deoxycholic acid
3,12-dihydroxycholanic acid
Identification
| Name | deoxycholic acid |
| CAS Number | 83-44-3 |
| EINECS | 201-478-5 |
| FDA UNII | 005990WHZZ |
| Molecular Formula | C24 H40 O4 |
| Molecular Weight | 392.57960000 |
| MDL Number | MFCD00003673 |
| Beilstein | 3219882 |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | 1975 |
| JECFA Food Additive | Desoxycholic Acid |
| FDA Mainterm (SATF) | 83-44-3 ; DESOXYCHOLIC ACID |
| FDA Regulation | FDA PART 178 -- INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS |
Physical Properties
| Appearance | white crystalline powder (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 172.00 to 177.00 °C. @ 760.00 mm Hg |
| logP (o/w) | 3.500 |
| Soluble in | water, 43.6 mg/L @ 20 °C (exp) |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-rat LD50 1000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | emulsifiers |
| Recommendation for deoxycholic acid usage levels up to | not for fragrance use. |
| Recommendation for deoxycholic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5-beta-
cholan-24-oic acid, 3-alpha,12-alpha-dihydroxy-
cholan-24-oic acid, 3,12-dihydroxy-, (3-alpha,5-beta,12-alpha)-
cholan-24-oic acid, 3,12-dihydroxy-, (3alpha,5beta,12alpha)-
5beta-
cholan-24-oic acid, 3alpha,12alpha-dihydroxy-
cholan-24-oic, 3,12-dihydroxy-(3alpha,5beta,12alpha)-
choleic acid
cholic acid, deoxy-
deoxy cholic acid
desoxycholic acid
4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-
dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
3-alpha,12-alpha-
dihydroxy-5-beta-cholan-24-oic acid
3-alpha,12-alpha-
dihydroxy-5-beta-cholanoic acid
3alpha,12alpha-
dihydroxy-5beta-cholan-24-oic acid
3,12-
dihydroxycholan-24-oic acid, (3alpha,5beta,12alpha)-
3,12-
dihydroxycholanic acid
dihydroxycholanoic acid
PubMed:
Obesity and the gut microbiome: pathophysiological aspects.
PubMed:
Self-aggregated nanoparticles of carboxylic curdlan-deoxycholic acid conjugates as a carrier of doxorubicin.
PubMed:
Bile salts act as effective protein-unfolding agents and instigators of disulfide stress in vivo.
PubMed:
Inhibitory effect of medicinal plant-derived carboxylic acids on the human transporters hOAT1, hOAT3, hOATP1B1, and hOATP2B1.
PubMed:
Use of sodium lauroyl sarcosinate (sarkosyl) in viable real-time PCR for enumeration of Escherichia coli.
PubMed:
Metabonomic analysis of quercetin against the toxicity of chronic exposure to low-level dichlorvos in rats via ultra-performance liquid chromatography-mass spectrometry.
PubMed:
Modification of intestinal microbiota and its consequences for innate immune response in the pathogenesis of campylobacteriosis.
PubMed:
Determination of bile acids by hollow fibre liquid-phase microextraction coupled with gas chromatography.
PubMed:
Injection of phosphatidylcholine and deoxycholic acid regulates gene expression of lipolysis-related factors, pro-inflammatory cytokines, and hormones on mouse fat tissue.
PubMed:
Effects of microwave (2.45 GHz) irradiation on some biological characters of Salmonella typhimurium.
PubMed:
Improvement of modified charcoal-cefoperazone-deoxycholate agar by addition of potassium clavulanate for detecting Campylobacter spp. in chicken carcass rinse.
PubMed:
The role of the gallbladder in humans.
PubMed:
Consumption of vitamin B(6) reduces fecal ratio of lithocholic acid to deoxycholic acid, a risk factor for colon cancer, in rats fed a high-fat diet.
PubMed:
Burdock fermented by Aspergillus awamori elevates cecal Bifidobacterium, and reduces fecal deoxycholic acid and adipose tissue weight in rats fed a high-fat diet.
PubMed:
Resistance to bile salts and sodium deoxycholate in macrolide- and fluoroquinolone-susceptible and resistant Campylobacter jejuni and Campylobacter coli strains.
PubMed:
Effects of efflux-pump inducers and genetic variation of the multidrug transporter cmeB in biocide resistance of Campylobacter jejuni and Campylobacter coli.
PubMed:
Variation of intragenic tandem repeat tract of tolA modulates Escherichia coli stress tolerance.
