3B-HYDROXY-20(29)-LUPENE-28-OIC ACID
betulinic acid
CAS: 472-15-1
Molecular Formula: C30H48O3
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID - Names and Identifiers
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID - Physico-chemical Properties
| Molecular Formula | C30H48O3 |
| Molar Mass | 456.71 |
| Density | 1.065±0.06 g/cm3(Predicted) |
| Melting Point | 295-298 °C (dec.) (lit.) |
| Boling Point | 550.0±33.0 °C(Predicted) |
| Specific Rotation(α) | D25 +7.5° (c = 0.37 in pyridine) |
| Flash Point | 299.4°C |
| Solubility | Insoluble in water, slightly soluble in methanol, ethanol, acetone, easily soluble in tetrahydrofuran, pyridine. |
| Vapor Presure | 2.67E-14mmHg at 25°C |
| Appearance | White crystal |
| Color | White or off-white |
| Merck | 14,1190 |
| pKa | 4.61±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. |
| Refractive Index | 7.8 ° (C=0.9, Pyridi |
| MDL | MFCD00009619 |
| Physical and Chemical Properties | Melting point 295-298°C (dec.). |
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29181985 |
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID - Reference
| Reference Show more | 1. Gao Ya, Yang Jie, Yang, Yingchun, sulitan, abakley. Determination of triterpene acids and cyclic nucleotides in different jujube cultivars [J]. Chinese patent medicine 2012 34(10): -1965. 2. Cui Yixuan, Liu Di, Zhou Qiqi, et al. Simultaneous determination of betulinic acid, oleanolic acid and ursolic acid in Jujube by dispersive liquid-liquid microextraction-high performance liquid chromatography [J]. Journal of Analytical Science, 2019, 035(003):34-351. 3. Han Yue, Li Zhanjun, Li Mengyuan, Yang Fengjian. Optimization of extraction of triterpenoids from Betula alnoides by response surface methodology [J]. Forest Engineering, 2021,37(02):79-85. 4. Wang Qingwei, Liu Qiling, Cui Shengwen. Effects of different drying methods on nutritional quality and antioxidant activity of jujube [J]. Food industry, 2020,41(12):218-222. 5. Dong Li, raiting Xue. Effect of high temperature and high humidity gas impact treatment on quality of mid-short wave infrared dried jujube [J]. Food Research and Development, 2020,41(22):107-112. 6. Liu Min, Wang Jianying, Wei Li, Pan Yingyi, Yuan Ying. Determination of eight components in bark, leaf and male flower of Eucommia ulmoides Oliv. By HPLC [J]. Chinese traditional medicines, 2021,43(03):686-691. 7. [IF = 5.645] Wenjia Zhao et al."Induction and cultivation of novel red Cyclocarya paliurs call and its unique physical and metabolic characteristics." Ind Crop Prod. 2020 May;147:112266 8. [IF = 2.833] Yangyang Guo et al."Chemopreventive effect of Betulinic acid via mTOR -Caspases/Bcl2/Bax apoptotic signaling in pancreatic cancer."Bmc Complem Altern M. 2020 Jun 8;20(1):178 9. [IF=1.175] Wang Meng et al."Mechanism of molecules crosstalk and the critical role of jasmonic acid on triterpenoid synthesis in Cyclocarya Paliurus cells under Aspergillus niger elicitor."J Plant Biochem Biot. 2022 Jan;:1-16 10. [IF=4.412] Shaodan Chen et al."Binding Interaction of Betulinic Acid to α-Glucosidase and Its Alleviation on Postprandial Hyperglycemia."MOLECULES. 2022 Jan;27(8):2517 |
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID - Reference Information
| Introduction | Betulinic acid is a pentacyclic triterpenoid compound, which is widely present in the natural world. It was first isolated from the bark of Rhamnaceae evergreen plants growing in eastern Africa, but the main source is extracted and purified from birch bark. In recent years, scientific research has found that BA is a very valuable natural product. BA and its derivatives have shown great potential in anti-cancer and HIV treatment as biological agents. They play an important role in the body's antioxidant damage and immune regulation process. They are a class of potential drug lead compounds and have important value for the research and development of new drugs. NCI of the American Cancer Institute has included them in the Rapid Research and Development Program (RAID). |
| properties | light yellow to white crystalline powder; The air is slight and the taste is bitter. |
