An oxysterol and bile acid precursor
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7α-hydroxy Cholesterol

Item No. 20098

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-ene-3β,7α-diol
CAS Number
566-26-7
Molecular Formula
C27H46O2
Formula Weight
402.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
SMILES
O[C@H](C1)CC[C@@]2(C)C1=C[C@@H](O)[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCCC(C)C
InChi Code
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChi Key
OYXZMSRRJOYLLO-RVOWOUOISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

    $236

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    25 mg

    $527

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    Product Description

    7α-hydroxy Cholesterol is an oxysterol and a precursor in the biosynthesis of the bile acids cholic acid (CA; Item No. 20250) and chenodeoxycholic acid (CDCA; Item No. 10011286).1,2 It is formed via the oxidation of cholesterol (Item No. 9003100) by cholesterol 7α-hydroxylase/CYP7A1 in rat liver microsomes.1 7α-hydroxy Cholesterol (40 µM) increases levels of the adhesion molecules ICAM-1, VCAM-1, and E-selectin in human umbilical vein endothelial cells (HUVECs).3 It increases secretion of chemokine (C-C motif) ligand 2 (CCL2) and matrix metalloproteinase-9 (MMP-9) in serum-deprived THP-1 cells when used at a concentration of 5 µg/ml.4 7α-hydroxy Cholesterol has been found in macrophages isolated from atherosclerotic lesions in rabbits fed a high-cholesterol diet.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mitropoulos, K.A., and Balasubramaniam, S. Cholesterol 7α-hydroxylase in rat liver microsomal preparations. Biochem. J. 128(1), 1-9 (1972).

    2. Chiang, J.Y.L. Bile acid metabolism and signaling in liver disease and therapy. Liver Res. 1(1), 3-9 (2017).

    3. Lemaire, S., Lizard, G., Monier, S., et al. Different patterns of IL-1β secretion, adhesion molecule expression and apoptosis induction in human endothelial cells treated with 7α-, 7β-hydroxycholesterol, or 7-ketocholesterol. FEBS Lett. 440(3), 434-439 (1998).

    4. Kim, S.M., Kim, B.Y., Son, Y., et al. 7α-Hydroxycholesterol induces inflammation by enhancing production of chemokine (C-C motif) ligand 2. Biochem. Biophys. Res. Commun. 467(4), 879-884 (2015).

    5. Hultén, L.M., Lindmark, H., Diczfalusy, U., et al. Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages. J. Clin. Invest. 97(2), 461-468 (1996).