PubMed:
Screening for cholesterol-lowering probiotic based on deoxycholic acid removal pathway and studying its functional mechanisms in vitro.
PubMed:
Role of anionic charges of periplasmic glucans of Shigella flexneri in overcoming detergent stress.
PubMed:
Role of anionic charges of osmoregulated periplasmic glucans of Salmonella enterica serovar Typhimurium SL1344 in mice virulence.
PubMed:
Effect of tween series on growth and Cis-9, trans-11 conjugated linoleic acid production of Lactobacillus acidophilus F0221 in the presence of bile salts.
PubMed:
Antibody-mediated inhibition of fibroblast growth factor 19 results in increased bile acids synthesis and ileal malabsorption of bile acids in cynomolgus monkeys.
PubMed:
Adverse events associated with 2010 CSL and other inactivated influenza vaccines.
PubMed:
Chemical composition and bile acid binding activity of products obtained from amaranth (Amaranthus cruentus) seeds.
PubMed:
Effects of synbiotic fermentation products on primary chemoprevention in human colon cells.
PubMed:
Injectable therapies for localized fat loss: state of the art.
PubMed:
Bile acid-binding ability of kaki-tannin from young fruits of persimmon (Diospyros kaki) in vitro and in vivo.
PubMed:
Comparison of chromogenic Biolog Rainbow agar Shigella/Aeromonas with xylose lysine desoxycholate agar for isolation and detection of Shigella spp. from foods.
PubMed:
Selective removal of monoterpenes from bergamot oil by inclusion in deoxycholic acid.
PubMed:
Separation of dipeptides with two chiral centers using 2-hydroxypropyl-beta-CD-modified MEKC.
PubMed:
Evaluation of Mycoplasma inactivation during production of biologics: egg-based viral vaccines as a model.
PubMed:
Discrimination of viable and dead Vibrio vulnificus after refrigerated and frozen storage using EMA, sodium deoxycholate and real-time PCR.
PubMed:
Fermented wheat aleurone inhibits growth and induces apoptosis in human HT29 colon adenocarcinoma cells.
PubMed:
Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer.
PubMed:
Bile acids as possible human carcinogens: new tricks from an old dog.
PubMed:
Fratricide in Streptococcus pneumoniae: contributions and role of the cell wall hydrolases CbpD, LytA and LytC.
PubMed:
An accelerated method for isolation of Salmonella enterica serotype Typhimurium from artificially contaminated foods, using a short preenrichment, immunomagnetic separation, and xylose-lysine-desoxycholate agar (6IX method).
PubMed:
Faecal steroid excretion in humans is affected by calcium supplementation and shows gender-specific differences.
PubMed:
Effect of putative efflux pump inhibitors and inducers on the antimicrobial susceptibility of Campylobacter jejuni and Campylobacter coli.
PubMed:
Culture of Campylobacter jejuni with sodium deoxycholate induces virulence gene expression.
PubMed:
Simultaneous characterization of bile acid, sterols, and determination of acylglycerides in feces from soluble cellulose-fed hamsters using HPLC with evaporative light-scattering detection and APCI-MS.
PubMed:
Virulence properties of Campylobacter jejuni isolates of poultry and human origin.
PubMed:
High hydrostatic pressure treatment impairs AcrAB-TolC pump resulting in differential loss of deoxycholate tolerance in Escherichia coli.
PubMed:
Interactions of high amylose starch and deoxycholic acid on gut functions in rats.
PubMed:
Effect of dried plums on colon cancer risk factors in rats.
PubMed:
In situ and in vivo efficacy of peroral absorption enhancers in rats and correlation to in vitro mechanistic studies.
PubMed:
Use of Fourier transform infrared spectra of crude bacterial lipopolysaccharides and chemometrics for differentiation of Salmonella enterica serotypes.
PubMed:
Cost advantage of voriconazole over amphotericin B deoxycholate for primary treatment of invasive aspergillosis.
PubMed:
Bile acid induced gene expression in LT97 colonic adenoma cells.
PubMed:
Comparative evaluation of the Desoxycholate Agar Nissui Food Stamp and swab methods for estimating coliform organisms in poultry processing plants after cleaning in Japan.
PubMed:
Evaluation of VIDAS Immuno-Concentration Salmonella (ICS) plus selective plate method (Hektoen enteric, bismuth sulfite, xylose lysine desoxycholate) for detection of Salmonella in selected foods (Method Modification 2001.08): collaborative study.
