1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE Chemical Properties

Melting point:

220°C(lit.)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

BRN 

3921768

Stability:

Stable, but heat sensitive - store at -20℃. Incompatible with strong oxidizing agents.

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 Information

WGK Germany 

3

F 

10-21

HS Code 

29232000

MSDS

• Language:English Provider:SigmaAldrich

1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE Usage And Synthesis

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 has been used as a standard for phospholipid analysis by LC-ESI-MS.

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

1,2-dimyristoyl-sn-glycero-3-phosphocholine is a synthetic phospholipid used in liposomes and lipid bilayers for the study of biological membranes.

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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