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Merck
CN

999992C

Avanti

16:0 Diether PC

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-O-hexadecyl-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C40H84NO6P
CAS Number:
36314-47-3
Molecular Weight:
706.07
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

16:0 Diether PC, Avanti Research™ - A Croda Brand 999992C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OCCCCCCCCCCCCCCCC)COCCCCCCCCCCCCCCCC)=O

InChI

1S/C40H84NO6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-35-44-38-40(39-47-48(42,43)46-37-34-41(3,4)5)45-36-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h40H,6-39H2,1-5H3

InChI key

MWTIGLPPQBNUFP-UHFFFAOYSA-N

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (999992C-10mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 999992C

concentration

10 mg/mL (999992C-10mg)

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

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General description

16:0 Diether PC (phosphocholine) is a zwitterionic lipid having two hexadecane chains attached to the sn-1 and sn-2 positions of the glycerol backbone by ether bonds. It has choline as the alcohol moiety, attached to the phosphate group.

Application

16:0 Diether PC or 1,2-di-O-hexadecyl-sn-glycero-3-phosphocholine might be used:
  • to examine the miscibility and phase behavior of the cationic 1,2-dipalmitoyl-sn-glycero-3-ethylphosphocholine (EDPPC)
  • as a component of unilamellar vesicles to study glycolipid transfer protein (GLTP)-mediated transfer of anthrylvinyl-galactosylceramide (AV-GalCer) from different ether phospholipid matrices
  • to compose large phospholipid bicelles to determine the three-dimensional backbone structure of the transmembrane domain of Vpu from human immunodeficiency virus (HIV)-1 by solid-state nuclear magnetic resonance (NMR) spectroscopy
  • as a non-ladderane phosphocholine (PC) lipid reference sample in reversed-phase liquid chromatography (LC) method to separate PC lipids

Biochem/physiol Actions

Ether linked phospholipids serve as precursors for important signaling molecules. Ether glycerolipids act as membrane molecules and cellular mediators. 16:0 Diether PC (phosphocholine) interdigitates even in the absence of chemical inducers or pressure.

Packaging

5 mL Clear Glass Sealed Ampule (999992C-10mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

Regulatory Information

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Ether-linked lipids and their bioactive species
Biochemistry of Lipids, Lipoproteins and Membranes, 9(2), 245-276 (2008)
Analysis of intact ladderane phospholipids, originating from viable anammox bacteria, using RP-LC-ESI-MS
Lanekoff I and Karlsson R
Analytical and Bioanalytical Chemistry, 397(8), 3543-3551 (2010)
Three-dimensional structure of the transmembrane domain of Vpu from HIV-1 in aligned phospholipid bicelles
Park SH, et al.
Biophysical Journal, 91(8), 3032-3042 (2006)
The interdigitated gel phase in mixtures of cationic and zwitterionic phospholipids
Smith EA and Dea PH
Biophysical Chemistry, 196(2), 86-91 (2015)
Molecular features of phospholipids that affect glycolipid transfer protein-mediated galactosylceramide transfer between vesicles
Nylund M, et al.
Biochimica et Biophysica Acta - Biomembranes, 1758(6), 807-812 (2006)
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