516-72-3
516-72-3
Chemical Structure
20(S)-Hydroxycholesterol
Synonym(s): 20α-Hydroxycholesterol
- CAS. Nr.: 516-72-3
- Formula:C27H46O2
- Molecular Weight:402.65
IUPAC Name: (3S,8S,9S,10R,13S,14S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChIKey: MCKLJFJEQRYRQT-APGJSSKUSA-N
SMILES: C[C@@]1([C@@]2([H])[C@@](C)(O)CCCC(C)C)[C@](CC2)([H])[C@@](CC=C3[C@@]4(CC[C@H](O)C3)C)([H])[C@]4([H])CC1
Biological Activity: 20(S)-Hydroxycholesterol (20α-Hydroxycholesterol) is an allosteric activator that selectively targets the Smoothened (Smo) of the Hedgehog pathway with an EC50 of ~30 μM (Hedgehog). 20(S)-Hydroxycholesterol binds to the extracellular cysteine-rich domain (CRD) of Smo in a stereoselective manner, activating downstream Gli transcription factors (without inducing transcription of receptor genes in the Wnt pathway). 20(S)-Hydroxycholesterol enhances osteogenic differentiation of bone marrow stromal cells and synergistically activates the Raf/MEK/ERK pathway with Simvastatin (HY-17502) to promote bone regeneration. 20(S)-Hydroxycholesterol can be used to study the mechanisms of developmental biology, oncology, bone, and angiogenesis[1][2][3].
| Art. -Nr. | Produktname | Reinheit | Beschreibung | Pricing | |||||||||||||||||||
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20(S)-Hydroxycholesterol | 99.63% | 20(S)-Hydroxycholesterol (20α-Hydroxycholesterol) is an allosteric activator that selectively targets the Smoothened (Smo) of the Hedgehog pathway with an EC50 of ~30 μM (Hedgehog). 20(S)-Hydroxycholesterol binds to the extracellular cysteine-rich domain (CRD) of Smo in a stereoselective manner, activating downstream Gli transcription factors (without inducing transcription of receptor genes in the Wnt pathway). 20(S)-Hydroxycholesterol enhances osteogenic differentiation of bone marrow stromal cells and synergistically activates the Raf/MEK/ERK pathway with Simvastatin (HY-17502) to promote bone regeneration. 20(S)-Hydroxycholesterol can be used to study the mechanisms of developmental biology, oncology, bone, and angiogenesis. | ||||||||||||||||||||
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20(S)-Hydroxycholesterol (Standard) | 98.69% | 20(S)-Hydroxycholesterol (Standard) is the analytical standard of 20(S)-Hydroxycholesterol. This product is intended for research and analytical applications. 20(S)-hydroxyCholesterol (20α-Hydroxycholesterol) is an allosteric activator of the oncoprotein smoothened (Smo) that activates the hedgehog (Hh) signaling pathway with an EC50 of 3 μM in a gene transcription reporter assay using NIH3T3 cells. | ||||||||||||||||||||
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25-Hydroxycholesterol (Standard) | ≥98% | 25-Hydroxycholesterol (Standard) is the analytical standard of 25-Hydroxycholesterol. This product is intended for research and analytical applications. 25-Hydroxycholesterol (25-OHC) is a metabolite of cholesterol that is produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells. | ||||||||||||||||||||
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22(R)-Hydroxycholesterol | 99.86% | 22 (R)-Hydroxycholesterol (Narthesterol) is a natural oxysterol, acting as a LXRα agonist that inhibits cancer cell proliferation. 22 (R)-Hydroxycholesterol activates LXRα-mediated upregulation of downstream ABCA1 expression, enhances apolipoprotein-dependent cholesterol efflux, reduces intracellular cholesterol content, and decreases the production of β-amyloid peptide. 22 (R)-Hydroxycholesterol induces the differentiation of human mesenchymal stem cells into functional dopaminergic neurons. 22 (R)-Hydroxycholesterol is applicable to research related to cancer, Alzheimer's disease, and Parkinson's disease. | ||||||||||||||||||||
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20α,22R-Dihydroxycholesterol | 98.48% | 20α,22R-Dihydroxycholesterol is an endogenous metabolic intermediate. 20α,22R-Dihydroxycholesterol involved in the biosynthesis of cholesterol to steroid hormones. | ||||||||||||||||||||
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Nat 20(S)-yne | Nat 20(S)-yne is a steroid with an alkyne group at the terminal end, and it can be used in click chemistry reactions. | |||||||||||||||||||||
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SGE-201 | SGE-201 is an allosteric modulator of N-methyl-D-aspartate receptors (NMDARs), demonstrating significant neuroprotective effects by enhancing NMDAR-mediated responses while differing in action among various blockers in neuronal networks. | |||||||||||||||||||||
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25-Flurocholesterol | 25-Flurocholesterol is an oxysterol. 25-Fluorocholesterol increases pigmentation. | |||||||||||||||||||||
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Cholesterol (Standard) | 99.91% | Cholesterol (Standard) is the analytical standard of Cholesterol. This product is intended for research and analytical applications. Cholesterol is the major sterol in mammals. It is making up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist. | ||||||||||||||||||||
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Cholesterol-13C5 | 99.5% | Cholesterol-13C5 is the 13C-labeled Cholesterol. Cholesterol is the major sterol in mammals. It is making up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist. | ||||||||||||||||||||
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Cholesterol-13C2 | 99.66% | Cholesterol-13C2 is the 13C labeled Cholesterol. Cholesterol is the major sterol in mammals. It is making up 20-25% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist. | ||||||||||||||||||||
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ent-25-Hydroxycholesterol | ent-25-Hydroxycholesterol is an enantiomer of 25-Hydroxycholesterol (HY-113134). | |||||||||||||||||||||
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References
- [1]. Nachtergaele S, et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat Chem Biol. 2012 Jan 8;8(2):211-20. [Content Brief]
- [2]. Huang Y, et al. 20(S)-hydroxycholesterol and simvastatin synergistically enhance osteogenic differentiation of marrow stromal cells and bone regeneration by initiation of Raf/MEK/ERK signaling. J Mater Sci Mater Med. 2019 Jul 19;30(8):87. [Content Brief]
- [3]. Nedelcu D, et al, Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat Chem Biol. 2013 Sep;9(9):557-64. [Content Brief]
