Hyodeoxycholic acid is an organic compound with the molecular formula C24H40O4 and CAS 83-49-8. It is a bile acid extracted from pig bile and is a white or slightly yellowish powder with a bitter taste. Stinky and slightly fishy. Slightly soluble in alcohol, slightly soluble in acetone, extremely slightly soluble in ether and chloroform, and almost insoluble in water. It can inhibit the formation of cholic acid and dissolve fat, reduce cholesterol and triglyceride in blood, and is suitable for type Ia or type Ib hyperlipidemia and atherosclerosis. It also has a certain antibacterial effect on pertussis bacillus, diphtheria bacillus, staphylococcus aureus, etc. It can also be used as an anti-inflammatory drug to treat chronic bronchitis, viral upper respiratory tract inflammation in children, etc. Can stimulate bile secretion, make bile thinner without increasing solid content, combined with adenosine methionine succinate, suitable for cholangitis, cholecystitis, cholelithiasis and other non obstructive bile stasis; It can also accelerate the excretion of gallbladder contrast agent from the liver and help with imaging. It can also promote the breakdown of intestinal fat and the absorption of fat soluble vitamins, and can be used for digestive disorders caused by liver and gallbladder diseases. At the same time, it can reduce blood cholesterol, treat and prevent coronary heart disease, hypertension, etc.
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Chemical Formula |
C24H40O4 |
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Exact Mass |
392 |
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Molecular Weight |
393 |
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m/z |
392 (100.0%), 393 (26.0%), 394 (2.7%) |
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Elemental Analysis |
C, 73.43; H, 10.27; O, 16.30 |
Chemical Properties
● Molecular Structure and Formula
HDCA has a molecular formula of C24H40O4 and a molar mass of 392.58 g/mol. Its structure consists of a steroid nucleus with hydroxyl groups at the 3α and 6α positions and a carboxyl group at the 24-position. The presence of the 6α-hydroxyl group makes HDCA a hydrophilic acid, which is a characteristic it shares with hyocholic acid. This hydrophilicity influences its solubility and biological activity, allowing it to interact with aqueous environments and biological membranes effectively.
● Physical Appearance and Solubility
HDCA typically appears as a white or off-white crystalline powder. In terms of solubility, it exhibits limited solubility in water, which is a common feature of many bile acids. However, it is slightly soluble in alcohol and very slightly soluble in ether, chloroform, and other organic solvents. The melting point of HDCA is around 200–201°C, indicating its relatively high thermal stability. These physical and chemical properties are crucial for its formulation and application in various products, from pharmaceuticals to dietary supplements.
Hyodeoxycholic acid is a bile acid extracted from pig bile, which has various biological activities and medicinal functions. The following is a detailed explanation of all functions of deoxycholic acid in pigs:
1. Promote fat digestion: It can emulsify fat, disperse fat molecules in water, form tiny fat droplets, thereby increasing the contact area between fat and digestive enzymes, and promoting fat digestion. This process helps to reduce the burden on the gastrointestinal tract and improve the efficiency of fat absorption.
2. Promote the absorption of fat soluble vitamins: It can combine with fat and fat soluble vitamins (such as vitamins A, D, E, K) to form water-soluble complexes, thereby promoting the absorption of these vitamins in the intestine. This is of great significance for maintaining normal physiological functions in the human body.
Regulating cholesterol metabolism
1. Lowering cholesterol levels in the blood: It can inhibit the formation of bile acids, reduce the reabsorption of cholesterol in the intestine, and thus lower cholesterol levels in the blood. This is of great significance for the prevention and treatment of cardiovascular diseases such as hyperlipidemia and atherosclerosis.
2. Preventing gallstones: Promoting bile excretion and reducing cholesterol deposition in the gallbladder can help prevent the formation of gallstones. This is crucial for maintaining the health of the biliary system.
1. Reducing the burden on the liver: It can stimulate the secretion of bile by the liver, making the bile thinner without increasing the solid content, which helps to alleviate the burden on the liver during bile secretion.
2. Promoting liver cell repair: It also has the function of promoting liver cell regeneration and repair, which can alleviate liver damage and promote the recovery of liver function. This is of great significance for the treatment of liver diseases such as hepatitis and cirrhosis.
Antibacterial and anti-inflammatory properties
1. Antibacterial effect: It has a certain inhibitory effect on various bacteria, including pertussis bacilli, diphtheria bacilli, Staphylococcus aureus, etc. This makes pig deoxycholic acid have certain application value in the treatment of infections caused by these bacteria.
2. Anti inflammatory effect: It can also be used as an anti-inflammatory drug, which can alleviate inflammatory symptoms and promote the resolution of inflammation. This makes it effective in treating inflammatory diseases such as chronic bronchitis and viral upper respiratory tract inflammation in children.
1. Treatment of biliary tract diseases: suitable for the treatment of cholangitis, cholecystitis, cholelithiasis, and other non obstructive cholestasis. It can stimulate bile secretion and promote bile excretion, helping to alleviate symptoms of biliary diseases and promote disease recovery.
2. Improving liver function abnormalities: It can also be used to improve symptoms such as yellowing complexion, lack of appetite, or fatigue caused by liver function abnormalities. By promoting the metabolism and detoxification function of the liver and reducing its burden, deoxycholic acid from pigs can help restore normal liver function and improve patients' symptoms.
3. Adjuvant treatment for other diseases: In addition to the above functions, it can also be used to assist in the treatment of other diseases such as eczema and skin diseases, as well as digestive disorders caused by certain liver and gallbladder diseases. These applications, although relatively rare, still have certain therapeutic effects and clinical application value.
