Antioxidant humic acid derivatives and methods of preparation and use

Patent metadata

Field	Value
Publication number	US-9932319-B2
Application number	US-201314894616-A
Country	US
Kind code	B2
Filing date	May 28, 2013
Priority date	May 28, 2013
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

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 selected from the group of at least one compound of a humic acid cleavage derivative, a salt, a chelate, or a combination thereof, wherein the humic acid cleavage derivative is selected from the group consisting of formula II, formula III, formula IV, formula V and formula VI:

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 a chelate thereof.

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

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

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

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

7. The antioxidant compound of claim 1 , wherein R 1 of the humic acid cleavage derivative of formula II, formula IV, and formula VI is a (C 1 -C 20 ) alkyl.

8. The antioxidant compound of claim 1 , wherein R 2 of the humic acid cleavage derivative of formula II, formula III, formula IV, and formula VI is hydrogen.

9. The antioxidant compound of claim 1 , wherein R 2 of the humic acid cleavage derivative of formula II, formula III, formula IV, and formula VI is iodide.

10. The antioxidant compound of claim 1 , wherein R 2 of the humic acid cleavage derivative of formula II, formula III, formula IV, and formula VI is hydroxyl.

11. The antioxidant compound of claim 1 , 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 claim 1 , wherein the compound is a transition metal ion chelate.

13. A method of preparing an antioxidant compound selected from the group of at least one compound of a humic acid cleavage derivative, a salt, a chelate, or a combination thereof, the method comprising:
reacting a humic acid with a cleaving agent to form a reaction mixture,
optionally heating the reaction mixture to about reflux to obtain a substantially homogeneous reaction mixture; and
isolating at least one antioxidant compound of the humic acid cleavage derivative, a salt, or a chelate thereof, wherein the humic acid cleavage derivative is selected from the group consisting of formula II, formula III, formula IV, formula V, and formula VI:

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

14. The method of claim 13 , wherein the humic acid comprises at least one compound having substructure of formula I:

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

15. The method of claim 13 , wherein the cleaving agent is selected from the group consisting of nickel catalyst, sodium borohydride, amide hydro halide salts, lithium chloride in dimethylformamide, hydrogen bromide, and hydrogen iodide.

16. The method of claim 13 , wherein reacting the humic acid with the cleaving agent comprises reacting the humic acid with aqueous hydrogen iodide and sodium hypophosphite to form a suspension.

17. The method of claim 16 , further comprising heating the suspension at about reflux until a substantially homogeneous reaction mixture is obtained.

18. The method of claim 13 , further comprising isolating the salt of the at least one antioxidant compound of the humic acid cleavage derivative.

19. The method of claim 13 , wherein isolating the at least one antioxidant compound of the humic acid cleavage derivative comprises isolating a salt of the antioxidant compound, and the salt is selected from the group consisting of a lithium salt, a sodium salt, an ammonium salt, a potassium salt, a calcium salt, a barium salt, a magnesium salt, a manganese salt, a zinc salt, an aluminum salt, and an iron salt.

20. The method of claim 13 , wherein isolating the at least one antioxidant compound of the humic acid cleavage derivative comprises isolating a derivative where R 1 is a (C 1 -C 20 ) alkyl.

21. The method of claim 13 , wherein isolating the at least one antioxidant compound of the humic acid cleavage derivative comprises isolating a derivative where R 2 is hydrogen.

22. The method of claim 13 , wherein isolating the at least one antioxidant compound of the humic acid cleavage derivative comprises isolating a derivative where R 2 is iodide.

23. The method of claim 13 , wherein isolating at least one antioxidant compound of the humic acid cleavage derivative comprises isolating a derivative where R 2 is hydroxyl.

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal
• Needham Scott Andrew

Classifications

• A61K2800/28

  Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants · CPC title

• A61Q19/001

  Preparations for care of the lips · CPC title

• C08K5/3417

  condensed with carbocyclic rings · CPC title

• C07D209/36

  in position 3, e.g. adrenochrome · CPC title

• C07D307/77 Primary

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title