An oxidized phospholipid
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PON-PC

Item No. 9000463

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7R-[(1,9-dioxononyl)oxy]-4-hydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphapentacosan-1-aminium, 4-oxide, inner salt
CAS Number
135726-46-4
Synonyms
  • 16:0/9:0-PC
  • PC(16:0/9:0)
  • 1-Palmitoyl-2-(9-oxo-Nonanoyl)-sn-glycero-3-PC
  • 1-Palmitoyl-2-(9-oxo-Nonanoyl)-sn-glycero-3-Phosphatidylcholine
  • 1-Palmitoyl-2-(9-oxo-Nonanoyl)-sn-glycero-3-Phosphocholine
Molecular Formula
C33H64NO9P
Formula Weight
649.4
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 10 mg/ml
SMILES
O=C(CCCCCCCCCCCCCCC)OC[C@@H](OC(CCCCCCCC=O)=O)COP([O-])(OCC[N+](C)(C)C)=O
InChi Code
InChI=1S/C33H64NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-18-21-24-32(36)40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-16-17-20-23-27-35/h27,31H,5-26,28-30H2,1-4H3/t31-/m1/s1
InChi Key
PPTNNIINSOQWCE-WJOKGBTCSA-N
Side Chain Carbon Sum
27:0
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $186

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    Product Description

    PON-PC is an oxidized phospholipid containing a truncated 9-carbon fatty acyl chain terminating in an aldehyde at the sn-2 position.1,2 It is a component of oxidized LDL formed by oxidation of palmitoyl oleoyl phosphatidylcholine (POPC) and can also be formed via a reaction with ozone in pulmonary surfactant.1,2,3 PON-PC decreases the production of TNF-α, nitric oxide (NO), and NADP+ in primary mouse alveolar macrophages, as well as reduces the bactericidal activity of RAW 264.7 cells, when used at a concentration of 40 µM.1 Bronchoalveolar lavage fluid (BALF) levels of PON-PC are elevated in mice exposed to cigarette smoke and in aged mice.2,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kimura, T., Shibata, Y., Yamauchi, K., et al. Oxidized phospholipid, 1-palmitoyl-2-(9'-oxo-nonanoyl)-glycerophosphocholine (PON-GPC), produced in the lung due to cigarette smoking, impairs immune function in macrophages. Lung 190(2), 169-182 (2012).

    2. da Costa Loureiro, L., da Costa Loureiro, L., Gabriel-Junior, E.A., et al. Pulmonary surfactant phosphatidylcholines induce immunological adaptation of alveolar macrophages. Mol. Immunol. 122, 163-172 (2020).

    3. Sasabe, N., Keyamura, Y., Obama, T., et al. Time course-changes in phosphatidylcholine profile during oxidative modification of low-density lipoprotein. Lipids Health Dis. 13, 48 (2014).

    4. Ke, Y., Karki, P., Kim, J., et al. Elevated truncated oxidized phospholipids as a factor exacerbating ALI in the aging lungs. The FASEB Journal 33(3), 3887-3900 (2019).