PL228421B1 - 1'-[(3,7-Dimethyl-3-vinylocta-6-enyl)]-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it - Google Patents
1'-[(3,7-Dimethyl-3-vinylocta-6-enyl)]-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining itInfo
- Publication number
- PL228421B1 PL228421B1 PL419068A PL41906816A PL228421B1 PL 228421 B1 PL228421 B1 PL 228421B1 PL 419068 A PL419068 A PL 419068A PL 41906816 A PL41906816 A PL 41906816A PL 228421 B1 PL228421 B1 PL 228421B1
- Authority
- PL
- Poland
- Prior art keywords
- vinylocta
- dimethyl
- phosphocholine
- glycero
- enyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 3,7-Dimethyl-3-vinylocta-6-enyl Chemical group 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 5
- SUHOQUVVVLNYQR-MRVPVSSYSA-O glycerylphosphorylcholine Chemical compound C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 2
- LVUOVZBYBQSRKR-UHFFFAOYSA-N 3-ethenyl-3,7-dimethyloct-6-enoic acid Chemical compound CC(C)=CCCC(C)(C=C)CC(O)=O LVUOVZBYBQSRKR-UHFFFAOYSA-N 0.000 description 5
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 4
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DCERRXLGNYIYNC-UHFFFAOYSA-N CC(CCC=C(C)C)(CC(Cl)=O)C=C Chemical compound CC(CCC=C(C)C)(CC(Cl)=O)C=C DCERRXLGNYIYNC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Description
Przedmiotem wynalazku jest 1'-[(3,7-dimetylo-3-winylookta-6-enylo]-2‘-hydroksy-sn-glicero-3'-fosfocholina, o wzorze 1, przedstawionym na rysunku.The present invention relates to 1 '- [(3,7-dimethyl-3-vinylocta-6-enyl] -2'-hydroxy-sn-glycero-3'-phosphocholine of formula 1 as shown in the drawing.
Przedmiotem wynalazku jest także sposób otrzymywania 1'-[(3,7-dimetylo-3-winylookta-6-enylo]-2’-hydroksy-sn-glicero-3’-fosfocholiny o wzorze 1.The invention also relates to a method for the preparation of 1 '- [(3,7-dimethyl-3-vinylocta-6-enyl] -2'-hydroxy-sn-glycero-3'-phosphocholine of formula 1.
Wynalazek może znaleźć zastosowanie w przemyśle kosmetycznym, farmaceutycznym oraz jako środek w terapii chorób nowotworowych.The invention may find application in the cosmetics and pharmaceutical industries as well as in the treatment of neoplastic diseases.
Celem wynalazku było opracowanie metody otrzymywania nowej lizofosfatydylocholiny zawierającej cząsteczkę kwasu 3,7-dimetylo-3-winylookta-6-enowego w pozycji sn-1 fosfatydylocholiny, która pełni w tym wypadku rolę nośnika aktywnego; biologicznie kwasu izoprenoidowego ułatwiając jego wnikanie do komórek żywych.The aim of the invention was to develop a method for the preparation of a new lysophosphatidylcholine containing a 3,7-dimethyl-3-vinylocta-6-enoic acid molecule at the sn-1 position of phosphatidylcholine, which in this case acts as an active carrier; biologically isoprenoidic acid, facilitating its penetration into living cells.
Ze zgłoszenia wynalazku P. 418652 znana jest fosfatydylocholina zwierająca dwie cząsteczki kwasu 3,7-dimetylo-3-winylookta-6-enowego jednocześnie w pozycji sn-1 i sn-2 fosfatydylocholiny. Z kolei z opisu wynalazku P. 418945 znana jest fosfatydylocholina zawierająca cząsteczkę kwasu palmitynowego w pozycji sn-1 i cząsteczkę kwasu 3,7-dimetylo-3-winylookta-6-enowego w pozycji sn-2.From the application of the invention, P. 418652, a phosphatidylcholine is known containing two 3,7-dimethyl-3-vinylocta-6-enoic acid molecules simultaneously in the sn-1 and sn-2 positions of phosphatidylcholine. On the other hand, from the description of the invention P. 418945 there is known phosphatidylcholine containing a palmitic acid molecule in the sn-1 position and a 3,7-dimethyl-3-vinylocta-6-enoic acid molecule in the sn-2 position.
