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

Item No. 20959

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,7R-dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18Z-en-1-aminium, 4-oxide, inner salt
CAS Number
19420-56-5
Synonyms
  • LPC(18:1)
  • 1-(9(Z)-Octadecenoyl)-2-hydroxy-sn-glycero-3-phosphocholine
  • 1-Oleoyl-2-hydroxy Phosphatidylcholine
  • PC(18:1/0:0)
  • PC(18:1(9Z)/0:0)
  • PtdCho-(1-oleoyl, 2-hydroxy)
Molecular Formula
C26H52NO7P
Formula Weight
521.7
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in chloroform
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 2 mg/ml
λmax
221 nm
SMILES
O[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)COC(CCCCCCC/C=C\CCCCCCCC)=O
InChi Code
InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
InChi Key
YAMUFBLWGFFICM-PTGWMXDISA-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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    1 mg

    $36

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    5 mg

    $75

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    10 mg

    $135

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    25 mg

    $303

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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-phosphocholine is a lysophospholipid containing oleic acid (Item Nos. 90260 | 24659) at the sn-1 position. It inhibits taurine uptake in Caco-2 cells when used at a concentration of 200 µM.1 Levels of 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine are increased in conditioned medium in VEGF-stimulated primary normal human bronchial epithelial (NHBE) cells, an effect that can be reversed by the phospholipase A2 (PLA2) inhibitor oleyloxyethyl phosphorylcholine (Item No. 70560).2 Plasma levels of 1-oleoyl-2-hydroxy-sn-glycero-3-phosphocholine are decreased in patients with lung cancer or abdominal aortic aneurysm.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ishizuka, K., Miyamoto, Y., Satsu, H., et al. Characteristics of lysophosphatidylcholine in its inhibition of taurine uptake by human intestinal Caco-2 cells. Biosci. Biotechnol. Biochem. 66(4), 730-736 (2002).

    2. Zhuge, Y., Yuan, Y., van Breemen, R., et al. Stimulated bronchial epithelial cells release bioactive lysophosphatidylcholine 16:0, 18:0, and 18:1. Allergy Asthma Immunol. Res. 6(1), 66-74 (2014).

    3. Dong, J., Xiaoming, C., Zhao, L., et al. Lysophosphatidylcholine profiling of plasma: Discrimination of isomers and discovery of lung cancer biomarkers. Metabolomics 6(4), 478-488 (2010).

    4. Xie, T., Lei, C., Song, W., et al. Plasma lipidomics analysis reveals the potential role of lysophosphatidylcholines in abdominal aortic aneurysm progression and formation. Int. J. Mol. Sci. 24(12), 10253 (2023).