PubMed:
Steroids in the intestinal tract of rats are affected by dietary-fibre-rich barley-based diets.
PubMed:
A new micellar electrokinetic capillary chromatography method for separation of the components of the aminoglycoside antibiotics.
PubMed:
Growth of autobioluminescent Campylobacter jejuni in response to various environmental conditions.
PubMed:
Alkaline adaptation induces cross-protection against some environmental stresses and morphological change in Vibrio parahaemolyticus.
PubMed:
Plasma deoxycholic acid concentration is elevated in postmenopausal women with newly diagnosed breast cancer.
PubMed:
Improvements in the measurement of stool decay-accelerating factor in the detection of colorectal cancer.
PubMed:
A prospective study of serum bile acid concentrations and colorectal cancer risk in post-menopausal women on the island of Guernsey.
PubMed:
Postprandial changes in serum unconjugated bile acid concentrations in healthy beagles.
PubMed:
Biosynthetic requirements for the repair of membrane damage in pressure-treated Escherichia coli.
PubMed:
Combined use of Lactobacillus reuteri and soygerm powder as food supplement.
PubMed:
Effect of environmental and chemotactic stimuli on the activity of the Campylobacter jejuni flaA sigma(28) promoter.
PubMed:
Dietary fibre, physicochemical properties and their relationship to health.
PubMed:
Rat colon ornithine and arginine metabolism: coordinated effects after proliferative stimuli.
PubMed:
Antitumorigenic effects of several food proteins in a rat model with colon cancer and their reverse correlation with plasma bile acid concentration.
PubMed:
Change in the positional specificity of lipoxygenase 1 due to insertion of fatty acids into phosphatidylcholine deoxycholate mixed micelles.
PubMed:
Feeding soybean resistant protein to rats raises fecal bile acid excretion but counteracts a deoxycholate-caused decrease in colonic aberrant crypt foci.
PubMed:
Effect of nondigestible oligosaccharides on large-bowel functions, blood lipid concentrations and glucose absorption in young healthy male subjects.
PubMed:
Faecal pH, bile acid and sterol concentrations in premenopausal Indian and white vegetarians compared with white omnivores.
PubMed:
Modulation of colonic xenobiotic metabolizing enzymes by feeding bile acids: comparative effects of cholic, deoxycholic, lithocholic and ursodeoxycholic acids.
PubMed:
Is the pig a good animal model for studying the human ileal brake?
PubMed:
Comparison of the productivity of cefoperazone amphotericin teicoplanin (CAT) agar and modified charcoal cefoperazone deoxycholate (mCCD) agar for various strains of Campylobacter, Arcobacter and Helicobacter pullorum.
PubMed:
Dietary diosgenin attenuates subacute intestinal inflammation associated with indomethacin in rats.
PubMed:
Dietary stearic acid reduces plasma and hepatic cholesterol concentrations without increasing bile acid excretion in cholesterol-fed hamsters.
PubMed:
Effects of different types of dietary fiber preparations isolated from bamboo shoots, edible burdock, apple and corn on fecal steroid profiles of rats.
PubMed:
Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology.
PubMed:
A new dietary model to study colorectal carcinogenesis: experimental design, food preparation, and experimental findings.
PubMed:
Evaluation of cell death in EBV-transformed lymphocytes using agarose gel electrophoresis, light microscopy and electron microscopy. I. Induction of classic apoptosis by the bile salt, sodium deoxycholate.
PubMed:
[Evaluation of selective culture media for the isolation of Salmonella from poultry].
PubMed:
Effects of rat bile-pancreatic juice on Fe2+ induced peroxidation of phospholipids.
PubMed:
Effects of bile acids and lectins on immunoglobulin production in rat mesenteric lymph node lymphocytes.
PubMed:
Influence of diet on experimental toxicity of amphotericin B deoxycholate.
PubMed:
Influence of dietary fat and feeding period on phosphoinositide metabolism in rat colonocytes.
PubMed:
Bile acids and pH values in total feces and in fecal water from habitually omnivorous and vegetarian subjects.
PubMed:
Use of inexpensive O antisera as the detecting antibodies for Salmonella antigens in the polymyxin-cloth enzyme immunoassay.
PubMed:
Deoxycholate is an important releaser of peptide YY and enteroglucagon from the human colon.
PubMed:
Effect of enteral feeding on intestinal epithelial proliferation and fecal bile acid profiles in the rat.
PubMed:
Sex differences in colonic function: a randomised trial.
