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880341C

Avanti

16:0-16:0 (16-F) PC

Avanti Research™ - A Croda Brand 880341C

Synonym(s):

1-palmitoyl-2-(16-fluoropalmitoyl)-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C40H79NO8PF
CAS Number:
215362-14-4
Molecular Weight:
752.03
UNSPSC Code:
12352211
NACRES:
NA.25

form

liquid

packaging

pkg of 1 × 1 mL (880341C-10mg)
pkg of 1 × 2.5 mL (880341C-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 880341C

concentration

10 mg/mL (880341C-10mg)
10 mg/mL (880341C-25mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

General description

16:0-16:0 (16-F) PC or 1-palmitoyl-2-(16-fluoropalmitoyl)-sn-glycero-3-phosphocholine is a monofluorinated analog of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC).

Application

16:0-16:0 (16-F) PC or 1-palmitoyl-2-(16-fluoropalmitoyl)-sn-glycero-3-phosphocholine is suitable for use as a rotational-echo double-resonance (REDOR) probe to analyze peptides integrated into phospholipid bilayers. It might be used to study its thermal and physical properties when combined with naturally occurring lipids through differential scanning calorimetry and fluorescence studies.

Biochem/physiol Actions

Fluorinated lipids are useful to study the characteristics of proteins and membranes. They act as drug carriers. 16:0-16:0 (16-F) PC or 1-palmitoyl-2-(16-fluoropalmitoyl)-sn-glycero-3-phosphocholine is known to interdigitate lipid bilayers in the absence of inducing agents. This is due to its hydrophilic nature because of the presence of highly polar C-F bond at the terminal end of the sn-2 acyl chain.

Packaging

5 mL Clear Glass Sealed Ampule (880341C-10mg)
5 mL Clear Glass Sealed Ampule (880341C-25mg)

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_germany

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

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D J Hirsh et al.
Biophysical journal, 75(4), 1858-1868 (1998-09-24)
16-Fluoropalmitic acid was synthesized from 16-hydroxypalmitic acid using diethylaminosulfur trifluoride. This monofluorinated fatty acid then was used to make 1-palmitoyl-2-[16-fluoropalmitoyl]-phosphatidylcholine (F-DPPC) as a fluorinated analog of dipalmitoylphosphatidylcholine (DPPC). Surprisingly, we found that the phase transition temperature (Tm) of F-DPPC occurs
Syed W H Shah et al.
Chemistry and physics of lipids, 230, 104918-104918 (2020-05-18)
The monolayer behavior of a l-DPPC derivative with a single fluorination in one of its terminal methyl groups (F-DPPC) at air-water interface was investigated by epifluorescence microscopy and infrared reflection absorption spectroscopy (IRRAS). Epifluorescence microscopy was utilized to study the
Babak Sanii et al.
The journal of physical chemistry. B, 114(1), 215-219 (2009-12-17)
In free bilayers, the fluid to gel main phase transition of a monofluorinated phospholipid (F-DPPC) transforms a disordered fluid bilayer into a fully interdigitated monolayer consisting of ordered acyl tails. This transformation results in an increase in molecular area and
Eric A Smith et al.
Biophysical chemistry, 147(1-2), 20-27 (2010-01-13)
In aqueous solution, the monofluorinated phospholipid 1-palmitoyl-2-[16-fluoropalmitoyl]sn-glycero-3-phosphocholine (F-DPPC) interdigitates without the use of inducing agents. To understand the thermal and physical properties of this unique lipid, F-DPPC was combined with the non-fluorinated 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and 1,2-diarachidoyl-sn-glycero-3-phosphocholine (DAPC). Differential scanning calorimetry
Eric A Smith et al.
Chemistry and physics of lipids, 165(2), 151-159 (2011-12-28)
Unlike the parent phospholipid, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), the monofluorinated analog, 1-palmitoyl-2-(16-fluoropalmitoyl)sn-glycero-3-phosphocholine (F-DPPC), spontaneously forms an interdigitated gel phase (L(β)I) below the main transition temperature (T(m)). We have examined the effects of introducing cholesterol to F-DPPC and 1:1 F-DPPC/DPPC membranes using a

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