Record Information
Version1.0
Creation date2015-10-09 22:30:57 UTC
Update date2017-01-19 02:36:26 UTC
FoodComEx IDPC000494
FoodDB RecordFDB011602
Chemical Information
NameAllocholic acid
DescriptionIsolated from many animal sources. Bile acid in sturgeon (Acipenser sturio) 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).
CAS Number2464-18-8
Structure
Thumb
Synonyms
SynonymSource
3,7,12-Trihydroxy-(3alpha,5alpha,7alpha,12alpha)-cholan-24-OateHMDB
3,7,12-Trihydroxy-(3alpha,5alpha,7alpha,12alpha)-cholan-24-Oic acidHMDB
3a,7a,12a-trihydroxy-(5a)-cholan-24-oatebiospider
3a,7a,12a-trihydroxy-(5a)-cholan-24-oic acidbiospider
3a,7a,12a-trihydroxy-5a-cholan-24-oatebiospider
3a,7a,12a-trihydroxy-5a-cholan-24-oic acidbiospider
3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholan-24-oic acidbiospider
5a-Allocholatebiospider
5a-Allocholic acidbiospider
5a-Cholatebiospider
5a-Cholic acidbiospider
Allocholatebiospider
Allocholic aciddb_source
Chemical FormulaC24H40O5
IUPAC name4-{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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 250-251°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 10 mg
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
Toronto Research Chemicals A545000