Deoxycholic acid

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 Y
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
ChemSpider ID	193196
Properties
Molecular formula	C24H40O4
Molar mass	392.57 g mol−1
Density	? g/cm3
Melting point	174 - 176 °C
Acidity (pKa)	6.58[1]
Y (what is this?)  (verify) 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.

Applications

Deoxycholic acid has been used since its discovery in various fields of human medicine. In the human body deoxycholic acid is used in the emulsification of fats for the absorption in the intestine. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry^[2], but it is no longer common. Outside the body it is used in experimental basis of cholagogues and is also in use to prevent and dissolve gallstones^[3][4].

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.^[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]

Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology.^[7] They also have found application in microlithography as photoresistant components.^[8][9]

Research in immunology

Many research reports consistently found that DCA was concentrated in the vicinity of tumors and inflammations. In conservative viewpoint, there was carcinogenicity suspected from DCA, but causality has not been demonstrated. The opinion of naturopaths and newer medical science is different.

In China, the traditional medicine "Niuhuang", which in Chinese means "Oxen Yellow" and is actually bilestone of oxen, has been in use for two millennia for the treatment of inflammations as well as to enhance the immune system^[10]. One of its main components is DCA.

Some european publications point towards the effect of DCA as an immunostimulant^[11][12] of the unspecific immune system, activating its main actors, the macrophages. According to these publications, a sufficient amount of DCA in the human body would correspond with a good immune reaction of the unspecific immune system. Clinical studies conducted in the 1970s and 1980s confirm the expectation, that DCA is involved in the natural healing prozesses of local inflammations^[13][14], different types of herpes^[15][16], and possibly cancer^[17][18].

See also

• Ursodiol (ursodeoxycholic acid)
• Bile acids

References

Weblinks

• www.dca-immunity.com: Information about the use of DCA in human medicine