A 15-LO product derived from cholesteryl linoleate
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(±)13-HODE cholesteryl ester

Item No. 38601

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-13-hydroxy-9Z,11E-octadecadienoic acid, cholesteryl ester
CAS Number
167354-91-8
Molecular Formula
C45H76O3
Formula Weight
665.1
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/mlDMSO: >50 mg/mlEthanol: >50 mg/mlEthanol:PBS (1:10): <10 µg/ml
λmax
234 nm
SMILES
CCCCCC(O)\C=C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@H]23)C1
InChi Code
InChI=1S/C45H76O3/c1-7-8-16-22-37(46)23-17-14-12-10-9-11-13-15-18-24-43(47)48-38-29-31-44(5)36(33-38)25-26-39-41-28-27-40(35(4)21-19-20-34(2)3)45(41,6)32-30-42(39)44/h12,14,17,23,25,34-35,37-42,46H,7-11,13,15-16,18-22,24,26-33H2,1-6H3/b14-12-,23-17+/t35-,37?,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChi Key
RZXYPSUQZUUHPD-ZCNQQENXSA-N
Side Chain Carbon Sum
18:2
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $108

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    50 µg

    $205

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    100 µg

    $387

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    Product Description

    (±)13-HODE cholesteryl ester was originally extracted from atherosclerotic lesions1 and shown to be produced by Cu2+-catalyzed oxidation of LDL.2 Later studies determined that 15-LO from rabbit reticulocytes and human monocytes were able to metabolize cholesteryl linoleate, a major component of LDL, to 13-HODE cholesteryl ester.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brooks, C.J.W., Harland, W.A., Steel, G., et al. Lipids of human atheroma: Isolation of hydroxyoctadecadienoic acids from advanced aortal lesions. Biochim. Biophys. Acta 202(3), 563-566 (1970).

    2. Lenz, M.L., Hughes, H., Mitchell, J.R., et al. Lipid hydroperoxy and hydroxy derivatives in copper-catalyzed oxidation of low density lipoprotein. J. Lipid Res. 31(6), 1043-1050 (1990).

    3. Belkner, J., Wiesner, R., Kühn, H., et al. The oxygenation of cholesterol esters by the reticulocyte lipoxygenase. FEBS Lett. 279(1), 110-114 (1991).

    4. Folcik, V.A., and Cathcart, M.K. Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL. J. Lipid Res. 35(9), 1570-1582 (1994).

    Product Citations

    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).