27-HydroxycholesterolAn oxysterol with cholesterol oxidation metabolite properties

27-Hydroxycholesterol (CAS 20380-11-4)

27-Hydroxycholesterol | CAS 20380-11-4 is rated 5.0 out of 5 by 1.
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Synonym: (25R)-26-Hydroxycholesterol; (25R)-Cholest-5-ene-3b,26-diol; 25(R)-27-hydroxy Cholesterol
Application: An oxysterol with cholesterol oxidation metabolite properties
CAS Number: 20380-11-4
Molecular Weight: 402.65
Molecular Formula: C27H46O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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27-Hydroxycholesterol, an oxysterol secreted from macrophages, has been shown to be capable of passing through the blood-brain barrier and entering the circulation via the brain. This compound has been shown to be a cholesterol oxidation metabolite that causes an increase in levels of GADD 153 and caspase-12 in ARPE-19 cells in vitro. 27-Hydroxycholesterol has also been reported to increase levels of Aβ peptide production, reduce mitochondrial membrane potential, and induce nuclear factor κB (NFκB) and heme-oxygenase 1 (HO-1). Overall, 27-Hydroxycholesterol displays apoptotic properties via reactive oxygen species (ROS) generation, glutathione depletion, and inflammation. 27-Hydroxycholesterol is an activator of LXR α and LXR β.


References

1. Dasari, B., et al. 2010. BMC Ophthalmol. 10: 22. PMID: 20836858

2. Karuna, R., et al. 2011. Atherosclerosis. 214: 448-455. PMID: 21130455

3. Mateos, L., et al. 2011. J Alzheimers Dis. [Epub ahead of print]. PMID: 21297254

Usage :
Stable for up to 1 year after receipt when stored at -20°C. Stock solutions should be aliquoted and stored at -20°C for up to 1 month.
Physical State :
Solid
Solubility :
Soluble in chloroform. Insoluble in water.
Storage :
Store at room temperature
Melting Point :
194.53° C (Predicted)
Boiling Point :
~517.1° C at 760 mmHg (Predicted)
Density :
~1.0 g/cm3 (Predicted)
Refractive Index :
n20D 1.54 (Predicted)
IC50 :
LXR-alpha: EC5050 = 250 nM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
123976
MDL Number :
MFCD00272990
SMILES :
C[C@H](CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)CO

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Certificate of Analysis

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27-Hydroxycholesterol  Product Citations

See how others have used 27-Hydroxycholesterol. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 20 total

PMID: # 30881285  2019. Front Mol Neurosci. 12: 14.

PMID: # 31139381  2019. Food Sci Nutr. 7: 1685-1694.

PMID: # 30563407  Liang, Z.|Chen, Y.|Wang, L.|Li, D.|Yang, X.|Ma, G.|Wang, Y.|Li, Y.|Zhao, H.|Liang, Y.|Niu, H.| et al. 2019. Cell Cycle. 18: 34-45.

PMID: # 30180878  Du, T. et al. 2018. Breast Cancer Res. 20: 106.

PMID: # 29130512  Tian, W.|Pang, W.|Ge, Y.|He, X.|Wang, D.|Li, X.|Hou, H.|Zhou, D.|Feng, S.|Chen, Z.|Yang, Y.| et al. 2018. J. Cell. Biochem. 119: 2929-2938.

PMID: # 28503095  Raza, S.|Meyer, M.|Goodyear, C.|Hammer, KDP.|Guo, B.|Ghribi, O.| et al. 2017. Cancer Cell Int. 17: 52.

PMID: # 28739487  2017. Toxicol In Vitro. 45: 10-18.

PMID: # 28257824  2017. Environ. Toxicol. Pharmacol. 51: 1-8.

PMID: # 28118975  Kylli, P. et al. 2017. J Chromatogr A. 1487: 147-152.

PMID: # 28167099  2017. Neurotoxicology. 59: 88-97.

Citations 1 to 10 of 20 total

I dissolved 27-hydroxycholesterol in DMSO (12mM) and from this stock 1 micromolar was prepared dissolving in DMEM. But it got re-precipitated. What can be done to prevent this??

Asked by: two2igm05
Thank you for your question. This chemical, 27-Hydroxycholesterol, is soluble in DMSO, however, we do not have any information regarding solubility in DMEM.
Answered by: Technical Support
Date published: 2017-03-09

What is the solubility of this product?

Asked by: hawkeye11
This product is soluble in DMSO.
Answered by: Chemical Support 4
Date published: 2017-02-25
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Rated 5 out of 5 by from Raza Raza, et al. (PubMed ID 26350565) reported that 27-Hydroxycholesterol (27-OHC) may play a role in estrogen receptor-positive breast cancer progression. It disrupts essential MDM2 modulated p53 signaling. -SCBT Publication Review
Date published: 2015-04-15
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