63-89-8

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine is used as a pulmonary surfactant and diagnostic aid for fetal lung maturity. It is utilized in the form of Colfosceril Palmitate, which helps in the treatment of respiratory distress syndrome in premature infants.
Used in Biomedical Research:
DPPC is used as a primary component in the generation of thymoquinone (TQ) liposomes, gold nanorods, and calcium chloride encapsulated liposomes and bilayers for biophysical studies. These applications contribute to the understanding of membrane biophysics and the development of novel drug delivery systems.
Used in Ultrasound Contrast Agents (UCA) Formulations:
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine is used as the main phospholipid component in vesicle preparation for all UCA formulations. It plays a crucial role in enhancing the effectiveness of ultrasound imaging by improving the visibility of blood flow and other internal structures.
Used in Microbubble Preparation:
DPPC is suitable for use as a component in the preparation of microbubbles, which are tiny gas-filled spheres used in various medical imaging techniques, particularly in ultrasound imaging to enhance the visualization of blood vessels and other tissues.
Used in Lipid Bilayer Studies:
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine is used in the preparation of lipid bilayers, which are essential models for studying biological membranes and their interactions with various molecules, including drugs and other bioactive compounds. This application aids in the development of new therapeutic strategies and understanding the mechanisms of membrane-related diseases.

Purification Methods

It has three crystalline forms 1, 2 and ' which change at 60-70o and at 229o, respectively. In order to obtain a fine powder, ~2 g are dissolved in CHCl3 (15mL) and pet ether (b 35-60o) is added; the solution is evaporated to dryness in vacuo at <20o and then dried at 0.1mm over CaCl2. [Baer & Maurukas J Am Chem Soc 74 158 1952, Baer & Kates J Biol Chem 185 615 1950, Beilstein 4 IV 1463.]

InChI:InChI=1/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

Synthetic route

sn-glycero-3-phosphocholine cadmium chloride complex + 1-hexadecylcarboxylic acid (57-10-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 40h; Inert atmosphere;	87%

1-α-glycerophosphocholine cadmium chloride salt + 1-hexadecylcarboxylic acid (57-10-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Stage #1: 1-α-glycerophosphocholine cadmium chloride salt; 1-hexadecylcarboxylic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: In dichloromethane	83%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 72h; Steglich Esterification;

L-glycero-3-phosphorylcholine (28319-77-9) + 1-hexadecylcarboxylic acid (57-10-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With dmap; Hyflo Supre-Cel; dicyclohexyl-carbodiimide In chloroform at 30℃;	80%
Stage #1: L-glycero-3-phosphorylcholine; 1-hexadecylcarboxylic acid With dmap In dichloromethane for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 8h;	80.3%
Stage #1: 1-hexadecylcarboxylic acid With 1,1'-carbonyldiimidazole In chloroform-d1 at 20℃; for 0.75h; Condensation; Stage #2: L-glycero-3-phosphorylcholine With 1,8-diazabicyclo[5.4.0]undec-7-ene In chloroform-d1 at 20℃; for 24h; Acylation;

2-chloroethyl phosphorodichloridate (1455-05-6) + 1,2-dipalmitoyl-sn-glycerol (30334-71-5) + trimethylamine (75-50-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Stage #1: 2-chloroethyl phosphorodichloridate; 1,2-dipalmitoyl-sn-glycerol With triethylamine In dichloromethane phosphorylation; Stage #2: With water; triethylamine In dichloromethane Hydrolysis; Stage #3: trimethylamine In ethanol at 70 - 80℃; for 72h; Substitution;	60.5%

2-(1',2'-dipalmitoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane (59540-20-4) + trimethylamine (75-50-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 16h; Ring cleavage; addition;	56%

palmitic anhydride (623-65-4) + 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8, 17364-17-9, 17364-18-0, 14863-27-5) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With dmap In chloroform for 42h; Ambient temperature;	0.21 g

choline tosylate (55357-38-5) + triethylammonium 1,2-di-O-hexadecanoyl-sn-glycerol 3-hydrogenphosphonate (147632-69-7) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With pyridine; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; water; iodine 2.) 5 min; Yield given. Multistep reaction;

Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-phosphoryloxy]-ethyl}-trimethyl-ammonium; (102152-55-6) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With trimethylamine In toluene for 10h; Ambient temperature; Yield given;

Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-chloro-phosphoryloxy]-ethyl}-trimethyl-ammonium; → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With sodium hydrogencarbonate In chloroform Ambient temperature; Yield given;

