Tauroursodeoxycholic acid is widely used in the field of disease treatment, especially for gallstones and liver diseases. Well, there are still many questions worth exploring about tauroursodeoxycholic acid. Such as solubility, source, application, etc. Now, Nature Micron will cover these issues in detail in this article.
What is tauroursodeoxycholic acid?
The chemical name of tauroursodeoxycholic acid (TUDCA) is 3α, 7β dihydroxycholanyl-N-taurine. It is a conjugated bile acid formed by shrinking the carboxyl group of ursodeoxycholic acid (UDCA) and the amino group of taurine. It occurs naturally in the human body and is also found in small amounts in bear bile.
Tauroursodeoxycholic acid solubility
The solubility of tauroursodeoxycholic acid will be affected by factors such as temperature, pH value, and the presence or absence of other substances in the solution.
In general, tauroursodeoxycholic acid is relatively soluble in water, and the solubility of TUDCA in water is usually about 50-60 milligrams per milliliter (mg/mL) at room temperature. However, this value will vary with temperature.
The solubility of TUDCA in organic solvents such as ethanol and methanol varies but is generally lower than its solubility in water. Specific data need to be tested experimentally.
Is TUDCA a bile salt?
The answer is YES. Tauroursodeoxycholic acid is a bile salt. Ursodeoxycholic acid, a natural bile acid produced by the liver, forms TUDCA when it is conjugated with taurine, a conjugate meaning an attached taurine molecule on the UDCA structure.
Where does tauroursodeoxycholic acid come from?
In 1902, tauroursodeoxycholic acid (TUDCA) was discovered in bear bile, and tauroursodeoxycholic acid is the active component of bear bile. There is only a small amount of tauroursodeoxycholic acid in bear bile, which is also a traditional Chinese medicine. In the pharmaceutical industry, tauroursodeoxycholic acid is often chemically synthesized for medical and research use. Synthetic TUDCA is chemically identical to the natural compound and can be used for a variety of therapeutic purposes.
In humans, UDCA is synthesized from bile acids. UDCA can then undergo further modifications, including conjugation with taurine, to form TUDCA. This conversion occurs in the liver as part of normal bile acid metabolism.
How is tauroursodeoxycholic acid made?
Tauroursodeoxycholic acid is produced primarily through two protocols.
- Tauroursodeoxycholic acid is obtained through artificial extraction of bear bile as the main method, but the purity is not high and is not conducive to large-scale production.
- Chemical synthesis of tauroursodeoxycholic acid, there are three main chemical semi-synthetic methods:
① Use ursodeoxycholic acid to react with ethyl chloroformate or pivaloyl chloride to form a mixed acid anhydride, which reacts with taurine under alkaline conditions. Then it was purified by ion exchange column to obtain tauroursodeoxycholic acid with a total yield of about 62%.
② Ursodeoxycholic acid and taurine are directly condensed under alkaline conditions under the action of N-ethoxy-carbonyl-ethoxy-1, 2-dihydroquinoline (EEDQ) or diethyl phosphorocyanidate (DEPC) respectively to obtain tauroursodeoxycholic acid. The yields were 67% and 90%, respectively.
③ After ursodeoxycholic acid and ethyl chloroformate form a mixed anhydride, they condense with p-hydroxypropiophenone to obtain the active phenolic ester of ursodeoxycholic acid, which is then reacted with taurine to obtain tauroursodeoxycholic acid. The total yield is about 64%. This method has many reaction steps.
Comparing the three chemical synthesis methods, the latter two require EEDQ and DEPC, which are expensive and cumbersome to prepare. Therefore utilize the method for artificially extracting bear bile to prepare and can not be replaced in a short time.
What is tauroursodeoxycholic acid used for?
Tauroursodeoxycholic acid not only has obvious effects in the treatment of liver diseases, gallstones, and gastrointestinal diseases but also has a wide range of applications in other aspects.
- Liver health: Tauroursodeoxycholic acid can protect the liver, improve liver function, and treat various liver diseases. Such as cholestasis, liver cirrhosis and non-alcoholic fatty liver disease.
