Record Information
Version1.0
Creation date2015-10-09 22:29:45 UTC
Update date2017-01-19 02:36:19 UTC
FoodComEx IDPC000300
FoodDB RecordFDB022211
Chemical Information
NameHyodeoxycholic 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) [HMDB]
CAS Number83-49-8
Structure
Thumb
Synonyms
SynonymSource
3a,6a-Dihydroxy-5b-cholan-24-oatehmdb
3a,6a-Dihydroxy-5b-cholan-24-oic acidhmdb
3a,6a-Dihydroxy-5b-cholanatehmdb
3a,6a-Dihydroxy-5b-cholanic acidhmdb
3a,6a-Dihydroxy-5b-cholanoatehmdb
3a,6a-Dihydroxy-5b-cholanoic acidhmdb
6a-Hydroxylithocholatehmdb
6a-Hydroxylithocholic acidhmdb
7-Deoxyhyocholatehmdb
7-Deoxyhyocholic acidhmdb
a-Hyodeoxycholatehmdb
a-Hyodeoxycholic acidhmdb
alpha-Hyodeoxycholatehmdb
alpha-Hyodeoxycholic acidhmdb
Hyodeoxycholatehmdb
Hyodeoxycholic acidhmdb
Hyodesoxycholatehmdb
Hyodesoxycholic acidhmdb
Iodeoxycholatehmdb
Iodeoxycholic acidhmdb
Chemical FormulaC24H40O4
IUPAC name(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20?,21+,23-,24-/m1/s1
InChI KeyDGABKXLVXPYZII-CDONHWFASA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C
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
  • 3-alpha-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 1 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 0003TG
AKSci J91554
AKSci K489
Cayman Chemical 20294
MetaSci HMDB0000733
Sigma-Aldrich HMDB0000733
Toronto Research Chemicals H998100