# US 5,705,618 A · Process for extracting lignans from flaxseed > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,618 A - Document ID: US5705618A - Status: Granted - Kind: A - Application number: 08/415,050 - Filed: 1995-03-31 - Granted: 1998-01-06 - Earliest claimed: 1995-03-31 - Assignees: Agriculture and Agri-Food Canada - Inventors: Neil D. Westcott; Alister D. Muir - Web page: https://patentgrep.com/patent/US5705618A ## CPC - C07H 1/08: from natural products - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) ## Abstract A process is described for extracting lignans from flaxseed which comprises contacting a substantially oil-free flaxseed meal with an aliphatic alcohol solvent, e.g. a mixture of methanol or ethanol with water, to extract lignans into the alcohol solvent and separating residual solids from the lignan-rich alcohol solvent. The lignan-rich alcohol solvent is concentrated by removing solvent therefrom and the lignan concentrate obtained is subjected to a base-catalyzed hydrolysis to liberate lignans therefrom in a non-complexed form. Thereafter, the hydrolyzed concentrate is subjected to either a liquid/liquid partition, e.g. by an ethyl acetate/water system, or anion exchange to further enrich the lignans and the lignan-enriched solution thus obtained is subjected to chromatographic separation to isolate lignans at a purity of greater than 90 percent. The lignan, secoisolariciresinol diglucoside, was found in amounts of up to 20 mg per gram of defatted flaxseed. ## Claims ### Claim 1 A process for extracting lignans and/or cinnamic acid derivatives from flaxseed which comprises contacting a substantially oil-free flaxseed meal with an aliphatic alcohol solvent to extract phenolics comprising secoisolariciresinol diglucoside (SDG) and cinnamic acid derivatives into the alcohol solvent, separating residual solids from the phenolic-rich alcohol solvent, subjecting the phenolic-rich alcohol extract obtained to an aqueous base-catalyzed hydrolysis to liberate SDG and cinnamic acid derivatives therefrom in a non-complexed form. ### Claim 2 (depends on 1) A process according to claim 1 wherein the aliphatic alcohol solvent is a mixture of said alcohol and water. ### Claim 3 (depends on 2) A process according to claim 2 wherein the alcohol is selected from methanol and ethanol. ### Claim 4 (depends on 1) A process according to claim 1 wherein the base-catalyzed hydrolysis is carried out by mixing the phenolic-rich alcohol extract with aqueous alkali metal hydroxide. ### Claim 5 (depends on 4) A process according to claim 4 wherein the phenolic-rich alcohol extract is concentrated by removal of solvent. ### Claim 6 (depends on 4) A process according to claim 4 wherein the aqueous base hydrolysate obtained containing SDG is contacted with an anion exchange resin, after which the resin is eluted with water to elute the SDG together with some organic and inorganic materials. ### Claim 7 (depends on 6) A process according to claim 6 wherein the aqueous base hydrolysate is neutralized to a pH in the range 3-7 before contacting the anion exchange resin. ### Claim 8 (depends on 6) A process according to claim 6 wherein the eluate containing SDG is further enriched in SDG by contacting with a reverse-phase resin, after which the resin is eluted with a dilute acid/alcohol gradient to obtain SDG at a purity greater than 90 percent. ### Claim 9 (depends on 6) A process according to claim 6 wherein after the resin is eluted with water to elute the SDG, it is further eluted with a dilute acid to remove a separate product containing glycosides of cinnamic acids and other cinnamic acid derivatives. ### Claim 10 (depends on 4) A process according to claim 4 wherein the aqueous base hydrolysate obtained containing SDG is contacted with a C-18 reverse-phase solid phase extraction resin at pH 3-5, after which the resin is washed with dilute acid and eluted with alcohol. ### Claim 11 (depends on 10) A process according to claim 10 wherein the alcohol eluate from the C-18 reverse-phase solid phase extraction resin is further contacted with a C-18 reverse-phase solid phase extraction resin equilibrated in water, after which the resin is washed with water and dilute alcohol to recover the cinnamic acid glycosides, and the resin eluted with alcohol or an alcohol water mixture to recover the SDG. ### Claim 12 A process for extracting lignans and/or cinnamic acid derivatives from flaxseed which comprises contacting a substantially oil-free flaxseed meal with an aliphatic alcohol solvent to extract phenolics comprising secoisolariciresinol diglucoside (SDG) and cinnamic acid derivatives into the alcohol solvent, separating residual solids from the phenolic-diglucoside (SDG) and cinnamic acid derivatives into the alcohol solvent, separating residual solids from the phenolic-rich alcohol solvent and removing solvent to obtain a phenolic-rich alcohol extract in dry form, subjecting the dry phenolic-rich extract to an anhydrous base-catalyzed hydrolysis to obtain a hydrolyzed anhydrous concentrate containing SDG and cinnamic acid derivatives in a non-complexed form and subjecting the hydrolyzed anhydrous concentrate obtained to liquid/liquid partition using an ethyl acetate/water system whereby SDG is isolated in the aqueous phase and cinnamic acid derivatives are in the ethyl acetate phase. ### Claim 13 (depends on 12) A process according to claim 12 wherein the base-catalyzed hydrolysis is carried out by slurrying the dried extract in anhydrous ethanol or methanol and in the presence of sodium alkoxide or triethylamine. ### Claim 14 (depends on 13) A process according to claim 13 wherein the base catalyzed anhydrous hydrolysate obtained containing SDG is contacted with an anion exchange resin, after which the resin is eluted with water to elute the SDG together with some organic and inorganic materials. ### Claim 15 (depends on 12) A process according to claim 12 wherein the aqueous phase from the liquid/liquid partition is further enriched in SDG by contacting with a reverse phase resin. ### Claim 16 (depends on 14) A process according to claim 14 wherein a separate product containing esters of cinnamic acid glycosides and other cinnamic acid derivatives is removed in the ethyl acetate fraction. ### Claim 17 (depends on 13) A process according to claim 13 wherein the anhydrous base hydrolysate obtained containing SDG is contacted with a C-18 reverse-phase solid phase extraction resin at pH 3-5, after which the resin is washed with dilute acid and eluted with alcohol to elute the SDG together with some organic materials.