Deoxycholic acid

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Deoxycholic acid
IUPAC name	(3α,​5β,​12α,​20R)-​3,​12-​dihydroxycholan-​24-​oic acid
Other names	Deoxycholic acid Deoxycholate
Identifiers
CAS number	[83-44-3]
PubChem	222528
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	392.57 g mol−1
Density	? g/cm3
Melting point	174 - 176 °C
Acidity (pKa)	6.58[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox 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.

Contents 1 Applications 2 Current applications 3 See also 4 References

[edit] 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.^{[citation needed]}

Sodium deoxycholate, the sodium salt of deoxycholic acid, is frequently used in mesotherapy injections, mixed with phosphatidylcholine.^{[citation needed]}

In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The critical micelle concentration for deoxycholic acid is approximately 2.4-4 mM.^[2]

Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology.^[3] They also have found application in microlithography as photoresist components.^[4][5]

Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent to lyse cells and solubilise cellular and membrane components.^[6]

Deoxycholic acid has been used since its discovery in various fields of human medicine and in the food industry. It has, in some countries (including Switzerland) been allowed as an emulsifier, but it is no longer commonly used. Currently it is part of predominantly gallstone reducing medicines (choleretics). Examples would be the European medicines Essentiale or Lipostabil from Casella Med. Recently, DCA has been approved as a food additive in Austria.^{[citation needed]}

Many research reports consistently found that DCA was concentrated in the vicinity of tumors and inflammations. In the conservative viewpoint, there was carcinogenicity suspected from DCA, but causality has not been demonstrated.^{[citation needed]}

[edit] Current applications

In China, the traditional medicine "Niuhuang", which in Chinese means "yellow thing of oxen" and is actually bilestones of oxen, has been in use for two millennia for the treatment of inflammation as well as to enhance the immune system. One of its main components is DCA.

• Chen X, Mellon RD, Yang L, Dong H, Oppenheim JJ, Howard OM. (The Laboratory of Molecular Immunoregulation, Center for Cancer Research, National Cancer Institute-Frederick, Bldg. 560, Rm. 31-19, Frederick, MD 21702-1201, USA): Regulatory effects of deoxycholic acid, a component of the anti-inflammatory traditional Chinese medicine Niuhuang, on human leukocyte response to chemoattractants. Biochemical Pharmacology 2002, 63(3), 533-541.

[edit] See also

• Ursodiol (ursodeoxycholic acid)
• Bile acids

[edit] References