Beverages and foodstuffs resistant to light induced flavour changes, processes for making the same, and compositions for imparting such resistance

Patent metadata

Field	Value
Publication number	US-9554592-B2
Application number	US-91010106-A
Country	US
Kind code	B2
Filing date	Mar 28, 2006
Priority date	Mar 29, 2005
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

One aspect of the present invention is concerned with a composition containing:
(A) at least 10 μg of particular substituted pyrroles per kg of dry matter; and (B) at least 100 mg per kg of dry matter of a pyranone selected from the group consisting of maltol, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one and combinations thereof;

which composition, when dissolved in water at a dry solids content of 0.1 wt. %, exhibits:
i. an absorption at 280 nm (A 280 ) that exceeds 0.01, preferably exceeds 0.05; and ii. an absorption ratio A 280/560 of at least 100, preferably of at least 200. The present composition can advantageously be used as an additive in beverages or foodstuffs to prevent or reduce light induced flavor changes. The invention also encompasses a process for the manufacture of the aforementioned composition.

First claim

The invention claimed is:

1. A method of manufacturing beer that is resistant to light induced flavour changes, comprising:
(a) obtaining a mixture comprising:
(i) 0.3-35 wt. % of amino compounds selected from the group consisting of amino acids, peptides, proteins and combination thereof;
(ii) 10-90 wt. % of carbohydrates, wherein 0.5-80 wt. % of the carbohydrates, by weight of the mixture, comprise one or more reducing sugars selected from the group consisting of maltose, isomaltose, maltotriose, glucose and fructose; and
(iii) 0-20 wt. % water;

wherein at least 20 wt. % of the dry components in the mixture are from a cereal selected from the group consisting of barley, wheat, rice, rye, maize, sorghum and combinations thereof;
(b) heating the mixture to at least 80° C. for at least 10 seconds to obtain a Maillard reaction product,
which Maillard reaction product, when dissolved in water at a dry solids content of 0.1 wt. %, exhibits an absorption at 560 nm of at least 0.1;
(c) subjecting the Maillard reaction product to ultrafiltration to obtain a filtered product, which filtered product, when dissolved in water at a dry solids content of 0.1 wt. %, exhibits:
i. an absorption at 280 nm (A 280 ) that exceeds 0.01; and
ii. an absorption ratio A 280/560 of at least 200,

wherein the filtered product contains less than 30%, by weight of dry matter, of components having a molecular weight in excess of 30 kDa and comprises:
(A) at least 30% cereal derived matter by weight of dry matter;
(B) at least 10 μg of substituted pyrroles per kg of dry matter, said substituted pyrroles being represented by the following formula:

wherein R 1 represents an optionally oxygenated hydrocarbyl comprising 1-6 carbon atoms; R 2 represents hydrogen or an optionally oxygenated hydrocarbyl comprising 1-6 carbon atoms; and R 3 re presents hydrogen or a linear or branched C 1 -C 5 alkyl residue; and
(C) at least 100 mg per kg of dry matter of a pyranone selected from the group consisting of maltol, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one and combinations thereof; and

(d) adding between 0.01 and 5 wt. %, based on the amount of dry matter being added, of the filtered product to a beer.

2. The method according to claim 1 , wherein the composition contains at least 50 μg of the substituted pyrroles per kg of dry matter.

3. The method according to claim 1 , wherein the composition comprises at least 500 mg per kg of dry matter of a pyranone selected from the group consisting of maltol, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one and combinations thereof.

4. The method according to claim 1 , wherein A 280 exceeds 0.05.

5. The method according to claim 1 , having an absorption ratio A 280/560 of at least 200.

6. The method according to claim 1 , wherein R 1 represents an oxygenated hydrocarbyl comprising 1-6 carbon atoms.

7. The method according to claim 6 , wherein R 1 represents an oxygenated hydrocarbyl comprising 1-4 carbon atoms.

8. The method according to claim 6 , wherein R 1 represents —(CO)CH 3 or —CHO.

9. The method according to claim 8 , wherein R 1 represents —(CO)CH 3 .

10. The method according to claim 8 , wherein R 1 represents —CHO.

11. The method according to claim 1 , wherein R 2 represents hydrogen, C 1 -C 2 alkyl or an oxygenated hydrocarbyl comprising 1-2 carbon atoms.