2-(N,N-dimethylamino)ethanol (108-01-0) + 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid (7091-44-3) + methyl iodide (74-88-4) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With dmap; 2,4,6-triisopropylphenylsulfonyl chloride; sodium tetraphenyl borate Yield given. Multistep reaction;

n-hexadecanoyl chloride (112-67-4) + phosphoric acid-<(R)-2,3-bis-dihydroxy-propyl ester>-<2-trimethylammonio-ethyl ester betaine → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With chloroform

phosphoric acid-<(R)-2,3-bis-hexadec-9c-enoyloxy-propyl ester>-<2-trimethylammonio-ethyl ester>-betaine → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With ethanol; platinum Hydrogenation;

trimethylamine (75-50-3) + phosphoric acid-<(R)-2,3-bis-palmitoyloxy-propyl ester>-<2-bromo-ethyl ester> → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With toluene Behandeln einer Loesung des Reaktionsprodukts in Methanol mit Silbercarbonat;

phosphoric acid-<(R)-2,3-bis-palmitoyloxy-propyl ester>-phenyl ester-<2-trimethylammonio-ethyl ester>-chloride → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With ethanol; platinum Hydrogenation;

phosphoric acid-<(R)-2,3-bis-palmitoyloxy-propyl ester>-phenyl ester-<2-trimethylammonio-ethyl ester>-sulfate → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With ethanol; platinum Hydrogenation;

palmitic acid carboimidazolide (26227-65-6) + L-glycero-3-phosphorylcholine (28319-77-9) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 24h;

1-hexadecylcarboxylic acid (57-10-3) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: DBU / 24 h View Scheme

1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol (30403-51-1) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 69.5 percent / BCl3 / CH2Cl2 / 20 °C 2.1: Et3N / CH2Cl2 2.2: H2O; Et3N / CH2Cl2 2.3: 60.5 percent / ethanol / 72 h / 70 - 80 °C View Scheme

1-O-hexadecanoyl-3-O-benzyl-sn-glycerol (1487-50-9) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 69.5 percent / DMAP; DCC / CH2Cl2 / 24 h / 20 °C 2.1: 69.5 percent / BCl3 / CH2Cl2 / 20 °C 3.1: Et3N / CH2Cl2 3.2: H2O; Et3N / CH2Cl2 3.3: 60.5 percent / ethanol / 72 h / 70 - 80 °C View Scheme

1,2-dipalmitoyl-sn-glycerol (30334-71-5) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Et3N / benzene / 16 h / 20 °C 2: 56 percent / Et3N / acetonitrile / 16 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: POCl3, Et3N / CHCl3 / Ambient temperature 2: pyridine / CHCl3 / Ambient temperature 3: 10percent aq. NaHCO3 / CHCl3 / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: Et3N / CHCl3 / 0.08 h / Ambient temperature 2: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 3: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 4: Me3N / toluene / 10 h / Ambient temperature View Scheme

1,2-dipalmitoyl-3-triphenylmethyl-sn-glycerol (33625-90-0) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / 12N HCl / CHCl3; methanol / 18 h / 0 °C 2: 90 percent / Et3N / benzene / 16 h / 20 °C 3: 56 percent / Et3N / acetonitrile / 16 h / 20 °C View Scheme

(R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitate (71321-85-2) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CHCl3 / Ambient temperature 2: 10percent aq. NaHCO3 / CHCl3 / Ambient temperature View Scheme

Hexadecanoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester (496808-59-4) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 2: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 3: Me3N / toluene / 10 h / Ambient temperature View Scheme

choline tosylate (55357-38-5) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) tetrazole / 1.) vacuum, 1 h, 2.) CH3CN, THF, 30 min 2: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 3: Me3N / toluene / 10 h / Ambient temperature View Scheme

Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-phosphanyloxy]-ethyl}-trimethyl-ammonium; → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: t-butyl hydroperoxide / toluene / 10 h / Ambient temperature 2: Me3N / toluene / 10 h / Ambient temperature View Scheme

hexadecanoic acid, glycidyl ester (7501-44-2) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOAc / various solvent(s) / 42 h / Heating 2: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme

sodium palmitate (408-35-5) → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / NEt4I / 0.42 h / Heating 2: KOAc / various solvent(s) / 42 h / Heating 3: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme

n-hexadecanoyl chloride (112-67-4) + ent-17-methyl-morphinan-3-ol → L-dipalmitoylphosphatidylcholine (63-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / diethyl ether / -15 °C 2: KOAc / various solvent(s) / 42 h / Heating 3: 0.21 g / DMAP / CHCl3 / 42 h / Ambient temperature View Scheme

L-dipalmitoylphosphatidylcholine (63-89-8) → 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8, 17364-17-9, 17364-18-0, 14863-27-5)

