Metal-complexing aroma compounds for use in aroma stabilization

Patent metadata

Field	Value
Publication number	US-9332783-B2
Application number	US-201313862449-A
Country	US
Kind code	B2
Filing date	Apr 14, 2013
Priority date	Apr 24, 2012
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The present invention relates to the use of one or more compounds of the formulae

and/or pharmaceutically acceptable salts thereof for inhibiting the oxidation of fatty acids and/or triacylglycerols; and/or the rancidification of products that includes one or more of fatty acids and/or one or a plurality of triacylglycerols; and/or chemical and/or sensory changes of products that includes one or more of fatty acids and/or one or a plurality of triacylglycerols, caused by the action of the oxygen of the air. Corresponding mixtures and orally consumable preparations and methods are also described.

First claim

What is claimed is:

1. A method for inhibiting the oxidation of fatty acids and/or triacylglycerols catalyzed by divalent or higher-valent metal ions or for inhibiting the rancidification of products that comprise one or more fatty acids and/or one or more triacylglycerols catalyzed by divalent or higher-valent metal ions comprising:
(a) forming a mixture of the fatty acids and/or triacylglycerols with one or more compounds selected from the group consisting of:
i) a compounds of formula (I)

wherein each R 1 independently denotes H, OH, or NH 2 ; and
each R 2 independently denotes OH, OCH 3 , OC 2 H 5 , OCH 2 CH 2 CH 3 , NHCH 3 , NHC 2 H 5 , or NHCH 2 CH 2 CH 3 ; or a pharmaceutically acceptable salt thereof;

ii) a compound of formula (II)

wherein each R 5 independently denotes H or CH 3 ; and
x denotes CH 2 or CO; or a pharmaceutically acceptable salt thereof; and

iii) a compound of formula (III)

 or a pharmaceutically acceptable salt thereof; and

(b) inhibiting the oxidation of the fatty acids and/or triacylglycerols catalyzed by divalent or higher-valent metal ions.

2. The method of claim 1 for inhibiting the oxidation of fatty acids, wherein the fatty acids are selected from the group consisting of saturated fatty acids and singly, doubly, triply, and more than triply unsaturated fatty acids.

3. The method of claim 1 for inhibiting the oxidation of triacylglycerols, wherein the triacylgycerols contain saturated fatty acid residues, singly unsaturated fatty acid residues, doubly unsaturated fatty acid residues, triply unsaturated and/or more than triply unsaturated fatty acid residues.

4. The method of claim 1 , wherein the total amount of compounds and salts of formula (I), formula (II), and formula (III) is in the range of 0.01 through 2.9 mmol per kg of the mixture.

5. The method of claim 1 , wherein the total amount of compounds and salts of formula (I), formula (II), and formula (III) is in the range of 0.05 through 0.20 mmol per kg of the mixture.

6. The method of claim 1 , wherein the total amount of fatty acids and triacylglycerols is in the range from 99.96400through 99.99972wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

7. The method of claim 1 , wherein the total amount of fatty acids and triacylglycerols is in the range from 99.987600 through 99.99820 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

8. The method of claim 1 , wherein the total amount of fatty acids and triacylglycerols is in the range from 99.99000 through 99.99640 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

9. The method of claim 1 , wherein the ratio of the compounds and salts of formula (I), formula (II), and formula (III) to the fatty acids and triacylglycerols is in the range from 1:1.25※10 6 through 1:6250.

10. The method of claim 1 , wherein the mixture further comprises one or more different metal ions selected from the group consisting of metal cations of the first and second main group with an atomic number above 20, transition metal cations and metallic and semi-metallic cations of the third, fourth, fifth and sixth main group.

11. The method of claim 10 , wherein the cations are selected from the group consisting of iron, copper, manganese, zinc, nickel, cadmium, lead, cobalt, arsenic and aluminum ions.

12. The method of claim 10 , wherein the cations are selected from the group consisting of iron, copper and zinc ions.

13. The method of claim 10 , wherein the total amount of iron, copper, manganese, zinc, nickel, cadmium, lead, cobalt, arsenic and aluminum ions is in the range from 0.00020 through 0.02000 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

14. The mixture of claim 10 , wherein the total amount of iron, copper, manganese, zinc, nickel, cadmium, lead, cobalt, arsenic and aluminum ions is in the range from 0.00100 through 0.01000 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

15. The method of claim 10 , wherein the total amount of iron, copper, manganese, zinc, nickel, cadmium, lead, cobalt, arsenic and aluminum ions is in the range from 0.00200 through 0.00800 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

16. The method of claim 10 , wherein the total amount of compounds and salts of formula (I), formula (II), and formula(III), of fatty acids and triacylglycerol, and of metal ions, is at least 99.96408 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

17. The method of claim 10 , wherein the total amount of compounds and salts of formula (I), formula (II), and formula(III), of fatty acids and triacylglycerols, and of metal ions, is at least 99.98840 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

18. The method of claim 10 , wherein the total amount of compounds and salts of formula (I), formula (II), and formula(III), of fatty acids and triacylglycerols, and of metal ions, is at least 99.99160 wt. %, wherein the percentage by weight is relative to the total weight of the mixture.

19. The method of claim 10 , wherein the ratio of the total weights (a) of compounds and salts of formula (I), formula (II), and formula(III), to the total weight of iron, copper, manganese, zinc, nickel, cadmium, lead, cobalt, arsenic and aluminum ions is in the range from 1:250 through 1:0.0125.

20. The method of claim 10 , wherein the mixture comprises a maximum of 3200 μg/kg hexanal.

21. The method of claim 10 , wherein the mixture comprises a maximum of 1600 μg/kg hexanal.

22. The method of claim 10 , wherein the mixture comprises a maximum of 320 μg/kg hexanal.

23. The method of claim 10 , wherein the mixture comprises a maximum of 40 μg/kg (E,Z)-2,4-decadienal.

24. The method of claim 10 , wherein the mixture comprises a maximum of 20 μg/kg (E,Z)-2,4-decadienal.

25. The method of claim 10 , wherein the mixture comprises a maximum of 4 μg/kg (E,Z)-2,4-decadienal.

26. The method of claim 10 , wherein the mixture comprises a maximum of 1800 μg/kg (E,E)-2,4-decadienal.

27. The method of claim 10 , wherein the mixture comprises a maximum of 900 μg/kg (E,E)-2,4-decadienal.

28. The method of claim 10 , wherein the mixture comprises a maximum of 180 μg/kg (E,E)-2,4-decadienal.

29. The method of claim 10 , wherein the composition of the mixture is such that it has an induction period longer than 6.0 hours according to DIN EN ISO 6886:2008, at a temperature of 110° C. or higher.

30. The method of claim 10 , wherein the composition of the mixture is such that it has an induction period longer than 12.0 hours according to DIN EN ISO 6886:2008, at a temperature of 110° C. or higher.

31. The method

Assignees

• Symrise Ag

Inventors

• Degenhardt Andreas
• Krammer Gerhard
• Backes Michael

Classifications

• A23B70/10

  by addition of preservatives · CPC title

• A23B2/754

  containing carboxyl groups · CPC title

• A23B2/75

  with doubly-bound oxygen · CPC title

• A23B2/762 Primary

  Organic compounds containing nitrogen · CPC title

• A23L3/3499

  Human Necessities · mapped topic