glycocholic acid
N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)glycine
Identification
| Name | glycocholic acid |
| CAS Number | 475-31-0 |
| EINECS | 207-494-9 |
| FDA UNII | G59NX3I3RT |
| Molecular Formula | C26 H43 N O6 |
| Molecular Weight | 465.63091000 |
| MDL Number | MFCD06408004 |
| Nikkaji Number | J12.411G |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | 1975 |
| FDA Mainterm (SATF) | 475-31-0 ; GLYCOCHOLIC ACID |
Physical Properties
| Food Chemicals Codex Listed | No |
| Melting Point | 166.00 to 167.00 °C. @ 760.00 mm Hg |
| Boiling Point | 692.04 °C. @ 760.00 mm Hg (est) |
| Flash Point | 702.00 °F. TCC ( 372.30 °C. ) (est) |
| logP (o/w) | 1.650 |
| Soluble in | water, 3.3 mg/L @ 20 °C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| 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 | food additive |
| Recommendation for glycocholic acid usage levels up to | not for fragrance use. |
| Recommendation for glycocholic acid flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
N-
choloylglycine
2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-
trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
N-((3alpha,5beta,7alpha,12alpha)-3,7,12-
trihydroxy-24-oxocholan-24-yl)glycine
PubMed:
Validated UPLC Method for Determination of Unbound Bile Acids in Colesevelam HCl Tablets.
PubMed:
Metabonomic analysis of the joint toxic action of long-term low-level exposure to a mixture of four organophosphate pesticides in rat plasma.
PubMed:
Comparative evaluation of in vitro efficacy of colesevelam hydrochloride tablets.
PubMed:
Genetic diversity of bile salt hydrolases among human intestinal bifidobacteria.
PubMed:
Factors affecting adhesion of lactic acid bacteria to Caco-2 cells and inhibitory effect on infection of Salmonella typhimurium.
PubMed:
Identification and characterization of a bile salt hydrolase from Lactobacillus salivarius for development of novel alternatives to antibiotic growth promoters.
PubMed:
Effects of bile salt deconjugation by probiotic strains on the survival of antibiotic-resistant foodborne pathogens under simulated gastric conditions.
PubMed:
All 4 bile salt hydrolase proteins are responsible for the hydrolysis activity in Lactobacillus plantarum ST-III.
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:
Chemical composition and bile acid binding activity of products obtained from amaranth (Amaranthus cruentus) seeds.
PubMed:
Molecular characterization of bile salt hydrolase from Bifidobacterium animalis subsp. lactis Bi30.
PubMed:
Relative gene expression of bile salt hydrolase and surface proteins in two putative indigenous Lactobacillus plantarum strains under in vitro gut conditions.
PubMed:
A sensitive method for qualitative screening of bile salt hydrolase-active lactobacilli based on thin-layer chromatography.
PubMed:
A novel vector for lactic acid bacteria that uses a bile salt hydrolase gene as a potential food-grade selection marker.
PubMed:
SigB plays a major role in Listeria monocytogenes tolerance to bile stress.
PubMed:
Bile acid-binding ability of kaki-tannin from young fruits of persimmon (Diospyros kaki) in vitro and in vivo.
PubMed:
Coexpression of bile salt hydrolase gene and catalase gene remarkably improves oxidative stress and bile salt resistance in Lactobacillus casei.
PubMed:
Bile salt deconjugation and cholesterol removal from media by Lactobacillus strains used as probiotics in chickens.
PubMed:
Functional and probiotic attributes of an indigenous isolate of Lactobacillus plantarum.
PubMed:
Differential proteomic analysis of Clostridium perfringens ATCC13124; identification of dominant, surface and structure associated proteins.
PubMed:
Molecular and probiotic characterization of bacteriocin-producing Enterococcus faecium strains isolated from nonfermented animal foods.
PubMed:
Molecular characterization of native isolates of lactic acid bacteria, bifidobacteria and yeasts for beneficial attributes.
