Record Information
Version1.0
Creation date2015-10-09 22:27:42 UTC
Update date2017-01-19 02:36:11 UTC
FoodComEx IDPC000047
FoodDB RecordFDB012810
Chemical Information
NameCholic acid
DescriptionEmulsifying agent in foods A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. ; 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); Cholic acid is a bile acid, a white crystalline substance insoluble in water (soluble in alcohol and acetic acid), with a melting point of 200-201 °C. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of two major bile acids produced by the liver where it is synthesized from cholesterol. Of the two major bile acids, cholate derivatives represent approximately eighty percent of all bile acids. These derivatives are made from cholyl-CoA which forms a conjugate with either glycine, or taurine, yielding glycocholic and taurocholic acid respectively.
CAS Number81-25-4
Structure
Thumb
Synonyms
SynonymSource
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-OateGenerator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-OateGenerator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acidChEBI
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-OateGenerator
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acidGenerator
17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triolbiospider
3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanatebiospider
3,7,12-Trihydroxy-cholan-24-oic acidbiospider
3,7,12-Trihydroxycholanic acidbiospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oatebiospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oic acidbiospider
3a,7a,12a-Trihydroxy-5b-cholanatebiospider
3a,7a,12a-Trihydroxy-5b-cholanic acidbiospider
3a,7a,12a-Trihydroxy-5b-cholanoatebiospider
3a,7a,12a-Trihydroxy-5b-cholanoic acidbiospider
3a,7a,12a-Trihydroxy-b-cholanatebiospider
3a,7a,12a-Trihydroxy-b-cholanic acidbiospider
3a,7a,12a-Trihydroxy-beta-cholanatebiospider
3a,7a,12a-Trihydroxy-beta-cholanic acidbiospider
3a,7a,12a-Trihydroxycholanatebiospider
3a,7a,12a-Trihydroxycholanic acidbiospider
3alpha,7alpha-Dihydroxy-5beta-cholanic acidbiospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanatebiospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acidbiospider
3alpha,7alpha,12alpha-Trihydroxycholanic acidbiospider
3α,7α,12α-trihydroxy-5β-cholanateGenerator
3α,7α,12α-trihydroxy-5β-cholanic acidGenerator
5b-Cholanic acid-3a,7a,12a-triolbiospider
5b-Cholatebiospider
5b-Cholic acidbiospider
5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-biospider
5beta-Cholanic acid-3alpha,7alpha-diolbiospider
Chenodiolbiospider
Cholagitdb_source
Cholalatebiospider
Cholalic aciddb_source
Cholalinbiospider
Cholan-24-oic acidbiospider
Cholanic acidbiospider
Cholatebiospider
Cholic aciddb_source
Cholic acid, 5beta-biospider
CholsaeureChEBI
Colalindb_source
Hypocholatedb_source
NSC 6135db_source
Chemical FormulaC24H40O5
IUPAC name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)
InChI KeyBHQCQFFYRZLCQQ-UHFFFAOYSA-N
Isomeric SMILESCC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP2.02RODA,A ET AL. (1990)
Experimental Water Solubility0.175 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 197° (anhyd.)DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 3 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci K446
Cayman Chemical 20250
Eastman Chemical Company HMDB0000619
Glentham GD0884
MetaSci HMDB0000619
Toronto Research Chemicals C432600