12. The method according to claim 11 , wherein R 2 represents hydrogen, methyl or —CH 2 OH.

13. The method according to claim 12 , wherein R 2 represents hydrogen.

14. The method according to claim 12 , wherein R 2 represents —CH 2 OH.

15. The method according to claim 1 , wherein R 3 represents hydrogen, methyl or —CH 2 CH 2 CH(CH 3 )CH 3 .

16. The method according to claim 15 , wherein R 3 represents hydrogen.

17. The method according to claim 15 , wherein R 3 represents methyl.

18. The method according to claim 15 , wherein R 3 represents —CH 2 CH 2 CH(CH 3 )CH 3 .

19. The method according to claim 1 , wherein the composition comprises at least 1,000 mg of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one per kg of dry matter.

20. The method according to claim 19 , wherein the composition comprises at least 5,000 mg of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one per kg of dry matter.

21. The method according to claim 1 , wherein the composition comprises at least 100 mg of maltol per kg of dry matter.

22. The method according to claim 21 , wherein the composition comprises at least 500 mg of maltol per kg of dry matter.

23. The method according to claim 1 , wherein the composition comprises at least 1 μg of 5-hydroxymethyl-1-(3-methyl-butyl)-1H-pyrrole-2-carbaldehyde per kg of dry matter.

24. The method according to claim 23 , wherein the composition comprises at least 3 μg of 5-hydroxymethyl-1-(3-methyl-butyl)-1H-pyrrole-2-carbaldehyde per kg of dry matter.

25. The method according to claim 1 , wherein the composition comprises at least 0.1% of reducing sugars by weight of dry matter.

26. The method according to claim 1 , wherein the composition is water soluble.

27. The method according to claim 1 , wherein the composition comprises less than 20%, by weight of dry matter, of components having a molecular weight in excess of 30 kDa.

28. The method according to claim 1 , wherein the composition comprises less than 30%, by weight of dry matter, of components having a molecular weight in excess of 5 kDa.

29. The method according to claim 1 , wherein the solids content of the composition is at least 10 wt. %.

30. The method according to claim 29 , wherein the solids content of the composition is at least 20 wt. %.

31. The method according to claim 30 , wherein the solids content of the composition is at least 30 wt. %.

32. The method according to claim 1 , wherein said composition comprises at least 50% cereal derived matter by weight of dry matter.

33. The method according to claim 1 , wherein the composition is introduced into beer in an amount of between 0.01 and 5 wt. %, calculated on the basis of the amount of dry matter introduced.

34. The method according to claim 33 , wherein the composition is introduced into the beer in an amount of between 0.02 and 3 wt. %, calculated on the basis of the amount of dry matter introduced.

35. A beer that is resistant to light induced flavour changes, wherein the beer is obtained by a method according to claim 1 .

Assignees

• Hughes Paul Shane
• Blokker Peter
• Brouwer Eric Richard
• Alewijn Martinus
• Van Der Ark Richard
• Heineken Supply Chain Bv

Inventors

• Hughes Paul Shane
• Blokker Peter
• Brouwer Eric Richard
• Alewijn Martinus
• Van Der Ark Richard

Classifications

• A23L2/58

  Colouring agents · CPC title

• C12C5/02

  Additives for beer · CPC title

• A23L5/41

  Retaining or modifying natural colour by use of additives, e.g. optical brighteners (A23L5/42 takes precedence) · CPC title

• A23L3/3544

  Human Necessities · mapped topic

• A23L3/3526 Primary

  Human Necessities · mapped topic