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EP-4736654-A2 - OLIGOSACCHARIDES FOR FLAVOUR GENERATION

EP4736654A2EP 4736654 A2EP4736654 A2EP 4736654A2EP-4736654-A2

Abstract

The present invention relates to the use of a special class of oligosaccharides, herein called iso-oligosaccharides, for flavour generation during thermal processing of food. The invention also relates to the use of such oligosaccharides in the form of individual compounds, or as mixtures thereof, or in the form of ingredients comprising the individual compounds or mixtures thereof, or as enzymatic or fermented preparations containing the individual compounds or mixtures thereof.

Inventors

  • DAVIDEK, TOMAS
  • Novotny, Ondrej
  • VAFEIADI, Christina

Assignees

  • Société des Produits Nestlé S.A.

Dates

Publication Date
20260506
Application Date
20171214

Claims (20)

  1. Use of an iso-oligosaccharides of formula (I) R--------------------B (I) Wherein R and B are connected via a 1→6 glycosidic linkage; B is an aldohexose or ketohexose monosaccharide unit comprising the carbon 6 bearing the -OH group forming the glycosidic linkage between R and B; R is a group X-A-* wherein A is an optionally functionalized monosaccharide unit comprising the carbon 1 bearing the -OH group forming the glyosidic linkage; wherein the sign * indicates the point of attachment for the group R to B; wherein X is connected to A via a covalent bond and is selected in the group consisting of: hydrogen, monosaccharide, and linear or branched oligosaccharide, wherein such monosaccharide or oligosaccharides may be further functionalized; or mixtures thereof as flavour precursors, for example in Maillard or caramelization reactions
  2. The use according to claim 1 for generating at least one odorant selected in the group consisting of: 4-hydroxy-2,5-dimethyl-3( 2H )-furanone; 2,3-butanedione; And mixtures thereof.
  3. The use according to claim 1 or 2 for generating at least one odorant selected in the group consisting of: 4-hydroxy-2,5-dimethyl-3( 2H )-furanone; 2,3-butanedione; 2- and 3-methylbutanal; Methional; Phenylacetaldehyde; 2-acetyl-1-pyrroline; And mixtures thereof.
  4. Use according to claim 1, 2 or 3 wherein the iso-oligosaccharide of formula (I) is a iso-oligosaccharide of formula (IB1):
  5. Use according to anyone of claims 1 to 4 wherein the iso-oligosaccharide of formula (IB1) is an iso-maltooligosaccharide or mixtures thereof.
  6. Use according to claim 1, 2 or 3 wherein the iso-oligosaccharide of formula (I) is a iso-oligosaccharide of formula (IB2):
  7. Use according to claim 1,2,3 or 6 wherein the iso-oligosaccharide of formula (IB2) is 6- O -α-D-glucopyranosyl- D-fructose (isomaltulose or Palatinose ™ ).
  8. Use according to anyone of claims 1 to 6 wherein R for iso-oligosaccharides of formula (I) is not functionalized.
  9. Use according to anyone of claims 1 to 6 wherein R for iso-oligosaccharides of formula (I) is functionalized so that one or more of the -OH groups in the monosaccharide unit R are absent (replaced by an hydrogen atom) or replaced with a moiety selected from the group consisting of: A-O-* and A-*, wherein A is as above defined and the asterisk sign (*) represents the point where the group A-O- or A- is linked to the remaining part of compounds of formula (I) via the carbon atom originally bearing the -OH group that is now replaced with the moiety A-* or A-O-*.
