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

chenodeoxycholic acid
(3a,5b,7a)-3,7-dihydroxycholan-24-oic acid

Supplier Sponsors

CAS Number: 474-25-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-481-8
FDA UNII: 0GEI24LG0J
Nikkaji Web:J2.053B
Beilstein Number:3219887
MDL:MFCD00064142
XlogP3-AA:4.90 (est)
Molecular Weight:392.57960000
Formula:C24 H40 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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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
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 119.00 °C. @ 760.00 mm Hg
Boiling Point: 547.15 °C. @ 760.00 mm Hg (est)
Flash Point: 570.00 °F. TCC ( 298.80 °C. ) (est)
logP (o/w): 4.150
Soluble in:
 water, 2.414 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Chenodeoxycholic acid 98%
BOC Sciences
For experimental / research use only.
Chenodeoxycholic acid >98%
Odor: characteristic
Use: Chenodeoxycholic Acid is a naturally occurring human bile acid.Chenodeoxycholic acid has been used as medical therapy to dissolve gallstones.
Carbosynth
For experimental / research use only.
Chenodeoxycholic Acid
ExtraSynthese
For experimental / research use only.
Chenodeoxycholic Acid
Glentham Life Sciences
Chenodeoxycholic acid
Pangaea Sciences
Chenodeoxycholic Acid
Santa Cruz Biotechnology
For experimental / research use only.
Chenodeoxycholic acid, free acid ≥95%
Sigma-Aldrich: Sigma
For experimental / research use only.
Chenodeoxycholic acid ≥97%
 
Safety Information:
Preferred SDS: View
 
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:
oral-dog LD50 > 1000 mg/kg
Drugs in Japan Vol. -, Pg. 397, 1990.

oral-hamster LD50 500 mg/kg
Drugs in Japan Vol. -, Pg. 464, 1995.

intramuscular-mouse LD50 > 1000 mg/kg
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 1157, 1982.

intraperitoneal-mouse LD50 86 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES
Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 915, 1978.

intravenous-mouse LD50 100 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 323, 1970.

oral-mouse LD50 > 2000 mg/kg
Drugs in Japan Vol. -, Pg. 464, 1995.

intramuscular-rat LD50 > 500 mg/kg
Drugs in Japan Vol. -, Pg. 397, 1990.

intraperitoneal-rat LD50 105 mg/kg
GASTROINTESTINAL: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 915, 1978.

intravenous-rat LD50 106 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 915, 1978.

oral-rat LD50 4000 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 915, 1978.

Dermal Toxicity:
subcutaneous-mouse LD50 > 4000 mg/kg
GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 11, Pg. 2499, 1977.

subcutaneous-rat LD50 > 4000 mg/kg
BLOOD: CHANGES IN SPLEEN SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Kiso to Rinsho. Clinical Report. Vol. 11, Pg. 2499, 1977.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for chenodeoxycholic acid usage levels up to:
 not for fragrance use.
 
Recommendation for chenodeoxycholic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10133
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
Chemidplus:0000474259
RTECS:FZ1980000 for cas# 474-25-9
 
References:
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:474-25-9
Pubchem (cid):10133
Pubchem (sid):134973140
 
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
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C02528
HMDB (The Human Metabolome Database):HMDB00518
FooDB:FDB022087
Export Tariff Code:2918.19.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 chenodiol
 cholan-24-oic acid, 3,7-dihydroxy-, (3a,5b,7a,8x)-
3a,7a-dihydroxy-5b-cholan-24-oic acid
3a,7a-dihydroxy-5b-cholanic acid
(3a,5b,7a)-3,7-dihydroxy-cholan-24-oic acid
(3a,5b,7a,8x)-3,7-dihydroxycholan-24-oic acid
(3a,5b,7a)-3,7-dihydroxycholan-24-oic acid
17b-(1-methyl-3-carboxypropyl)etiocholane-3a,7a-diol
 

Articles:

