601-53-6 Usage
Description
5β-Cholestan-3-one, also known as cholestan-3-one, is a steroidal ketone and a metabolite of cholesterol. It is a white crystalline solid with a molecular formula of C27H46O and a molecular weight of 386.66 g/mol. It is soluble in organic solvents such as ethanol, methanol, and acetone but insoluble in water. 5BETA-CHOLESTAN-3-ONE has a unique structure with a cyclohexane ring and a side chain, which makes it a valuable compound for various applications.
Uses
Used in Pharmaceutical Industry:
5β-Cholestan-3-one is used as a pharmaceutical intermediate for the synthesis of various cholesterol-lowering drugs. It is used in the production of statins, a class of drugs that inhibit the enzyme HMG-CoA reductase, which is involved in cholesterol biosynthesis. By inhibiting this enzyme, statins reduce the levels of low-density lipoprotein (LDL) cholesterol in the blood, thus helping to prevent cardiovascular diseases.
Used in Research and Development:
5β-Cholestan-3-one is used as a research tool in the study of cholesterol metabolism and its role in various diseases. It is used to assess the biosynthesis of cholesterol and to investigate the mechanisms of cholesterol regulation in the body. 5BETA-CHOLESTAN-3-ONE is also used in the development of new drugs and therapies targeting cholesterol-related disorders.
Used in Analytical Chemistry:
5β-Cholestan-3-one is used as an internal standard in the analysis of cholesterol and other sterols by gas chromatography and mass spectrometry. It helps to improve the accuracy and precision of the analysis by providing a reference point for the quantification of the target compounds.
Used in Cosmetics Industry:
5β-Cholestan-3-one is used as an ingredient in some cosmetics and personal care products due to its emollient and moisturizing properties. It helps to improve the skin's hydration and elasticity, providing a smooth and youthful appearance.
Check Digit Verification of cas no
The CAS Registry Mumber 601-53-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 1 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 601-53:
(5*6)+(4*0)+(3*1)+(2*5)+(1*3)=46
46 % 10 = 6
So 601-53-6 is a valid CAS Registry Number.
InChI:InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20-,22+,23-,24+,25+,26+,27-/m1/s1
601-53-6Relevant articles and documents
Reduction of a Δ4-steroid with diborane
D'Alessandro,Giacopello,Seldes,Deluca
, p. 2703 - 2708 (1995)
Reported here is a boron process equivalent to stereoselective olefin reduction and concomitant protecting group cleavage.
Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones
Lator, Alexis,Gaillard, Sylvain,Poater, Albert,Renaud, Jean-Luc
supporting information, p. 5770 - 5774 (2018/03/26)
An iron-catalyzed chemo- and diastereoselective reduction of α,β-unsaturated ketones into the corresponding saturated ketones in mild reaction conditions is reported herein. DFT calculations and experimental work underline that transfer hydride reduction is a more facile process than hydrogenation, unveiling the fundamental role of the base.
Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids
Ramachary, Dhevalapally B.,Sakthidevi, Rajasekar,Reddy, P. Srinivasa
, p. 13497 - 13506 (2013/09/02)
Kinetically controlled and organocatalytic syn-selective transfer hydrogenation has been successfully demonstrated for the reduction of the enone functional group of various steroids. Herein, diastereoselective synthesis of many 5β-steroids have been reported through organocatalysis, which have broad medicinal and pharmaceutical applications. The mechanistic studies and the selectivity of the products clearly indicated that the catalyst 1b·d-CSA is mild enough to activate the various chiral cyclic enones through iminium ion formation during the organocatalytic transfer hydrogenations with Hantzsch ester 2a as a hydrogen source. Further, clear evidence for the selective formation of intermediate iminium species [I]+ have been characterized through on-line monitoring of controlled experiments by NMR and ESI-HRMS analyses.