Bilirubin
Bilirubin
CAS: 635-65-4
Molecular Formula: C33H36N4O6
Bilirubin - Names and Identifiers
Bilirubin - Physico-chemical Properties
| Molecular Formula | C33H36N4O6 |
| Molar Mass | 584.66 |
| Density | 1.2163 (rough estimate) |
| Melting Point | 192 °C |
| Boling Point | 641.7°C (rough estimate) |
| Flash Point | 513.3°C |
| Water Solubility | practically insoluble |
| Solubility | Insoluble in water, insoluble in alcohol, ether, soluble in alkali. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Red or brownish red powder |
| Color | orange |
| Merck | 14,1218 |
| BRN | 74376 |
| pKa | 4.62±0.10(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable. Refrigerate. |
| Sensitive | Light Sensitive |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00005499 |
| Physical and Chemical Properties | In addition to the natural bilirubin IX Alpha, it also contains the III {alpha and XIII {alpha isomers. IX {the two vinyl groups on the pyrrole ring in the α molecule are in the medial and lateral positions, respectively, under acidic conditions, isomer III{α with both vinyl groups in the lateral position or isomer XIII{α with both vinyl groups in the medial position can be formed. In the production process, the type, concentration and operation of the acid used in the acidification are different, and the degree of isomerization is also different. This product is mainly derived from the aging of red blood cells after the disintegration of hemoglobin in the heme through a series of catabolism reduction products. For the golden yellow or dark red-brown monoclinic crystals, odorless and tasteless. Soluble in benzene, chloroform and carbon disulfide and other organic solvents; Can also be dissolved in hot ethanol and chloroform mixture; Sodium salt soluble in water, but calcium salt, magnesium salt and barium salt insoluble in water. Dry solid is more stable; Chloroform solution is more stable in the dark; In the alkali solution (such as 0.1mmol/L sodium hydroxide) or in the case of ferric ion is unstable, quickly oxidized to biliverdin, biliverdin can be reduced to bilirubin by an in vitro chemical reaction or Biliverdin Reductase. Bilirubin may be conjugated to glycine, alanine, or histidine. Bilirubin is a potent endogenous antioxidant at normal serum concentrations. The molecular structure of bilirubin can be ketone type and alcohol type, because bilirubin shows a specific coil structure, so that the hydrophobicity is increased, and can enter the lipid molecule. Bilirubin has an extended conjugated double bond system and an active hydrogen atom that prevents oxidation. The results show that bilirubin can inhibit the oxidative modification of LDL (low density lipoprotein) to a certain extent in vitro, which can inhibit and alleviate the formation of atherosclerosis caused by LDL oxidative modification, so as to achieve the purpose of prevention and treatment of coronary heart disease. |
| Use | Bilirubin has a variety of pharmacological effects, is the main raw material for the manufacture of artificial bezoar. Pharmacological experiments have proved that it has a good inhibitory effect on W256 Tumor. The inactivation rate and inhibitory index of Japanese encephalitis Virus are 1~1.5 times higher than those of deoxycholic acid and cholic acid; it is also an effective drug for the treatment of liver disease, without destroying the liver tissue, the role of the proliferation of new cells, can treat serum hepatitis, cirrhosis |
Bilirubin - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R62 - Possible risk of impaired fertility R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | DU3038000 |
| FLUKA BRAND F CODES | 8 |
| TSCA | Yes |
| HS Code | 29339990 |
Bilirubin - Reference
| Reference Show more | 1. Xing Junfen, Wang Tao, Zhang Ying, et al. Study on the chromogenic gene chip of CYP2C19 [J]. China medical biotechnology 2015 10(001):39-44. 2. Liu Zhiyun, fan Junxiu, Yao Lifei et al. Performance Verification of PCR-Chip hybridization system for CYP2C9 and VKORC1 gene polymorphism detection [J]. Jiangxi Medicine 2018 53(10):145-148. 3. Yu-Mei Wang, Jun-fen Xing, Tao Wang, et al. Detection of aldehyde dehydrogenase 2 gene polymorphism in Chinese by gene chip [J]. Chinese pharmacist, no.1447 -1450 pages, 2014(9):1447-1450. 4. Xiaokui Huo, Xiangge Tian, Yannan Li, Lei Feng, Yongle I Cui, Chao Wang, Jingnan Cui, Chengpeng Sun, Kexin Liu, Xiaochi Ma, A highly selective ratiometric fluorescent probe for real-time imaging of β-glucuronidase in living cells and zebrafish, Sensors and 5. [IF=7.46] Xiaokui Huo et al."A highly selective ratiometric fluorescent probe for real-time imaging of β-glucuronidase in living cells and zebrafish."Sensor Actuat B- Chem. 2018 Jun;262:508 |
Bilirubin - Nature
Open Data Verified Data
- This product is golden yellow or dark red-brown monoclinic crystal. The dry solid is relatively stable, and its chloroform solution is also relatively stable in the dark; It is extremely unstable in the alkali solution or in the case of Fe3 ion, and is quickly oxidized to biliverdin. It can be combined with glycine, alanine and histidine, and bilirubin can be stabilized by adding serum protein, vitamin C or EDTA. This product is insoluble in water, soluble in benzene, chloroform, chlorobenzene, carbon disulfide, alkali and fat, ethanol-soluble and ether. Its sodium salt is soluble in water and insoluble in chloroform. Calcium, magnesium or barium salts are insoluble in water. Heating gradually Black does not melt.
