Deoxycholic acid

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Structural formula
Structural formula of deoxycholic acid
General
Surname Deoxycholic acid
other names
  • (4 R ) -4 - [(3 R , 5 R , 8 R , 9 S , 10 S , 12 S , 13 R , 14 S , 17 R ) -3,12-dihydroxy-10,13-dimethylhexadecahydro-1 H -cyclopenta [a] phenanthren-17-yl] pentanoic acid ( IUPAC )
  • 3 α , 12 α -dihydroxycholanic acid
Molecular formula C 24 H 40 O 4
Brief description

beige solid

External identifiers / databases
CAS number 83-44-3
EC number 201-478-5
ECHA InfoCard 100.001.344
PubChem 222528
ChemSpider 193196
DrugBank DB03619
Wikidata Q425680
properties
Molar mass 392.58 g mol −1
Physical state

firmly

Melting point

177 ° C

pK s value

5.15 (20 ° C)

solubility

almost insoluble in water (43.6 mg l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: 301-312-330
Toxicological data

1000 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Deoxycholic acid (DCA) is a secondary bile acid . Chemically it is a steroid belonging to the group of sterols (sterols) . Their salts are called deoxycholates.

biochemistry

Biochemically, it is a so-called secondary bile acid , which is synthesized from cholesterol with the intermediate stage of the primary bile acid glycocholic acid through various remodeling processes in the liver and through the activity of certain intestinal bacteria . As a bile acid, it has an important function in fat digestion .

With the structural relationship to the steroid hormones , there are hypotheses about their involvement in the body's hormonal balance. Above all, there could be an antagonistic interaction with the stress hormones ( glucocorticoids ).

use

Structure of the DCA tetramer

The sodium salt of deoxycholic acid, sodium deoxycholate, is used in biochemistry as an anionic surfactant for cell disruption and for the solubilization of membrane proteins .

In some countries (including Switzerland), deoxycholic acid is approved as an emulsifier that is no longer in use .

In medicine, deoxycholic acids, specifically ursodeoxycholic acid, are used as a drug to dissolve gallstones and to treat liver diseases that are associated with biliary stasis. Nowadays it is a component of mainly choleretic drugs ( choleretics ). In in-vitro laboratory tests on cell cultures, bile acids also showed growth-inhibiting and cancer-cell-inhibiting properties. On the other hand, there are studies that show that DCA can act as a tumor promoter in colon cancer. About 25% of all colorectal cancers in humans have specific receptors for deoxycholic acid. In the model organism of the rat , significantly more tumors formed in the animals that received deoxycholic acid in addition to the carcinogenic azoxymethane . Deoxycholic acid is considered a risk factor for the development of colon cancer.

However, based on the work of the Czech chemist Bohuslav Vlček (1923–1998) from the 1970s, who noticed an immunomodulatory effect of deoxycholic acid, the substance is occasionally used in alternative medicine against infections and cancer. Deoxycholic acid has anti-inflammatory effects.

In 2015, deoxycholic acid was approved in the USA under the trademark Kybella for the treatment of the double chin.

Individual evidence

  1. a b c Data sheet Deoxycholic acid from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
  2. a b c Entry on deoxycholic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-51.
  4. ^ Database entry of the National Cancer Institute of the USA
  5. Festi D, Montagnani M, Azzaroli F, et al. : Clinical efficacy and effectiveness of ursodeoxycholic acid in cholestatic liver diseases . In: Curr Clin Pharmacol . 2, No. 2, May 2007, pp. 155-177. PMID 18690863 .
  6. Trauner M, Fickert P, Halilbasic E, Moustafa T: Lessons from the toxic bile concept for the pathogenesis and treatment of cholestatic liver diseases . In: Wien Med Wochenschr . 158, No. 19-20, 2008, pp. 542-8. doi : 10.1007 / s10354-008-0592-1 . PMID 18998069 .
  7. Shiraki K, Ito T, Sugimoto K, et al. : Different effects of bile acids, ursodeoxycholic acid and deoxycholic acid, on cell growth and cell death in human colonic adenocarcinoma cells . In: Int. J. Mol. Med . 16, No. 4, October 2005, pp. 729-33. PMID 16142412 .
  8. V. Milovic include: Deoxycholic acid Stimulates migration in colon cancer cells. In: Eur J Gastroenterol Hepatol 13, 2001, pp. 945-949. PMID 11507360
  9. ^ J. Summerton et al .: Effect of deoxycholic acid on the tumor incidence, distribution, and receptor status of colorectal cancer in the rat model. In: Digestion 31, 1985, pp. 77-81. PMID 4039693
  10. ^ Y. Han et al: Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer. In: J Agric Food Chem 57, 2009, pp. 8587-8590. PMID 19711910
  11. Healthy intestinal flora and defenses with DCA . immunvitamin.de. Retrieved July 18, 2012.
  12. ^ Chen X, Mellon RD, Yang L, Dong H, Oppenheim JJ, Howard OM: Regulatory effects of deoxycholic acid, a component of the anti-inflammatory traditional Chinese medicine Niuhuang, on human leukocyte response to chemoattractants . In: Biochem. Pharmacol. . 63, No. 3, February 2002, pp. 533-41. PMID 11853704 .
  13. ^ Report of the pharmaceutical newspaper