Cholic Acid CAS 81-25-4

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Cholic Acid Supplement

Basic Info of Cholic Acid

What is Cholic Acid?

Cholic acid is an organic acid with a steroid structure existing in bile, and is one of the components of bile acid, also known as CholaticAcid. Molecular formula C24H40O5. Molecular weight 408.59. Orthorhombic crystals can be obtained from ether or crystals obtained from dilute ethanol (monohydrate). It exists in the gallbladder of mammals, fish, amphibians and reptiles in the form of taurocholic acid and glycocholic acid. It can form binary eutectic with n-hexadecanol, palmitic acid, stearic acid, stearic acid, basalic acid, docosa-13-ynoic acid, etc.

In dilute acetic acid or sodium bicarbonate solution with bromine to obtain 3,7,12-tricarbonyl-5β-cholan-24-acid (dehydrocholic acid). It is acylated with acetyl chloride in acetic acid to obtain 12α-hydroxy-3α, 7α-diacetoxy-5β-cholan-24-acid, which is blue-violet when reacted with dilute hydrochloric acid or dilute hydrochloric acid in acetic acid, and its concentrated sulfuric acid solution It is orange-red and has green fluorescence. Cholic acid consists of a rigid steroid ring and an aliphatic side chain, and is a general term for a large class of cholanoic acids in bile.

Studies have shown that the bile acid-conjugated prodrug has a liver-targeting effect and improved metabolic stability. In recent years, with the in-depth research on cholic acid, the structure-activity relationship between cholic acid as a carrier and transportases and drugs has become more and more clear. Research has entered a whole new stage.

Cholic Acid Uses

  1. Cholic acid is utilized as an emulsifier.
  2. Cholic acid is used in biochemical research, pharmaceutical intermediates. Salt cholate is a choleretic medication for the treatment of cholecystitis, bile deficiency, as well as intestinal dyspepsia.
  3. An organic acid with a steroid structure that emulsifies fats and facilitates their digestion.
  4. Cholic acid is a non-denaturing ionic detergent for membrane protein extraction.
  5. A non-denaturing ionic cleaning agent for the removal of membrane proteins.
  6. Cholic acid can stimulate bile secretion, boost bile circulation, and have a choleretic result.

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Application of Cholic Acid

As a drug carrier, cholic acid has two applications: one is to utilize the high-efficiency recovery of cholic acid in the small intestine to improve the oral availability of drugs. Second, bile acid can be taken up by NTCP in hepatocytes and reabsorbed by ASBT in small intestinal cells, which can improve the liver and intestine targeting of drugs. In addition, taking advantage of the bile acid amphiphilic molecule can help to improve the permeability of the drug to the cell membrane.

As an oral drug carrier, cholic acid can improve the oral availability of the drug and its stability in the small intestine. Gabapentin [13] (gabapentin) is an anxiolytic drug, but it has a low absorption rate and is easy to be hydrolyzed during oral administration. Five kinds of gabapentin derivatives conjugated with cholic acid carrier were synthesized to target ASBT. The experiment showed that the monovalent anionic compound had better ASBT targeting function, and the dianionic compound had general ASBT affinity.

In vitro analysis experiments showed that gabapentin conjugated cholic acid, its stability in vivo was greatly improved compared with the parent drug, but a certain amount of conjugates would release the parent drug, proving that the release was caused by the action of enzymes in vivo. caused. By coupling gabapentin to cholic acid, its degradation rate in the body was successfully delayed, and the oral availability was improved. However, drugs linked to cholic acid through amide bonds or ester bonds can be degraded in vivo to release the parent drug.

Heparin is a highly effective anticoagulant. Recent studies have reported that it has anti-tumor activity, but heparin is difficult to be absorbed in the intestinal tract, making it difficult to make oral drugs. Molecular heparin conjugate LHD, in vivo experiments show that the oral availability of LHD has been greatly improved compared with heparin, and nude mice experiments show that LHD can significantly inhibit the metastasis of melanoma B16F10 cells and human lung cancer A549 cells.

