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 |
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 biliary 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.
Promote digestion and absorption
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 biliary 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.
Protecting the liver
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.
Other functions
Treatment of biliary tract diseases: Hyodeoxycholic acid is clinically suitable for the systematic treatment of cholangitis, cholecystitis, cholesterol gallstones and various types of non-obstructive cholestasis. As a natural biliary acid component, it can effectively stimulate the secretion of thin and low-viscosity bile by liver cells, relax biliary smooth muscle, and accelerate the smooth excretion of accumulated bile inside bile ducts and gallbladder. It can relieve typical biliary symptoms including right upper abdominal pain, abdominal distension and bitter mouth caused by bile stasis and inflammatory stimulation.
Moreover, it can prevent secondary bile salt deposition and biliary inflammation aggravation, effectively relieve clinical discomfort of biliary tract diseases and speed up the overall recovery of biliary system lesions.
Improving liver function abnormalities: This ingredient is widely applied to ameliorate typical discomforts induced by mild to moderate liver function damage, including sallow complexion, poor appetite, general fatigue and hypodynamia. It enhances liver metabolic capacity and accelerates the clearance of metabolic wastes and toxic substances in liver tissues, which significantly reduces the detoxification and metabolic burden of damaged liver cells.
Besides, it can protect hepatocytes from inflammatory damage caused by long-term bile reflux and cholestasis. Through comprehensively regulating liver internal circulation and repairing partial injured hepatocytes, it helps gradually restore normal physiological liver function and improve systemic physical discomfort of patients with liver dysfunction.
Adjuvant treatment for other diseases: Apart from core hepatobiliary therapeutic effects, it also serves as a practical adjuvant therapy drug for refractory eczema, chronic inflammatory skin diseases and gastrointestinal digestive disorders secondary to hepatobiliary dysfunction.
The therapeutic mechanism for skin lesions is mainly related to its mild anti-inflammatory and lipid metabolism regulating effects, which can relieve skin inflammatory exudation and itching symptoms. For digestive problems triggered by insufficient bile secretion, it improves fat emulsification and nutrient absorption in the gastrointestinal tract to relieve indigestion, bloating and diarrhea. Though these clinical applications are not first-line treatment regimens and relatively less common than hepatobiliary treatments, they possess definite pharmacological efficacy and stable auxiliary 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 biliary acids in bile into soluble biliary 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 biliary 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 biliary acids
Operation: Remove the emulsion, collect the precipitate, rinse with tap water to make it hard and brittle, and obtain crude pig biliary acid.
Chemical change: This step is mainly a physical process that involves acidification to precipitate biliary acids from the solution, followed by washing to remove impurities.
Step 4: Saponification of Pig Bile Acids
Objective: To convert pig biliary acids into more manageable sodium bile acid salts.
Operation: Take crude pig biliary 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 biliary acid to the sodium salt of biliary 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 biliary 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 Hyodeoxycholic acid.
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 biliary 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.
In the early 20th century, biliary acid research flourished under German steroid chemists Windaus and Wieland. In 1923, Windaus and Bohne first separated and purified HDCA from pig bile, identifying it as a unique dihydroxy biliary acid exclusive to swine and naming it after its porcine source.
They distinguished its 3α,6α-dihydroxyl structure from chenodeoxycholic acid's 3α,7α configuration, laying the foundation for structural research of atypical bile acids.
In the 1930s–1950s, Japanese scholars supplemented related research, isolating stereoisomers of HDCA and verifying its complete steroid skeleton via oxidation and epimerization experiments.
Later biologists confirmed HDCA exists as both primary and secondary bile acids in pigs, produced by intestinal flora transformation. After the 1950s, industrial extraction technology matured; HDCA was widely used as the core synthetic precursor of ursodeoxycholic acid, pushing its transition from laboratory compound to critical pharmaceutical raw material.
FAQ
What is hyodeoxycholic acid?
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Hyodeoxycholic acid is defined as a bile acid that is included in the total secondary bile acids (SBAs) circulating in the enterohepatic circulation.
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