GB877031A - A process for the production of natural phospholipids and related substances - Google Patents
A process for the production of natural phospholipids and related substancesInfo
- Publication number
- GB877031A GB877031A GB21837/58A GB2183758A GB877031A GB 877031 A GB877031 A GB 877031A GB 21837/58 A GB21837/58 A GB 21837/58A GB 2183758 A GB2183758 A GB 2183758A GB 877031 A GB877031 A GB 877031A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphoric acid
- choline ester
- ester
- fatty acids
- essential
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940042880 natural phospholipid Drugs 0.000 title abstract 2
- 239000000126 substance Substances 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 12
- -1 choline ester Chemical class 0.000 abstract 9
- 229960001231 choline Drugs 0.000 abstract 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 7
- 230000001476 alcoholic effect Effects 0.000 abstract 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 239000011261 inert gas Substances 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- 150000004665 fatty acids Chemical class 0.000 abstract 3
- 150000003904 phospholipids Chemical class 0.000 abstract 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000007717 exclusion Effects 0.000 abstract 2
- 229940067606 lecithin Drugs 0.000 abstract 2
- 239000000787 lecithin Substances 0.000 abstract 2
- 235000010445 lecithin Nutrition 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000002002 slurry Substances 0.000 abstract 2
- 239000003998 snake venom Substances 0.000 abstract 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 abstract 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 235000004626 essential fatty acids Nutrition 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940055076 parasympathomimetics choline ester Drugs 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A natural phospholipid is obtained from soya bean crude lecithin by extracting the crude lecithin with acetone, extracting the residual ester mixture with alcohol, allowing the alcoholic solution to stand for several days to clarify it from suspended colloidal particles, removing the alcoholic solution containing, as predominantly the basic component, a choline ester of diglyceride phosphoric acid, and recovering the said phospholipid from the alcohol solution, all steps being carried out in the presence of an inert gas at a temperature not exceeding 35 DEG C. whilst excluding the presence of oxygen and light. The phospholipid obtained has a content of substantially 60% essential and other unsaturated fatty acids relative to the total fatty acid content. The clarified alcoholic solution containing the choline ester of diglyceride phosphoric ester may be distilled under vacuum with exclusion of light and oxygen and in the presence of an inert gas e.g. nitrogen or CO2 and the product may be further treated to complete the separation of cephalin by passing an alcoholic solution thereof of 2-3% concentration at a temperature not exceeding 35 DEG C. with the exclusion of light and oxygen and in the presence of an inert gas such as nitrogen through an absorption column containing an alcoholic slurry of a carbonate and/or oxide of one or more elements of the second, third or fourth group of the Periodic Table, preferably Al and/or Mg and/or Si and eluting the slurry with alcohol. On distillation of the alcoholic eluate under vacuum in the presence of an inert gas while excluding oxygen and light a chemically pure choline ester of diglyceride phosphoric acid is obtained which has a high content of essential fatty acids and is suitable for intravenous administration. The chemically pure choline ester may be treated with snake venom to form monoglyceride phosphoric acid choline esters, the treatment with snake venom being carried out in a solvent medium, e.g. peroxide-free ether, in which the monoglyceride phosphoric acid choline ester is insoluble and the fatty acids which are split off in the alpha position are soluble. The invention also includes (a) a phospholipid containing a choline ester of diglyceride phosphoric acid as the basic component and containing substantially 60% essential unsaturated fatty acids, (b) a substantially chemically pure cephalin-free choline ester of diglyceride phosphoric acid containing substantially 66-70% essential unsaturated fatty acids, and (c) a choline ester of monoglyceride phosphoric acid having substantially 28% essential unsaturated fatty acid content, the percentage-essential unsaturated fatty acid content being based in each case on the total fatty acid content and an example is given in which such products are obtained from crude soya bean phosphaltides.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEN13867A DE1047597B (en) | 1957-07-09 | 1957-07-09 | Process for the production of natural choline phosphoric acid diglyceride esters poor in colaminphosphoric acid diglyceride esters |
Publications (1)
Publication Number | Publication Date |
---|---|
GB877031A true GB877031A (en) | 1961-09-13 |
Family
ID=7339787
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21837/58A Expired GB877031A (en) | 1957-07-09 | 1958-07-08 | A process for the production of natural phospholipids and related substances |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1047597B (en) |
GB (1) | GB877031A (en) |
NL (1) | NL229049A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5214171A (en) * | 1988-12-08 | 1993-05-25 | N.V. Vandemoortele International | Process for fractionating phosphatide mixtures |
US7465717B2 (en) | 2004-09-27 | 2008-12-16 | Soymor | Process for releasing and extracting phosphatides from a phosphatide-containing matrix |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE617508C (en) * | 1932-06-22 | 1935-08-20 | I G Farbenindustrie Akt Ges | Process for the production of pure lecithin |
-
1957
- 1957-07-09 DE DEN13867A patent/DE1047597B/en active Pending
-
1958
- 1958-06-26 NL NL229049A patent/NL229049A/nl unknown
- 1958-07-08 GB GB21837/58A patent/GB877031A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5214171A (en) * | 1988-12-08 | 1993-05-25 | N.V. Vandemoortele International | Process for fractionating phosphatide mixtures |
US7465717B2 (en) | 2004-09-27 | 2008-12-16 | Soymor | Process for releasing and extracting phosphatides from a phosphatide-containing matrix |
Also Published As
Publication number | Publication date |
---|---|
DE1047597B (en) | 1958-12-24 |
NL229049A (en) | 1963-07-15 |
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