Conditions	Yield
With sodium docusate; phospholipase A2 In aq. buffer at 40℃; for 0.5h; pH=8.5;	99%
With Tris-HCl buffer; calcium chloride; phospholipase A2 In diethyl ether; ethanol at 20℃; for 7h; pH=8.0; deacylation;	77%

L-dipalmitoylphosphatidylcholine (63-89-8) → 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine

Conditions	Yield
With water In ethanol at 25℃; Enzymatic reaction; regioselective reaction;	93%

L-dipalmitoylphosphatidylcholine (63-89-8) → 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid (7091-44-3)

Conditions	Yield
With calcium chloride In dichloromethane; tris hydrochloride at 35℃; for 16h; pH=8; Inert atmosphere; Darkness;	89%

L-homoserine (672-15-1) + L-dipalmitoylphosphatidylcholine (63-89-8) → choline (62-49-7) + Hexadecanoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester (108865-87-8)

Conditions	Yield
With acetate buffer; phospholipase D In chloroform; water at 45℃; for 2h;	A n/a B 83%

D-glucose (50-99-7) + L-dipalmitoylphosphatidylcholine (63-89-8) → Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-2-[hydroxy-((2R,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxo-hexyloxy)-phosphoryloxy]-ethyl ester

Conditions	Yield
With sodium chloride In diethyl ether; water at 30℃; for 24h; phospholipase D from Actinomadura sp. strain No. 362;	76%

L-dipalmitoylphosphatidylcholine (63-89-8) + uridine (58-96-8) → Hexadecanoic acid (R)-2-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester (107110-39-4)

Conditions	Yield
With acetate buffer; calcium chloride; phospholipase D-P In chloroform; water at 45℃; for 6h; pH 6.0;	75%
With acetate buffer; phospholipase D-P In chloroform; water at 25℃; for 0.166667h; Rate constant; pH 6.0; Linewaever-Burk plots; further nucleosides;

L-dipalmitoylphosphatidylcholine (63-89-8) + thymidine (50-89-5) → C41H73N2PO12(CH2)4

Conditions	Yield
With D-glucose In chloroform; acetate buffer at 37℃; for 2h; pH=6.0;	54.3%

L-dipalmitoylphosphatidylcholine (63-89-8) + 1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)cytosine (135598-68-4) → C45H78N4O11P(1-)*Na(1+)

Conditions	Yield
In chloroform; water at 40℃; phospholipase D from Streptomyces sp. AA 586;	42%

6-hydroxyhexyl β-lactoside (757238-05-4) + L-dipalmitoylphosphatidylcholine (63-89-8) → hexadecanoic acid 2-({6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexyloxy}-hydroxy-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

Conditions	Yield
With Streptomyces sp. phospholipase D (EC 3.1.4.4); calcium chloride In phosphate buffer; chloroform at 30℃; for 80h; pH=5.5;	36%

6-hydroxyhexyl β-N-acetyllactosaminide + L-dipalmitoylphosphatidylcholine (63-89-8) → hexadecanoic acid 2-({6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexyloxy}-hydroxy-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

Conditions	Yield
With Streptomyces sp. phospholipase D (EC 3.1.4.4); calcium chloride In phosphate buffer; chloroform at 30℃; pH=5.5;	33%

pentan-1-ol (71-41-0) + L-dipalmitoylphosphatidylcholine (63-89-8) → C40H78O8P(1-)*Na(1+) (92609-93-3)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;	30%

methanol (67-56-1) + L-dipalmitoylphosphatidylcholine (63-89-8) → C36H70O8P(1-)*Na(1+) (92609-89-7)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;

propan-1-ol (71-23-8) + L-dipalmitoylphosphatidylcholine (63-89-8) → C38H74O8P(1-)*Na(1+) (92609-91-1)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phopholipase-D;

ethanol-d6 (1516-08-1) + L-dipalmitoylphosphatidylcholine (63-89-8) → C37H67(2)H5O8P(1-)*Na(1+) (92609-95-5)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;

ethanol (64-17-5) + L-dipalmitoylphosphatidylcholine (63-89-8) → (R)-1-(ethoxy-hydroxy-phosphoryloxy)-2,3-bis-palmitoyloxy-propane; sodium-salt (92609-90-0)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;

d(4)-methanol (811-98-3) + L-dipalmitoylphosphatidylcholine (63-89-8) → C36H67(2)H3O8P(1-)*Na(1+) (92609-94-4)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;

L-dipalmitoylphosphatidylcholine (63-89-8) + neplanocin A (72877-50-0) → C46H79N5O10P(1-)*Na(1+) (116696-44-7)

