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860042P

Avanti

16:0-d31-18:1 PI

1-palmitoyl-d31-2-oleoyl-sn-glycero-3-phosphoinositol (ammonium salt), powder

Synonym(s):

110923

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About This Item

Empirical Formula (Hill Notation):
C43H53NO13PD31
CAS Number:
799812-61-6
Molecular Weight:
885.29
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 100 μg (with stopper and crimp cap (860042P-100ug))
pkg of 1 × 500 μg (with stopper and crimp cap (860042P-500ug))

manufacturer/tradename

Avanti Polar Lipids 860042P

shipped in

dry ice

storage temp.

−20°C

SMILES string

[NH4+].[2H]C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C(=O)OC[C@H](COP([O-])(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI

1S/C43H81O13P.H3N/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(45)55-35(34-54-57(51,52)56-43-41(49)39(47)38(46)40(48)42(43)50)33-53-36(44)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2;/h17-18,35,38-43,46-50H,3-16,19-34H2,1-2H3,(H,51,52);1H3/b18-17-;/t35-,38?,39-,40?,41?,42?,43-;/m1./s1/i2D3,4D2,6D2,8D2,10D2,12D2,14D2,16D2,19D2,21D2,23D2,25D2,27D2,29D2,31D2;

InChI key

NPOZNLWSCICHRX-MPQXHUEUSA-N

General description

16:0-d31-18:1 PI or 1-palmitoyl-d31-2-oleoyl-sn-glycero-3-phosphoinositol is a deuterated phospholipid. This lipid consists of a phosphatidylinositol group attached to palmitic acid and oleic acid.
Deuterated fatty acids experience exchange of the deuteriums on the alpha carbon to the carbonyl, i.e., C2 position, and will therefore be a mixture of compounds that are fully deuterated and partially deuterated at that position.

Application

16:0-d31-18:1 PI or 1-palmitoyl-d31-2-oleoyl-sn-glycero-3-phosphoinositol has been used as an internal standard:
  • in yeast lipid profiling
  • for the quantification of lipids using electrospray ionization tandem mass spectrometry (ESI-MS/MS)
  • for the extraction of lipids from human bronchus tissue and epithelium samples using Bligh and Dyer method and for liquid chromatography-mass spectrometry (LC-MS) analysis

Biochem/physiol Actions

Phosphatidylinositol (PI) is phosphorylated at their hydroxyls group and the phosphorylated PIs regulate several biological processes including membrane trafficking, recruitment of proteins and autophagy.

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (860042P-100ug)
2 mL Amber Serum Vial with Stopper and Crimp Cap (860042P-500ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

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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Nicole Zehethofer et al.
Chromatographia, 78(5-6), 403-413 (2015-03-10)
Airway epithelial cells play an important role in the pathogenesis of inflammatory lung diseases such as asthma, cystic fibrosis and COPD. Studies concerning the function of the lipid metabolism of the airway epithelium are so far based only on the
Nicholas J Blunsom et al.
Biochimica et biophysica acta. Molecular and cell biology of lipids, 1865(1), 158471-158471 (2019-06-08)
Phosphatidylinositol (PI) is a minor phospholipid with a characteristic fatty acid profile; it is highly enriched in stearic acid at the sn-1 position and arachidonic acid at the sn-2 position. PI is phosphorylated into seven specific derivatives, and individual species
Sarah Spiegel et al.
Nature reviews. Molecular cell biology, 4(5), 397-407 (2003-05-03)
The evolutionarily conserved actions of the sphingolipid metabolite, sphingosine-1-phosphate (S1P), in yeast, plants and mammals have shown that it has important functions. In higher eukaryotes, S1P is the ligand for a family of five G-protein-coupled receptors. These S1P receptors are
Michael Maceyka et al.
Trends in cell biology, 22(1), 50-60 (2011-10-18)
The bioactive sphingolipid metabolite sphingosine-1-phosphate (S1P) is now recognized as a critical regulator of many physiological and pathophysiological processes, including cancer, atherosclerosis, diabetes and osteoporosis. S1P is produced in cells by two sphingosine kinase isoenzymes, SphK1 and SphK2. Many cells
Maria Makarova et al.
Current biology : CB, 30(3), 367-380 (2020-01-21)
Membrane function is fundamental to life. Each species explores membrane lipid diversity within a genetically predefined range of possibilities. How membrane lipid composition in turn defines the functional space available for evolution of membrane-centered processes remains largely unknown. We address
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