Deoxycholic acid
Encyclopedia
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 chenodeoxycholic acid
. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid
, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol
and acetic acid
. When pure, it comes in a white to off-white crystalline powder form.
deoxycholic acid is used in the emulsification of fat
s for the absorption in the intestine
. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry, but it is no longer common. Outside the body it is used in experimental basis of cholagogue
s and is also in use to prevent and dissolve gallstone
s.
Sodium deoxycholate, the sodium salt of deoxycholic acid, is frequently used in mesotherapy
injections, mixed with phosphatidylcholine
.
In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The critical micelle concentration
for deoxycholic acid is approximately 2.4-4 mM.
Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent
to lyse cells and solubilise cellular and membrane components.
Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology. They also have found application in microlithography as photoresistant components.
vaccine was produced using the same method.
In China, the traditional medicine "Niuhuang", which in Chinese means "Oxen Yellow" and is actually bilestone of oxen, has been in use for two millennia in the unproven belief that it treats inflammation
s and enhances the immune system. One of its main components is DCA.
Some European publications point towards the effect of DCA as an immunostimulant of the unspecific immune system
, activating its main actors, the macrophage
s. According to these publications, a sufficient amount of DCA in the human body would correspond with a good immune reaction of the unspecific immune system. Clinical studies conducted in the 1970s and 1980s confirm the expectation, that DCA is involved in the natural healing processes of local inflammation
s, different types of herpes, and possibly cancer
.
Bile acid
Bile acids are steroid acids found predominantly in the bile of mammals. Bile salts are bile acids compounded with a cation, usually sodium. In humans, the salts of taurocholic acid and glycocholic acid represent approximately eighty percent of all bile salts. The two major bile acids are cholic...
. 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
Cholic acid
Cholic acid is a bile acid, a white crystalline substance insoluble in water , 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...
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...
. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid
Lithocholic acid
Lithocholic acid is a bile acid that acts as a detergent to solubilize fats for absorption. It is made from chenodeoxycholic acid by bacterial action in the colon.It has been implicated in human and experimental animal carcinogenesis....
, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
and acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...
. When pure, it comes in a white to off-white crystalline powder form.
Applications
Deoxycholic acid has been used since its discovery in various fields of human medicine. In the human bodyHuman body
The human body is the entire structure of a human organism, and consists of a head, neck, torso, two arms and two legs.By the time the human reaches adulthood, the body consists of close to 100 trillion cells, the basic unit of life...
deoxycholic acid is used in the emulsification of fat
Fat
Fats consist of a wide group of compounds that are generally soluble in organic solvents and generally insoluble in water. Chemically, fats are triglycerides, triesters of glycerol and any of several fatty acids. Fats may be either solid or liquid at room temperature, depending on their structure...
s for the absorption in the intestine
Intestine
In human anatomy, the intestine is the segment of the alimentary canal extending from the pyloric sphincter of the stomach to the anus and, in humans and other mammals, consists of two segments, the small intestine and the large intestine...
. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry, but it is no longer common. Outside the body it is used in experimental basis of cholagogue
Cholagogue
A cholagogue is a medicinal agent which promotes the discharge of bile from the system, purging it downward.In Patrick O'Brian's book "The Post Captain," which is set in the Napoleonic era, Stephen Maturin, one of the book's main characters sits in the snug of the Rose and Crown in Deal and drinks...
s and is also in use to prevent and dissolve gallstone
Gallstone
A gallstone is a crystalline concretion formed within the gallbladder by accretion of bile components. These calculi are formed in the gallbladder, but may pass distally into other parts of the biliary tract such as the cystic duct, common bile duct, pancreatic duct, or the ampulla of...
s.
Sodium deoxycholate, the sodium salt of deoxycholic acid, is frequently used in mesotherapy
Mesotherapy
Mesotherapy is a non-surgical cosmetic medicine treatment. Mesotherapy employs multiple injections of pharmaceutical and homeopathic medications, plant extracts, vitamins, and other ingredients into the subcutaneous fat...
injections, mixed with phosphatidylcholine
Phosphatidylcholine
Phosphatidylcholines are a class of phospholipids that incorporate choline as a headgroup.They are a major component of biological membranes and can be easily obtained from a variety of readily available sources such as egg yolk or soy beans from which they are mechanically extracted or chemically...
.
In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The critical micelle concentration
Critical micelle concentration
In colloidal and surface chemistry, the critical micelle concentration is defined as the concentration of surfactants above which micelles form and almost all additional surfactants added to the system go to micelles....
for deoxycholic acid is approximately 2.4-4 mM.
Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent
Detergent
A detergent is a surfactant or a mixture of surfactants with "cleaning properties in dilute solutions." In common usage, "detergent" refers to alkylbenzenesulfonates, a family of compounds that are similar to soap but are less affected by hard water...
to lyse cells and solubilise cellular and membrane components.
Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology. They also have found application in microlithography as photoresistant components.
Research in immunology
Its function as a detergent and isolating agent for membrane proteins also suits it for production of Outer Membrane Protein (OMP) vaccines such as MenB, a Norwegian vaccine developed in the early 1990's. The MeNZBMeNZB
MeNZB was a vaccine against a specific strain of group B meningococcus, used to control an epidemic of meningococcal disease in New Zealand. Most people are able to carry the meningococcus bacteria safely with no ill effects...
vaccine was produced using the same method.
In China, the traditional medicine "Niuhuang", which in Chinese means "Oxen Yellow" and is actually bilestone of oxen, has been in use for two millennia in the unproven belief that it treats inflammation
Inflammation
Inflammation is part of the complex biological response of vascular tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. Inflammation is a protective attempt by the organism to remove the injurious stimuli and to initiate the healing process...
s and enhances the immune system. One of its main components is DCA.
Some European publications point towards the effect of DCA as an immunostimulant of the unspecific immune system
Immune system
An immune system is a system of biological structures and processes within an organism that protects against disease by identifying and killing pathogens and tumor cells. It detects a wide variety of agents, from viruses to parasitic worms, and needs to distinguish them from the organism's own...
, activating its main actors, the macrophage
Macrophage
Macrophages are cells produced by the differentiation of monocytes in tissues. Human macrophages are about in diameter. Monocytes and macrophages are phagocytes. Macrophages function in both non-specific defense as well as help initiate specific defense mechanisms of vertebrate animals...
s. According to these publications, a sufficient amount of DCA in the human body would correspond with a good immune reaction of the unspecific immune system. Clinical studies conducted in the 1970s and 1980s confirm the expectation, that DCA is involved in the natural healing processes of local inflammation
Inflammation
Inflammation is part of the complex biological response of vascular tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. Inflammation is a protective attempt by the organism to remove the injurious stimuli and to initiate the healing process...
s, different types of herpes, and possibly cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
.