Antioxidant humic acid derivatives and methods of preparation and use

Patent metadata

Field	Value
Publication number	US-2016102069-A1
Application number	US-201314894616-A
Country	US
Kind code	A1
Filing date	May 28, 2013
Priority date	May 28, 2013
Publication date	Apr 14, 2016
Grant date	—

Abstract

Disclosed are antioxidative, natural compounds, their salts, chelates and cleavage derivatives that exhibit a superior combination of properties. The compounds can be used for a variety of purposes, including stabilizing foods, cosmetics, beverages and nutritional supplement. The compounds can be prepared by substantially cleaving a humic acid of formula I to provide at least one antioxidant compounds of formula II, formula III, formula IV, formula V, formula VI, salts, or chelates thereof.

First claim

What is claimed is:

1 . An antioxidant compound comprising at least one compound of formula II, formula III, formula IV, formula V, formula VI, a salt, chelate, or combination thereof:

wherein R 1 is alkyl or substituted alkyl; and R 2 is hydrogen, iodide, or hydroxyl.

2 . The antioxidant compound of claim 1 , wherein the compound is formula II, a salt, or chelate thereof.

3 . The antioxidant compound of claim 1 , wherein the compound is formula III, a salt, or chelate thereof.

4 . The antioxidant compound of claim 1 , wherein the compound is formula IV, a salt, or chelate thereof.

5 . The antioxidant compound of claim 1 , wherein the compound is formula V, a salt, or chelate thereof.

6 . The antioxidant compound of claim 1 , wherein the compound is formula VI, a salt, or chelate thereof.

7 . The antioxidant compound of any one of claims 1 , 2 , 4 , and 6 , wherein R 1 is a (C 1 -C 2 o)alkyl.

8 . The antioxidant compound of any one of claims 1 - 4 , and 6 - 7 , wherein R 2 is hydrogen.

9 . The antioxidant compound of any one of claims 1 - 4 , and 6 - 7 , wherein R 2 is iodide.

10 . The antioxidant compound of any one of claims 1 - 4 , and 6 - 7 , wherein R 2 is hydroxyl.

11 . The antioxidant compound of any one of claims 1 - 10 , wherein the compound is a lithium salt, sodium salt, ammonium salt, potassium salt, calcium salt, barium salt, magnesium salt, manganese salt, zinc salt, aluminum salt, iron salt, or a combination thereof.

12 . The antioxidant compound of any one of claims 1 - 10 , wherein the compound is a sodium salt, potassium salt, calcium salt, ammonium salt, or a combination thereof.

13 . The antioxidant compound as of one of claims 1 - 10 , wherein the compound is a transition metal ion chelate.

14 . A method of preparing an antioxidant compound, the method comprising cleaving covalent bonds of a humic acid to form at least one antioxidant compound of formulas II-VI a salt, or chelate thereof:

wherein R 1 is alkyl; and R 2 is hydrogen, iodide, or hydroxyl.

15 . The method of claim 14 , wherein the humic acid comprises at least one compound of having the substructure of formula I:

a salt, or chelate thereof, wherein each R 1 is independently alkyl.

16 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by nickel catalyzed hydrogenolysis.

17 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by sodium borohydride.

18 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by amide hydro halide salts.

19 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by lithium chloride in dimethylformamide

20 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by hydrogen bromide.

21 . The method of any one of claims 14 - 15 , wherein the cleaving of covalent bonds is by hydrogen iodide.

22 . The method of claim 21 , wherein cleaving comprises reacting the humic acid with aqueous hydrogen iodide and sodium hypophosphite to form a suspension.

23 . The method of claim 22 , wherein cleaving further comprises heating the suspension at about reflux until a substantially homogeneous reaction is obtained.

24 . The method of any one of claims 14 - 23 , further comprising forming a salt of the at least one compound.

25 . The method of any one of claims 14 - 24 , wherein the salt is a lithium salt, sodium salt, ammonium salt, potassium salt, calcium salt, barium salt, magnesium salt, manganese salt, zinc salt, aluminum salt, iron salt, or a combination thereof.

26 . The method of any one of claims 14 - 25 , further comprising isolating the at least one antioxidant compound.

27 . The method of any one of claims 14 - 26 , wherein R 1 is a (C 1 -C 20 )alkyl.

28 . The method of any one of claims 14 - 27 , wherein R 2 is hydrogen.

29 . The method of any one of claims 14 - 27 , wherein R 2 is iodide.

30 . The method of any one of claims 14 - 27 , wherein R 2 is hydroxyl.

31 . A stabilized food product comprising at least one antioxidant compound of formula II-VI, a salt, or chelate thereof:

in a food product matrix, wherein R 1 is alkyl; and R 2 is hydrogen, iodide, or hydroxyl.

32 . The stabilized food product of claim 31 , wherein the food product matrix is a dairy product, fat, oil, fat emulsion, edible ice, fruit, vegetable, fungi, seaweed, nuts, seeds, confectionery, cereal, cereal product derived from cereal grains, bakery ware, meat, meat byproduct, fish, fish product, egg product, sugar, artificial sweetener, spices, condiment, soup, sauce, salad, protein mix, non-dairy beverage, savory snack, or combinations thereof.

33 . The stabilized food product of claim 31 , wherein the food product matrix is a vegetable oil, animal fat, processed cheeses, chewing gum base, processed meat products, dried meats, sausages, beef patties, meatballs, frozen seafood, pizza toppings, protein, yeast, bakery products, dry cereals, spices, dehydrated potatoes, potato chips, beverage mixes, nonalcoholic beverages, mixed nuts, fruit, vegetables, butter, margarine, dairy products, or combinations thereof.

34 . The stabilized food product of claim 31 , wherein the antioxidant compound extends the shelf-life of the food product matrix.

35 . The stabilized food product of claim 31 , wherein the stabilized food product is stable to about 250-300° C.

36 . The stabilized food product of claim 31 , wherein the antioxidant compound is present in the food product matrix at a concentration of less than 3000 ppm.

37 . The stabilized food product of claim 31 , wherein the antioxidant compound is present in the food product matrix at a concentration of less than 300 ppm.

38 . The stabilized food product of claim 31 , wherein the antioxidant compound is present in the food product matrix at a concentration of less than 100 ppm.

39 . The stabilized food product of claim 31 , wherein the antioxidant compound is present in the food product matrix at a concentration of less than 10 ppm.

40 . The stabilized food product of any one of claims 31 - 39 , wherein R 1 is a (C 1 -C 20 )alkyl.

41 . The stabilized food product of any one of claims 31 - 40 , wherein R 2 is hydrogen.

42 . The stabilized food product of any one of claims 31 - 40 , wherein R 2 is iodide.

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal
• Needham Scott Andrew

Classifications

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C08K5/3417

  condensed with carbocyclic rings · CPC title

• A61K2800/522

  Antioxidants; Radical scavengers · CPC title

• A61Q1/06

  Lipsticks · CPC title

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title