CH615191A5 - Process for the preparation of synthetic phospholipids, and their use - Google Patents

Process for the preparation of synthetic phospholipids, and their use Download PDF

Info

Publication number: CH615191A5
Authority: CH; Switzerland
Prior art keywords: ester; phosphoric acid; alk; phospholipids; prepared
Prior art date: 1974-08-06

Application number

CH1028375A

Other languages

German (de)

English (en)

Inventor

Hansjoerg Dr Eibl

Walter Diembeck

Stefan Kovatchev

Original Assignee

Max Planck Gesellschaft

Priority date (The priority date 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 date listed.)

1974-08-06

Filing date

1975-08-06

Publication date

1980-01-15

1975-08-06 Application filed by Max Planck Gesellschaft filed Critical Max Planck Gesellschaft

1980-01-15 Publication of CH615191A5 publication Critical patent/CH615191A5/de

Links

238000000034 method Methods 0.000 title claims description 35
230000008569 process Effects 0.000 title claims description 19
150000003904 phospholipids Chemical class 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 31
239000007795 chemical reaction product Substances 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
230000007717 exclusion Effects 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229940042880 natural phospholipid Drugs 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000011630 iodine Chemical group 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 23
-1 B. from egg yolk Natural products 0.000 description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000787 lecithin Substances 0.000 description 15
235000010445 lecithin Nutrition 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 10
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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 description 8
230000015572 biosynthetic process Effects 0.000 description 8
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
235000019197 fats Nutrition 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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241001465754 Metazoa Species 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
150000001924 cycloalkanes Chemical class 0.000 description 3
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235000014113 dietary fatty acids Nutrition 0.000 description 3
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150000004670 unsaturated fatty acids Chemical class 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
UDIPIOHLDFSMLR-UHFFFAOYSA-N 2-phenylmethoxypropane-1,3-diol Chemical compound OCC(CO)OCC1=CC=CC=C1 UDIPIOHLDFSMLR-UHFFFAOYSA-N 0.000 description 2
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WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
230000007910 cell fusion Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
229940079919 digestives enzyme preparation Drugs 0.000 description 2
235000013345 egg yolk Nutrition 0.000 description 2
210000002969 egg yolk Anatomy 0.000 description 2
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125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
239000000568 immunological adjuvant Substances 0.000 description 2
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238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
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230000035484 reaction time Effects 0.000 description 2
230000007420 reactivation Effects 0.000 description 2
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235000017281 sodium acetate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000021122 unsaturated fatty acids Nutrition 0.000 description 2
238000009736 wetting Methods 0.000 description 2
ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
JFBCSFJKETUREV-LJAQVGFWSA-N 1,2-ditetradecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCC JFBCSFJKETUREV-LJAQVGFWSA-N 0.000 description 1
PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 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 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
206010057248 Cell death Diseases 0.000 description 1
DMKDRSIXSDKEFQ-KDXMTYKHSA-N Cephaline Natural products CCCCCCCCCCCCCCCCCOC(=O)C[C@@H](COP(=O)(O)CCN)C(=O)OCCCCCCCC=CCCCCCCCC DMKDRSIXSDKEFQ-KDXMTYKHSA-N 0.000 description 1
102220517418 DDIT3 upstream open reading frame protein_C47H_mutation Human genes 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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239000004386 Erythritol Substances 0.000 description 1
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ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
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235000015173 baked goods and baking mixes Nutrition 0.000 description 1
230000031709 bromination Effects 0.000 description 1
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125000004122 cyclic group Chemical group 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
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210000002216 heart Anatomy 0.000 description 1
CBCIHIVRDWLAME-UHFFFAOYSA-N hexanitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O CBCIHIVRDWLAME-UHFFFAOYSA-N 0.000 description 1
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XOYXELNNPALJIE-UHFFFAOYSA-N trimethylazanium phosphate Chemical compound C[NH+](C)C.C[NH+](C)C.C[NH+](C)C.[O-]P([O-])([O-])=O XOYXELNNPALJIE-UHFFFAOYSA-N 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Organic Chemistry (AREA)
Biophysics (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Birds (AREA)
Oral & Maxillofacial Surgery (AREA)
Dermatology (AREA)
Cosmetics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

