A lysophospholipid
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1-Oleoyl-2-hydroxy-sn-glycero-3-PE

Item No. 25596

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-oleoyl-2-hydroxy-sn-glycero-3-phosphatidylethanolamine
CAS Number
89576-29-4
Synonyms
  • 18:1 LPE
  • 18:1 Lyso-PE
  • 1-Oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine
Molecular Formula
C23H46NO7P
Formula Weight
479.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 3 mg/ml
SMILES
O[C@@H](COP(OCC[NH3+])([O-])=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
InChi Code
InChI=1S/C23H46NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(26)29-20-22(25)21-31-32(27,28)30-19-18-24/h9-10,22,25H,2-8,11-21,24H2,1H3,(H,27,28)/b10-9-/t22-/m1/s1
InChi Key
PYVRVRFVLRNJLY-MZMPXXGTSA-N
Side Chain Carbon Sum
18:1
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $54

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    10 mg

    $96

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    25 mg

    $209

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    50 mg

    $315

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

    1-Oleoyl-2-hydroxy-sn-glycero-3-PE is a naturally-occurring lysophospholipid and an analog of plasmalogen lysophosphatidylethanolamine.1,2,3 It induces transient increases in intracellular calcium in PC12 rat neuronal cells in a concentration-dependent manner, an effect that can be blocked by the lysophosphatidic acid receptor 1 (LPA1) antagonist AM095 (Item No. 22141).2 1-Oleoyl-2-hydroxy-sn-glycero-3-PE (100 ng/ml) increases IL-2 production in CD1d-stimulated murine natural killer T (NKT) cell hybridoma 2H4 cells.3 It also induces production of IL-4, but not IFN-γ, in murine splenocytes when used at a concentration of 100 ng/ml and in mouse serum when administered at a dose of 1 μg per animal, indicating induction of the T helper 2 (Th2) response. 1-Oleoyl-2-hydroxy-sn-glycero-3-PE levels increase in interscapular brown adipose tissue (iBAT) in mice following three-day cold exposure.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Marcher, A.B., Loft, A., Nielsen, R., et al. RNA-Seq and mass-spectrometry-based lipidomics reveal extensive changes of glycerolipid pathways in brown adipose tissue in response to cold. Cell. Rep. 13(9), 2000-2013 (2015).

    2. Lee, J.M., Park, S.J., and Im, D.S. Lysophosphatidylethanolamine increases intracellular Ca2+ through LPA1 in PC-12 neuronal cells. Biochem. Biophys. Res. Commun. 461(2), 378-382 (2015).

    3. Ni, G., Li, Z., Liang, K., et al. Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells. Bioorg. Med. Chem. 22(11), 2966-2973 (2014).