The detailed process of making pig Hyodeoxycholic acid from fresh pig bile involves multiple chemical steps and physical treatments. Here, we will describe these steps and their possible chemical principles in detail. However, please note that the specific chemical equation may be difficult to give accurately due to the complexity of reaction conditions and by-products. I will focus on describing the reaction process and principles.
Step 1: Raw material collection and pretreatment
Raw material: Fresh pig bile
Operation: Ensure that pig bile is fresh and free of contamination, and proceed to the next step of processing as soon as possible after collection to prevent the degradation of bioactive components in the bile.
Step 2: Alkalization of bile
Objective: To convert bile acids in bile into soluble bile acid sodium salts through alkalization, facilitating subsequent extraction.
Operation: Add saturated lime water (calcium hydroxide solution) to bile, adjust the pH to 11-12, heat to boiling, and combine bilirubin with calcium ions to form bilirubin calcium salt precipitate. The mother liquor (i.e. the remaining liquid after removing the precipitate) is acidified by adding hydrochloric acid while hot until the Congo red test paper turns blue. At this point, a black gel like precipitate bound to pig bile acid will precipitate.
Possible chemical equations (simplified representation):
Bile acid+Ca (OH) 2 → Calcium bilirubinate+water
Calcium bilirubinate+HCl → bound pig bile acid+calcium chloride+water
Step 3: Precipitation and collection of pig bile acids
Operation: Remove the emulsion, collect the precipitate, rinse with tap water to make it hard and brittle, and obtain crude pig bile acid.
Chemical change: This step is mainly a physical process that involves acidification to precipitate bile acids from the solution, followed by washing to remove impurities.
Step 4: Saponification of Pig Bile Acids
Objective: To convert pig bile acids into more manageable sodium bile acid salts.
Operation: Take crude pig bile acid, add 1.5 times the mass of sodium hydroxide and 9 times the volume of water, heat for more than 16 hours, and completely saponifie the bile acid to the sodium salt of bile acid. After cooling, let it stand and separate into layers. Pour out the upper layer of light yellow liquid, dissolve the precipitate in a small amount of water, and then acidify it with dilute hydrochloric acid or sulfuric acid (2:1) until the Congo red test paper turns blue. The precipitate is filtered, washed with water until neutral, and vacuum dried to obtain the crude product.
Possible chemical equations (simplified representation):
Pig bile acid+NaOH → bile acid sodium salt+water
Sodium Bile Acid+HCl → Pig Bile Acid+Sodium Chloride+Water
Step 5: Preparation of crude pig deoxycholic acid
Method: Starting from bilirubin waste or crude pig bile acid, crude pig deoxycholic acid is prepared through steps such as saponification, acidification, extraction, decolorization, concentration, and crystallization.
Operation example: Take 100g of bilirubin residue, add 30g of sodium hydroxide or potassium hydroxide, 200ml of water, saponification at 98 ℃ for 20 hours. After cooling, let it stand. Siphon out the supernatant and discard it. Add 200ml of water to the lower layer of the paste and stir to dissolve. Then acidify it with concentrated hydrochloric acid until the Congo red test paper turns blue. Add ethyl acetate for extraction, and after filtration, dehydration, decolorization, concentration, cooling crystallization and other steps, obtain crude pig deoxycholic acid.
Possible chemical equations (involving multiple steps, simplified representation):
Bilirubin waste+NaOH → intermediate products
Intermediate product+HCl → Porcine deoxycholic acid and its mixture
Mixture+ethyl acetate → extract
Step 6: Purification of crude product
Objective: To improve the purity of deoxycholic acid in pigs.
Operation: Take crude pig deoxycholic acid, add anhydrous ethanol, triethylamine and other reagents for further processing, and then obtain high-purity pig deoxycholic acid through acid-base adjustment, filtration, drying and other steps.
Possible chemical equations (simplified representation, involving multiple steps):
Crude pig deoxycholic acid+ethanol → dissolved substance
Dissolved substance+triethylamine → precipitate
After completing the above steps, it is necessary to conduct quality inspection on the final product to ensure that it meets relevant standards. The inspection items may include purity determination (such as HPLC method), melting point determination, structural identification (such as infrared spectroscopy, mass spectrometry, etc.), etc.
The process of making it from fresh pig bile is a complex and sophisticated chemical process involving multiple steps and chemical reactions. From the collection and pretreatment of raw materials, to the extraction and purification of bile acids, to the preparation and purification of deoxycholic acid from pigs, each step requires strict control of reaction conditions and operating procedures to ensure the quality and purity of the product. At the same time, due to the possible involvement of toxic and harmful substances as well as flammable and explosive solvents in the process, it must be carried out in a professional laboratory or production environment, and strictly follow safety operating procedures.
Hyodeoxycholic acid, also known as HDCA powder, is a naturally occurring bile acid derived primarily from the metabolism of cholesterol in pigs. It belongs to the family of secondary bile acids and plays a crucial role in the digestive process by facilitating the emulsification and absorption of fats in the small intestine.
This powdered form is highly concentrated and widely used in various industries, particularly in the pharmaceutical and dietary supplement sectors. In pharmaceuticals, HDCA powder is sometimes incorporated into medications designed to treat conditions related to gallstone formation or to aid in fat digestion for patients with certain digestive disorders.
Moreover, it has gained attention in the cosmetics industry due to its potential skin-benefiting properties, though its use in this field requires further research and regulation approval. As a dietary supplement, it is marketed to support liver health and enhance fat metabolism, though claims should be evaluated with caution and supported by medical evidence.
The powder is typically sourced through meticulous extraction processes ensuring purity and safety. It is stored under controlled conditions to maintain its stability and potency. Handling HDCA powder should involve appropriate safety measures, including the use of protective gear, as it can be irritant to skin and eyes.
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