A cholesterol ester
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Cholesteryl Eicosapentaenoate

Item No. 22719

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-en-3β-ol, 3-[(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoate]
CAS Number
74892-97-0
Synonyms
  • 20:5 Cholesteryl ester
Molecular Formula
C47H74O2
Formula Weight
671.1
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in chloroform
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/ml
SMILES
C[C@]12C(C[C@@H](OC(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)CC2)=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)C
InChi Code
InChI=1S/C47H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/b9-8-,12-11-,15-14-,18-17-,21-20-/t38-,40+,41+,42-,43+,44+,46+,47-/m1/s1
InChi Key
XZFUGMCJZFRBKF-BDJFIEMMSA-N
Side Chain Carbon Sum
20:5
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $178

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    10 mg

    $312

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    25 mg

    $680

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    Product Description

    Cholesteryl eicosapentaenoate is a cholesterol ester.1 It induces cytotoxicity in human monocyte-macrophages in a concentration-dependent manner at concentrations ranging from 88 to 880 μM. Cholesteryl eicosapentaenoate levels are elevated 1.89-fold in the serum of pediatric patients with extrahepatic biliary atresia and decreased in the serum and plasma of patients with Alzheimer’s disease and abetalipoproteinemia, respectively, compared with healthy individuals.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hardwick, S.J., Carpenter, K.L., Law, N.S., et al. Toxicity of polyunsaturated fatty acid esters for human monocyte-macrophages: The anomalous behaviour of cholesteryl linolenate. Free Radic. Res. 26(4), 351-362 (1997).

    2. Robberecht, E., Koletzko, B., and Christophe, A. Several mechanisms contribute to the abnormal fatty acid composition of serum phospholipids and cholesterol esters in cholestatic children with extrahepatic biliary atresia. Prostaglandins Leukot. Essent. Fatty Acids 56(3), 199-204 (1997).

    3. Tully, A.M., Roche, H.M., Doyle, R., et al. Low serum cholesteryl ester-docosahexaenoic acid levels in Alzheimer’s disease: A case-control study. Br. J. Nutr. 89(4), 483-489 (2003).

    4. Subbaiah, P.V., Banerji, B., Gregg, R.E., et al. Molecular species of cholesteryl esters formed in abetalipoproteinemia: Effect of apoprotein B-containing lipoproteins. J. Lipid Res. 31(5), 927-932 (1990).