Methods for the production of ferulic acid

A method or process of manufacturing ferulic acid, comprising the steps of:

• (a) providing a starting material comprising:
• oryzanol, a mixture of ferulic acid esters of phytosterols and triterpenoids, cycloartenyl ferulate, 24-methylenecycloartanyl ferulate, and/or campesteryl ferulate;
• and
• (b) hydrolyzing the starting material by adding an alkali to the starting material and agitating or stirring the resultant mixture, wherein sufficient alkali is added such that the resultant mixture reaches a pH of about 10, or between about pH 8 and 11, thereby producing
• a first saponified mixture,
• (c) extracting the first saponified mixture with a first solvent and removing materials soluble in said first solvent, thereby creating or generating a first solvent phase,
• (d) mixing the first solvent phase with an ion swapping agent and agitating or stirring the resultant mixture to generate a first precipitate mixture and fatty acid soaps with counterions that are monovalent, divalent, or trivalent,
• (e) extracting the first precipitate mixture with a second solvent and removing materials soluble in said second solvent, thereby generating a second solvent phase,
• wherein the second solvent comprises hexane, heptane, methanol, ethanol, propanol, isopropanol, a butanol or a combination thereof,
• (f) separating the second solvent phase from the first precipitate mixture,
• (g) mixing a second alkali with the second solvent phase and agitating or stirring the resultant mixture, to generate a second saponified mixture comprising a ferulate salt,
• (h) removing the ferulate salt from the second saponified mixture,
• and
• (i) dissolving the ferulate salt in water or an aqueous solution, to generate a first ferulate salt solution;
• and
• (j) acidifying the first ferulate salt solution to substantially precipitate the ferulic acid,
• thereby producing a precipitated ferulic acid.

A method or process of manufacturing ferulic acid, comprising the steps of:

• (a) preparing or having provided a starting material comprising an oryzanol, or a γ-oryzanol, or a mixture of ferulic acid esters of phytosterols and triterpenoids;
• (b) contacting the starting material with an alkali, thereby converting glycerides, if present, to alkali soaps and thereby generating a hydrolyzed starting material,
• (c) solvent extracting or substantially extracting the hydrolyzed material from step b,
• (d) removing or substantially removing the solvent from step d to generate a first solvent extract containing oryzanol, and
• (e) subjecting the first solvent extract to a hydrolysis process in the presence of an enzyme or mixture of enzymes, water, or water and a polar solvent, wherein the hydrolysis process comprises the steps of:
• (i) mixing the first solvent extract with a first enzyme or mixture of enzymes and agitating or stirring the resultant mixture while heating to produce a first hydrolyzed mixture,
• (ii) extracting or substantially extracting ferulic acid from the first hydrolyzed with a first cation, thereby generating a ferulate salt and creating or generating a first precipitate phase,
• (iii) separating the first solvent phase from the first precipitate mixture and/or first precipitate,
• (iv) substantially dissolving the ferulate salt in water or an aqueous solution to generate a first ferulate salt mixture
• and
• (v) acidifying the ferulate salt mixture, thereby substantially precipitating the ferulic acid.