A bile acid alcohol
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5β-Cholestane-3α,7α,12α,25-tetrol

Item No. 42577

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
18866-87-0
Synonyms
  • 3α,7α,12α,25-Tetrahydroxycoprostane
Molecular Formula
C27H48O4
Formula Weight
436.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥ 10 mg/mlEthanol: Soluble: ≥ 10 mg/ml
SMILES
O[C@H]1[C@@]2([H])[C@@]3([H])[C@@]([C@]([C@@H](CCCC(C)(O)C)C)([H])CC3)([C@H](C[C@]2([H])[C@@]4([C@](C[C@@H](CC4)O)([H])C1)C)O)C
InChi Code
InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChi Key
NTIXPPFPXLYJCT-RNUSRIHUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    Product Description

    5β-Cholestane-3α,7α,12α,25-tetrol is a bile acid alcohol.1,2,3 It induces activation of G protein-coupled bile acid receptor 1 (GPBAR1), also known as TGR5, in HEK293 cells expressing the human receptor when used at concentrations ranging from 0.1 to 10 µM.1 Blood, fecal, and bile levels of 5β-cholestane-3α,7α,12α,25-tetrol are increased in patients with cerebrotendinous xanthomatosis (CTX), a progressive metabolic leukodystrophy.1,2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iguchi, Y., Yamaguchi, M., Sato, H., et al. Bile alcohols function as the ligands of membrane-type bile acid-activated G protein-coupled receptor. J. Lipid Res. 51(6), 1432-1441 (2010).

    2. DeBarber, A.E., Kalfon, L., Fedida, A., et al. Newborn screening for cerebrotendinous xanthomatosis is the solution for early identification and treatment. J. Lipid Res. 59(11), 2214-2222 (2018).

    3. Dayal, B., Shefer, S., Tint, G.S., et al. Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 24ξ, 25-pentol. J. Lipid Res. 17(1), 74-77 (1976).