Nie jest znana lizofosfatydylocholina zawierająca kwas 3,7-dimetylo-3-winylookta-6-enowy tylko w pozycji sn-1.There is no known lysophosphatidylcholine containing 3,7-dimethyl-3-vinylocta-6-enoic acid only at the sn-1 position.
Istotą wynalazku jest 1 ’-[(3,7-dimetylo-3-winylookta-6-enylo]-2’-hydroksy-sn-glicero-3’-fosfocholina przedstawiona na rysunku oraz sposób jej otrzymywania.The essence of the invention is the 1 '- [(3,7-dimethyl-3-vinylocta-6-enyl] -2'-hydroxy-sn-glycero-3'-phosphocholine shown in the drawing and the method of its preparation.
Istotą sposobu otrzymywania lizofosfatydylocholiny z cząsteczką kwasu 3,7-dimetylo-3-winylookta-6-enowego, jest to, że mieszaninę sn-glicero-3-fosfocholiny (GPC) i tlenku dibutylocyny (DBTO) rozpuszczonych w bezwodnym 2-propanolu poddaje się reakcji z chlorkiem kwasu 3,7-dimetylo-3-winylookta-6-enowego, również rozpuszczonym w propan-2-olu, w obecności trietyloaminy (TEA). Całość miesza się przez co najmniej 1 godzinę w temperaturze wrzenia rozpuszczalnika, a następnie wydziela powstały produkt i oczyszcza go za pomocą chromatografii kolumnowej.The essence of the method of obtaining lysophosphatidylcholine with a molecule of 3,7-dimethyl-3-vinylocta-6-enoic acid is that a mixture of sn-glycero-3-phosphocholine (GPC) and dibutyltin oxide (DBTO) dissolved in anhydrous 2-propanol is subjected to reaction with 3,7-dimethyl-3-vinylocta-6-enoic acid chloride, also dissolved in propan-2-ol, in the presence of triethylamine (TEA). The mixture is stirred for at least 1 hour at the reflux temperature of the solvent, and then the resulting product is isolated and purified by column chromatography.
Sposób, według wynalazku, objaśniony jest bliżej na przykładzie wykonania.The method according to the invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d 1P r z k ł a d 1
Do kolby okrągłodennej zawierającej 8 cm3 2-propanol dodaje się 300 mg (1,16 mmol) osuszonej sn-glicero-3-fosfocholiny (GPC) oraz 290 mg (1,17 mmol) tlenku dibutylocyny (DBTO) i całość ogrzewa się w temperaturze wrzenia rozpuszczalnika przez 1 godzinę. Po tym czasie mieszaninę reakcyjną ochładza się i dodaje 242 mg (2,4 mmol) trietyloaminy (TEA) oraz 515 mg (2,4 mmol) chlorku kwasu 3,7-dimetylo-3-winylookta-6-enowego rozpuszczonego w 4 cm3 bezwodnego 2-propanolu. Zawiesinę miesza się intensywnie w temperaturze pokojowej w atmosferze N2 przez 1 godzinę. Po tym czasie mieszaninę poreakcyjną odsącza się pod zmniejszonym ciśnieniem na lejku Schotta przez warstwę celitu, a następnie odparowuje się rozpuszczalnik pod zmniejszonym ciśnieniem. Surowy produkt oczyszcza się za pomocą chromatografii kolumnowej na żelu krzemionkowym stosując jako eluent mieszaninę rozpuszczalników CHCl3:MeOH:H2O, 65:25:4 (v/v/v). Otrzymuje się 162 mg (0,37 mmol) 1’-[(3,7-dimetylo-3-winylookta-6-enylo]-2’-hydroksy-sn-3-gIicero-3'-fosfocholiny z wydajnością 32% w postaci mazistej substancji o czystości >98% (wg HPLC).To a round bottom flask containing 8 cm 3 of 2-propanol was added 300 mg (1.16 mmol) of dried sn-glycero-3-phosphocholine (GPC) and 290 mg (1.17 mmol) of dibutyltin oxide (DBTO) and the mixture heated at the boiling point of the solvent for 1 hour. After this time, the reaction mixture is cooled and 242 mg (2.4 mmol) of triethylamine (TEA) and 515 mg (2.4 mmol) of 3,7-dimethyl-3-vinylocta-6-enoic acid chloride dissolved in 4 cm 3 are added. anhydrous 2-propanol. The suspension is vigorously stirred at room temperature under N2 atmosphere for 1 hour. After this time, the reaction mixture was filtered under reduced pressure on a Schott funnel through a celite pad, and then the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using a solvent mixture of CHCl3: MeOH: H2O, 65: 25: 4 (v / v / v) as the eluent. 162 mg (0.37 mmol) of 1 '- [(3,7-dimethyl-3-vinylocta-6-enyl] -2'-hydroxy-sn-3-glycero-3'-phosphocholine are obtained with a yield of 32% in greasy form of> 98% purity (by HPLC).