CH1028375A 1974-08-06 1975-08-06 Process for the preparation of synthetic phospholipids, and their use CH615191A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2437832A DE2437832C2 (de)	1974-08-06	1974-08-06	Phospholipide, Verfahren zu ihrer Herstellung sowie ihre Verwendung

Publications (1)

Publication Number	Publication Date
CH615191A5 true CH615191A5 (en)	1980-01-15

Family

ID=5922578

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1028375A CH615191A5 (en)	1974-08-06	1975-08-06	Process for the preparation of synthetic phospholipids, and their use

Country Status (13)

Country	Link
JP (1)	JPS5143723A (fr)
AU (1)	AU8370575A (fr)
BE (1)	BE832182A (fr)
CA (1)	CA1063615A (fr)
CH (1)	CH615191A5 (fr)
DE (1)	DE2437832C2 (fr)
DK (1)	DK355575A (fr)
FR (1)	FR2372631A1 (fr)
GB (1)	GB1522664A (fr)
IE (1)	IE41597B1 (fr)
IT (1)	IT1044020B (fr)
LU (1)	LU73148A1 (fr)
NL (1)	NL7509359A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE442014B (sv) *	1976-10-12	1985-11-25	Barry D Sears	Syntetisk fosfatidyl-kvarter ammoniumforening till anvendning for solubilisering eller emulgering av vattenolosliga foreningar
DE2752125A1 (de) *	1977-11-22	1979-05-23	Max Planck Gesellschaft	Neue phosphororganische ringverbindungen, ihre herstellung und verwendung
EP0122151B1 (fr) *	1983-04-11	1989-02-15	Meito Sangyo Kabushiki Kaisha	Production de dérivés phospholipidiques d'alcools primaires ou secondaires par la technique enzymatique
DE3417235A1 (de) *	1983-12-15	1985-06-27	Rudolf V. Dr.rer.nat Dipl.-Chem. 5024 Pulheim Noronha	Zahnpflegemittel enthaltend phosphatide
DE3663255D1 (en) *	1985-07-26	1989-06-15	Sankyo Co	Phosphate ester derivatives, their preparation and their therapeutic use
GB2267033B (en) *	1992-03-07	1996-01-24	David Garnett	Lysophospholipid Animal Feed Supplement
GB9301701D0 (en) *	1993-01-28	1993-03-17	Biocompatibles Ltd	New zwitterionic materials
AU2245295A (en) *	1994-04-15	1995-11-10	Hemagen/Pfc	Fluorochemical emulsions containing 1,3-dialkylglycerophosphoryl choline surfactants and methods of use
US6828306B2 (en) *	2000-07-31	2004-12-07	Ottawa Heart Institute Research Corporation	Charged lipid compositions and methods for their use

1974
- 1974-08-06 DE DE2437832A patent/DE2437832C2/de not_active Expired
1975
- 1975-08-04 IT IT26086/75A patent/IT1044020B/it active
- 1975-08-05 IE IE1733/75A patent/IE41597B1/en unknown
- 1975-08-05 CA CA232,801A patent/CA1063615A/fr not_active Expired
- 1975-08-05 DK DK355575A patent/DK355575A/da unknown
- 1975-08-05 GB GB32664/75A patent/GB1522664A/en not_active Expired
- 1975-08-05 LU LU73148A patent/LU73148A1/xx unknown
- 1975-08-06 CH CH1028375A patent/CH615191A5/de not_active IP Right Cessation
- 1975-08-06 NL NL7509359A patent/NL7509359A/xx not_active Application Discontinuation
- 1975-08-06 AU AU83705/75A patent/AU8370575A/en not_active Expired
- 1975-08-06 FR FR7524487A patent/FR2372631A1/fr active Granted
- 1975-08-06 JP JP50095095A patent/JPS5143723A/ja active Pending
- 1975-08-06 BE BE158989A patent/BE832182A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE41597L (en)	1976-02-06
IE41597B1 (en)	1980-02-13
FR2372631B1 (fr)	1979-06-22
DE2437832A1 (de)	1976-02-26
DK355575A (da)	1976-02-07
LU73148A1 (fr)	1977-04-13
NL7509359A (nl)	1976-02-10
BE832182A (fr)	1976-02-06
GB1522664A (en)	1978-08-23
FR2372631A1 (fr)	1978-06-30
JPS5143723A (en)	1976-04-14
AU8370575A (en)	1977-02-10
CA1063615A (fr)	1979-10-02
DE2437832C2 (de)	1986-04-10
IT1044020B (it)	1980-02-29

