A glycerophospholipid
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Lysophosphatidylcholine

Item No. 24331

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
9008-30-4
Synonyms
  • Lyso-Lecithins
Molecular Formula
C24H50NO7P (for palmitoyl)
Formula Weight
495.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): 2:1Chloroform:Methanol (2:1): soluble
SMILES
O[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)COC([R])=O
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $42

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    25 mg

    $94

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    50 mg

    $161

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

    Lysophosphatidylcholines are produced by hydrolysis of the fatty acid of phosphatidylcholine (PC; Item Nos. 24343 | 24370) at either the sn-1 or sn-2 position by phospholipase A2 (PLA2) or by lecithin-cholesterol acyltranferase (LCAT), which transfers the fatty acid to cholesterol.1 Lysophosphatidylcholine has effects on a variety of cell types, including smooth muscle cells, endothelial cells, T lymphocytes, monocytes, and macrophages among others. It is a major phospholipid component of oxidized low-density lipoprotein (ox-LDL), and it accumulates in animal models of atherosclerosis. Lysophosphatidylcholine also has pro-inflammatory properties through its activation and modulation of various signaling pathways, including the ERK pathway as well as through protein tyrosine kinase and G protein-coupled receptor (GPCR) signal transduction. It is released from apoptotic cells in vitro following caspase-3 activation of the calcium-independent PLA2 and acts as a chemoattractant for monocytes.2 Lysophosphatidylcholine (2 µl, 1%) injected into the caudal cerebellar peduncle of rats induces demyelination of axons in vivo, which are extensively remyelinated by oligodendrocytes six weeks following injection.3 This product contains lysophosphatidylcholine molecular species with primarily C16:0 fatty acyl chain lengths acylated to the sn-1 position. [Matreya, LLC. Catalog No. 1046]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Matsumoto, T., Kobayashi, T., and Kamata, K. Role of lysophosphatidylcholine (LPC) in atherosclerosis. Curr. Med. Chem. 14(30), 3209-3220 (2007).

    2. Lauber, K., Bohn, E., Kröber, S.M., et al. Apoptotic cells induce migration of phagocytes via caspase-3-mediated release of a lipid attraction signal. Cell. 113(6), 717-730 (2003).

    3. Woodruff, R.H., and Franklin, R.J. Demyelination and remyelination of the caudal cerebellar peduncle of adult rats following stereotaxic injections of lysolecithin, ethidium bromide, and complement/anti-galactocerebroside: A comparative study. Glia. 25(3), 216-228 (1999).