An oxysterol metabolite of cholesterol
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Labeled Version(s)
259685α,6β-Dihydroxycholestanol-d7
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5α,6β-Dihydroxycholestanol

Item No. 25538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholestane-3β,5α,6β-triol
CAS Number
1253-84-5
Synonyms
  • Cholestanetriol
  • NSC 124751
  • NSC 18178
  • 5α,6β-di-OHC
Molecular Formula
C27H48O3
Formula Weight
420.7
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](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
InChi Code
InChI=1S/C27H48O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28-30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1
InChi Key
YMMFNKXZULYSOQ-RUXQDQFYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $90

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    10 mg

    $168

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    25 mg

    $392

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    50 mg

    $740

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    Product Description

    5α,6β-Dihydroxycholestanol is an oxysterol metabolite of cholesterol formed from conversion of cholesterol epoxides by 5,6-epoxysterol hydrolase.1,2 It inhibits NMDA-mediated calcium influx in HEK293 cells expressing NR1/NR2B NMDA receptors in a concentration-dependent manner. It also binds to voltage-gated sodium (Nav) channels and decreases action potentials in hippocampal neurons in vitro when used at a concentration of 10 µM.2 It increases survival of spinal cord motoneurons, cortical neurons, and cerebellar granule neurons in vitro when used at concentrations ranging from 5 to 15 µM.3 5α,6β-Dihydroxycholestanol is neuroprotective in a rat model of cerebral ischemia when administered at a dose of 12 mg/kg and increases latency to seizure onset and reduces severity of seizures induced by pentylenetetrazole (PTZ; Item No. 18682) in rats. 5α,6β-Dihydroxycholestanol has been used as a replacement for cholesterol in the study of cholesterol binding proteins.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aringer, L., and Eneroth, P. Formation and metabolism in vitro of 5,6-epoxides of cholesterol and β-sitosterol. J. Lipid Res. 15(4), 389-398 (1974).

    2. Tang, L., Yan, M., Leng, T., et al. Cholestane-3β, 5α, 6β-triol suppresses neuronal hyperexcitability via binding to voltage-gated sodium channels. Biochem. Biophys. Res. Commun. 496(1), 95-100 (2018).

    3. Hu, H., Zhou, Y., Leng, T., et al. The major cholesterol metabolite cholestane-3β,5α,6β-triol functions as an endogenous neuroprotectant. J. Neurosci. 34(34), 11426-11438 (2014).

    4. Sheng, R., Kim, H., Lee, H., et al. Cholesterol selectively activates canonical Wnt signalling over non-canonical Wnt signalling. Nat. Commun. 5:4393, (2014).