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Cholic acid

Cholic acid

Overview
Cholic acid is a bile acid
Bile acid
Bile acids are steroid acids found predominantly in the bile of mammals. Bile salts are bile acids conjugated to glycine or taurine. In humans, taurocholic acid and glycocholic acid represent approximately eighty percent of all bile salts. The two major bile acids are cholic acid, and...

, a white crystalline substance insoluble in water (soluble in alcohol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug, best known as the type of alcohol found in alcoholic beverages and in modern thermometers. Ethanol is one of the oldest recreational drugs...

 and acetic acid
Acetic acid
Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. It is a weak acid, in that it is only partially dissociated acid in aqueous solution...

), with a melting point of 200-201 °C. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid
Chenodeoxycholic acid
Chenodeoxycholic acid is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates...

, is one of two major bile
Bile
Bile or gall is a bitter yellowish, blue and green fluid secreted by hepatocytes from the liver of most vertebrates. In many species, bile is stored in the gallbladder between meals and upon eating is discharged into the duodenum where the bile aids the process of digestion of lipids by...

 acid
Acid
An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion activity greater than in pure water, i.e. a pH less than 7.0...

s produced by the liver
Liver
The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...

 where it is synthesized from cholesterol
Cholesterol
Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes, where it is required to establish proper membrane permeability and fluidity...

. 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
Conjugated system
A conjugated system occurs in an organic compound where atoms covalently bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization. In this region electrons do not belong to a single bond or atom, but rather a group...

 with either glycine
Glycine
Glycine is an organic compound with the formula NH2CH2COOH. With only a hydrogen atom as its side chain, glycine is the smallest of the 20 amino acids commonly found in proteins....

, or taurine
Taurine
Taurine, or 2-aminoethanesulfonic acid, is an organic acid. It is also a major constituent of bile and can be found in the lower intestine and in small amounts in the tissues of many animals, including humans. Taurine is a derivative of the sulfur-containing amino acid, cysteine...

, yielding glycocholic
Glycocholic acid
Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate....

 and taurocholic acid
Taurocholic acid
Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine...

 respectively.

Cholic acid and chenodeoxycholic acid
Chenodeoxycholic acid
Chenodeoxycholic acid is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates...

 are the most important human bile acids.
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Encyclopedia
Cholic acid is a bile acid
Bile acid
Bile acids are steroid acids found predominantly in the bile of mammals. Bile salts are bile acids conjugated to glycine or taurine. In humans, taurocholic acid and glycocholic acid represent approximately eighty percent of all bile salts. The two major bile acids are cholic acid, and...

, a white crystalline substance insoluble in water (soluble in alcohol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug, best known as the type of alcohol found in alcoholic beverages and in modern thermometers. Ethanol is one of the oldest recreational drugs...

 and acetic acid
Acetic acid
Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. It is a weak acid, in that it is only partially dissociated acid in aqueous solution...

), with a melting point of 200-201 °C. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid
Chenodeoxycholic acid
Chenodeoxycholic acid is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates...

, is one of two major bile
Bile
Bile or gall is a bitter yellowish, blue and green fluid secreted by hepatocytes from the liver of most vertebrates. In many species, bile is stored in the gallbladder between meals and upon eating is discharged into the duodenum where the bile aids the process of digestion of lipids by...

 acid
Acid
An acid is traditionally considered any chemical compound that, when dissolved in water, gives a solution with a hydrogen ion activity greater than in pure water, i.e. a pH less than 7.0...

s produced by the liver
Liver
The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...

 where it is synthesized from cholesterol
Cholesterol
Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes, where it is required to establish proper membrane permeability and fluidity...

. 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
Conjugated system
A conjugated system occurs in an organic compound where atoms covalently bond with alternating single and multiple bonds and influence each other to produce a region called electron delocalization. In this region electrons do not belong to a single bond or atom, but rather a group...

 with either glycine
Glycine
Glycine is an organic compound with the formula NH2CH2COOH. With only a hydrogen atom as its side chain, glycine is the smallest of the 20 amino acids commonly found in proteins....

, or taurine
Taurine
Taurine, or 2-aminoethanesulfonic acid, is an organic acid. It is also a major constituent of bile and can be found in the lower intestine and in small amounts in the tissues of many animals, including humans. Taurine is a derivative of the sulfur-containing amino acid, cysteine...

, yielding glycocholic
Glycocholic acid
Glycocholic acid, or cholylglycine, is a crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with glycine. Its anion is called glycocholate....

 and taurocholic acid
Taurocholic acid
Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine...

 respectively.

Cholic acid and chenodeoxycholic acid
Chenodeoxycholic acid
Chenodeoxycholic acid is a bile acid. It occurs as a white crystalline substance insoluble in water but soluble in alcohol and acetic acid, with melting point at 165-167 °C. Salts of this carboxylic acid are called chenodeoxycholates...

 are the most important human bile acids. Some other mammals synthesize predominantly deoxycholic acid
Deoxycholic acid
Deoxycholic acid, also known as deoxycholate, cholanoic acid, and 3α,12α-dihydroxy-5β-cholanate, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and...

.