Dane spektroskopowe otrzymanego związku są następujące;The spectroscopic data of the obtained compound are as follows;
1H NMR (600 MHz, CDCla/CDaOD 2:1 (v/v)), 5:0.91 (s, 6H, CHs-11 (A), CHs-11 (B)), 1.17-1.21 (m, 4H, CH2-4 (a), CH2-4 (B)), 1.35, 1.44 (dwa s, 12H, CH3-8 (A), CH3-8 (B), CH3-12 (A), CH3-12 (B)), 1.68 (m, 4H, CH2-5 (A), CH2-5 (B)), 2.12-2.17 (dwa d, J = 13,8 Hz, 4H, układ AB, CH2-2 (A), CH2-2 (B)), 2.99 (s, 18H, -N(CH3)3 (A), -N(CH3)3 (B)), 3.38 (m, 4H, CH2-3 (A), CH2-3 (B)), 3.63-3.66 (m, 2H, jeden z CH2-3' (A), jeden z CH2-3' (B)), 3.66-3.73 (m, 4H, H-2' (A), H-2' (B), jeden z CH2-3' (A), jeden z CH2-3') (B)), 3.83-3.91 (dwa m, 4H, CH2-1' (A), CH2-1' (B)), 4.01-4.06 (szeroki m, 4H, CH2-a (A), CH2-a (B)), 4.74 (d, J = 18,0 Hz, 2H, jeden z CH2-10 (A), jeden z CH2-10 (B)), 4.81 (d, J = 10,8 Hz, 2H, jeden z CH2-10 (A), jeden z CH2-10 (B)) 4.84 (t, J = 7.2 Hz, 2H, H-6 (A), H-6 (B)), 5.92 (dd, J = 18.0, 10,8 Hz, 2H, H-9 (A), H-9 (B));1 3C NMR (151 MHz, CDCI3/CD3OD 2:1 (v/v)) 5: 16.86, 24.93 (C-8 (A), C-8 (B), C-12 (A), C-12 (B)), 22.40 (C-11 (A), C-11 (B)), 22.43 (C-5 (A), C-5 (B)), 38.75 (C-3 (A), C-3 (B)), 40.35, 40.38 (C-4 (A), C-4 (B)), 44.48, 44.50 (C-2 (a), C-2 (B)), 53.67 (t, J = 3.6 Hz, -N(CH3)3 (A), -N(CH3)3 (B)), 58.64 (d, J = 4.9 Hz, C-α (A), C-α (B)), 64.37 (C-1' (A), C-1' (B)), 66.09 (m, C-β (A), C-β (B)), 66.55 (d, J = 5.7 Hz, 1 H NMR (600 MHz, CDCl / CDaOD 2: 1 (v / v)), 5: 0.91 (s, 6H, CHs-11 (A), the CH-11 (B)), 1.17-1.21 (m, 4H , CH2-4 (a), CH2-4 (B)), 1.35, 1.44 (two s, 12H, CH3-8 (A), CH3-8 (B), CH3-12 (A), CH3-12 ( B)), 1.68 (m, 4H, CH2-5 (A), CH2-5 (B)), 2.12-2.17 (two d, J = 13.8 Hz, 4H, AB system, CH2-2 (A) , CH2-2 (B)), 2.99 (s, 18H, -N (CH3) 3 (A), -N (CH3) 3 (B)), 3.38 (m, 4H, CH2-3 (A), CH2 -3 (B)), 3.63-3.66 (m, 2H, one of CH2-3 '(A), one of CH2-3' (B)), 3.66-3.73 (m, 4H, H-2 '(A ), H-2 '(B), one of CH2-3' (A), one of CH2-3 ') (B)), 3.83-3.91 (two m, 4H, CH2-1' (A), CH2 -1 '(B)), 4.01-4.06 (m broad, 4H, CH2-a (A), CH2-a (B)), 4.74 (d, J = 18.0 Hz, 2H, one of CH2-10 (A), one of CH2-10 (B)), 4.81 (d, J = 10.8 Hz, 2H, one of CH2-10 (A), one of CH2-10 (B)) 4.84 (t, J = 7.2 Hz, 2H, H-6 (A), H-6 (B)), 5.92 (dd, J = 18.0, 10.8 Hz, 2H, H-9 (A), H-9 (B)) ; 1 3 C NMR (151 MHz, CDCl 3 / CD 3 OD 2: 1 (v / v)) 5: 16.86, 24.93 (C-8 (A), C-8 (B), C-12 (A), C-12 (B)), 22.40 (C-11 (A), C-11 (B)), 22.43 (C-5 (A), C-5 (B)), 38.75 (C-3 (A), C- 3 (B)), 40.35, 40.38 (C-4 (A), C-4 (B)), 44.48, 44.50 (C-2 (a), C-2 (B)), 53.67 (t, J = 3.6 Hz, -N (CH3) 3 (A), -N (CH3) 3 (B)), 58.64 (d, J = 4.9 Hz, C-α (A), C-α (B)), 64.37 ( C-1 '(A), C-1' (B)), 66.09 (m, C-β (A), C-β (B)), 66.55 (d, J = 5.7 Hz,