As a targeted drug carrier, bile acid can increase the concentration of drugs in the liver and small intestine, deliver drugs in a targeted manner, and reduce the toxic and side effects of drugs. Organic nitrates are clinical drugs for the treatment of liver cirrhosis, but in clinical application, the nitric oxide releasing drugs of organic nitrates have poor portal specificity and often cause systemic side effects. Therefore, NCX1000, a conjugate of nitrate and liver targeting carrier ursodeoxycholic acid, was designed.

Using a more efficient microwave-assisted Cu(I) catalyzed cycloaddition reaction, the antibacterial drug fluconazole was linked at the C-24 position (the carboxyl group was reduced) and C-3 position of cholic acid, respectively. The newly obtained derivatives exhibited good antibacterial ability. Then, after the C-24 position (carboxyl group is retained), the ester bond or amide bond is doubled, and the β-lactam antibiotics are connected by microwave-assisted Cu(I) catalyzed cycloaddition reaction. Compared with the pharmacophore activity, it is greatly enhanced, and the pharmacological research on the cell membrane permeability of the drug is currently being carried out.

Preparation Method of Cholic Acid

A preparation method for directly extracting and synthesizing chenodeoxycholic acid or ursodeoxycholic acid from pig bile ointment or leftovers. The deficiency of the existing technology is solved, and chenodeoxycholic acid and ursodeoxycholic acid are directly obtained. Therefore, the present invention has simple process and low cost, and is suitable for clinical application. The preparation method includes the following steps:

  1. Take pig bile paste (called pig bile paste is saponified and used after extracting hyodeoxycholic acid), or leftovers (after pig bile paste is extracted hyodeoxycholic acid, it is leftover material, which contains lower chenodeoxycholic acid in 15-35% range) 50-200kg as raw material, directly pre-treated and clarified to remove non-cholic acid impurities. Dissolve in 15-20 times alkaline water, heat, add 1+1 natural clarifying agent (produced by Shandong Yaosheng Biological Technology Co., Ltd.), 1°/10°/10,000, calculated as mother liquor. After 24 hours, the mother liquor was clarified, cooled, filtered by pressure, and removed non-cholic acid impurities, protein, mucus, foreign impurities, sand, heavy metal ions, organic residues, etc., to obtain a clarified mother liquor. Cool down and adjust ph3 4.
  2. Use the leftovers of the above pretreatment as raw materials, dissolve them in 5.15 times the amount of methanol and cool down to 0.10°, add bromine solution with an equal molar ratio, and after reacting for 610 hours, add 5.10% sodium carbonate to wash and remove Impurity cholic acid below chenodeoxycholic acid in thin layer chromatography. Apply strong alkali or weak alkali adsorption resin in alkaline alcohol solution to remove impurities such as bromate and hypobromite that have not been washed with water. Obtained 7 keto lithocholic acid, containing a small amount of C3, C7 diketone compounds. Alternatively, it is oxidized by conventional chromate oxidation method, and after that, strong acid or weak acid adsorption resin is applied to remove the heavy metal ions that have not been washed with water. Obtained 7 keto lithocholic acid, containing a small amount of C3, C7 diketone compounds.
  3. Take the above 7-keto lithocholic acid, add sodium borohydride, potassium, etc., reduce, and remove the impurity cholic acid above the chenodeoxycholic acid in thin layer chromatography with an organic solvent such as methyl chloride or ethane, and prepare. Obtain chenodeoxycholic acid. Or, take the above-mentioned 7 keto lithocholic acid, add metal potassium sodium or sapphire, etc., reduce, and remove the impurity cholic acid above ursodeoxycholic acid in thin-layer chromatography with an organic solvent such as methyl chloride or ethane, to prepare Ursodeoxycholic acid.

Renference

  1. Cholic Acid – ChemicalBook
  2. Cholic Acid – PubChem
  3. Research progress of cholic acid as drug carrier

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