An endogenous agonist for LXR
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25(S)-27-hydroxy Cholesterol

Item No. 14791

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(25S)-cholest-5-ene-3β,26-diol
CAS Number
56845-83-1
Synonyms
  • (25S)-26-hydroxy Cholesterol
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
O[C@@H]1CC2=CC[C@]3([H])[C@@](CC[C@]4([C@@]3([H])CC[C@]4([H])[C@@H](CCC[C@H](C)CO)C)C)([H])[C@](C)2CC1
InChi Code
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19+,21-,22-,23+,24-,25-,26-,27+/m0/s1
InChi Key
FYHRJWMENCALJY-VICXTREFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    The liver x receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands, oxysterols, induce the expression of genes involved in cholesterol and fatty acid metabolism.1 27-hydroxy Cholesterol, a sterol 27-hydroxylase-mediated cholesterol hydroxylation product, activates LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM, respectively, and is a potent suppressor of cholesterol biosynthesis.2,3 25(S)-27 hydroxy Cholesterol is the less predominant-occurring (~20%) stereoisomer of the endogenous oxysterol 27-hydroxy cholesterol.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, Y., and Mangelsdorf, D.J. LuXuRies of lipid homeostasis: The unity of nuclear hormone receptors, transcription regulation, and cholesterol sensing. Mol. Interv. 2(2), 78-87 (2002).

    2. Fu, X., Menke, J.G., Chen, Y., et al. 27-Hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. The Journal of Biological Chemisty 276(42), 38378-38387 (2001).

    3. Axelson, M., and Larsson, O. Low density lipoprotein (LDL) cholesterol is converted to 27-hydroxycholesterol in human fibroblasts. The Journal of Biological Chemisty 270(25), 15102-15110 (1995).

    4. Javitt, N.B. 26-Hydroxycholesterol: Synthesis, metabolism, and biologic roles. J. Lipid Res. 31(9), 1527-1533 (1990).

    5. Javitt, N.B. 25R,26-Hydroxycholesterol revisited: Synthesis, metabolism, and biologic roles. J. Lipid Res. 43(5), 665-670 (2002).