# US 2016/0256503 A1 · Isolation of omega-7 fatty acid ethyl esters from natural oils > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2016/0256503 A1 - Document ID: US20160256503A1 - Status: Published application - Kind: A1 - Application number: 15/157,047 - Filed: 2016-05-17 - Published: 2016-09-08 - Earliest claimed: 2013-11-22 - Assignees: Heliae Development, LLC - Applicants: Heliae Development LLC - Inventors: Sandip SHINDE; Stephen VENTRE; Jennifer LLOYD-RANDOLFI; Mike LAMONT - Web page: https://patentgrep.com/patent/US20160256503A1 ## CPC - A61K 36/02: Algae - A61K 8/37: Esters of carboxylic acids - A61K 31/231: having one or two double bonds - A61Q 19/00: Preparations for care of the skin - C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)} - C12P 7/6458: by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis - 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) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM - C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)} ## Abstract Methods of producing high purity palmitoleic acid esters from natural oils are disclosed. The natural oils may comprise plant oil, nut oil, microalgae oil, and fish oil. The methods of processing the natural oil comprise transesterification with ethanol as the reacting solvent to produce ethyl esters. Methods of producing a high purity fraction of Omega-3, 6, & 9 fatty acid esters from natural oils are also disclosed. The high purity fatty acid esters may be used in nutrition, cosmetic, and nutraceutical products. ## Claims ### Claim 1 A method of producing high purity palmitoleic acid ethyl esters, comprising: a. Providing a microalgae oil; b. Transesterifying the microalgae oil with a catalyst and ethanol as a reacting solvent in a reaction comprising at least one stage to produce ethyl esters; c. Distilling the ethyl esters to produce a first fraction comprising C18:1n9, C20:4n6, and C20:5n3 ethyl esters, and a second fraction comprising C16:0 and C16:1n7 ethyl esters; and d. Separating the C16:0 and C16:1n7 ethyl esters of the second fraction to produce a third fraction of C16:0 ethyl esters and a fourth fraction comprising at least 35% w/w C16:1n7 ethyl esters. ### Claim 2 (depends on 1) The method of claim 1, wherein the microalgae oil consists of a natural microalgae oil comprising at least 5% C16:1n7 fatty acid. ### Claim 3 (depends on 2) The method of claim 2, wherein the natural microalgae oil comprises oil derived from at least one microalga from a genus selected from the group consisting of Nannochloropsis, Nitzschia, Thalasossira, and Phaeodactylum. ### Claim 4 (depends on 1) The method of claim 1, wherein the catalyst of the transesterifying step comprises at least one catalyst selected from the group consisting of: NaOH, KOH, sodium ethoxide, HCl, BF3, H3PO4, an organic sulfonic acid, sulphuric acid, a metal oxide, Mg—Al hydrolalcite, and an immobilized enzyme. ### Claim 5 (depends on 1) The method of claim 1, wherein the molar ratio of ethanol in the transesterifying step is in the range of 1:3 to 1:15. ### Claim 6 (depends on 5) The method of claim 5, wherein the molar ratio of ethanol in the transesterifying step is in the range of 1:6 to 1:8. ### Claim 7 (depends on 1) The method of claim 1, wherein the transesterifying step comprises two stages of transesterification reactions. ### Claim 8 (depends on 7) The method of claim 7, wherein the two stages of transesterification reactions use different catalysts. ### Claim 9 (depends on 1) The method of claim 1, wherein the transesterifying step has a yield in the range of 60-80%. ### Claim 10 (depends on 1) The method of claim 1, wherein the transesterifying step is performed at a temperature in the range of 75-85° C. ### Claim 11 (depends on 1) The method of claim 1, wherein the distillation step comprises at least one selected from the group consisting of one pass vacuum distillation, two pass vacuum distillation, fractional distillation, and simple molecular distillation. ### Claim 12 (depends on 1) The method of claim 1, wherein the separation step comprises at least one selected from the group consisting of urea complexation, crystallization, filtration, extraction, and adsorption chromatography. ### Claim 13 (depends on 1) The method of claim 1, wherein the fourth fraction comprises 35-50% w/w C16:1n7 ethyl esters. ### Claim 14 (depends on 3) The method of claim 3, wherein the second fraction derived from natural Nannochloropsis oil comprises less than 50% w/w C16:0 ethyl esters. ### Claim 15 (depends on 14) The method of claim 14, wherein the first fraction derived from natural Nannochloropsis oil further comprises less than 10% w/w C16:0 ethyl esters. ### Claim 16 (depends on 3) The method of claim 3, wherein the first fraction derived from natural Nannochloropsis oil comprises less than 30% w/w C18:1n9 ethyl esters. ### Claim 17 (depends on 16) The method of claim 16, wherein the second fraction derived from natural Nannochloropsis oil further comprises less than 10% w/w C18:1n9 ethyl esters. ### Claim 18 (depends on 3) The method of claim 3, wherein the second fraction derived from natural Nannochloropsis oil further comprises at least 40% w/w of C16:1n7 and C18:1n9 ethyl esters combined. ### Claim 19 (depends on 1) The method of claim 1, further comprising including the C16:1n7 ethyl esters in a product selected from the group consisting of a nutrition product, cosmetic product, and nutraceutical product. ### Claim 20 (depends on 11) The method of claim 11, wherein the distillation step is performed at a pressure in the range of 0.3-5 mm Hg and a temperature in the range of 140-280° C.