An internal standard for the quantification of cholesteryl arachidonate
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Unlabeled Version(s)
22595Cholesteryl Arachidonate
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Cholesteryl Arachidonate-d8

Item No. 39085

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β)-cholest-5-en-3-ol-d8 3-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate]
Synonyms
  • Arachidonic Acid cholesteryl ester-d8
  • Cholesterol Arachidonate-d8
  • Cholesterol 5Z,8Z,11Z,14-Z Eicosatetraenoic Acid ester-d8
  • 20:4 Cholesteryl ester-d8
Molecular Formula
C47H68D8O2
Formula Weight
681.2
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 100 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/mlMethyl Acetate: 1 mg/ml
SMILES
C[C@]12C(C[C@@H](OC(CCC/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\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/i11D,12D,14D,15D,17D,18D,20D,21D
InChi Key
IMXSFYNMSOULQS-WOUNVMDJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $29

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    100 µg

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    250 µg

    $106

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    Product Description

    Cholesteryl arachidonate-d8 is intended for use as an internal standard for the quantification of cholesteryl arachidonate (Item No. 22595) by GC- or LC-MS. 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 oxidation 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).