A cholesterol ester
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Labeled Version(s)
39085Cholesteryl Arachidonate-d8
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Cholesteryl Arachidonate

Item No. 22595

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β)-cholest-5-en-3-ol 3-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate]
CAS Number
604-34-2
Synonyms
  • Arachidonic Acid cholesteryl ester
  • Cholesterol Arachidonate
  • Cholesterol 5Z,8Z,11Z,14Z-Eicosatetraenoic Acid ester
  • 20:4 Cholesteryl ester
Molecular Formula
C47H76O2
Formula Weight
673.1
Purity
≥98%
Formulation (Request formulation change)
A neat oil
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\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/C47H76O2/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/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11-,15-14-,18-17-,21-20-/t38-,40+,41+,42-,43+,44+,46+,47-/m1/s1
InChi Key
IMXSFYNMSOULQS-BEDFLICRSA-N
Side Chain Carbon Sum
20:4
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Product Description

    Cholesteryl arachidonate is a cholesterol ester that is found in plasma and the adrenal gland.1 It is a component of low-density lipoprotein (LDL) and oxidiation of the arachidonate moiety contributes to macrophage activation and foam cell formation in atherosclerosis.2 Cholesteryl arachidonate undergoes hydrolysis to release arachidonic acid during ACTH-stimulated prostaglandin synthesis in rat adrenocortical cells.3 Levels of cholesteryl arachidonate are increased in the bronchoalveolar lavage fluid (BALF) in pediatric cystic fibrosis patients compared to healthy controls as well as in placentas of women with chorioamnionitis.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cheng, B., Al-Shammari, F.H., Ghader, I.A., et al. Fundamental studies of adrenal retinoid-X-receptor: Protein isoform, tissue expression, subcellular distribution, and ligand availability. J. Steroid. Biochem. Mol. Biol. 171, 110-120 (2017).

    2. Choi, S.-H., Yin, H., Ravandi, A., et al. Polyoxygenated cholesterol ester hydroperoxide activates TLR4 and SYK dependent signaling in macrophages. PLoS One 8(12), e83145 (2013).

    3. Vahouny, G.V., Chanderbhan, R., Hodges, V.A., et al. Cholesterol arachidonate as a prostaglandin precursor in adrenocortical cells. Prostaglandins 16(2), 207-220 (1978).

    4. Ma, D.C., Yoon, A.J., Faull, K.F., et al. Cholesteryl esters are elevated in the lipid fraction of bronchoalveolar lavage fluid collected from pediatric cystic fibrosis patients. PLoS One 10(4), e0125326 (2015).

    5. Delmis, J. Placental lipid contents in preterm labor complicated by chorioamnionitis. J. Perinat. Med. 17(6), 417-422 (1989).

    Product Citations

    Lange, M., Wagner, P.V., and Fedorova, M. Lipid composition dictates the rate of lipid peroxidation in artificial lipid droplets. Free Radic. Res. 55(4), 469-480 (2021).