A precursor of cholesterol
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Zymostenol

Item No. 26209

Technical Information
Formal Name
(5α)-cholest-8-en-3β-ol
CAS Number
566-97-2
Synonyms
  • Δ8-Cholesterol
Molecular Formula
C27H46O
Formula Weight
Purity
≥95%
Formulation
A crystalline solid
DMF: 3 mg/mlEthanol: 2 mg/ml
SMILES
C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]([C@]1(C)CC2)([H])C3=C2[C@]4(C)[C@](CC3)([H])C[C@@H](O)CC4
InChi Code
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChi Key
QETLKNDKQOXZRP-XTGBIJOFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Zymostenol is a late-stage precursor in the biosynthesis of cholesterol.1 It is an agonist of retinoic acid receptor-related orphan receptor γ (RORγ) with an EC50 value of 1 µM in a RORγ coactivator recruitment assay in the presence of ursolic acid (Item No. 10072). It increases the number of myelin basic protein-positive oligodendrocytes generated from oligodendrocyte precursor cells in vitro.2 Zymostenol accumulates in cells following administration of microsomal antiestrogen-binding site (AEBS) ligands, such as tamoxifen (Item No. 13258), which are associated with cell differentiation and a protective type of autophagy.3,4 When used alone at a concentration of 20 µM, zymostenol halts the cell cycle at the G0/G1 phase and increases the levels of free sterols, esterified sterols, and triacylglycerols in MCF-7 cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hu, X., Wang, Y., Hao, L.-Y., et alSterol metabolism controls TH17 differentiation by generating endogenous RORγ agonists. Nat. Chem. Biol. 11(9), 141-147 (2015).

    2. Hubler, Z., Allimuthu, D., Bederman, I., et alAccumulation of 8,9-unsaturated sterols drives oligodendrocyte formation and remyelination. Nature 560(7718), 372-376 (2018).

    3. Payré, B., de Medina, P., Boubekeur, N., et alMicrosomal antiestrogen-binding site ligands induce growth control and differentiation of human breast cancer cells through the modulation of cholesterol metabolism. Mol. Cancer Ther. 7(12), 3707-3718 (2008).

    4. Poirot, M., and Silvente-Poirot, S. The tumor-suppressor cholesterol metabolite, dendrogenin A, is a new class of LXR modulator activating lethal autophagy in cancers. Biochem. Pharmacol. 153, 75-81 (2018).