PubMed:
Simplified methods for the synthesis of 2-hexadecanoylthio-1-ethylphosphorylcholine and for the determination of phospholipase A2 activity.
PubMed:
Soluble fecal acidic lipids and colorectal epithelial cell proliferation in normal subjects and in patients with colon cancer.
PubMed:
Sensitivity of Helicobacter pylori to different bile salts.
PubMed:
Feeding diets containing 2% cheno- or urso-deoxycholic acid or cholestyramine to rats for two weeks alters intestinal morphology and bile acid absorption.
PubMed:
Diarrhetic shellfish toxins: improvement of sample clean-up for HPLC determination.
PubMed:
Use of detergents in the preparation of Salmonella samples for enzyme immunoassay on polymyxin-coated polyester cloth.
PubMed:
Medical management of gallstones: a cost-effectiveness analysis.
PubMed:
Effect of ursodeoxycholic acid (UDCA) on pancreatic enzyme secretion and gallbladder emptying.
PubMed:
Serum unconjugated primary and secondary bile acids in patients with cholangiocarcinoma and hepatocellular carcinoma.
PubMed:
Effect of aging and dietary restriction on bile acid metabolism in rats.
PubMed:
Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects.
PubMed:
Steroid catechol degradation: disecoandrostane intermediates accumulated by Pseudomonas transposon mutant strains.
PubMed:
Cholelithiasis in hamsters: effects of cholic acid and calcium on gallstone formation.
PubMed:
Ursodiol: a cholesterol gallstone solubilizing agent.
PubMed:
In vitro transformation of cheno- and ursodeoxycholic acids and their 7-oleyl esters by human intestinal microflora.
PubMed:
Age and diet effects on fecal bile acids in infants.
PubMed:
The action of sodium deoxycholate on Escherichia coli.
PubMed:
Intestinal permeability changes in rodents: a possible mechanism for degraded carrageenan-induced colitis.
PubMed:
Feeding rats diets containing cheno- or ursodeoxycholic acid or cholestyramine modifies intestinal uptake of glucose and lipids.
PubMed:
Influence of the intake and composition of elemental diets on bile acid metabolism and hepatic lipids in the rat.
PubMed:
Acute effects of dietary cholic acid and methylazoxymethanol acetate on colon epithelial cell proliferation; metabolism of bile salts and neutral sterols in conventional and germfree SD rats.
PubMed:
Comparative effects of cimetidine on biliary lipid secretion in fasted and fed rats.
PubMed:
Ornithine decarboxylase induction in rat colon: synergistic effects of intrarectal instillation of sodium deoxycholate and starvation-refeeding.
PubMed:
Faecal weight, constituents, colonic motility, and lactose tolerance in the irritable bowel syndrome.
PubMed:
A treatment of non-ketotic hyperglycinaemia.
PubMed:
Effect of a standard test meal on serum bile acid levels in healthy nonpregnant and pregnant women and in patients with intrahepatic cholestasis of pregnancy.
PubMed:
Hepatic uptake of bile acids in man. Fasting and postprandial concentrations of individual bile acids in portal venous and systemic blood serum.
PubMed:
Postprandial serum concentration of individual bile acids in man. Influence of ileal resection.
PubMed:
Age dependent differences in human bile acid metabolism and 7 alpha-dehydroxylation.
PubMed:
Plasma bile acid levels and liver disease.
PubMed:
Effect of cecum and appendix on 7 alpha-dehydroxylation and 7 beta-epimerization of chenodeoxycholic acid in the rabbit.
PubMed:
Cholesterol gallstone formation and prevention by chenodeoxycholic and ursodeoxycholic acids. A new hamster model.
PubMed:
Brilliant green deoxycholate agar as an improved selective medium for the isolation of Salmonella.
PubMed:
Effect of fasting and lleal resection on the concentration of deoxycholic acid in rat portal blood.
PubMed:
In vitro effects of amphotericin B on growth and ultrastructure of the amoeboflagellates Naegleria gruberi and Naegleria fowleri.
PubMed:
Environmental degradation of the insect growth regulator methoprene. VII. Bovine metabolism to cholesterol and related natural products.
PubMed:
In virto adsorption of bile salts to food residues, salicylazosulfapyridine, and hemicellulose.
PubMed:
Duodenal bile acids after a test meal.
PubMed:
Protein synthesis in pancreas of fasted pigeons.
PubMed:
Evaluation of Bacto-strip technique for the detection of coliforms in pasteurized milk.