An ω-carboxylated 7-ketocholesteryl ester and a lipid component of oxLDL
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oxLig-1 (technical grade)

Item No. 40740

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-[(8-carboxy-1-oxooctyl)oxy]-cholest-5-en-7-one
CAS Number
352523-18-3
Synonyms
  • 7-Ketocholesteryl-9-carboxynonanoate
Molecular Formula
C36H58O5
Formula Weight
570.8
Purity
≥80%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C(C=C4C[C@@H](OC(CCCCCCCC(O)=O)=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
InChi Code
InChI=1S/C36H58O5/c1-24(2)12-11-13-25(3)28-16-17-29-34-30(19-21-36(28,29)5)35(4)20-18-27(22-26(35)23-31(34)37)41-33(40)15-10-8-6-7-9-14-32(38)39/h23-25,27-30,34H,6-22H2,1-5H3,(H,38,39)/t25-,27+,28-,29+,30+,34+,35+,36-/m1/s1
InChi Key
YEWAZFNDLCTTDN-FJQOAEFNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $138

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    5 mg

    $654

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    10 mg

    $963

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    Product Description

    oxLig-1 is an ω-carboxylated 7-ketocholesteryl ester and a lipid component of oxidized LDL (oxLDL).1 It binds to the ligand-binding domain of peroxisome proliferator-activated receptor γ (PPARγ), an effect that can be reversed by the PPARγ agonist troglitazone (Item No. 71750), and also binds to CD36, also known as scavenger receptor B2, when used at a concentration of 50 µg/ml.2,3 oxLig-1 (20 µg/ml) increases cholesterol efflux and protein levels of liver X receptor α (LXRα) and ATP-binding cassette transporter 1 subfamily A (ABCA1) in THP-1 macrophages. Liposomes containing oxLig-1 and complexed with apolipoprotein H, also known as β2-glycoprotein I (β2-GPI), bind to an anti-apolipoprotein H antibody, which mediates uptake by J774A.1 macrophages.1 oxLig-1 decreases intracellular lipid accumulation induced by oleic acid (Item Nos. 90260 | 24659) in HepG2 cells, as well as hepatic lipid accumulation in mice fed a high-fat diet.3 Serum levels of IgG autoantibodies targeting a complex of oxLig-1 and apolipoprotein H are increased in patients with antiphospholipid syndrome with a history of arterial thrombosis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kobayashi, K., Matsuura, E., Liu, Q., et al. A specific ligand for β2-glycoprotein I mediates autoantibody-dependent uptake of oxidized low density lipoprotein by macrophages. J. Lipid Res. 42(5), 697-709 (2001).

    2. Chi, Y., Wang, L., Liu, Y., et al. 7-ketocholesteryl-9-carboxynonanoate enhances ATP binding cassette transporter A1 expression mediated by PPARγ in THP-1 macrophages. Atherosclerosis 234(2), 461-468 (2014).

    3. Fu, C., Xiang, M.-L., Chen, S., et al. Molecular drug simulation and experimental validation of the CD36 receptor competitively binding to long-chain fatty acids by 7-ketocholesteryl-9-carboxynonanoate. ACS Omega 8(31), 28277-28289 (2023).

    4. Lopez, D., Kobayashi, K., Merrill, J.T., et al. IgG autoantibodies against β2-glycoprotein I complexed with a lipid ligand derived from oxidized low-density lipoprotein are associated with arterial thrombosis in antiphospholipid syndrome. Clin. Dev. Immunol. 10(2-4), 203-211 (2003).