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Deoxycholic acid



Deoxycholic acid
IUPAC name (3α,5β,12α)-3,12-
Dihydroxycholan-24-oic acid
Other names Deoxycholic acid
Deoxycholate
Identifiers
CAS number 83-44-3
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

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.

Additional recommended knowledge

Contents

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.[2][3]

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.[4]

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.

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.

Current applications

In China, the plant "Niuhuang" (Schisandra chinensis) 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.

Newer approaches are therefore assumed that DCA has a central function in the immune system, possibly as an activator of macrophages in tumor tissue and in inflammation, and that is why it is found concentrated in trouble spots in the body. DCA would then be a non-specific immunomodulator for the immune system. Evidence of this is its property in acidic tissue (pH <7.33) by self-association to a tetramer (two DCA-molecules and two DCA-ions) of being able to pass through membranes, for example, to selectively activate enzymatic processes in immune cells.[citation needed]

Because of this, recently an application for DCA as a natural immunstimulant for the healing of inflammation, cancer and wounds is being discussed. There are various published scientific success reports, but because of the lack of patentability of DCA, a commercial marketing of it has not yet been undertaken.[citation needed]

See also

  • Ursodiol (ursodeoxycholic acid)
  • Bile acids

References

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Deoxycholic_acid". A list of authors is available in Wikipedia.
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