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810601C

Avanti

16:0-5 Doxyl PC

Avanti Research™ - A Croda Brand 810601C

Synonym(s):

1-palmitoyl-2-stearoyl-(5-doxyl)-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C46H90N2O10P
CAS Number:
188004-24-2
Molecular Weight:
862.19
UNSPSC Code:
51321705
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (810601C-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 810601C

concentration

1 mg/mL (810601C-1mg)

lipid type

ESR probes
phospholipids

shipped in

dry ice

storage temp.

−20°C

General description

Avanti′s nitroxide spin product listing is a group of compounds designed to act as membrane probes. A variety of positions down the hydrophobic chain are labeled with the nitroxide functional groups to allow probing the membrane at various depths. These compounds have been synthesized from 1-palmitoyl-2-hydroxy-sn-glycerol-3-phosphocholine with the product being purified by column chromatography. Various n-doxyl phosphocholines have been recently used as biophysical tools to elucidate membrane trafficking with phosphatidylinositol transfer proteins and as fluorescent quenchers in lipid bilayer structural studies.
Phosphatidylcholine (PC), a strong bilayer-forming lipid is the most common phospholipid in mammalian membranes. It is also an important component of the mucosal layer of the colon. The 5th carbon of the sn-2 stearic acid chain of 1-palmitoyl-2-stearoyl-(5-doxyl)-sn-glycero-3-phosphocholine analog has a Doxyl PC, a spin probe attached to it covalently.

Application

16:0-5 Doxyl PC may be used:
  • as a component in virus-like large unilamellar vesicles (VL LUVs) to quench 4-chloro-7-nitrobenz-2-oxa-1,3-diazole (NBD) fluorescence emission
  • in the preparation of multi-lamellar vesicles (MLVs) as a site-specific quencher to perform fluorescence quenching studies
  • in the preparation of spin-labelled multi-lamellar vesicles (MLVs)

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.

Packaging

5 mL Clear Glass Sealed Ampule (810601C-1mg)

Preparation Note

To prevent aggregation, prepare water-based solutions of 2 mM stock solutions of n-DOXYL PCs and store in plastic. Dilute stock solutions to 0.03- 0.1 mM solutions for EPR studies. For liposome preparations in fluorescent quenching measurements, dissolve the doxyl lipid in 150 μl absolute ethanol for a concentration of 40.3 mM., Supplemental information

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Liver,Kidney

WGK

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

810601C-VAR:
810601C-1MG:
810601C-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Membranes of Cells (2016)
Edurne Rujas et al.
The Journal of biological chemistry, 292(13), 5571-5583 (2017-02-19)
The 4E10 antibody displays an extreme breadth of HIV-1 neutralization and therefore constitutes a suitable model system for structure-guided vaccine design and immunotherapeutics against AIDS. In this regard, the relevance of autoreactivity with membrane lipids for the biological function of
Alexander Kyrychenko et al.
The journal of physical chemistry. B, 117(19), 5875-5885 (2013-04-26)
Spin-labeled lipids are commonly used as fluorescence quenchers in studies of membrane penetration of dye-labeled proteins and peptides using depth-dependent quenching. Accurate calculations of depth of the fluorophore rely on the use of several spin labels placed in the membrane
Alexander Vogel et al.
Biophysical journal, 85(3), 1691-1701 (2003-08-29)
The distribution of the lipid-attached doxyl electron paramagnetic resonance (EPR) spin label in 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine membranes has been studied by (1)H and (13)C magic angle spinning nuclear magnetic resonance relaxation measurements. The doxyl spin label was covalently attached to the 5th
Diego E Sastre et al.
The Journal of biological chemistry, 295(7), 2136-2147 (2019-12-05)
PlsX plays a central role in the coordination of fatty acid and phospholipid biosynthesis in Gram-positive bacteria. PlsX is a peripheral membrane acyltransferase that catalyzes the conversion of acyl-ACP to acyl-phosphate, which is in turn utilized by the polytopic membrane
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