An internal standard for the quantification of 1-palmitoyl-2-hydroxy-sn-glycero-3-PC
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1-Palmitoyl-d3-2-hydroxy-sn-glycero-3-PC

Item No. 28229

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7R)-4,7-dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphapentacosan-25,25,25-d3-1-aminium, inner salt, 4-oxide
CAS Number
2692624-19-2
Synonyms
  • 1-Hexadecanoyl-sn-glycero-3-Phosphatidylcholine-d3
  • 1-Hexadecanoyl-sn-glycero-3-Phosphocholine-d3
  • LPC-d3
  • 16:0/0:0(d3) Lyso-PC
  • 1-Palmitoyl-sn-glycero-3-Phosphocholine-d3
  • PC(16:0/0:0)-d3
  • 16:0/0:0-PC-d3
Molecular Formula
C24H47D3NO7P
Formula Weight
498.7
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (1:1): solubleDMF: solubleDMSO: solubleEthanol: 2 mg/mlPBS (pH 7.2): soluble
SMILES
O[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)COC(CCCCCCCCCCCCCCC([2H])([2H])[2H])=O
InChi Code
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1/i1D3
InChi Key
ASWBNKHCZGQVJV-MVIJBLFRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $702

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    Cayman Chemical
    Learn More About Leveraging Helper Lipids to Achieve Versatile LNPs
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    Product Description

    1-Palmitoyl-d3-2-hydroxy-sn-glycero-3-PC is intended for use as an internal standard for the quantification of 1-palmitoyl-2-hydroxy-sn-glycero-3-PC (Item No. 10172) by GC- or LC-MS. 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC is the ubiquitous lipid species generated following phospholipase A2 (PLA2) hydrolysis of phosphatidylcholine.1 It increases the production of reactive oxygen species (ROS) and decreases superoxide dismutase (SOD) and endothelial nitric oxide synthase (eNOS) protein levels and phosphorylation of ERK1/2 in human umbilical vein endothelial cells (HUVECs) when used at a concentration of 125 µM.2 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC potentiates the secretion of IL-6, IL-1β, IL-12, and TNF-α in LPS-stimulated M1 macrophages, but has no effect on CD163, CD206, CD36, or IL-10 in LPS-stimulated M2 macrophages when used at concentrations of 0.3 and 1.0 µM.3 It increases TGF-β1 production and enhances Foxp3 protein levels in Treg cells in isolated human peripheral blood when used at a concentration of 10 µM.4 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC enhances neutrophil function, bacterial clearance, and survival in mouse models of sepsis when administered at a dose of 10 mg/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Balsinde, J., Winstead, M.V., and Dennis, E.A. Phospholipase A2 regulation of arachidonic acid mobilization. FEBS Lett. 531(1), 2-6 (2002).

    2. Choi, S., Park, S., Liang, G.H., et al. Superoxide generated by lysophosphatidylcholine induces endothelial nitric oxide synthase downregulation in human endothelial cells. Cell Physiol. Biochem. 25(2-3), 233-240 (2010).

    3. Qin, X., Qiu, C., and Zhao, L. Lysophosphatidylcholine perpetuates macrophage polarization toward classically activated phenotype in inflammation. Cell. Immunol. 289(1-2), 185-190 (2014).

    4. Hasegawa, H., Lei, J., Matsumoto, T., et al. Lysophosphatidylcholine enhances the suppressive function of human naturally occurring regulatory T cells through TGF-β production. Biochem. Biophys. Res. Commun. 415(3), 526-531 (2011).

    5. Yan, J.-J., Jung, J.-S., Lee, J.-E., et al. Therapeutic effects of lysophosphatidylcholine in experimental sepsis. Nat. Med. 10(2), 161-167 (2004).