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1. WO2005077929 - PHENOLIC COMPOUND PURIFICATION

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CLAIMS
What is claimed is:

1. A process for the production of purified isoflavones from a starting material resulting from a biological source, the starting material comprising at least one isoflavone in its conjugate form and at least one impurity, the process comprising: (a) adjusting the concentration of the starting material in an aqueous medium so that the concentration of the isoflavone conjugates therein is greater than about 20 percent (%) of saturation, but smaller than saturation, whereby there is formed an isoflavone purified solution comprising a purified isoflavone conjugate and an isoflavone -depleted precipitate containing the impurity, wherein the isoflavone -depleted precipitate contains, after washing, less than about 20 percent (%) of the isoflavone conjugate present in the starting material; (b) separating the isoflavone purified solution from the isoflavone -depleted precipitate; and (c) separating the isoflavone from the isoflavone purified solution.

2. A process for the purification of a starting material resulting from a biological source, the starting material comprising at least one polyphenol glycoside in its conjugate form and at least one non-phenolic compound, comprising: (a) adjusting the concentration of the starting material in an aqueous medium so that the concentration of the polyphenol glycoside in its conjugate form is greater than about 20 percent (%) of saturation, but smaller than saturation, in order to induce the formation of a polyphenol purified solution containing the conjugate and a polyphenol-depleted precipitate containing the non-phenolic compound, wherein the polyphenol-depleted precipitate contains less than about 20 percent (%) of the conjugate present in the starting material; and (b) separating the formed polyphenol purified solution from the polyphenol-depleted precipitate.

3. The process of Claim 2 further comprising the step of: (c) separating the polyphenol from the purified solution.

4. The process of Claim 3 wherein separating the polyphenol comprises a step (c(i)) of hydrolyzing the conjugate in the polyphenol purified solution to its glycoside or aglycone form, inducing thereby formation of a polyphenol enriched precipitate enriched in the polyphenol in glycoside or aglycone form from the purified solution.

5. The process of Claim 4 comprising the further step (c(ii)) of separating the polyphenol enriched precipitate from the purified solution.

6. The process of Claim 5 wherein the polyphenol is a flavonoid.

7. The process of Claim 6 wherein the flavonoid is an isoflavone.
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8. The process of Claim 6 wherein the flavonoid is a flavonoid glycoside in its conjugate form and comprises at least one of malonyls of genistin, daidzin and glycitin.

9. The process of Claim 7 wherein the biological source comprises at least one of a plant, an extract thereof, and a processed material derived therefrom.

10. The process of Claim 7 wherein the plant comprises the family Glycine.

11. The process of Claim 7 wherein the plant comprises Glycine max.

12. The process of Claim 7 wherein the biological source comprises at least one of soybean, non-oil products of soybean processing, defatted soy flakes, soybean meal, soy molasses, soy solubles soy whey and soy germ.

13. The process of Claim 7 wherein the biological source comprises at least one of cocoa and citrus.

14. The process of Claim 7 wherein the biological source is initially subjected to ultrafiltration processing to provide a permeate, the permeate comprising the starting material.

15. The process of Claim 14 wherein the permeate is further concentrated, the permeate concentrate comprising the starting material.

16. The process of Claim 7 wherein the starting material is a solid.

17. The process of Claim 7 wherein the solid is a product of co-precipitation of the conjugate and the non-phenolic compound.

18. The process of Claim 7 wherein the starting material also contains polyphenol in its glycoside or aglycones form.

19. The process of Claim 7 wherein the conjugate forms at least about 20 percent (%) of the total polyphenols in the starting material.

20. The process of Claim 7 wherein a total solids concentration of the solution in (c(ii)) is about the same as that of the solution in step (b) or smaller.

21. The process of Claim 7 wherein the temperature of the solution in (c(ii)) is about the same as that of the solution in step (b) or higher.

22. The process of Claim 7 wherein the concentration and the temperature of the solution in (c(ii)) are about the same as those of the solution in step (b).

23. The process of Claim 7 wherein the starting material is formed during the production of purified soy protein.

24. The process of Claim 23 wherein the production comprises extraction with a solvent.

25. The process of Claim 24 wherein the production comprises dissolution of soy protein in an aqueous solution followed by separation of dissolved protein comprising at least one of protein precipitation at about the isoelectric point, membrane separation, and a combination thereof.

26. The process of Claim 7 wherein the starting material comprises at least one of soy solubles, soy whey, soy molasses, precipitates obtained from those, and solutions obtained from those.

27. The process of Claim 7 wherein the adjusted concentration of step (a) is between about 10 percent (%) and about 40 percent (%). The process of Claim 7 wherein the hydrolyzing in (c(i)) is conducted by at least one of treatment at alkaline pH, enzymatic hydrolysis, and a combination thereof.

28. The process of Claim 7 wherein the hydrolyzing in (c(i)) is conducted at pH greater than about 9 and wherein the formation of the polyphenol enriched precipitate further comprises the step of: (d) adjusting the pH of the solution to less than that of hydrolyzing by at least about 0.2 pH units.

