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25-hydroxy Cholesterol New

Cayman Chemical Item Number 11097

(CAS 2140-46-7)

25-hydroxy Cholesterol (CAS 2140-46-7)

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Description

25-hydroxy Cholesterol is a side-chain substituted oxysterol derived from dietary cholesterol that inhibits the cleavage of sterol regulatory element binding proteins (SREBPs) to suppress endogenous cholesterol synthesis in various cell types.1 It has been implicated in a variety of metabolic events including cholesterol homeostasis and atherosclerosis as well as antitumor activities as it has been shown to induce apoptosis through down-regulation of Bcl-2 expression and activation of caspases.2 Immunomodulating capabilities have also been observed as the oxysterol can act as a LXR-RXR ligand coupling cholesterol synthesis to T cell proliferation, can reduce (EC50 ~ 65 nM) IgA production by B cells in response to IL-2, and can suppress differentiation of monocytes into macrophages.3,4,5

1 Adams, C.M., Reitz, J., De Brabander, J.K., et al. Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs. J Biol Chem 279(50) 52772-52780 (2004).

2 Bischoff, P.L., Holl, V., Coelho, D., et al. Apoptosis at the interface of immunosuppressive and anticancer activities: The examples of two classes of chemical inducers, oxysterols and alkylating agents. Curr Med Chem 7 693-713 (2000).

3 McDonald, J.G., and Russell, D.W. Editorial: 25-Hydroxycholesterol: A new life in immunology. J Leukoc Biol 88(6) 1071-1072 (2010).

4 Bauman, D.R., Bitmansour, A.D., McDonald, J.G., et al. 25-Hydroxycholesterol secreted by macrophages in response to toll-like receptor activation suppresses immunoglobulin A production. Proc Natl Acad Sci USA 106(39) 16764-16769 (2009).

5 Bensinger, S.J., Bradley, M.N., Joseph, S.B., et al. LXR signaling couples sterol metabolism to proliferation in the acquired immune response. Cell 134 97-111 (2008).

Formal Name 25-​diol-​cholest-​5-​ene-​3β
CAS Number 2140-46-7
Molecular Formula C27H46O2
Formula Weight 402.7
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O[C@H]​(C1)​CC[C@@]​2(C)​C1=CCC3C2CC[C@@]​4(C)​C3CCC4[C@H]​(C)​CCCC(C)​(O)​C
Size Price Quantity Subtotal
5 mg $25.00 $0.00
10 mg $48.00 $0.00
25 mg $113.00 $0.00
100 mg $350.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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