88179-71-9Relevant academic research and scientific papers
PROCESS FOR PRODUCTION OF STEROIDS
-
Page/Page column 64, (2008/12/04)
It is an object of the present invention to provide a novel method for producing a steroid compound. The present invention provides a method for producing 5β-3,7-dioxocholanic acid or an ester derivative thereof, using, as a raw material, a sterol having double bonds at position 5 and at position 24, such as cholesta-5,7,24-trien-3β-ol, ergosta-5,7,24(28)-trien-3β-ol, desmosterol, fucosterol, or ergosta-5,24(28)-dien-3β-ol, via the following 4 steps: (I) a step involving oxidation of a hydroxyl group at position 3 and isomerization of a double bond at position 5 to position 4; (II) a step involving the oxidative cleavage of a side chain to convert position 24 to a carboxyl group or an ester derivative thereof; (III) a step of introducing an oxygen functional group into position 7; and (IV) a step of constructing a 5β configuration by reductive saturation of a double bond at position 4.
Bile acid transformations by Alcaligenes recti
Mazumder, Ipsita,Mahato, Shashi B.
, p. 79 - 86 (2007/10/02)
Metabolism of cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid by the grown cells of the bacterium Alcaligenes recti suspended in water was studied.Each isolated metabolite was characterized by the application of various spectroscopic methods.Cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid yielded methylated derivatives 3α-methoxy-7α,12α-dihydroxy-5β-cholanoic acid, 3α-methoxy-7α-hydroxy-5β-cholanoic acid, 3α-methoxy-7β-hydroxy-5β-cholanoic acid, and 3α-methoxy-12α-hydroxy-5β-cholanoic acid, respectively.In addition, cholic acid furnished 7α,12α-dihydroxy-3-oxochol-4-en-24-oic acid; chenodeoxycholic acid gave 7α-hydroxy-3-oxo-5β-cholanoic acid and 7α-hydroxy-3-oxochol-4-en-24-oic acid while ursodeoxycholic acid yielded 7β-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxochola-4,6-dien-24-oic acid.The formation of various metabolites showed that two competitive enzymic reactions, i.e., selective methylation of the 3α-hydroxy group and dehydrogenation in the A/B rings, were operative.The methylation process was found to be enzymic involving an S-adenosyl-L-methionine (AdoMet)-dependent methyl transferase, and this reaction appeared to be inhibitory to the process of degradation of the ring system.In the other reaction sequence, degradation of the ring system was initiated by dehydrogenation of the 3α-hydroxy group.A 7β-dehydratase activity producing the Δ6 double bond was also noticeable in the metabolism of ursodeoxycholic acid. Keywords: sterols; bile acids; metabolites; microbial transformation; Alcaligenes recti; bacterial transformation
POTENTIAL BILE ACID METABOLITES. X. SYNTHESES OF STEREOISOMERIC 3,7-DIHYDROXY-5α-CHOLANIC ACIDS
Iida, Takashi,Momose, Toshiaki,Nambara, Toshio,Chang, Frederic C.
, p. 1929 - 1933 (2007/10/02)
New synthetic routes to allochenodeoxycholic (3α,7α-dihydroxy-5α-cholanic) and alloursodeoxycholic (3α,7β-dihydroxy-5α-cholanic) acids, and their stereoisomers are described.Treatments of allo 7α-hydroxy-3β-tosyloxy ester with N,N-dimethylformamide and of allo 7α-mesyloxy-3β-tosyloxy and 3β-cathyloxy-7α-mesyloxy esters with potassium superoxide-crown ether afforded the desired 3α,7α-, 3α,7β-, and 3β,7β-dihydroxy stereoisomers, respectively, in high yield.Highperformance liquid chromatography was of key importance in characterizing the compounds and determining their purity.Keywords--bile acid; allo bile acid; 3,7-dihydroxy-5α-cholanic acid; allochenodeoxycholic acid; alloursodeoxycholic acid; N,N-dimethylformamide reaction; potassium superoxide-18-crown-6 ether reaction; HPLC
