FComEx: Cholic acid (PC000047)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:42 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000047

FoodDB Record

FDB012810

Chemical Information

Name

Cholic acid

Description

Emulsifying 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 Number

81-25-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid	ChEBI
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate	Generator
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid	Generator
17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol	biospider
3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate	biospider
3,7,12-Trihydroxy-cholan-24-oic acid	biospider
3,7,12-Trihydroxycholanic acid	biospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oate	biospider
3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid	biospider
3a,7a,12a-Trihydroxy-5b-cholanate	biospider
3a,7a,12a-Trihydroxy-5b-cholanic acid	biospider
3a,7a,12a-Trihydroxy-5b-cholanoate	biospider
3a,7a,12a-Trihydroxy-5b-cholanoic acid	biospider
3a,7a,12a-Trihydroxy-b-cholanate	biospider
3a,7a,12a-Trihydroxy-b-cholanic acid	biospider
3a,7a,12a-Trihydroxy-beta-cholanate	biospider
3a,7a,12a-Trihydroxy-beta-cholanic acid	biospider
3a,7a,12a-Trihydroxycholanate	biospider
3a,7a,12a-Trihydroxycholanic acid	biospider
3alpha,7alpha-Dihydroxy-5beta-cholanic acid	biospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oic acid	biospider
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate	biospider
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanic acid	biospider
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid	biospider
3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid	biospider
3alpha,7alpha,12alpha-Trihydroxycholanic acid	biospider
3α,7α,12α-trihydroxy-5β-cholanate	Generator
3α,7α,12α-trihydroxy-5β-cholanic acid	Generator
5b-Cholanic acid-3a,7a,12a-triol	biospider
5b-Cholate	biospider
5b-Cholic acid	biospider
5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-	biospider
5beta-Cholanic acid-3alpha,7alpha-diol	biospider
Chenodiol	biospider
Cholagit	db_source
Cholalate	biospider
Cholalic acid	db_source
Cholalin	biospider
Cholan-24-oic acid	biospider
Cholanic acid	biospider
Cholate	biospider
Cholic acid	db_source
Cholic acid, 5beta-	biospider
Cholsaeure	ChEBI
Colalin	db_source
Hypocholate	db_source
NSC 6135	db_source

Chemical Formula

C24H40O5

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 Identifier

InChI=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 Key

BHQCQFFYRZLCQQ-UHFFFAOYSA-N

Isomeric SMILES

CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C

Average Molecular Weight

408.5714

Monoisotopic Molecular Weight

408.28757439

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:16359 )
trihydroxy-5beta-cholanic acid (CHEBI:16359 )
C24 bile acids, alcohols, and derivatives (C00695 )
Cholane and derivatives (C00695 )
C24 bile acids, alcohols, and derivatives (LMST04010001 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	2.02	RODA,A ET AL. (1990)
Experimental Water Solubility	0.175 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 197° (anhyd.)	DFC

Foods of Origin