# US 11,306,271 B2 · Process for producing extracted lipid comprising docosahexaenoic acid

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- Number: US 11,306,271 B2
- Document ID: US11306271B2
- Status: Granted
- Kind: B2
- Application number: 16/868,324
- Filed: 2020-05-06
- Published: 2020-11-26
- Granted: 2022-04-19
- Earliest claimed: 2012-06-15
- Assignees: Commonwealth Scientific and Industrial Research Organisation; Grains Research and Development Corporation; Nuseed Nutritional Australia Pty Ltd
- Applicants: Commonwealth Scientific and Industrial Research Organisation; Grains Research and Development Corporation; Nuseed Nutritional Australia Pty Ltd.
- Inventors: James Robertson Petrie; Surinder Pal Singh; Robert Charles de Feyter
- Web page: https://patentgrep.com/patent/US11306271B2

## CPC

- C11B 1/10: by extracting
- A01H 1/104: {involving modified lipid metabolism, e.g. seed oil composition}
- A01H 5/10: Seeds
- A01H 6/20: Brassicaceae, e.g. canola, broccoli or rucola
- A61K 36/31: Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 3/02: Nutrients, e.g. vitamins, minerals
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/06: Antiarrhythmics
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 13/12: of the kidneys
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 17/06: Antipsoriatics
- A61P 17/08: Antiseborrheics
- A61P 19/10: for osteoporosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/18: for HIV
- A61P 35/00: Antineoplastic agents
- C07C 57/02: with only carbon-to-carbon double bonds as unsaturation
- C07C 57/03: Monocarboxylic acids
- C07C 67/02: by interreacting ester groups, i.e. transesterification
- C11B 1/00: Production of fats or fatty oils from raw materials
- C11C 1/002: {Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids}
- C11C 3/00: Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom (sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F)
- C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)}
- C11C 3/06: with glycerol
- C12N 9/1025: {Acyltransferases (2.3)}
- C12N 15/8247: {involving modified lipid metabolism, e.g. seed oil composition}
- C12Y 203/01: transferring groups other than amino-acyl groups (2.3.1)
- C12Y 203/01075: Long-chain-alcohol O-fatty-acyltransferase (2.3.1.75)
- A23K 20/158: Fatty acids; Fats; Products containing oils or fats
- A23L 33/12: Fatty acids or derivatives thereof
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K 31/231: having one or two double bonds
- A61K 31/232: having three or more double bonds, e.g. etretinate
- A61K 2236/35: Extraction with lipophilic solvents, e.g. Hexane or petrol ether
- C07K 14/415: from plants
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- A01H: NEW PLANTS OR {NON-TRANSGENIC} PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- 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
- 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
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12Y: ENZYMES
- A23K: FODDER
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

The present invention relates to a process for producing ethyl esters of polyunsaturated fatty acids, comprising transesterifying triacylglycerols in extracted plant lipid.

## Claims

### Claim 1

A process for producing extracted lipid, comprising the steps of:
a) obtaining Brassica napus or Camelina sativa seed comprising extractable lipid having a total fatty acid content, the lipid comprising fatty acids esterified as triacylglycerols (TAG), the fatty acids comprising oleic acid, palmitic acid, linoleic acid (LA), γ-linolenic acid (GLA), α-linolenic acid (ALA), stearidonic acid (SDA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA) and eicosatetraenoic acid (ETA), wherein at least 70% by weight of the DHA which is esterified in the form of TAG is esterified at the sn-1 or sn-3 position of TAG, and
b) extracting lipid from the seed.

### Claim 2 (depends on 1)

The process of claim 1, wherein EPA, DPA and DHA, and optionally arachidonic acid (ARA), are each present at a level in the total fatty acid content, each level being expressed as a percentage of the total fatty acid content, whereby the sum total of the levels of ARA, EPA, DPA and DHA in the extractable lipid is between 7% and 25% by weight of the total fatty acid content.

### Claim 3 (depends on 1)

The process of claim 1, wherein GLA is present in the extracted lipid at a level of less than 2% by weight of the total fatty acid content.

### Claim 4 (depends on 3)

The process of claim 3, wherein at least 80% by weight of the DHA esterified in the form of TAG in the extracted lipid is at the sn-1 or sn-3 position of TAG.

### Claim 5 (depends on 1)

The process of claim 1, wherein SDA, ETA, EPA, DPA and DHA are each present at a level in the total fatty acid content, each level being expressed as a percentage by weight of the total fatty acid content, whereby the sum of the percentages for ETA, EPA, DPA and DHA divided by the sum of the percentages for SDA, ETA, EPA, DPA and DHA, expressed as a percentage, is at least 75%.

### Claim 6 (depends on 5)

The process of claim 5, wherein at least 80% by weight of the DHA esterified in the form of TAG in the extracted lipid is at the sn-1 or sn-3 position of TAG.

### Claim 7 (depends on 1)

The process of claim 1, wherein ETA, EPA, DPA and DHA are each present at a level in the total fatty acid content, each level being expressed as a percentage by weight of the total fatty acid content, whereby the sum of the percentages for EPA, DPA and DHA divided by the sum of the percentages for ETA, EPA, DPA and DHA, expressed as a percentage, is between 75% and 98%.

### Claim 8 (depends on 7)

The process of claim 7, wherein at least 80% by weight of the DHA esterified in the form of TAG in the extracted lipid is at the sn-1 or sn-3 position of TAG.

### Claim 9 (depends on 1)

The process of claim 1, wherein DHA is present in the extracted lipid at a level of between 2.7% and 3.3% by weight of the total fatty acid content.

### Claim 10 (depends on 1)

The process of claim 1, wherein DHA is present in the extracted lipid at a level of between 7% and 20% by weight of the total fatty acid content.

### Claim 11 (depends on 1)

The process of claim 1, further comprising a step of purifying the extracted lipid.

### Claim 12 (depends on 2)

The process of claim 2, further comprising a step of purifying the extracted lipid.

### Claim 13 (depends on 3)

The process of claim 3, further comprising a step of purifying the extracted lipid.

### Claim 14 (depends on 4)

The process of claim 4, further comprising a step of purifying the extracted lipid.

### Claim 15 (depends on 1)

The process of claim 1, further comprising a step of transesterifying the extracted lipid to thereby produce fatty acid esters.

### Claim 16 (depends on 15)

The process of claim 15, further comprising a step of fractionating the fatty acid esters.

### Claim 17 (depends on 1)

The process of claim 1, wherein the Brassica napus or Camelina sativa seeds of step a) are obtained from Brassica napus or Camelina sativa plants grown in a field as a population of at least 1,000 plants.

### Claim 18 (depends on 17)

The process of claim 17, wherein the process comprises, prior to step a), a step of cultivating the at least 1000 Brassica napus or Camelina sativa plants in the field, and step a) comprises harvesting Brassica napus or Camelina sativa seeds from the at least 1000 Brassica napus or Camelina sativa plants.