Biomaterial Database

New bile acid analogs: 3 alpha, 7 alpha-dihydroxy-7 beta-methyl-5 beta-cholanoic acid, 3 alpha, 7 beta-dihydroxy-7 alpha-methyl-5 beta-cholanoic acid, and 3 alpha-hydroxy-7 xi-methyl-5 beta-cholanoic acid. 1984

M Une, and B I Cohen, and E H Mosbach

Methods are described for the chemical synthesis of three new bile acid analogs, namely, 3 alpha, 7 alpha-dihydroxy-7 beta-methyl-5 beta-cholanoic acid, 3 alpha, 7 beta-dihydroxy-7 alpha-methyl-5 beta-cholanoic acid and 3 alpha-hydroxyl-7 xi-methyl-5 beta-cholanoic acid. The starting material, 2-(3 alpha, 7 xi-dihydroxy-7 xi-methyl-24-nor-5 beta- cholanyl )-4, 4-dimethyl-2-oxazoline upon mild hydrolysis in aqueous HCl yields the two epimeric 3 alpha, 7-dihydroxy-7-methyl-5 beta-cholanoic acids which can be separated as the methyl esters by silica gel column chromatography. More rigorous hydrolysis in boiling methanolic HCl yields a mixture of unsaturated compounds which can be separated as their methyl esters into three fractions by silica gel-AgNO3 column chromatography. The fractions containing 3 alpha-hydroxy-7-methyl-5 beta-chol-6-enoic acid and 3 alpha-hydroxy-7-methylene-5 beta-cholanoic acid when subjected to catalytic hydrogenation yield 3 alpha-hydroxy-7 xi-methyl-5 beta-cholanoic acid.

UI	MeSH Term	Description	Entries
D008095	Lithocholic Acid	A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.	Lithocholate,Isolithocholic Acid,Acid, Isolithocholic,Acid, Lithocholic
D008401	Gas Chromatography-Mass Spectrometry	A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds.	Chromatography, Gas-Liquid-Mass Spectrometry,Chromatography, Gas-Mass Spectrometry,GCMS,Spectrometry, Mass-Gas Chromatography,Spectrum Analysis, Mass-Gas Chromatography,Gas-Liquid Chromatography-Mass Spectrometry,Mass Spectrometry-Gas Chromatography,Chromatography, Gas Liquid Mass Spectrometry,Chromatography, Gas Mass Spectrometry,Chromatography, Mass Spectrometry-Gas,Chromatography-Mass Spectrometry, Gas,Chromatography-Mass Spectrometry, Gas-Liquid,Gas Chromatography Mass Spectrometry,Gas Liquid Chromatography Mass Spectrometry,Mass Spectrometry Gas Chromatography,Spectrometries, Mass-Gas Chromatography,Spectrometry, Gas Chromatography-Mass,Spectrometry, Gas-Liquid Chromatography-Mass,Spectrometry, Mass Gas Chromatography,Spectrometry-Gas Chromatography, Mass,Spectrum Analysis, Mass Gas Chromatography
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D002621	Chemistry	A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002793	Cholic Acids	The 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholanic acid family of bile acids in man, usually conjugated with glycine or taurine. They act as detergents to solubilize fats for intestinal absorption, are reabsorbed by the small intestine, and are used as cholagogues and choleretics.	Cholalic Acids,Acids, Cholalic,Acids, Cholic
D006868	Hydrolysis	The process of cleaving a chemical compound by the addition of a molecule of water.
D001647	Bile Acids and Salts	Steroid acids and salts. The primary bile acids are derived from cholesterol in the liver and usually conjugated with glycine or taurine. The secondary bile acids are further modified by bacteria in the intestine. They play an important role in the digestion and absorption of fat. They have also been used pharmacologically, especially in the treatment of gallstones.	Bile Acid,Bile Salt,Bile Salts,Bile Acids,Acid, Bile,Acids, Bile,Salt, Bile,Salts, Bile
D014580	Ursodeoxycholic Acid	An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.	Deoxyursocholic Acid,3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-oic Acid,Cholit-Ursan,Cholofalk,Delursan,Destolit,Sodium Ursodeoxycholate,Urdox,Ursacholic Acid,Urso,Urso Heumann,Ursobilane,Ursochol,Ursodiol,Ursofalk,Ursogal,Ursolite,Ursolvan,3 alpha,7 beta Dihydroxy 5 beta cholan 24 oic Acid,Acid, Deoxyursocholic,Acid, Ursacholic,Acid, Ursodeoxycholic,Ursodeoxycholate, Sodium
D055598	Chemical Phenomena	The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes.	Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical