Record Information
Version1.0
Creation date2015-10-09 22:27:43 UTC
Update date2017-01-19 02:36:11 UTC
FoodComEx IDPC000049
FoodDB RecordFDB022087
Chemical Information
NameChenodeoxycholic acid
DescriptionA 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]
CAS Number474-25-9
Structure
Thumb
Synonyms
SynonymSource
(+)-chenodeoxycholatehmdb
(+)-chenodeoxycholic acidhmdb
(3a,5b,7a)-3,7-dihydroxy-cholan-24-oatehmdb
(3a,5b,7a)-3,7-dihydroxy-cholan-24-oic acidhmdb
3a,7a-dihydroxy-5b-cholan-24-oatehmdb
3a,7a-dihydroxy-5b-cholan-24-oic acidhmdb
3a,7a-dihydroxy-5b-cholanatehmdb
3a,7a-dihydroxy-5b-cholanic acidhmdb
3a,7a-dihydroxy-5b,14a,17b-cholanatehmdb
3a,7a-dihydroxy-5b,14a,17b-cholanic acidhmdb
3alpha,7alpha-Dihydroxy-5beta-cholanateGenerator
3α,7α-dihydroxy-5β-cholanateGenerator
3α,7α-dihydroxy-5β-cholanic acidGenerator
7a-Hydroxy-desoxycholsaeurehmdb
7a-HydroxylithocholateGenerator
7a-Hydroxylithocholic acidGenerator
7alpha-HydroxylithocholateGenerator
7alpha-Hydroxylithocholic acidChEBI
7α-hydroxylithocholateGenerator
7α-hydroxylithocholic acidGenerator
AnthropodeoxycholateGenerator
Anthropodeoxycholic acidChEBI
AnthropodesoxycholateGenerator
Anthropodesoxycholic acidChEBI
CDCAChEBI
ChenateGenerator
Chenic acidChEBI
ChenixChEBI
Chenodeoxycholatehmdb
Chenodesoxycholsaeurehmdb
GallodesoxycholateGenerator
Gallodesoxycholic acidChEBI
Chemical FormulaC24H40O4
IUPAC name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChI KeyRUDATBOHQWOJDD-BSWAIDMHSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
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 500 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
AKSci H680
AKSci J10019
AKSci J93264
Cayman Chemical 10011286
Glentham GP7061
Toronto Research Chemicals C291900