Deoxycholic acid
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Overview
| Deoxycholic acid | |
|---|---|
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| IUPAC name | (3α,5β,12α)-3,12- Dihydroxycholan-24-oic acid |
| Other names | Deoxycholic acid Deoxycholate |
| Identifiers | |
| CAS number | |
| SMILES | C[C@@]34[C@] (CC[C@@H]4[C@@H](CCC (O)=O)C)([H])[C@]2([H]) CC[C@]1([H])C [C@H](O)CC[C@@](C)1[C@] ([H])2C[C@@H]3O |
| Properties | |
| Molecular formula | C24H40O4 |
| Molar mass | 392.58 g/mol |
| Density | ? g/cm3 |
| Melting point |
174 - 176 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3α,12α-dihydroxy-5β-cholanate, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it comes in a white to off-white crystalline powder form.
Applications
In the human body deoxycholic acid is used in the emulsification of fats for the absorption in the intestine. Outside the body it is used in experimental basis of cholagogues and is also use to prevent and dissolve gallstones.
Sodium deoxycholate, the sodium salt of deoxycholic acid, is frequently used in mesotherapy injections, mixed with phosphatidylcholine.
In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins.
Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology.[1] They also have found application in microlithography as photoresist components.[1][1]
The critical micelle concentration for deoxycholic acid is approximately 0.2%.
Sodium deoxycholate, the sodium salt of deoxychlic acid, is often used as a biological detergent to lyse cells and solubilise cellular and membrane components.[1]
See also
- Ursodiol (ursodeoxycholic acid)
- Bile acids
References
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
