63-89-8

Basic information

• Product Name: 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
• Synonyms: 16:0 PC;1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE;1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE;1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHATIDYLCHOLINE;1,2-DIHEXADECANOYL-SN-GLYCERO-3-PHOSPHOCHOLINE;L-A-LECITHIN DIPALMITOYL;L-ALPHA-DIPALMITOYL PHOSPHATIDYLCHOLINE;L-ALPHA-LECITHIN, DIPALMITOYL
• CAS NO: 63-89-8
• Molecular Formula: C₄₀H₈₀NO₈P
• Molecular Weight: 734.04
• EINECS: 232-642-4
• Product Categories: Amines;Fatty Acid Derivatives & Lipids;Glycerols;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 63-89-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 229-229.5 °C
• Appearance: white powder
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2477
• CAS DataBase Reference: 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(63-89-8)
• EPA Substance Registry System: 1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE(63-89-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 63-89-8(Hazardous Substances Data)

Usage

Description

DPPC, also known as 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine, is a phospholipid containing the 16 carbon fatty acid/palmitic acid (16:0) at the sn-1 and sn-2 positions. It is commonly used in the generation of micelles, liposomes, and other types of artificial membranes. Due to the medium size of fatty acid chain, DLPC is used to form thinner membranes or lipid bilayers.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 63-89-8 differently. You can refer to the following data:
1. 1,2-dipalmitoyl-sn-glycero-3-phosphocholine is a major phospholipid constituent and primary surface tension lowering component of natural lung surfactant. Colfosceril Palmitate is used as pulmonary surfactant and diagnostic aid (fetal lung maturity).
2. 16:0 PC (DPPC) has been used in the generation of thymoquinone (TQ) liposomes, gold nanorods and calcium chloride encapsulated liposomes and bilayers for biophysical studies.
3. 16:0 PC (DPPC) is suitable for use:in vesicle preparationas the main phospholipid component for all ultrasound contrast agents (UCA) formulationsas a component for microbubble preparationin the preparation of lipid bilayers

Definition

ChEBI: A phosphatidylcholine 32:0 in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl). A synthetic phospholipid used in liposomes and lipid bilayers to study biological membranes. It is also a major constituent of pulmonary surfactants.

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

• 59540-20-4 2-(1',2'-dipalmitoyl-sn-glycero)-2-oxo-1,3,2-dioxaphospholane 
• 75-50-3 trimethylamine 
• 1455-05-6 2-chloroethyl phosphorodichloridate 
• 30334-71-5 1,2-dipalmitoyl-sn-glycerol 
• 26227-65-6 palmitic acid carboimidazolide 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 623-65-4 palmitic anhydride 
• 28319-77-9 L-α-glycerophosphorylcholine 
• 112-67-4 n-hexadecanoyl chloride 
• 408-35-5 sodium palmitate 
• 7501-44-2 hexadecanoic acid, glycidyl ester 
• 496808-59-4 Hexadecanoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester 
• 33625-90-0 1,2-dipalmitoyl-3-triphenylmethyl-sn-glycerol 

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⁺⁾ 
• 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 
• 26662-95-3 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 
• 28319-77-9 L-glycero-3-phosphorylcholine 

Relevant articles and documents

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.

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 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).