PubMed:Cyclosporin A induced toxicity in mouse liver slices is only slightly aggravated by Fxr-deficiency and co-occurs with upregulation of pro-inflammatory genes and downregulation of genes involved in mitochondrial functions.
PubMed:Dioxin-Produced Alteration in the Profiles of Fecal and Urinary Metabolomes: A Change in Bile Acids and Its Relevance to Toxicity.
PubMed:Simultaneous quantification of the major bile acids in artificial Calculus bovis by high-performance liquid chromatography with precolumn derivatization and its application in quality control.
PubMed:Novel splice-affecting variants in CYP27A1 gene in two Chilean patients with Cerebrotendinous Xanthomatosis.
PubMed:Bile acid mediated effects on gut integrity and performance of early-weaned piglets.
PubMed:Bile acids are nutrient signaling hormones.
PubMed:L-arginine conjugates of bile acids-a possible treatment for non-alcoholic fatty liver disease.
PubMed:Enhancement of brown fat thermogenesis using chenodeoxycholic acid in mice.
PubMed:Determination of bile acids by hollow fibre liquid-phase microextraction coupled with gas chromatography.
PubMed:[Rapid identification of two new isomers in bear bile powder by LC-Q-TOF-MS combined with PCC oxidation].
PubMed:The role of the gallbladder in humans.
PubMed:Effects of Korean red ginseng as an adjuvant to bile acids in medical dissolution therapy for gallstones: a prospective, randomized, controlled, double-blind pilot trial.
PubMed:A novel chenodeoxycholic acid-verticinone ester induces apoptosis and cell cycle arrest in HepG2 cells.
PubMed:Glucocorticoid receptor mediates the gluconeogenic activity of the farnesoid X receptor in the fasting condition.
PubMed:Probiotics decreased the bioavailability of the bile acid analog, monoketocholic acid, when coadministered with gliclazide, in healthy but not diabetic rats.
PubMed:Characterization of porcine pregnane X receptor, farnesoid X receptor and their splice variants.
PubMed:Sub-lethal stress effects on virulence gene expression in Enterococcus faecalis.
PubMed:Dietary procyanidins enhance transcriptional activity of bile acid-activated FXR in vitro and reduce triglyceridemia in vivo in a FXR-dependent manner.
PubMed:The mechanism of the cholesterol-lowering effect of water-insoluble fish protein in ovariectomised rats.
PubMed:Retrograded tapioca starch prevents ovarian hormone deficiency-induced hypercholesterolemia.
PubMed:Modulation of cholesterol metabolism by the green tea polyphenol (-)-epigallocatechin gallate in cultured human liver (HepG2) cells.
PubMed:Hepatoprotective bile acid 'ursodeoxycholic acid (UDCA)' Property and difference as bile acids.
PubMed:Xanthohumol, the chalcone from beer hops (Humulus lupulus L.), is the ligand for farnesoid X receptor and ameliorates lipid and glucose metabolism in KK-A(y) mice.
PubMed:Increasing ursodeoxycholic acid in the enterohepatic circulation of pigs through the administration of living bacteria.
PubMed:Bile acid induced gene expression in LT97 colonic adenoma cells.
PubMed:Cerebrotendinous xanthomatosis: clinical course, genotypes and metabolic backgrounds.
PubMed:Bile acid composition in snake bile juice and toxicity of snake bile acids to rats.
PubMed:Cholestanol metabolism, molecular pathology, and nutritional implications.
PubMed:Influence of breast feeding, and adapted and hydrolyzed formulas on biliary bile acids in newborn guinea pigs.
PubMed:Effect of chenodeoxycholic acid on the toxicity of 5alpha-cyprinol sulfate in rats.
PubMed:Postprandial changes in serum unconjugated bile acid concentrations in healthy beagles.
PubMed:Green tea upregulates the low-density lipoprotein receptor through the sterol-regulated element binding Protein in HepG2 liver cells.
PubMed:[3-oxo-delta 4-steroid 5 beta-reductase deficiency].
PubMed:[3 beta-Hydroxysteroid-delta 5-oxidoreductase/isomerase deficiency].
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:Taurochenodeoxycholic acid ameliorates and ursodeoxycholic acid exacerbates small intestinal inflammation.
PubMed:Comparison of hypolipidemic effect of refined konjac meal with several common dietary fibers and their mechanisms of action.
PubMed:Inducing cholesterol precipitation from pig bile with beta-cyclodextrin and cholesterol dietary supplementation.
