A pro-atherogenic cholesterol ester
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Labeled Version(s)
37920Cholesteryl Linoleate-d11
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Cholesteryl Linoleate

Item No. 22597

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-en-3β-ol, 3-[(9Z,12Z)-9,12-octadecadienoate]
CAS Number
604-33-1
Synonyms
  • 18:2(9,12) CE
  • CE(18:2)
  • 18:2(9,12) Cholesterol ester
  • Cholesterol Linoleate
  • Linoleic Acid cholesteryl ester
  • NSC 18183
Molecular Formula
C45H76O2
Formula Weight
649.1
Purity
≥98%
Formulation (Request formulation change)
A waxy crystal
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/ml
λmax
232 nm
SMILES
C[C@]12C(C[C@@H](OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)CC2)=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@@]4([C@@H](CCCC(C)C)C)[H]
InChi Code
InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChi Key
NAACPBBQTFFYQB-LJAITQKLSA-N
Side Chain Carbon Sum
18:2
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 mg

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    250 mg

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    500 mg

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    Product Description

    Cholesteryl linoleate is a pro-atherogenic cholesterol ester.1,2 It has been found in the plasma membrane of macrophages as a component of LDL, where it undergoes oxidation to form cholesteryl linoleate hydroperoxides (Item No. 48001).1 Cholesteryl linoleate levels are increased in apoB-lipoproteins and positively correlated with hepatic cholesterol levels and the number of atherosclerotic lesions in transgenic mice overexpressing human ABCA1.2 Lipoprotein levels of cholesteryl linoleate are increased and associated with lipid radical formation in patients with β-thalassemia.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takahashi, Y., Zhu, H., Xu, W., et al. Selective uptake and efflux of cholesteryl linoleate in LDL by macrophages expressing 12/15-lipoxygenase. Biochem. Biophys. Res. Commun. 338(1), 128-135 (2005).

    2. Joyce, C.W., Wagner, E.M., Basso, F., et al. ABCA1 overexpression in the liver of LDLr-KO mice leads to accumulation of pro-atherogenic lipoproteins and enhanced atherosclerosis. The Journal of Biological Chemisty 281(44), 33053-33065 (2006).

    3. Lerksaipheng, P., Paiboonsukwong, K., Sanvarinda, P., et al. Kinetics of lipid radical formation in lipoproteins from β-thalassemia: Implication of cholesteryl esters and α-tocopherol. Biomed. Pharmacother. 154, 113624 (2022).