Deoxycholic acid
[CAS# 83-44-3]

Identification

• Classification: Biochemical >> Chinese herbal medicine ingredients
• Name: Deoxycholic acid
• Synonyms: (3alpha,5beta,12alpha)-3,12-Dihydroxy-cholan-24-oic acid
• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.58
• CAS Registry Number: 83-44-3
• EC Number: 201-478-5
• SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C

Properties

• Melting point: 172-178 °C
• alpha: 55 ° (c=1, EtOH)
• Water solubility: 0.24 g/L (15 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Deoxycholic acid is a secondary bile acid that plays a crucial role in the emulsification and absorption of dietary fats in the human digestive system. It is chemically classified as a steroidal carboxylic acid with the molecular formula C₂₄H₄₀O₄. Structurally, it is derived from cholic acid by the removal of a hydroxyl group at the 7-position, resulting in hydroxyl groups at the 3α- and 12α-positions of the steroid nucleus. This compound is naturally produced in the body through bacterial metabolism of primary bile acids in the colon.

The discovery of deoxycholic acid dates back to the 19th century, when bile constituents were first isolated and characterized. Early research into bile acids was driven by an interest in understanding digestion and liver function. Deoxycholic acid was recognized as a component of bile that formed through the dehydroxylation of cholic acid by intestinal microbiota. It was one of the first bile acids identified as a secondary bile acid, meaning it is not synthesized directly by the liver but is produced from primary bile acids after their secretion into the intestine.

In the human body, deoxycholic acid is involved in the solubilization of dietary lipids. Bile acids, including deoxycholic acid, are amphipathic molecules that form micelles with fats, facilitating their digestion and absorption by pancreatic enzymes. After serving its digestive role, deoxycholic acid is reabsorbed in the ileum and returned to the liver via enterohepatic circulation, where it can be reconjugated with amino acids such as glycine or taurine and secreted again.

Beyond its physiological role, deoxycholic acid has been investigated and applied in several medical and pharmaceutical contexts. One of the most prominent applications is in the field of aesthetic medicine. Deoxycholic acid has been developed as an injectable treatment for the reduction of submental fat, commonly known as a "double chin." In this context, it acts as a cytolytic agent that disrupts the membranes of adipocytes, leading to cell lysis and a localized reduction in fat deposits. A pharmaceutical formulation of deoxycholic acid received regulatory approval in several countries and is marketed for cosmetic fat reduction under various brand names.

In addition to aesthetic use, deoxycholic acid has been explored as an excipient or active agent in pharmaceutical formulations. It may serve as a permeation enhancer in transdermal and oral drug delivery systems due to its ability to interact with lipid membranes. Its surfactant properties are also employed in laboratory research for solubilizing membrane proteins and lipids.

Deoxycholic acid and its derivatives have been used in the synthesis of steroid-based drugs and as intermediates in the preparation of certain biochemical reagents. Furthermore, it has been utilized in the study of bile acid signaling pathways, particularly those involving the farnesoid X receptor (FXR) and G protein-coupled bile acid receptor 1 (GPBAR1, also known as TGR5), which are implicated in lipid metabolism, glucose homeostasis, and inflammation.

Despite its beneficial roles, excessive or dysregulated levels of deoxycholic acid have been associated with pathological conditions. High concentrations of secondary bile acids in the colon have been linked to mucosal irritation and increased risk of colorectal cancer. The cytotoxic and detergent-like effects of deoxycholic acid at high concentrations can damage epithelial cells and promote inflammation, contributing to gastrointestinal disorders.

In summary, deoxycholic acid is a biologically significant secondary bile acid with essential roles in fat digestion, medical applications in fat reduction, and various uses in pharmaceutical and biochemical research. Its discovery and continued study have contributed to the understanding of bile acid metabolism and the development of novel therapeutic approaches in medicine.

References

1979. Structural and kinetic studies on the solubilization of lecithin by sodium deoxycholate. Biochemistry, 18(18).
DOI: 10.1021/bi00583a013

1991. Transient enhancement of multidrug resistance by the bile acid deoxycholate in murine fibrosarcoma cells in vitro. Biochemical Pharmacology, 41(5).
DOI: 10.1016/0006-2952(91)90083-h

2024. Taurodeoxycholic acid alleviates diquat-induced intestinal barrier function injury in mice through the upregulation of Nrf2-mediated signaling pathway. Animal Diseases, 4(1).
DOI: 10.1186/s44149-024-00139-6