  10. Use according to anyone of claims 1 to 9 wherein the iso-oligosaccharide of formula (I) is selected in the group consisting of: 6- O -β-D-glucopyranosyl- β-D-glucopyranose; 6- O -α-D-galactopyranosyl-α-D-glucopyranose; 6- O -α-D-galactopyranosyl- β-D-glucopyranose; 6- O -α-D-glucopyranosyl-α-D-glucopyranose; 6- O -β-D-galactopyranosyl-D-galactopyranose; 6- O -α-D-galactopyranosyl-D-galactopyranose; 6- O -β-D-galactopyranosyl-D-glucopyranose; 6- O -a-D-galactopyranosyl-D-glucopyranose; 6- O -β-D-glucopyranosyl- D-glucopyranose; 6- O -α-D-mannopyranosyl- D-glucopyranose; 6- O -α-D-glucopyranosyl- D-glucopyranose; 6- O -α-D-glucopyranosyl- D-glucose; 6- O -β-D-glucopyranosyl- D-glucose; 6-O-α-D-galactopyranosyl- D-glucose; 6-O-β-D-galactopyranosyl- D-galactose; 6- O -α-D-mannopyranosyl- D-mannose; 6- O - α-D-galactopyranosyl- D-galactose; 6- O -β-D-galactopyranosyl- D-glucose; 6- O -β-D-mannopyranosyl- D-mannose; 6- O -β-D-glucopyranosyl- D-mannose; 6- O -α-D-glucopyranosyl- D-fructose; 6- O -β-D-glucopyranosyl- D-fructose; 6- O -α-D-galactopyranosyl- D-fructose; O -α-D-glucopyranosyl-(1→6)- O -α-D-glucopyranosyl-(1→6)- D-glucose; O -α-D-galactopyranosyl-(1→6)- O -α-D-galactopyranosyl-(1→6)- D-glucose; O -α -D-glucopyranosyl-(1→4)- O -α-D-glucopyranosyl-(1→6)- D-glucose; O -α-D-glucopyranosyl-(1→6)- O -α-D-glucopyranosyl-(1→6)- O -α-D-glucopyranosyl-(1→6)- D-glucose; 6- O -α-D-glucopyranosyl-α-D-fructofuranose; 6- O -α-L-Rhamnopyranosyl- D-glucose; 6- O -α-L-Rhamnopyranosyl- D-fructose; Or mixtures thereof.
  11. Method for flavour generation in a heat-treated food product which comprises a step a) where a compound of formula (I) as described in anyone of claims 1 to 10, or mixtures thereof, is reacted under thermal treating.
  12. Method for flavour generation according to claim 11 which comprises a step a) where a compound of formula (I) as described in anyone of claims 1 to 10, or mixtures thereof, is mixed with an ingredient providing free amino groups and reacted under thermal treating.
  13. Method according to claim 11 or 12, wherein the iso-oligosaccharide of formula (I) is provided for step a) of the method in the form of an ingredient constituted by the compound of formula (I) or mixtures thereof.
  14. Method according to claim 11 or 12, wherein the iso-oligosaccharide of formula (I) is provided for step a) of the method in the form of an ingredient comprising the compound of formula (I) or mixtures thereof.
  15. Method according to claim 11 or 12, wherein the iso-oligosaccharide of formula (I) is provided for step a) of the method in the form of an ingredient comprising the compound of formula (I), (IB1), (IB2) or mixtures thereof which are prepared by enzymatic or fermentation process.
  16. Method according to claim 15, and comprising the following steps: b) an enzymatic preparation of an ingredient comprising the compound of formula (I) is performed; a) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step b) is directly reacted under thermal treating.
  17. Method according to claim 15 or 16, and comprising the following steps: b) an enzymatic preparation of an ingredient comprising the compound of formula (I) is performed; a) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step b) is directly mixed with an ingredient providing free amino groups and reacted under thermal treating.
  18. Method according to claim 15, comprising the following steps: b) an enzymatic preparation of an ingredient comprising the compound of formula (I) or mixtures thereof is performed; c) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step b) is stored for further use; a) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step c) is reacted under thermal treating.
  19. Method according to claim 15 or 18, comprising the following steps: b) an enzymatic preparation of an ingredient comprising the compound of formula (I) or mixtures thereof is performed; c) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step b) is stored for further use; a) the ingredient comprising the compound of formula (I) or mixtures thereof, obtained from step c) is mixed with an ingredient providing free amino groups and reacted under thermal treating.
  20. Method according to anyone of claims 11 to 19 wherein at least one odorant is generated which is selected in the group consisting of: 4-hydroxy-2,5-dimethyl-3( 2H )-furanone; 2,3-butanedione; And mixtures thereof.

