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Merck
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850464P

Avanti

18:0-14:0 PC

Avanti Research™ - A Croda Brand

Synonym(s):

1-octadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine; SMPC; PC(18:0/14:0)

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About This Item

Empirical Formula (Hill Notation):
C40H80NO8P
CAS Number:
206640-20-2
Molecular Weight:
734.04
MDL number:
MFCD00674329
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

18:0-14:0 PC, 1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine, powder

InChI

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

InChI key

MZWGYEJOZNRLQE-KXQOOQHDSA-N

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CCCCCCCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O)=O

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 25 mg (850464P-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 850464P

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

Application

18:0-14:0 PC (1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine) has been used:
  • as a standard for ultraperformance liquid chromatography-triple quadrupole time-of-flight mass spectrometry (UPLC–QTOF) for the lipid profiling of human plasma
  • as a standard for liquid chromatography-mass spectrometry(LC-MS)
  • in vesicle preparation

18:0-14:0 PC (1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine) may be used in liposomes to study its interference in the proliferation of several cell lines by transmission electron microscopy (TEM).

Biochem/physiol Actions

Phosphatidylcholine (PC) is the precursor for the synthesis of sphingomyelin and phosphatidylserine. PC is essential for the synthesis of second messengers like fatty acids, diacylglycerol (DAG), phosphatidic acid (PA) and lysophosphatidylcholine. The primary source of PC in the mammals is through Cytidine diphosphate (CDP)-choline/Kennedy pathway by the utilization of choline. 18:0-14:0 PC (1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine/SMPC) has two saturated chains of stearoyl (C18) and myristoyl (C14). The vesicles formed by SMPC behaves like solid shells and exhibit only weak shape fluctuations.
Phosphatidylcholine (PC) may participate in the signaling of neuronal differentiation.

General description

Phosphatidylcholine (PC) is a choline containing, zwitterionic phospholipid. It is the abundant phospholipid, constituting between 30-60%. PC has a head group consisting of phosphate, choline and glycerol esterified at C1 and C2 positions with long-chain fatty acyl alcohol. In the structure, quaternary amine choline is essential for its function. The tail group contains both saturated and unsaturated long-chain fatty acyl alcohol. In eukaryotes, the fatty acid chain length may vary up to C26.
Phosphatidylcholines (PCs) are phospholipids, that are abundantly present in the membrane. The fatty acids in the sn-1 and sn-2 positions of PCs are covalently attached to a glycerol with the help of ester bonds.

Packaging

5 mL Amber Glass Screw Cap Vial (850464P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Microenvironmental differences and changes in bilayers of unilamellar vesicles probed by spectroscopic and kinetic parameters
Wen S, et al.
Journal of Colloid and Interface Science, 278(2), 488-496 (2004)
Development of lipidomic platform and phosphatidylcholine retention time index for lipid profiling of rosuvastatin treated human plasma
Choi JM, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 944, 157-165 (2014)
Bending stiffness of biological membranes: What can be measured by neutron spin echo?
Mell M, et al.
The European physical journal. E, Soft matter, 36(7), 75-75 (2013)
Biochemistry of Lipids, Lipoproteins and Membranes (2015)
Regulation of endogenic metabolites by rosuvastatin in hyperlipidemia patients: An integration of metabolomics and lipidomics
Lee H, et al.
Chemistry and Physics of Lipids, 214, 69-83 (2018)
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