- Gastrointestinal disorders: Tauroursodeoxycholic acid can treat certain gastrointestinal disorders, such as gallstones and irritable bowel syndrome. The underlying reason is that it regulates bile acid and aids in digestion.
- Neuroprotection: Tauroursodeoxycholic acid may have applications in the treatment of neurodegenerative diseases such as Parkinson’s disease and Alzheimer’s disease. Because it has potential neuroprotective effects.
- Metabolic health: Tauroursodeoxycholic acid can regulate glucose and lipid metabolism. Therefore, it has great potential in improving metabolic health, and treating type 2 diabetes and obesity.
- Gallstone prevention: Tauroursodeoxycholic acid can be used to prevent the formation of gallstones and to dissolve small cholesterol gallstones.
- Weight Loss: Tauroursodeoxycholic acid regulates body metabolism and therefore has great potential as a weight loss supplement.
What are tauroursodeoxycholic acid side effects?
As a naturally occurring compound in the human body, tauroursodeoxycholic acid generally does not have any side effects. When taken in appropriate doses, tauroursodeoxycholic acid is relatively mild and safe. Relatively speaking, TUDCA also has some potential side effects.
- Gastrointestinal problems: Some people may experience mild gastrointestinal side effects, such as nausea, diarrhea, or stomach upset. These symptoms are usually temporary and can usually be controlled by adjusting the dose or taking tauroursodeoxycholic acid with food.
- Anaphylaxis: Although very rare, an allergic reaction to tauroursodeoxycholic acid may occur.
- Interactions: Tauroursodeoxycholic acid may interact with certain medications or supplements. Therefore, you need to consult a professional before taking it.
- Pregnancy and Breastfeeding: It is unknown whether there are any side effects from taking tauroursodeoxycholic acid during pregnancy and breastfeeding. Therefore, it should be avoided as much as possible during this period.
- Liver enzyme changes: In some cases, tauroursodeoxycholic acid may cause changes in liver enzyme levels. These changes are usually reversible and are not associated with liver damage. Periodic monitoring of liver function is recommended for individuals taking TUDCA.
Tauroursodeoxycholic acid VS Ursodeoxycholic acid
Tauroursodeoxycholic acid and ursodeoxycholic acid differ only by one taurine in the name, but there are some key differences in their actual properties and uses.
Chemical Composition:
Tauroursodeoxycholic acid is a bile acid combined with the amino acid taurine.
Ursodeoxycholic acid is a bile acid derived from ursodeoxycholic acid.
Source:
Tauroursodeoxycholic acid is a minor bile acid found in very small amounts in the human body.
Ursodeoxycholic acid is a naturally occurring bile acid that is abundant in human bile.
Medical Use:
Tauroursodeoxycholic acid is primarily used to treat cholestasis, a condition in which the flow of bile from the liver is reduced or blocked.
Ursodeoxycholic acid is approved to treat a variety of liver diseases, including gallstones, primary biliary cirrhosis, and primary sclerosing cholangitis.
Tauroursodeoxycholic acid VS Ox bile
Both tauroursodeoxycholic acid and ox bile are related to bile acids, but there are great differences in chemical composition, source, and use. The following is the specific content.
Tauroursodeoxycholic acid
The chemical composition, source, and use are partly the same as tauroursodeoxycholic acid vs. ursodeoxycholic acid
Ox bile
Chemical Composition: Bovine bile is a mixture of bile acids, salts, and other compounds extracted from the gallbladder of cattle. It contains several bile acids, including cholic acid and chenodeoxycholic acid.
Source: Bovine bile comes from the gallbladder of cattle.
Medical Uses: Ox bile itself is not usually used as medicine. It is sometimes used in dietary supplements as a digestive aid. Some people take ox gall supplements to support the digestion of dietary fat, especially if they have a condition that impairs fat absorption, such as cholecystectomy (cholecystectomy).
In the end
Tauroursodeoxycholic acid is very important and widely used in the field of medicine. As a natural compound with almost no side effects, TUDCA is well worth researching and developing its different uses. Natural Micron now offers high-purity and quality tauroursodeoxycholic acid, if you would like more information, you can check out this page, or contact us directly.