PubMed:
In vitro analysis of protection of the enzyme bile salt hydrolase against enteric conditions by whey protein-gum arabic microencapsulation.
PubMed:
Characterization of the cholesterol-reducing activity in a cell-free supernatant of Lactobacillus acidophilus ATCC 43121.
PubMed:
Functional analysis of four bile salt hydrolase and penicillin acylase family members in Lactobacillus plantarum WCFS1.
PubMed:
Genetic analysis of a bile salt hydrolase in Bifidobacterium animalis subsp. lactis KL612.
PubMed:
Influence of sodium glycocholate on production of conjugated linoleic acid by cells of Lactobacillus reuteri ATCC 55739.
PubMed:
Cloning and characterization of a bile salt hydrolase (bsh) from Bifidobacterium adolescentis.
PubMed:
Genetic analysis of two bile salt hydrolase activities in Lactobacillus acidophilus NCFM.
PubMed:
Cloning of the bile salt hydrolase (bsh) gene from Enterococcus faecium FAIR-E 345 and chromosomal location of bsh genes in food enterococci.
PubMed:
sigmaB-dependent gene induction and expression in Listeria monocytogenes during osmotic and acid stress conditions simulating the intestinal environment.
PubMed:
Cloning and characterization of the bile salt hydrolase genes (bsh) from Bifidobacterium bifidum strains.
PubMed:
Purification and characterization of three different types of bile salt hydrolases from Bifidobacterium strains.
PubMed:
Sigma(B)-dependent expression patterns of compatible solute transporter genes opuCA and lmo1421 and the conjugated bile salt hydrolase gene bsh in Listeria monocytogenes.
PubMed:
Binding of free bile acids by cells of yogurt starter culture bacteria.
PubMed:
Listeria monocytogenes bile salt hydrolase is a PrfA-regulated virulence factor involved in the intestinal and hepatic phases of listeriosis.
PubMed:
Bile salt hydrolase activity of Enterococci isolated from food: screening and quantitative determination.
PubMed:
Duodenogastric reflux and foregut carcinogenesis: analysis of duodenal juice in a rodent model of cancer.
PubMed:
Dietary inulin lowers plasma cholesterol and triacylglycerol and alters biliary bile acid profile in hamsters.
PubMed:
Effect of different varieties of pectin and guar gum on plasma, hepatic and biliary lipids and cholesterol gallstone formation in hamsters fed on high-cholesterol diets.
PubMed:
Studies on N-nitroso bile acid amides in relation to their possible role in gastrointestinal cancer.
PubMed:
Dietary antibiotics decrease taurine loss in cats fed a canned heat-processed diet.
PubMed:
Maillard reaction products in purified diets induce taurine depletion in cats which is reversed by antibiotics.
PubMed:
Influence of dietary taurine on vitamin D absorption.
PubMed:
Bile acid conjugation pattern in the isolated perfused rat liver during infusion of an amino acid formulation.
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:
Bile composition of adult baboons is influenced by breast versus formula feeding.
PubMed:
Serum unconjugated primary and secondary bile acids in patients with cholangiocarcinoma and hepatocellular carcinoma.
PubMed:
Effect of cholecystectomy on mouth-to-cecum transit of a liquid meal.
PubMed:
Combined effects of the mycotoxins aflatoxin B1 and cyclopiazonic acid on Sprague-Dawley rats.
PubMed:
Delayed postprandial plasma bile acid response in coeliac patients with slow mouth-caecum transit.
PubMed:
Diagnostic value of serum primary bile acids in detecting bile acid malabsorption.
PubMed:
[Radioimmunoassay of bile acids. Normal fasting values and changes after eating].
PubMed:
Binding of bile salts to fibre-enriched wheat bran.
PubMed:
Effects of a meal on plasma clearance of [14C]glycocholic acid and indocyanine green in man.
PubMed:
Clinical value of bile salt tests in anicteric liver disease.
PubMed:
Bile acid clearance in liver disease.
PubMed:
In virto adsorption of bile salts to food residues, salicylazosulfapyridine, and hemicellulose.