PubMed:Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology.
PubMed:Free bile acids inhibit IgE production by mouse spleen lymphocytes stimulated by lipopolysaccharide and interleukins.
PubMed:A food-grade silicon dioxide is hypocholesterolemic in the diet of cholesterol-fed rats.
PubMed:Effects of bile acids and lectins on immunoglobulin production in rat mesenteric lymph node lymphocytes.
PubMed:Effects of different formula feeds on the developmental pattern of urinary bile acid excretion in infants.
PubMed:Preweaning diet affects bile lipid composition and bile acid kinetics in infant baboons.
PubMed:Gallstone lithotripsy.
PubMed:Current management of symptomatic gallstones.
PubMed:Increased gallbladder residual volume in nonresponders to extracorporeal shock wave lithotripsy of gallbladder stones.
PubMed:[The effect of soy bran on the bile acid spectrum of patients with cholelithiasis].
PubMed:The bile acids binding of the fibre-rich fractions of three starchy legumes.
PubMed:Effect of taurine on total parenteral nutrition-associated cholestasis.
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: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:Steroid catechol degradation: disecoandrostane intermediates accumulated by Pseudomonas transposon mutant strains.
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:Transformation of sulfated bile acids by human intestinal microflora.
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:Effect of petroleum hydrocarbons on the biliary bile acid composition of rainbow trout (Salmo gairdneri).
PubMed:Serum bile acids in Gilbert's syndrome after oral load of chenodeoxycholic acid.
PubMed:Fasting and postprandial serum bile acid concentration with special reference to variations in the conjugate profile.
PubMed:Epimerization of the four 3,7-dihydroxy bile acid epimers by human fecal microorganisms in anaerobic mixed cultures and in feces.
PubMed:Management of gallstones. The new option of bile acid therapy.
PubMed:Feeding the low-birth-weight infant. III. Diet influences bile acid metabolism.
PubMed:Feeding the low-birth weight infant: V. Effects of taurine, cholesterol, and human milk on bile acid kinetics.
PubMed:Is normal pregnancy cholestatic?
PubMed:The GI drug column. The ACG committee on FDA related matters.
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:Diagnostic value of serum primary bile acids in detecting bile acid malabsorption.
PubMed:Postprandial serum concentration of individual bile acids in man. Influence of ileal resection.
PubMed:Dissolution of cholesterol gallstones by bile acids in hamsters.
PubMed:Effects of intestinal secretagogues and distension on small bowel myoelectric activity in fasted and fed conscious dogs.
PubMed:Plasma bile acid levels and liver disease.
PubMed:Differential timing of maximal postprandial concentrations of plasma chenodeoxycholate and cholate: its variability and implications.
PubMed:Evaluation of a commercial enzymatic method for the determination of total serum bile acids.
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:[Gastroenterology and internal medicine].
PubMed:Diurnal serum levels of primary conjugated bile acids. Assessment by specific radioimmunoassays for conjugates of cholic and chenodeoxycholic acid.
PubMed:Binding of bile acids by dietary fiber.
PubMed:Further investigations of indomethacin and intestinal ulcers in the rat.
PubMed:Fasting and postprandial serum bile acid concentrations in normal persons using an improved GLC method.
PubMed:The fda controversy.
PubMed:Pharmacology of chenodeoxycholic acid. II. Absorption and metabolism.
PubMed:Dietary cholesterol affects chenodeoxycholic acid action on biliary lipids.
PubMed:Gallstones.
PubMed:Bile production in fasted and fed primates.
PubMed:In virto adsorption of bile salts to food residues, salicylazosulfapyridine, and hemicellulose.
PubMed:Duodenal bile acids after a test meal.
 
Notes:
a bile acid, usually conjugated with either glycine or taurine. it acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. it is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones. A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) Usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones. [HMDB]
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