# US 10,945,983 B2 · Oleocanthal isolation and cancer treatment > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,945,983 B2 - Document ID: US10945983B2 - Status: Granted - Kind: B2 - Application number: 16/079,122 - Filed: 2017-07-21 - Published: 2019-06-27 - Granted: 2021-03-16 - Earliest claimed: 2016-07-21 - Assignees: Board of Supervisors for the University of Louisia - Applicants: Board of Supervisors for the University of Louisiana System - Inventors: Khalid A. El Sayed; Abu Bakar Siddique; Hassan Y. Ebrahim - Web page: https://patentgrep.com/patent/US10945983B2 ## CPC - A61K 31/222: with compounds having aromatic groups, e.g. dipivefrine, ibopamine - A61P 17/00: Drugs for dermatological disorders - A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like - A61P 35/00: Antineoplastic agents - C07C 67/56: by solid-liquid treatment; by chemisorption - C07C 67/58: by liquid-liquid treatment - A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)} - C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A method for extracting S (-)-Oleocanthal from olive oil comprising mixing a first volume of water with a second volume of olive oil to form an olive oil/water mixture; letting the olive oil/water mixture stand; removing an aqueous fraction from the olive oil/water mixture leaving a reduced S (-)-Oleocanthal containing olive oil; and filtering the aqueous fraction to create aqueous S (-)-Oleocanthal. ## Claims ### Claim 1 A method for extracting S (-)-oleocanthal from olive oil comprising: (a) mixing a first volume of water with a second volume of olive oil to form an olive oil/water mixture; (b) letting the olive oil/water mixture stand for a period of time sufficient for phase separation; (c) removing an aqueous fraction from the olive oil/water mixture of step (b), thereby leaving an olive oil fraction containing a reduced amount of S (-)-oleocanthal; and (d) filtering the aqueous fraction to obtain a purified aqueous solution of S (-)-oleocanthal. ### Claim 2 (depends on 1) The method of claim 1 further comprising the step of separating the water from the filtered aqueous S (-)-oleocanthal solution to obtain a dry S (-)-oleocanthal residue. ### Claim 3 (depends on 2) The method of claim 2 further comprising the step of stable freezing under nitrogen the dry S (-)-Oleocanthal residue. ### Claim 4 (depends on 1) The method of claim 1 wherein the olive oil is extra virgin olive oil. ### Claim 5 (depends on 1) The method of claim 1 where the mixing of the volume of water with the volume of olive oil is via vigorous shaking or agitating. ### Claim 6 (depends on 1) The method of claim 1 wherein a total amount of water mixed with the olive oil is at least three times the second volume of olive oil. ### Claim 7 (depends on 1) The method of claim 1 further comprising the step of ultra freezing the aqueous fraction after removal from the olive oil/water mixture. ### Claim 8 (depends on 1) The method of claim 1 wherein the water is separated from the aqueous fraction by freeze drying. ### Claim 9 (depends on 1) The method of claim 1 wherein the water is separated from the aqueous fraction by passing the aqueous fraction over a resin, entrapping the S (-)-oleocanthal, and then eluting the S (-)-oleocanthal from the resin. ### Claim 10 (depends on 9) The method of claim 9 wherein the resin is one of a macroporous styrenic polymeric bead resin allowing for adsorption/desorption process scale applications and having a matrix that provides an aromatic non-polar surface. ### Claim 11 (depends on 9) The method of claim 9 further comprising the steps of washing the resin with water and eluting with acetone. ### Claim 12 (depends on 11) The method of claim 11 further comprising the step of collecting a first portion of acetone elution separate from a second portion of acetone elution, where the first portion of acetone elution is a volume between 15% and 25% of the second portion of acetone elution. ### Claim 13 (depends on 1) The method of claim 1 further comprising performing size exclusion chromatography to obtain a chromatographically purified S (-)-oleocanthal. ### Claim 14 (depends on 13) The method of claim 13 wherein said performing size exclusion chromatography comprises providing CH2 Cl2 an isocratic eluent. ### Claim 15 (depends on 1) The method of claim 1 further comprising the steps of: (e) mixing a second volume of water with a volume of the remaining S (-)-oleocanthal reduced olive oil fraction of step (c), to form a second olive oil/water mixture; (f) letting the second olive oil/water mixture stand for a period of time sufficient for phase separation; (g) removing an aqueous fraction from the second olive oil/water mixture of step (f), thereby leaving an olive oil fraction further reduced in S (-)-oleocanthal; and (h) adding the further aqueous fraction of step (g) to the aqueous fraction of steps (c) or (d). ### Claim 16 (depends on 15) The method of claim 15 further comprising the steps of: (i) mixing a third volume of water with a volume of the remaining S (-)-oleocanthal reduced containing olive oil fraction of step (g) to form a third further olive oil/water mixture; (j) letting the third olive oil/water mixture stand for a period of time sufficient for phase separation; (k) removing an aqueous fraction from the third olive oil/water mixture of step (j), thereby leaving an olive oil fraction further reduced in S (-)-oleocanthal; and (l) adding the aqueous fraction of step (k) to the aqueous fraction of steps (c) or (d). ### Claim 17 (depends on 1) The method of claim 1 further comprising the steps of: (e) separating the water from the aqueous fraction by mixing the aqueous fraction with a non-hexane organic solvent to form an aqueous fraction solvent mixture, (f) letting the mixture of step (e) stand for a period of time to sufficient for phase separation, (g) evaporating an organic phase of the mixture of step (e) to obtain dry S-oleocanthal residue. ### Claim 18 (depends on 1) The method of claim 1, wherein hexane is not used to remove S (-)-oleocanthal from the olive oil.