Conditions	Yield
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction;

L-dipalmitoylphosphatidylcholine (63-89-8) + Mizoribine<*> (50924-49-7) → C44H78N3O13P(2-)*H(1+)*Na(1+) (116539-54-9)

Conditions	Yield
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction;

L-dipalmitoylphosphatidylcholine (63-89-8) + butan-1,1,2,2,3,3,4,4,4-d9-1-ol-d (34193-38-9) → C39H67(2)H9O8P(1-)*Na(1+) (92628-18-7)

Conditions	Yield
With CH3COONa-buffer; calcium chloride In diethyl ether Ambient temperature; phospholipase-D;

L-dipalmitoylphosphatidylcholine (63-89-8) + 5-fluorouridine (316-46-1) → C44H77FN2O13P(1-)*Na(1+) (116696-69-6)

Conditions	Yield
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 6.0, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction;

L-dipalmitoylphosphatidylcholine (63-89-8) + cordycepin (73-03-0) → C45H79N5O10P(1-)*Na(1+) (116595-57-4)

Conditions	Yield
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 5.6, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction;

L-dipalmitoylphosphatidylcholine (63-89-8) + 5-fluorocytidine (2341-22-2) → C44H78FN3O12P(1-)*Na(1+) (116661-29-1)

Conditions	Yield
With acetate buffer; Diaion WK-20 resin ; calcium chloride; phospholipase D-P 1.) H2O, CHCl3, 45 deg C, 6 h, pH 5.6, 2.) CHCl3, MeOH, H2O; Yield given. Multistep reaction;

Upstream product

• 623-65-4 palmitic anhydride 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 55357-38-5 choline tosylate 
• 147632-69-7 triethylammonium 1,2-di-O-hexadecanoyl-sn-glycerol 3-hydrogenphosphonate 
• 102152-55-6 Toluene-4-sulfonate{2-[((R)-2,3-bis-hexadecanoyloxy-propoxy)-methoxy-phosphoryloxy]-ethyl}-trimethyl-ammonium; 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 7091-44-3 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid 
• 74-88-4 methyl iodide 
• 59540-20-4 2-(1',2'-dipalmitoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane 
• 75-50-3 trimethylamine 
• 112-67-4 n-hexadecanoyl chloride 
• 1455-05-6 2-chloroethyl phosphorodichloridate 
• 30334-71-5 1,2-dipalmitoyl-sn-glycerol 
• 28319-77-9 L-glycero-3-phosphorylcholine 

Downstream Products

• 92609-89-7 C₃₆H₇₀O₈P^(1-)*Na⁽¹⁺⁾ 
• 92609-91-1 C₃₈H₇₄O₈P^(1-)*Na⁽¹⁺⁾ 
• 92609-90-0 (R)-1-(ethoxy-hydroxy-phosphoryloxy)-2,3-bis-palmitoyloxy-propane; sodium-salt 
• 62-49-7 choline 
• 108865-87-8 Hexadecanoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 83208-25-7 1-β-D-arabinofuranosylcytosine 5'-monophosphate-L-1,2-dipalmitin sodium salt 
• 92609-92-2 C₃₉H₇₆O₈P^(1-)*Na⁽¹⁺⁾ 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 17364-16-8 1-palmitoyl-sn-glycero-3-phosphocholine 
• 57-10-3 1-hexadecylcarboxylic acid 
• 7091-44-3 1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid 
• 17708-90-6 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine 
• 17364-16-8 1-palmitoyl-L-α-lysophosphatidylcholine 

Relevant academic research and scientific papers

FT-IR and NMR studies on the conformational and structural properties of 1,2-dipalmitoyl-sn-glycero-3-phosphatidyloligoglycerols

The conformational behavior of membranes derived from a new class of phospholipids, 1,2-dipalmitoyl-sn-glycero-phosphatidyloligoglycerols DPPGx, is studied for the first time by FT-IR spectroscopy in the liquid crystalline and gel state. The phospholipids examined here are characterized by oligoglycerol chains of variable length in the headgroup, ranging from one (x = 1, DPPG1 = DPPG) to four glycerol units (x = 4, DPPG4). The transition from the gellike to the liquid crystalline phase is monitored via CH2 and CD2 stretching bands as well as CH2 wagging band progressions. CH2 wagging bands are used to determine the relative amounts, i.e., integral values over the whole chains, of kink/gauche-trans-gauche, double gauche, and end gauche conformers in the acyl chain region. Information about the absolute amount of gauche conformers at a specific chain segment is obtained by a quantitative analysis of the CD2 rocking band region for phospholipid samples with selectively deuterated acyl chains. These latter data are combined with the results from an independent 2H NMR study on the same compounds, which allows a distinction between the overall chain order and the local conformational order of the phospholipid chains. In addition, results from solid state 31P and 13C NMR studies are presented which provide additional support for the conclusions based on the FT-IR data. The present work clearly shows that the conformational and structural properties strongly depend on the headgroup structure and hydrophilicity, sample composition as well as sample temperature. The derived data are discussed by considering related phospholipid systems, such as DPPC, to demonstrate the particular impact of the headgroup length and hydrophilicity on the ordering characteristics of the acyl chains.

