|Jmol-3D images||Image 1|
|Molar mass||392.57 g mol−1|
|Melting point||174 - 176 °C|
|Solubility in water||0.24%|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3α,12α-dihydroxy-5β-cholan-24-oic acid, 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.
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, 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.
Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology. They also have found application in microlithography as photoresistant components.
There is promising research to suggest the use of deoxycholic acid may be a viable alternative to surgical excision in the treatment of lipomas.
Research in immunology
Its function as a detergent and isolating agent for membrane proteins also suits it for production of Outer Membrane Protein (OMP) vaccines such as MenB, a Norwegian vaccine developed in the early 1990s. The MeNZB vaccine was produced using the same method.
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 in the unproven belief that it treats inflammations and enhances the immune system. One of its main components is DCA.
Some European publications point towards the effect of DCA as an immunostimulant 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 processes of local inflammations, different types of herpes, and possibly cancer. Due to the same acronym as another potential cancer treatment, DCA is often confused with Dichloroacetic acid.
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- Sodium deoxycholate
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- e.g., see PR from NZ immunology group, http://www.scoop.co.nz/stories/GE0506/S00048.htm
- 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.
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- Chyle M., Chyle P., Dolezal V. (Inst. f. hygiene and epidemiology, Prag): Deoxycholic acid – Therapy of viral infections and a toxicological inquiry 2nd Symp. on Prevention and Treatment of Viral Infections, Bechyne Castle 1988, p. 56f.
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- Vlček B., Reif A., Seidlova B.: Evidence of the participation of deoxycholate in cancer immunity, Z.Naturforsch. 26 b, 419-424 (1971)