Legal Events

Date	Code	Title	Description
1987-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4159988A (en)	1979-07-03	Synthetic phospholipids, a process for their manufacture and their use
DE60005241T2 (de)	2004-07-01	Verfahren zur Herstellung von Phosphatidylserinen
DE69429093T2 (de)	2002-07-11	Rückgewinnung von tocopherolen
DE69815581T2 (de)	2003-12-24	Verfahren zur Herstellung von pflanzlichen Lysolecithinen
DE1900959A1 (de)	1970-08-27	Verfahren zur Herstellung von Pflanzenphosphatiden mit universeller Emulgierkraft
CH637528A5 (de)	1983-08-15	Verfahren zur gewinnung von oelhaltigen hochgereinigten phosphatidylcholinen.
DE69426114T2 (de)	2001-05-10	Verfahren zur gewinnung hochreinen phosphatidylcholins
EP0036583B1 (fr)	1984-07-18	Ester halogénoalcoyle d'acide glycérine-3-phosphorique et procédé pour sa préparation et son post-traitement
DE102005003625A1 (de)	2006-07-27	Verfahren zur Herstellung einer DHA-haltigen Fettsäure-Zusammensetzung
DE3307925A1 (de)	1984-09-06	Neue 0-acyl-alkandiol-phospholipide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
DE2437832C2 (de)	1986-04-10	Phospholipide, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE3248167A1 (de)	1984-06-28	Trehaloselipidtetraester
EP0002062A1 (fr)	1979-05-30	Composés cycliques organophosphorés, procédé pour leur préparation et leur utilisation
DE1919855A1 (de)	1970-09-10	Diacylglycerine,ihre Zwischenprodukte und Verfahren zu ihrer Herstellung
EP1531182B1 (fr)	2009-10-21	Procédé d'obtention de stérols et de lipides polaires à partir de lécithine par ultrafiltration et prétraitement par amylases et glucosidases
DE3813805A1 (de)	1989-11-02	Verfahren zur desodorierung von fettsaeureestergemischen
DE4027334A1 (de)	1991-03-07	Verfahren zur herstellung von phosphatidylinosit hoher reinheit
DE3639084A1 (de)	1987-06-04	Phosphorsaeureester und verfahren zu deren herstellung
DE2147327A1 (de)	1972-05-04	Verfahren zur Trennung von Phos phatiden aus Phosphaüdmischungen
AT382623B (de)	1987-03-25	Verfahren zur herstellung von kephalinen und kephalin analogen verbindungen und phosphatidyl- glykolverbindungen und deren analogen
DE4210611C2 (de)	1995-09-14	Verfahren zur Abtrennung bzw. Anreicherung von Phosphatidylcholin (PC) aus bzw. in einer Phosphatidmischung durch Extraktion
CH619962A5 (en)	1980-10-31	Process for the preparation of synthetic alkyl esters of phosphatidic acids and their structural analogues.
DE2041932B2 (de)	1973-09-06	Verfahren zur gewinnung von saccharoseestern hoeherer fettsaeuren
DE1958710C3 (de)	1974-05-16	Phosphonatgruppenhaltige Ester
DE3641603C2 (de)	1996-07-04	Verfahren zur Herstellung von gereinigten Phosphorsäureestersalzen