- bilirubin is the main pigment of bile, is the reduction product of hemoglobin catabolism, and is also the main component of gallstones. It is a linear tetrapyrrole compound, belonging to the class of Diene cholines, mainly produced in the liver, followed by the kidney. In fresh bile with 1 or 2 glucuronic acid combined to form the presence of bilirubin ester. The conjugated bilirubin is weakly acidic, soluble in water, large in molecule and charged. In the blood, it mainly exists in the form of bilirubin albumin, which is "fixed" by plasma proteins and cannot penetrate the cell membrane. Free bilirubin is insoluble in water, soluble in fat, easily through the cell membrane into the cell. It is easy to combine with nerve cells rich in lipids, invade the nucleus of brain and nerve tissue, and cause dysfunction to present toxicity. Bilirubin bound to glucuronic acid cannot pass through the cell membrane, is almost non-toxic, and can be excreted with urine through the glomerular filtration membrane.
- There are two propionic acid side chains in the bilirubin molecule, which are weakly acidic and can form insoluble salts with alkaline earth metal ions, such as CA2. This insoluble salt reacts with a strong acid and can be substituted for bilirubin. Bilirubin may be conjugated to glycine, alanine, or histidine. Bilirubin is a potent endogenous antioxidant at normal serum concentrations. Since bilirubin exhibits a specific coiled structure, the hydrophobicity is increased and it can enter the interior of the lipid molecule. Bilirubin has an extended conjugated double bond system and an active hydrogen atom that prevents oxidation. The results show that bilirubin can inhibit the oxidative modification of LDL (low density lipoprotein) to a certain extent in vitro, which can inhibit and alleviate the formation of atherosclerosis caused by LDL oxidative modification, so as to achieve the purpose of prevention and treatment of coronary heart disease.
Last Update：2024-01-02 23:10:35
Bilirubin - Preparation Method
Open Data Verified Data
The Fresh pig bile was added into 3 to 3.5 times the amount of clear saturated lime water under stirring, stirred evenly, and the pH value was 11 to 12, the foam that appeared upon heating to 50 °c was skimmed off with gauze, continued to heat to boiling for 2min, cooled, and filtered to give a calcium salt. Calcium salt in the right amount of water, milled into a paste, and then 30~40 mesh sieve, add 1% of sodium bisulfite. Then, 1:1 industrial salt acid solution was slowly added dropwise with stirring to pH 1-2, and the mixture was allowed to stand for 0.5 H. Acidic water was leached out with double-layer gauze to obtain mud. To the sludge, an appropriate amount of 95% ethanol was added to form a thin paste, and then about 20kg of 95% ethanol and an aqueous solution of lOg sodium bisulfite were added, and the mixture was stirred well. The obtained ethanol solution had a pH value between 3.0 and 3.5, and was allowed to stand and precipitate at about 3 ° C. For 18 hours. The upper layer of ethanol is removed by siphoning, and warm water at 45 to 50 ° C. Is added to the lower layer, and the layer is left to stand and layered to enrich the floating matter of bilirubin (I. E., floating on the liquid surface). The lower layer of wastewater is removed by siphoning. About 30kg of chloroform was added to the floatation, and the mixture was refluxed for 2H. The extract was separated into layers in a liquid separator, and the lower chloroform solution was filtered, followed by evaporation of chloroform at normal pressure. An appropriate amount of 95% ethanol was added to the residue, and evaporation was continued until the ethanol was distilled off without a chloroform odor. The product was filtered, washed with warm ethanol and ether, dried and dried to obtain bilirubin.
Last Update：2022-01-01 11:14:14
Bilirubin - Application
Open Data Verified Data
One of the raw materials for the synthesis of artificial bezoar, has inhibitory effect on W256 tumor, has the inactivation effect on Japanese encephalitis Virus, can treat serum hepatitis, liver cirrhosis, with sedation, sedation, antipyretic, antihypertensive effect, can promote the newborn red blood cells.
Last Update：2025-08-19 16:24:40
Bilirubin - Safety
Open Data Verified Data
sealed storage.
Last Update：2022-01-01 11:14:15
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