17320-10-4 Usage
Description
4-BETA-HYDROXYCHOLESTEROL, also known as an oxysterol, is a metabolite of cholesterol formed by the drug-metabolizing enzyme cytochrome P450 3A4. It is characterized by the replacement of the hydrogen at the 4-beta position with a hydroxy group, making it one of the major oxysterols in human circulation. This white solid possesses unique chemical properties and has been identified as a potential ligand for the nuclear receptor LXR, as well as a new endogenous CYP3A marker.
Uses
Used in Pharmaceutical Industry:
4-BETA-HYDROXYCHOLESTEROL is used as a potential ligand for the nuclear receptor LXR, playing a crucial role in the regulation of cellular processes and gene expression. Its interaction with LXR can have implications in the development of therapeutic strategies for various diseases.
Used in Drug Metabolism Research:
As a new endogenous CYP3A marker, 4-BETA-HYDROXYCHOLESTEROL is used in the study of drug metabolism, particularly in understanding the role of cytochrome P450 3A4 enzyme in the metabolism of various drugs and compounds. This can help in the development of more effective and safer medications.
Used in Chemical and Analytical Research:
4-BETA-HYDROXYCHOLESTEROL, being a white solid with distinct chemical properties, is used as a research compound in chemical and analytical studies. Its unique structure and properties make it a valuable tool for investigating various chemical reactions and processes.
Used in Cholesterol Metabolism Studies:
As a metabolite of cholesterol, 4-BETA-HYDROXYCHOLESTEROL is used in research to understand the complex pathways and mechanisms involved in cholesterol metabolism. This knowledge can contribute to the development of treatments for conditions related to cholesterol imbalance, such as atherosclerosis and hypercholesterolemia.
Biological Activity
4β-hydroxy cholesterol is an endogenous marker for cyp3a4/5 activity [1].cytochome p450 3a4 (cyp3a4) and cyp3a5 are important drug-metabolizing enzymes that oxidize small foreign organic molecules, such as toxins or drugs, and remove them from the body. they exhibit a large variation in hepatic expression and biological activity between different individuals. patients treated with drugs known to be strong inducers of cyp3a4/5 have highly elevated levels of 4β-hydroxycholesterol in the circulation [1].4β-hydroxy cholesterol, an endogenous oxysterol found in human circulation, is formed from cholesterol by cytochrome p450 (cyp) 3a4 and cyp3a5. in 12 different occasions during a 3-month period, the cvs for 4β-hydroxycholesterol ranged from 4.8 to 13.2% with an average cv of 7.1% at an average concentration of 30.8 ng/ml. in 24 volunteers treated with rifampicin, a strong cyp3a4/5 inducer, 4β-hydroxycholesterol increased in a dose-dependent way, while the isomer 4α-hydroycholesterol was not influenced by rifampicin treatment. these results suggested that 4β-hydroxy cholesterol is an endogenous marker for cyp3a4/5 activity [1].
references
[1]. diczfalusy u, kanebratt kp, bredberg e, et al. 4beta-hydroxycholesterol as an endogenous marker for cyp3a4/5 activity. stability and half-life of elimination after induction with rifampicin. br j clin pharmacol. 2009 jan;67(1):38-43.
Check Digit Verification of cas no
The CAS Registry Mumber 17320-10-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,3,2 and 0 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 17320-10:
(7*1)+(6*7)+(5*3)+(4*2)+(3*0)+(2*1)+(1*0)=74
74 % 10 = 4
So 17320-10-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3
17320-10-4Relevant articles and documents
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Dahl,T.,Stevenson,R.
, p. 3243 - 3246 (1971)
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Cholesterol transformations during heat treatment
Derewiaka,Molińska
, p. 233 - 240 (2015/01/09)
The aim of the study was to characterise products of cholesterol standard changes during thermal processing. Cholesterol was heated at 120 °C, 150 °C, 180 °C and 220 °C from 30 to 180 min. The highest losses of cholesterol content were found during thermal processing at 220 °C, whereas the highest content of cholesterol oxidation products was observed at temperature of 150 °C. The production of volatile compounds was stimulated by the increase of temperature. Treatment of cholesterol at higher temperatures i.e. 180 °C and 220 °C led to the formation of polymers and other products e.g. cholestadienes and fragmented cholesterol molecules. Further studies are required to identify the structure of cholesterol oligomers and to establish volatile compounds, which are markers of cholesterol transformations, mainly oxidation.
Oxidation with selenium dioxide: The first report of solvent-selective steroidal aromatization, efficient access to 4β,7α-dihydroxy steroids, and syntheses of natural diaromatic ergosterols
Ghosh, Pranab,Das, Jayanta,Sarkar, Antara,Ng, Seik Weng,Tiekink, Edward R.T.
experimental part, p. 6485 - 6491 (2012/09/07)
Selenium dioxide oxidation of cholesterol reveals a solvent-dependent product selectivity and facile one-pot synthesis of three derivatives, including aromatic analogues of naturally occurring ergosterol. Efficient access to 4β,7α-dihydroxy cholesterol is
