A phospholipid
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Labeled Version(s)
383841-Palmitoyl-d9-2-Arachidonoyl-sn-glycero-3-PC
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1-Palmitoyl-2-Arachidonoyl-sn-glycero-3-PC

Item No. 25658

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7R,13Z,16Z,19Z,22Z)-4-hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphaoctacosa-13,16,19,22-tetraen-1-aminium 4-oxide, inner salt
CAS Number
35418-58-7
Synonyms
  • 1-Palmitoyl-2-Arachidonoyl-sn-glycero-3-Phosphocholine
  • PAPC
  • PC(16:0/20:4)
Molecular Formula
C44H80NO8P
Formula Weight
782.1
Purity
≥95%
Formulation (Request formulation change)
A 50 mg/ml solution in chloroform
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble
SMILES
O=C(CCCCCCCCCCCCCCC)OC[C@@H](OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O
InChi Code
InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h14,16,20-21,23,25,29,31,42H,6-13,15,17-19,22,24,26-28,30,32-41H2,1-5H3/b16-14-,21-20-,25-23-,31-29-/t42-/m1/s1
InChi Key
IIZPXYDJLKNOIY-JXPKJXOSSA-N
Side Chain Carbon Sum
36:4
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $109

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    25 mg

    $382

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    100 mg

    $1,198

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    Product Description

    1-Palmitoyl-2-arachidonoyl-sn-glycero-3-PC (PAPC) is a phospholipid containing palmitic acid (16:0) (Item No. 10006627) and arachidonic acid (20:4) (Item No. 90010) at the sn-1 and sn-2 positions, respectively, that is found in biological membranes.1 PAPC is oxidized in vivo, and its oxidation products are involved in chronic inflammation and vascular disease.1,2,3 PAPC has been used to study signaling of oxidized phospholipids. Levels of PAPC are decreased in isolated human multiple myeloma cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bretscher, P., Egger, J., Shamshiev, A., et al. Phospholipid oxidation generates potent anti-inflammatory lipid mediators that mimic structurally related pro-resolving eicosanoids by activating Nrf2. EMBO Mol. Med. 1-15 (2015).

    2. Miller, Y.I., and Shyy, J.Y.-J. Context-dependent role of oxidized lipids and lipoproteins in inflammation. Trends Endocrinol. Metab. 28(2), 143-152 (2017).

    3. Gugiu, B.G., Mouiflesseaux, K., Duong, V., et al. Protein targets of oxidized phospholipids in endothelial cells. J. Lipid Res. 49, 510-520 (2008).

    4. Hossen, M.A., Nagata, Y., Waki, M., et al. Decreased level of phosphatidylcholine (16:0/20:4) in multiple myeloma cells compared to plasma cells: A single-cell MALDI-IMS approach. Anal. Bioanal. Chem. 407(18), 5273-5280 (2015).