EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

glycocholic acid
N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)glycine

Supplier Sponsors

CAS Number: 475-31-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-494-9
FDA UNII: G59NX3I3RT
Nikkaji Web:J12.411G
MDL:MFCD06408004
XlogP3-AA:2.90 (est)
Molecular Weight:465.63091000
Formula:C26 H43 N O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:food additive
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
1975 Glycocholic acid View - review
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Glycocholic acid ≥99% (HPLC)
ExtraSynthese
For experimental / research use only.
Glycocholic Acid
Glentham Life Sciences
Glycocholic acid
Santa Cruz Biotechnology
For experimental / research use only.
Glycocholic Acid ≥97%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10140
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
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
Chemidplus:0000475310
 
References:
 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
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10140
Pubchem (sid):134973317
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C01921
HMDB (The Human Metabolome Database):HMDB00138
FooDB:FDB012346
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
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
 

Articles:

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.
 
Notes:
the glycine conjugate of cholic acid. it acts as a detergent to solubilize fats for absorption and is itself absorbed. Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate. [Wikipedia]
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