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Cholic acid
Identifiers
CAS number 81-25-4 Yes check.svgY
ChemSpider 192176
ATC code A05AA03
SMILES
InChI
InChI key BHQCQFFYRZLCQQ-OELDTZBJBZ
Properties
Molecular formula C24H40O5
Molar mass 408.57 g/mol
Melting point

200-201 °C

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cholic acid is a bile acid, a white crystalline substance insoluble in water (soluble in alcohol and acetic acid), with a melting point of 200-201 °C. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of two major bile acids produced by the liver where it is synthesized from cholesterol. Of the two major bile acids, cholate derivatives represent approximately eighty percent of all bile acids. These derivatives are made from cholyl-CoA which forms a conjugate with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively. Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis) and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Some other mammals synthesize predominantly deoxycholic acid.

References

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