Polyelectrolyte adsorption on heterogeneously charged surfaces

The adsorption transition of a uniformly charged polyelectrolyte onto heterogeneously charged surfaces has been investigated using off-lattice Monte Carlo simulations. Each of these surfaces contains both positive and negative charges. In addition to the usual case of adsorption of a polyelectrolyte to a surface with net charge opposite to that of the polymer, we show that a polyelectrolyte can adsorb onto a surface with net surface charge density similar to that of the polyelectrolyte. This adsorption is caused by the spatial inhomogeneity of the surface charges, which creates attractive regions with charge density different from the overall charge density of the surface. The spatial inhomogeneity of the surface charges also leads to differences in the conformation of the adsorbed polyelectrolyte. The critical conditions of strength and range of electrostatic interactions and chain length necessary for adsorption of a polyelectrolyte to a heterogeneously charged surface are demonstrated.

Preparation method of dipalmitoyl phosphatidylcholine

The invention belongs to the technical field of compound preparation, and particularly relates to a dipalmitoyl phosphatidylcholine preparation method, which comprises: step 1, carrying out a condensation reaction on GPC and palmitic acid in the presence of an organic solvent, a condensation reagent and an organic alkali to generate a DPPC crude product solution; step 2, filtering the DPPC crude product solution, taking filtrate, stirring in a non-polar solvent I, filtering, taking filtrate, and concentrating; wherein the non-polar solvent I is one or more of petroleum ether, normal hexane andcyclohexane; step 3, pulping and filtering the crude product prepared in the step 2 in a mixed solvent II, taking a filter cake, repeatedly pulping and filtering, and drying the filter cake to obtaina white powder solid; wherein the mixed solvent II is a mixed solvent of acetone/butanone; and step 4, re-crystallizing the powder solid twice by using a mixed solvent III; wherein the mixed solventIII is a butanone/isopropanol mixed solvent. The preparation and purification process is easy to operate, a hot-pressing filtration process is not needed, the requirement on production equipment is not high, and the finally obtained product is high in yield and purity.

Synthesis and biological evaluation of novel phosphatidylcholine analogues containing monoterpene acids as potent antiproliferative agents

The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59-87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards noncancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.

Synthesis of phosphatidylcholine with conjugated linoleic acid and studies on its cytotoxic activity

Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82%) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87% yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety

Dehydroepiandrosterone (DHEA) and its metabolite 7α-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7α-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl).

Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine

An improved safe method that does not contaminate the environment with cadmium chloride, a toxic heavy metal salt, was developed for the synthesis of phosphatidylcholine (PC). PC was synthesized from sn-glycero-3-phosphocholine (GPC) and fatty acid in one step under mild conditions without the use of cadmium chloride. GPC was prepared from egg yolk PC and adsorbed by kieselguhr in a Teflon vessel. The GPC on kieselguhr was acylated with fatty acid in the presence of two reagents, dicyclohexylcarbodiimide for synthesis of fatty acid anhydride and 4-dimethylaminopyridine as an acylating catalyst, at 30°C overnight. The PC thus produced was purified by silica gel column chromatography. The yield of dioleoyl PC was 90% based on the starting material, GPC.

A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives

A new stereospecific synthesis of phospholipid derivatives of 1,2- diacyl-sn-glycerols is reported. The synthesis is based on (1) the use of L- glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2- dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal ω-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

Synthesis of a small library of mixed-acid phospholipids from D-mannitol as a homochiral starting material

Synthesis of a series of mixed-acid phospholipids containing a polyunsaturated fatty acid using a newly protecting strategy are described. Thus, benzyl and methyl α-(2,4-dinitrophenyl)acetic acid which were respectively removed by BCl3 and 354 nm light are used as protecting groups.

Method for producing liposomes with increased percent of compound encapsulated

The efficiency of encapsulating a drug into a liposomal formulation is increased by use of a lipid having a carbon chain containing from about 13 to about 28 carbons during preparation of the liposomes. Preferably the liposomes are multivesicular liposomes.