Chenodeoxycholic Acid (CDCA) CAS 474-25-9

CDCA was originally isolated from the bile of animals, and its structure and biological activity have been fully confirmed. At present, the production of most CDCA is still isolated from the bile of animals through extraction or refining. For example, CDCA from bovine and porcine bile can be refined by the acetic acid method or the ferrous bromide method. In these processes, CDCA will be confused with other bile acids during the separation and purification process, so this method has difficulties in obtaining high-quality and high-purity CDCA.

With the continuous development of chemical synthesis technology, many chemists began to explore the chemical synthesis method of CDCA.

2.1 Photochemical synthesis method:

The photochemical synthesis method is a relatively novel CDCA synthesis method in recent years. Its principle is that the excitation of the photosensitive reactant by ultraviolet rays in the photochemical reaction can promote the chemical reaction. Shimizu et al. (1991) first reported the preparation of CDCA by photochemical reaction. The method first considers the use of an aromatic compound and sodium chloroacetate to initiate a photochemical reaction, and then obtains CDCA by hydrolyzing and oxidizing the photochemical product. This method has the advantages of high yield and high selectivity.

2.2 Stereoselective synthesis method:

There is a key stereoselective problem in the synthesis of CDCA, that is, the specific stereoisomer structure of the obtained product has an important influence on the biological activity of CDCA. Therefore, many chemists use stereoselective synthesis to control the stereoisomeric structure of the resulting product. For example, Jiang et al. (2018) reported a synthetic method starting from 5α, 6β-dihydroalkaloids, and synthesized CDCA using the addition reaction of BF3 catalyst under acidic conditions. Compared with other synthetic methods, this method has higher yield and better reaction conditions.

2.3 Metal-catalyzed method:

Many researchers use metal-catalyzed synthesis of CDCA, which uses metal catalysts to promote the reaction and improve the yield and selectivity. For example, Murayama et al. (2008) prepared a new catalyst [Pd2(dba)3] and PCy3/PPh3, which achieved carbon-carbon bond formation and established the entire CDCA framework.

In addition to optimizing existing methods, there are some new developments that deserve attention.

3.1 Microbial fermentation method:

With the development of biotechnology, microbial fermentation is considered as a green and sustainable method for synthesizing CDCA. Current research reports have shown that some bacteria and fungi can enrich CDCA under specific conditions. For example, Keshari et al. (2017) reported a method to obtain CDCA from Clostridium butyricum L7, which accounted for about 3.2% (w/w) yield. The method has the advantages of simple process and high waste utilization rate.

3.2 Synthesis of bioactive molecular probes:

In recent years, CDCA has been recognized as a bioactive molecule and widely used in applications such as drug therapy and molecular probes. For example, Zhao et al. (2021) developed a technique for color-coding DNA watermarking using CDCA. This method has the advantages of multifunctional molecular assembly and bioimaging.