29. The process of Claim 28 wherein the hydrolyzing induces formation of the polyphenol depleted precipitate containing less than about 20 percent (%) of the polyphenol present in the starting material.

30. The process of Claim 28 comprising the further step of separating the polyphenol depleted precipitate from the solution before step (d).

31.The process of Claim 28 wherein the total solids concentration in the step of separating the polyphenol depleted precipitate is similar to that of step (d) or greater.

32. The process of Claim 28 wherein the temperature in the step of separating the polyphenol depleted precipitate is similar to that of step (d) or smaller

33. The process of Claim 7 wherein the starting material is a solution with total solutes concentration of less than about 3 percent (%).

34. The process of Claim 7 wherein the adjusting of concentration is conducted by water removal comprising at least one of evaporation, multiple-effect evaporation, reverse osmosis, and a combination thereof.

35. The process of Claim 7 wherein the starting material is solid, and step (a) further comprises introduction of the starting material into water and/or solution using mixing, ultrasound or combinations of those.

36. The process of Claim 7 wherein the polyphenol forms less than about 5 percent (%) of the starting material on dry basis.

37. The process of laim 7 wherein the polyphenol enriched precipitate contains at least about 30 percent (%) of the polyphenol in the starting material.

38. The process of Claim 7 further comprising re-crystallization of the polyphenol enriched precipitate according to the steps of: (e) addition of water and alkali to the polyphenol enriched precipitate to form a solution having pH of at least about pKa - 1.5, wherein pKa is that of the polyphenol and having a total solid concentration of between about 1 percent (%) and about 40 percent (%), whereby there is formed a purified solution containing the polyphenol and the polyphenol depleted precipitate containing the non-phenolic compound, wherein the polyphenol depleted precipitate contains less than 20 percent (%) of the polyphenol present in the polyphenol enriched precipitate; (f) separating the purified solution from polyphenol depleted precipitate and (g) adjusting the pH of the purified solution resulting from step (f) to smaller than that of step (e) by at least about 0.2 pH units, inducing thereby precipitation of a precipitate further enriched in the polyphenol, the further enriched precipitate comprising at least 30 percent (%) phenolic compound on a dry basis.

39. The processof Claim 38 further comprising at least one recrystallization of the precipitate further enriched in the polyphenol.

40. The processof Claim 39 wherein the recrystallizations are conducted in a counter-current mode.

41. The process of Claim 40 further comprising a step of purifying the precipitate further enriched in the polyphenolcomprising at least one of solvent extraction,
chromatographic separation, ion-exchange, adsorption on resin of low polarity and a combination thereof.

42. A purified polyphenol produced from a starting material resulting from a biological source, the starting material comprising a mixture of at least one isoflavone in its conjugate form and at least one impurity, wherein the purified polyphenol is made by the process comprising: (a) adjusting the concentration of the starting material in an aqueous medium so that the concentration of the isoflavone conjugates therein is greater than about 20 percent (%) of saturation, but smaller than saturation, whereby there is formed a purified solution containing the isoflavone conjugate and an isoflavone depleted precipitate containing the at least one impurity, wherein the isoflavone-depleted precipitate contains, after washing, less than about 20 percent (%) of the isoflavone conjugate present in the starting material; (b) separating the formed purified solution from the isoflavone-depleted precipitate; and (c) separating the isoflavone from the purified solution.

43. The purified polyphenol of Claim 42 wherein the steps (a) and (b) are conducted at pH less than about 9.5.

44. The process of Claim 42 wherein the steps (a) and (b) are conducted at about neutral pH.

45. The purified polyphenol of Claim 42 >vherein the steps (a) and (b) are conducted at about acidic pH.

46. The purified polyphenol of Claim 42 wherein the starting solution comprises a protein and the steps (a) and (b) are conducted at pH of between about pi minus 1 and about pi plus 1, wherein pi is the isoelectric point of the protein present in the starting solution.

47. The purified polyphenol of Claim 42 wherein the steps (a) and (b) are conducted at pH between about 3 and about 6.

48. A process for the production of purified isoflavones from a starting material resulting from a biological source, the starting material comprising a mixture of at least one isoflavone conjugate and at least one impurity, comprising: (a) adjusting the concentration of the starting material in an aqueous medium so that the concentration of the at least one isoflavone conjugates therein is greater than about 20 percent (%) of solubility, but less than saturation, whereby there is formed a purified solution containing the isoflavone conjugate and insolubles containing the impurity, wherein the insolubles contain after washing less than about 20 percent (%) of the isoflavone conjugate present in the starting material; (b) separating the formed purified solution from the insolubles; and (c) hydrolyzing the isoflavone conjugate in the purified solution to its glycoside or aglycones form, inducing thereby precipitation of a precipitate enriched in the isoflavone in glycoside or aglycones form.