above,in which U represents a lower thioac
Altena Gerrit Hendrik
Apeldoorn Willem
Fitz Wolfgang
Hesp Theodorus Gerardus Maria
Kerler Josef
Fitch Even Tabin & Flannery
Quest International B.V.
Wong Leslie
LandOfFree
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