547-98-8 Usage
Uses
3α,7α,12α-Trihydroxycoprostanic Acid is a precursor of Cholic Acid (C432600), it undergoes side chain oxidation during the synthesis of bile acids. It was found that Zellweger’s syndrome patients have abnormal mitochondrial structure, the organelle that is responsible for the side chain oxidation, and as a consequence, excess amounts of 3α,7α,12α-Trihydroxycoprostanic Acid.
Definition
ChEBI: A steroid acid that is 5beta-cholestan-26-oic acid which is substituted by hydroxy groups as the 3alpha, 7alpha, and 12alpha positions.
General Description
Trihydroxycholestanoic acid (THCA) is an oxidative metabolite of cholesterol and a precursor to bile acids. Very long-chain acyl-CoA synthetase (VLCS) associated with endoplasmic reticulum and peroxisomes activates THCA, the C27 bile acid intermediate.
Biochem/physiol Actions
Trihydroxycholestanoic acid (THCA) and dihydroxycholestanoic (DHCA) accumulation is observed in Zellweger syndrome and cholestatic liver disease. The synthesis of (25R)-isomer of DHCA and THCA is favored by mitochondrial 27-hydroxylase.
Check Digit Verification of cas no
The CAS Registry Mumber 547-98-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 7 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 547-98:
(5*5)+(4*4)+(3*7)+(2*9)+(1*8)=88
88 % 10 = 8
So 547-98-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h5,7H,1-4,6,8H2,(H,11,12)(H,13,14)
547-98-8Relevant articles and documents
A convenient synthesis of 5β-cholestan-26-oic and 5β-cholestan-26,27-dioic acids
Starchenkov,Trapencieris,Kauss,Jas,Kalvinsh
, p. 143 - 147 (2007/10/03)
A new method for the preparation of 5β-cholestan-26-oic acids 7 and their analogs is described. The key steps in the synthesis are: iodination of bis- and tris-formyloxy-5β-cholan-24-ols 3; nucleophilic substitution of iodides 4 with diethyl sodiomalonate; complete alkaline hydrolysis of esters 5; and subsequent decarboxylation of geminal diacids 6 in DMSO. Copyright (C) 2000 Elsevier Science Inc.
Synthesis and metabolism of 5-beta-cholestane-3-alpha, 7-alpha, 12-alpha-triol-26-al. Bile acids and steroids 161.
Okuda,Danielsson
, p. 2160 - 2165 (2007/10/21)
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