PL 228 421 Β1PL 228 421 Β1
C-3' (A), C-3‘ (B)), 68.36 (d, J = 6,5 Hz, C-2’ (A), C-2’ (B)), 111.71 (C-10 (A), C-10 (B)), 123.93 (C-6 (A), C-6 (B)), 130.95 (C-7 (A), C-7 (B)), 144.94 (C-9 (A), C-9 (B)), 171.75 (C-1 (A), C-1 (B));C-3 '(A), C-3' (B)), 68.36 (d, J = 6.5 Hz, C-2 '(A), C-2' (B)), 111.71 (C-10 (A), C-10 (B)), 123.93 (C-6 (A), C-6 (B)), 130.95 (C-7 (A), C-7 (B)), 144.94 (C- 9 (A), C-9 (B)), 171.75 (C-1 (A), C-1 (B));
31P NMR (243 MHz, CDCI3/CD3OD 2:1 (ν/ν)) δ: -0.04; 31 P NMR (243 MHz, CDCl3 / CD3OD 2: 1 (ν / ν)) δ: -0.04;
(α, β) - oznacza sygnały pochodzące od choliny(α, β) - indicates choline-derived signals
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419068A PL228421B1 (en) | 2016-10-11 | 2016-10-11 | 1'-[(3,7-Dimethyl-3-vinylocta-6-enyl)]-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419068A PL228421B1 (en) | 2016-10-11 | 2016-10-11 | 1'-[(3,7-Dimethyl-3-vinylocta-6-enyl)]-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL419068A1 PL419068A1 (en) | 2017-03-27 |
| PL228421B1 true PL228421B1 (en) | 2018-03-30 |
Family
ID=58360359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL419068A PL228421B1 (en) | 2016-10-11 | 2016-10-11 | 1'-[(3,7-Dimethyl-3-vinylocta-6-enyl)]-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL228421B1 (en) |
-
2016
- 2016-10-11 PL PL419068A patent/PL228421B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL419068A1 (en) | 2017-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2681345T3 (en) | Method to produce sepiapterin and tetrahydrolactoylpterin | |
| CN107021985A (en) | The synthetic method of pharmaceutical intermediate R 9 [2 (diethylphosphono methoxyl) propyl group] adenine | |
| PL228423B1 (en) | 1'-(3,7,11,15-Tetramethyl-3-vinylhexadecyl)-2'-hydroxy-sn-glycero-3'-phosphatidylcholine and method for obtaining it | |
| CN108864148B (en) | Rapamycin-40-malic acid sodium salt and preparation method and application thereof | |
| EA010021B1 (en) | Process for the preparation of metal salts of medium –chain fatty acids | |