Description

Field of the invention The present invention relates to the use of a special class of oligosaccharides, herein called iso-oligosaccharides, for flavour generation during thermal processing of food. The invention also relates to the use of such oligosaccharides in the form of individual compounds, or as mixtures thereof, or in the form of ingredients comprising the individual compounds or mixtures thereof, or as enzymatic or fermented preparations containing the individual compounds or mixtures thereof. Background of the invention The flavour of a product, comprising the aroma (volatile compounds) and the taste (non-volatile compounds) of a product, has been recognised as one of the main drivers for consumers' food preference. There are several means how to modulate flavour during production of foods. Use of raw materials rich in intrinsic flavour as well as addition of various spices, natural or artificial flavourings or flavour enhancers are the most common approaches. Typical flavour characteristics of many foodstuffs are generated during thermal processes such as roasting, frying, drying, baking, toasting, cooking, extrusion etc. In all these processes, Maillard reaction plays a central role in the formation of flavours and colour. Anyways, existing approaches present some drawbacks. Use of pure flavour active molecules such as commercial flavourings in several product categories is intricate (e.g. in the production of wafer or extruded cereals), because many desirable volatile flavour components are lost. This is either due to thermal degradation or flashing off (stripping) during the cooking. Several aroma active compounds are not stable and undergo decomposition and/or reaction with other compounds in the food matrix upon thermal processing. Large volume of steam is also vented during the baking or extrusion process which carries away volatiles aroma compounds. In baked goods that comprise other components, such as a filling or a chocolate coating, it is possible to add flavour active molecules into the non-baked component. However, such solution may be perceived as artificial by consumers due to the mismatch in expectations (consumers expect certain flavour notes such as biscuity/baked note to be perceived form baked component and not from other components). Similarly, in extruded products, flavours can be added to the coating. Yet, as these products are consumed with the milk, the flavour is partially washed out to the milk before the consumption that consequently decreases the flavour intensity of the consumed product. Thus, there would be a need for a method for generation of flavour active compounds directly during the process, especially in the right component where the flavour is expected by the consumers, so that lost during processing is minimized. Furthermore, there is a common trend driven by consumer perception to eliminate or replace flavouring ingredients that are not natural. Thus, there is also a need to remove flavouring ingredients which are not natural. Apart from using natural flavours, thermal flavour generation upon food processing appears to be a promising approach for flavour modulation. Content of Maillard reactants (flavour precursors) in raw materials is often a limiting factor responsible for moderate flavour generation and consequently inferior flavour of several thermally treated products. Addition of pure flavour precursors (Maillard reactants) can boost flavour generation during thermal processes and thus can be used as a tool for flavour modulation. Our invention describes new class of very potent flavour precursors that are commercially available as food ingredients. Several approaches how to boost flavour generation during thermal processes have been described based on addition of Maillard precursors. EP2000032 disclosed use of various amino acids and reducing sugars in order to improve flavour during preparation of baked foodstuff such as wafer, extruded cereal or biscuit. GB1421397A and US3930045 disclosed use sulphur-containing amino acids and reducing sugars for preparation expanded porous food product having a meat-like flavour. US4022920 described use of Amadori compounds (intermediate products of Maillard reaction) as flavour precursors for flavour modulation of the foodstuff heated to at least 90°C before the consumption. EP1266581 described the method for bioconversion of amino acids, peptides and reducing sugar in the presence of yeasts and use of thereof in baking in order to enhance typical baked aroma. Several groups have reported on effect of sugars and free amino acids on the flavour development during extrusion. Impact on sensory attributes and on volatile composition of extruded wheat flour was observed after addition of glucose (5%) and individual amino acids (2%) such as alanine or leucine or lysine or threonine or cysteine. Strong impact of sucrose (0.6%) and cystein or proline (0.5%) on sensory attributes and volatile profile of extruded corn flo