14772-92-0 Usage
Description
Methyl 3-ketoallocholate is a synthetic derivative of Petromyzonol, a bile salt derivative that is isolated from the sea lamprey (Petromyzon marinus) ammocoete, which is the larval form of the species. Methyl 3-ketoallocholate is characterized by its slightly yellow solid appearance and is primarily used for research purposes to study the biochemical characteristics of compounds containing the allocholic acid ring nucleus.
Uses
Used in Research and Development:
Methyl 3-ketoallocholate is used as a research compound for studying the biochemical properties and characteristics of allocholic acid ring-containing compounds. Its application in this field aids in understanding the structure, function, and potential applications of these compounds in various scientific and medical contexts.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3-ketoallocholate may be utilized as a starting material or intermediate in the synthesis of other compounds with potential therapeutic applications. Its unique structure and properties make it a valuable tool for drug discovery and development.
Used in Biochemical Studies:
Methyl 3-ketoallocholate is also used as a biochemical research tool to investigate the interactions and mechanisms of action of compounds containing the allocholic acid ring nucleus. This can provide insights into the development of new drugs or therapies targeting specific biological pathways.
Check Digit Verification of cas no
The CAS Registry Mumber 14772-92-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,7 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14772-92:
(7*1)+(6*4)+(5*7)+(4*7)+(3*2)+(2*9)+(1*2)=120
120 % 10 = 0
So 14772-92-0 is a valid CAS Registry Number.
InChI:InChI=1/C25H40O5/c1-14(5-8-22(29)30-4)17-6-7-18-23-19(13-21(28)25(17,18)3)24(2)10-9-16(26)11-15(24)12-20(23)27/h14-15,17-21,23,27-28H,5-13H2,1-4H3/t14?,15-,17?,18?,19?,20-,21+,23?,24?,25?/m1/s1
14772-92-0Relevant articles and documents
Potential bile acid metabolites. XXI. A new synthesis of allochenodeoxycholic and allocholic acids
Iida,Nishida,Chang,Niwa,Goto,Nambara
, p. 763 - 765 (1993)
A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3α-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo bydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.
Allomerization of cholic acid and conversion to petromyzonol
Zhu, Xingpei,Amouzou, Etchri,McLean, Stewart
, p. 2447 - 2449 (2007/10/02)
Petromyzonol, a rare bile substance, has been prepared from an abundant starting material, cholic acid.The critical conversion, the inversion of the configuration at C-5, was accomplished by oxidizing a suitably protected derivative of cholic acid to a 1,4-dien-3-one, which was then stereoselectively reduced to methyl allocholate.In a single oxidation step, the 3-hydroxy steroid was converted to the dienone by Barton's procedure using a catalytic amount of benzeneseleninic anhydride and m-iodoxybenzoic acid as the stoichiometric oxidant.The stereoselective reduction employed two steps: hydrogenation of the dienone to the saturated ketone (5α) in the presence of the Wilkinson catalyst, followed by reduction of the ketone with K-Selectride.Finally, methyl allocholate was reduced to petromyzonol with lithium aluminum hydride.
A convenient synthesis of 3-keto bile acids by selective oxidation of bile acids with silver carbonate-Celite
Tserng
, p. 501 - 504 (2007/10/14)
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