Deoxycholic acid is a

bile acid Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile acids are synthesized in the liver. Bile acids are conjugated with taurine or glycine residues to give anions called bile salts. Primary b ...

. 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, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Ch ...

and

chenodeoxycholic acid Chenodeoxycholic acid (CDCA; also known as chenodesoxycholic acid, chenocholic acid and 3α,7α-dihydroxy-5β-cholan-24-oic acid) is a bile acid. Salts of this carboxylic acid are called chenodeoxycholates. Chenodeoxycholic acid is one of the mai ...

. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid

lithocholic acid Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydro ...

, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as

ursodeoxycholic acid Ursodeoxycholic acid (UDCA), also known as ursodiol, is a secondary bile acid, produced in humans and most other species from metabolism by intestinal bacteria. It is synthesized in the liver in some species, and was first identified in bile of ...

. Deoxycholic acid is soluble in

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

and

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...

. When pure, it comes in a white to off-white crystalline powder form. Deoxycholic acid is available as a

generic medication A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active ch ...

in the United States as of April 2021, sold under the brand name Kybella among others.

Applications

Deoxycholic acid has been used since its discovery in various fields of human medicine. In the

human body The human body is the structure of a Human, human being. It is composed of many different types of Cell (biology), cells that together create Tissue (biology), tissues and subsequently organ systems. They ensure homeostasis and the life, viabi ...

deoxycholic acid is used in the

emulsification An emulsion is a mixture of two or more liquids that are normally Miscibility, immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloi ...

fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers spec ...

s for absorption in the

intestine The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans ...

. 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 A cholagogue is a substance that is purported by humoral practitioners to encourage the discharge of bile from the system, purging it downward. Deployment is no longer recommended because the biliary purge, like the traditional kidney purge, can c ...

s and is also in use to prevent and dissolve

gallstone A gallstone is a calculus (medicine), stone formed within the gallbladder from precipitated bile components. The term cholelithiasis may refer to the presence of gallstones or to any disease caused by gallstones, and choledocholithiasis refers to ...

s. In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The

critical micelle concentration In colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles. The CMC is an important ch ...

for deoxycholic acid is approximately 2.4–4 mM. Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological

detergent A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are more ...

to lyse cells and solubilise cellular and membrane components. Sodium deoxycholate mixed with

phosphatidylcholine Phosphatidylcholines (PC) 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 soyb ...

, is used in

mesotherapy Mesotherapy (from Greek ''mesos'', "middle", and therapy from Greek ''therapeia'') is a non-invasive non-surgical technique that uses micro-injections of pharmaceutical preparations, plant extracts, vitamins, and other ingredients into subcutaneo ...

injections to produce lipolysis, and has been used as an alternative to surgical excision in the treatment of lipomas. 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. In the United States, deoxycholic acid, under the brand name Kybella, is approved by the

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...

for reducing moderate-to-severe fat below the chin. When injected into submental fat, deoxycholic acid helps destroy (adipocytes) fat cells, which are metabolized by the body over the course of several months. Kybella is produced by Kythera Biopharmaceuticals.

Research in immunology

Its function as a detergent and isolating agent for membrane proteins also suits it for production of

outer membrane protein Virulence-related outer membrane proteins, or outer surface proteins (Osp) in some contexts, are expressed in the outer membrane of gram-negative bacteria and are essential to bacterial survival within macrophages and for eukaryotic cell invasion ...

(OMP) vaccines such as MenB, a Norwegian vaccine developed in the early 1990s. The

MeNZB 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. However, meningoco ...

vaccine was produced using the same method. Deoxycholic acid binds and activates the membrane enzyme

NAPE-PLD NAPE-PLD may refer to: * N-acyl phosphatidylethanolamine-specific phospholipase D, an enzyme * N-acetylphosphatidylethanolamine-hydrolysing phospholipase D, an enzyme {{Short pages monitor