| CN104892372A (en) | Synthetic method of micromolecule polyethylene glycol | |
| PL229270B1 (en) | 1'-{2-[(2''E)-2''-Butylidene-1'',3'',3''trimethyl]cyclohexyl}acetyl-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL236836B1 (en) | 1-Cinnamoyl-2-hydroxy-sn-glycero-3-phosphocholine and method of preparing 1-cinnamoyl-2-hydroxy-sn-glycero-3-phosphocholine | |
| DE112014001871B4 (en) | Process for the preparation of 3,4,5-tricaffeoylquinic acid | |
| CN111819170B (en) | Methods for synthesizing pulmonary acid and its analogs | |
| JP6212462B2 (en) | Method for producing 3,4,5-tricaffeoylquinic acid | |
| RU2394830C1 (en) | 6-(n-alkylfluorophosphonyloxy)-5,5-dialkyl-6-aza-7-substituted bicyclo[2,2,1]heptene-2 - new class of physiologically active substances and method of obtaining said compounds | |
| PL240744B1 (en) | 1-(3-Methoxycinnamoyl)-2-hydroxy-sn-glycero-3-phosphocholine and method of preparing 1-(3-methoxycinnamoyl)-2-hydroxy-sn-glycerol-3-phosphocholine | |
| PL227314B1 (en) | 1-Veratroyl-2-hydroxy-sn-glycero-3-phosphocholine and method for obtaining it | |
| PL228424B1 (en) | 1'-(3,7-Dimethyl-3-vinylocta-6-enyl)-2'-palmitoyl-sn-glycero-3'-phosphocholine and method for obtaining it | |
| US20260008761A1 (en) | Process for the preparation of taxane derivatives | |
| PL236557B1 (en) | 1'-(3,7,11-Trimethyl-3-vinyldodeca-6,10-dienyl)-2'-hydroxy-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL238965B1 (en) | Method for obtaining 2-lysophosphatidylcholine containing ibuprofen in position sn-1 | |
| PL231816B1 (en) | 1'Palmitoyl-2'-(3,7-Dimethyl-3-vinylocta-6-enyl)-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL229556B1 (en) | 1-Citronelloyl-sn-glycero-3-phosphocholine and method for obtaining it | |
| JP4488161B2 (en) | Process for producing optically active α-silylmethyl-β-hydroxysulfoxide compound | |
| PL230423B1 (en) | 1'2'-Di-[3,7-dimethyl-3-vinylocta-6-enyl]-sn-glycero-3'-phosphocholine and method for obtaining 1',2'-di-[3,7-dimethyl-3-vinylocta-6-enyl]-sn-glycero-3'-phosphocholine | |
| PL229557B1 (en) | 1-Citronelloyl-2-palmitoyl-sn-glycero-3-phosphocholine and method for obtaining it | |
| PL235462B1 (en) | 1,2-Dicinnamoyl-sn-glycerol-3-phosphocholine and method of preparing 1,2-dicinnamoyl-sn-glycerol-3-phosphocholine | |
| PL232663B1 (en) | Phosphatidylcholines and method for obtaining them |