An oxysterol
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Isomer(s)
200987α-hydroxy Cholesterol
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5α,6α-epoxy Cholestanol

Item No. 25539

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,6α)-5,6-epoxy-cholestan-3-ol
CAS Number
1250-95-9
Synonyms
  • Cholesterol 5α,6α-epoxide
  • 5α,6α-Epoxycholesterol
  • NSC 18176
Molecular Formula
C27H46O2
Formula Weight
402.7
Purity
≥95%
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
C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C[C@H]4[C@@]5(O4)C[C@@H](O)CC[C@]5(C)[C@@]3([H])CC[C@@]21C
InChi Code
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24+,25-,26-,27+/m1/s1
InChi Key
PRYIJAGAEJZDBO-ZEQHCUNVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    100 mg

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    250 mg

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    Product Description

    5α,6α-epoxy Cholestanol is an oxysterol and a metabolite of cholesterol produced by oxidation.1 5α,6α-epoxy Cholestanol accumulates in MCF-7 breast cancer cells in a reactive oxygen species-dependent manner following tamoxifen and PBPE application and induces triacylglycerol biosynthesis by binding to liver x receptor β (LXRβ).2 5α,6α-epoxy Cholestanol levels are increased in rat aorta and mesenteric artery following orchidectomy, an effect that can be prevented by a DHA-supplemented diet.1 Levels are also increased in post-mortem frontal and occipital cortex of patients with Alzheimer’s disease.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Villalpando, D.M., Rojas, M.M., García, H.S., et al. Dietary docosahexaenoic acid supplementation prevents the formation of cholesterol oxidation products in arteries from orchidectomized rats. PLoS One 12(10), e0185805 (2017).

    2. Segala, G., de Medina, P., Iuliano, L., et al. 5,6-Epoxy-cholesterols contribute to the anticancer pharmacology of tamoxifen in breast cancer cells. Biochem. Pharmacol. 86(1), 175-189 (2013).

    3. Testa, G., Staurenghi, E., Zerbinati, C., et al. Changes in brain oxysterols at different stages of Alzheimer’s disease: Their involvement in neuroinflammation. Redox Biol. 10, 24-33 (2016).