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1-Myristoyl-sn-glycero-3-phosphocholine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

1-Myristoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine derivative, which is found in plasma and oxidized low-density lipoprotein (Ox-LDL). It can be used as a biomarker for detecting lipid metabolism.

Category

Peptide Synthesis Reagents

Catalog number

BAT-006369

CAS number

20559-16-4

Molecular Formula

C22H46NO7P

Molecular Weight

467.58

Specification
Reference Reading

IUPAC Name

[(2R)-2-hydroxy-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate

Synonyms

3-sn-Lysophosphatidylcholine; lysomyristoyl phosphatidylcholine; Lysolecithin,tetradecanoyl; 1-Myristoyl-2-hydroxy-sn-glycero-3-phosphatidylcholine; M-lyso-PC; 1-Tetradecanoyl-sn-glycero-3-phosphocholine; (7R)-,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphatricosan-1-aminium Inner salt 4-Oxide; (R)-,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphatricosan-1-aminium Inner salt 4-Oxide; 1-Myristoyl-L-α-phosphorylcholine; 1-Tetradecanoyl-sn-glycero-3-phosphorylcholine; L-α-Myristoyllysophosphatidylcholine; M-LysoPC; Myristoyl L-α-lysolecithin; Myristoyl L-α-Lysophosphatidylcholine; LPC(14:0); LyPC(14:0); PC(14:0/0:0)

Appearance

White to Off-white Powder

Purity

>99% by HPLC

Melting Point

> 142 °C (dec.)

Storage

-20 °C under inert atmosphere

Solubility

Slightly soluble in Chloroform, Methanol.

InChI

InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1

InChI Key

VXUOFDJKYGDUJI-OAQYLSRUSA-N

Canonical SMILES

CCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O

1.Lipid-protein interactions. Effect of apolipoprotein A-I on phosphatidylcholine polar group conformation as studied by proton nuclear magnetic resonance.

Reijngoud DJ, Lund-Katz S, Hauser H, Phillips MC. Biochemistry. 1982 Jun 8;21(12):2977-83.

Spin-spin coupling constants derived from high-resolution 1H NMR spectra of pure 1-myristoyl-sn-glycero-3-phosphocholine (MLPC) micelles and 60:1 mol/mol been analyzed in order to determine the effects of apoprotein on phosphatidylcholine (PC) polar group conformation. The shift ratios of the polar group proton resonances after addition of the paramagnetic shift reagent Fe(CN)6(3-) to the above MLPC systems, egg PC small unilamellar vesicles, and human HDL3 have been used to compare the PC polar group conformations in all systems. The location of the largely alpha-helical apo A-I molecules in the complex with MLPC was deduced from its effects on the chemical shifts and spin-lattice relaxation times (T1) of the well-resolved 1H resonances from the various parts of the lipid molecules. The data are consistent with the apo A-I molecules lying in the surface fo the MLPC micelle with their amphipathic, alpha-helical segments intercalated among the glycerophosphocholine groups of the lipid molecules so that aromatic amino acid side chains are interspersed among the lipid hydrocarbon chains.