ChemicalBook CAS DataBase List 18194-24-6

18194-24-6

Name	1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
CAS	18194-24-6
EINECS(EC#)	242-085-9
Molecular Formula	C36H72NO8P
MDL Number	MFCD00036901
Molecular Weight	677.93
MOL File	18194-24-6.mol

Synonyms

1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHATIDYLCHOLINE 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE 1,2-DITETRADECANOYL-SN-GLYCERO-3-PHOSPHOCHOLINE 14:0 PC BETA-GAMMA-DIMYRISTOYL-L-ALPHA-LECITHIN DIMYRISTOYL-L-3-LECITHIN DIMYRISTOYL LECITHIN DMPC L-ALPHA-PHOSPHATIDYLCHOLINE, DIMYRISTOYL L-ALPHA-PHOSPHATIDYLCHOLINE, DIMYRISTOYL (C14:0) L-BETA,GAMMA-DIMYRISTOYL-ALPHA-LECITHIN dimyristoyl l-a-phosphatidylcholinedimyristoyl (R)-(7-myristoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphatricosyl)trimethylammonium 4-oxide L-a-Lecithin-b,g-dimyristoyl=b,g-Dimyristoyl-L-a-Lecithin=Dimyristoyl-L-a-Lecithin=Dimyristoyl-L-3-Lecithin Lecithin-b,g-Dimyristoyl-L-a-=Dimyristoyl-L-a-L 1,2-Dimyristoyl-SN-Glycero-3-Phospho-Choline-D54 DIMYRISTOYL-L-3-LECITHIN Synthetic 1,2-Ditetradecanoyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, 1,2-dimyristoyl, L-β,γ-Dimyristoyl-α-lecithin

Chemical Properties

Appearance	white powder
Melting point	220°C(lit.)
storage temp.	−20°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
color	White to Off-White
Stability:	Stable, but heat sensitive-store at-20 C. Incompatible with strong oxidizing agents.
BRN	3921768
InChI	InChI=1/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/s3
InChIKey	CITHEXJVPOWHKC-UUWRZZSWSA-N
SMILES	[C@@H](OC(=O)CCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C \|&1:0,r\|
CAS DataBase Reference	18194-24-6(CAS DataBase Reference)

Safety Data

WGK Germany	3
F	10-21
HS Code	29232000

Hazard Information

Description

1,2-Dimyristoyl-sn-glycero-3-PC (DMPC) is a phospholipid containing 14:0 fatty acids at the sn-1 and sn-2 positions. It is a synthetic phosopholipid that has been used for liposome production in order to study the properties of lipid bilayer.

Chemical Properties

white powder

Uses

1,2-dimyristoyl-sn-glycero-3-phosphocholine is a phospholipid containing 14:0 fatty acids at the sn-1 and sn-2 positions. It is a synthetic phosopholipid that can be used for liposome production in order to study the properties of lipid bilayer.[Cayman Chemical]

Definition

ChEBI: A 1,2-diacyl-sn-glycero-3-phosphocholine where the two phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).

General Description

Phosphatidylcholine (PC) is a strong bilayer-forming lipid. It the most common phospholipid in mammalian membranes. It is also an important component of the mucosal layer of the colon.

Biochem/physiol Actions

Phosphatidylcholine (PC) functions as a surfactant within the mucus to form a hydrophobic surface to inhibit bacterial penetrance. It is used to treat fat embolism. Phosphatidylcholine lowers the levels of cholesterol and triglycerides.

Purification Methods

It has three forms 1, 2 and '. Recrystallise it from aqueous EtOH or EtOH/Et2O. Its solubility at 22-23o in Et2O is 0.03%, in Me2CO it is 0.06% and in pyridine it is 1.3%. [Baer & Kates J Am Chem Soc 72 942 1950, Baer & Maurakas J Am Chem Soc 74 158 1952, IR: Marinetti & Stotz J Am Chem Soc 76 1347 1954.] The S-isomer with 1H2O is recrystallised from 2,6-dimethylheptan-4-one and has m 226-227o (sintering at 90-95o), and [] 20D -7o (c 6, MeOH/CHCl3 1:1). [Baer & Martin J Biol Chem 193 835 1951, Beilstein 4 IV 1463.]

References

[1] AKIKO UEMURA. Induction of immune responses against glycosphingolipid antigens: comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids.[J]. Journal of Veterinary Medical Science, 2005, 67 12: 1197-1201. DOI: 10.1292/jvms.67.1197
[2] P MéLéARD. Bending elasticities of model membranes: influences of temperature and sterol content.[J]. Biophysical journal, 1997, 72 6: 2616-2629. DOI: 10.1016/s0006-3495(97)78905-7
[3] JOHN F. NAGLE Stephanie T N. Structure of lipid bilayers[J]. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 2000, 1469 3: Pages 159-195. DOI: 10.1016/s0304-4157(00)00016-2

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