| use | has anti-tumor, lowering blood pressure, anti-peptic ulcer and gastrointestinal dysfunction, and treats liver diseases. 1. Anti-inflammatory effect Most pentacyclic triterpenoids have anti-inflammatory activity. The anti-inflammatory effect of betulinic acid has been verified in the model system in vivo and in vitro. It can inhibit PGE2 production and reduce inflammatory response. 2. The antibacterial effect has a certain antibacterial effect, which can inhibit a variety of bacteria including Escherichia coli, Bacillus subtilis, Staphylococcus aureus and Staphylococcus epidermidis. 3. Antiviral effect has more prominent antiviral activity, especially anti-HIV activity, and has an effective effect on anti-hepatitis C virus, anti-spore rash virus, anti-Eco virus, anti-influenza virus, etc. 4. Anti-hyperlipidemia effects Studies have found that betulinic acid and its derivatives can play an anti-hyperlipidemia effect by regulating adipokines, reducing lipid production, and reducing triacylglycerol and total cholesterol levels. 5. Anti-diabetic effect has shown good efficacy in the treatment of diabetes, which is mainly treated by inhibiting α-amylase and α-glucosidase to reduce the hydrolysis of polysaccharides and promote glycogen synthesis. 6. Antioxidant stress activity BA has protective effect on normal cells and body, which is related to antioxidant stress. For example, betulinic acid has a protective effect on ischemia-reperfusion injury in the brain, kidney and heart. BA has protective effects on ischemia-reperfusion brain injury in mice by anti-oxidative stress, anti-nitriding stress and increasing blood flow. Other diseases have now been found to improve Alzheimer's disease. Its protective effect is mainly through weakening neurobehavioral and cognitive dysfunction, reducing pro-inflammatory cytokines in the hippocampus, and reducing oxidation and nitrosation. At the same time, there are also reports that betulinic acid has a certain anti-anxiety effect, and some anti-anxiety drugs have been used in its components. Betulinic acid has a strong inhibitory effect on human melanoma, human colon cancer, and completely inhibits the growth of athymic mice with human melanoma. A pentacyclic triterpenoid compound that selectively induces tumor cell apoptosis through the mitochondrial pathway that directly activates apoptosis through p53 and CD95 independent mechanisms. |
| production method | first, extracted and separated from natural plants. This method consumes a large amount of solvent, the yield is low, and the impurities are not easy to separate, so it is rarely used; second, betulinic acid is obtained by organic synthesis with betulin as the precursor. This method has been applied to industrial production, and industrial-scale betulinic acid can be obtained, which is the main source of betulinic acid on the market; third, betulinic acid is generated by microbial transformation with betulinic alcohol as a precursor. This method represents the new direction of the future plant extraction industry, but there are still many technical problems that cannot be solved. |
| Preparation | Microbial transformation method uses enzymes produced in the metabolic process to catalyze the substrate to obtain the target product. Compared with chemical synthesis methods, microbial transformation has high stereoselectivity, mild reaction conditions, low pollution and low cost. This method has the potential for industrialization. Feng et al. catalyzed betulin direct microbial transformation to produce BA by culturing Armillaria luteovirens ZJUQH100-6 and Cunninghamella blakesleeana cells. In addition, some studies have used the biotechnology of inducing BA production from callus of Ocimi species for the first time to improve the yield of BA. This study provides a new method for the preparation of BA and other anticancer triterpenes. Recently, it has been reported that the whole metabolic pathway of BA in plants was substituted into yeast cells, and BA was successfully synthesized by microorganisms. Studies have found that the metabolic flow balance of fatty acid and terpenoid precursor synthesis pathways has a significant effect on BA synthesis, and the production of BA is significantly increased by co-expression of key regulatory genes (HFA1, HMG1 and ERG9) in these two metabolic pathways. The engineering bacteria can synthesize mg-level BA per liter of culture medium, thus, the preparation and synthesis of BA has risen to a new level. |
Last Update：2024-04-09 20:49:11
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View History
3B-HYDROXY-20(29)-LUPENE-28-OIC ACID
5-三氟甲基嘧啶-2,4-二醇
Bicyclo[4.1.0]hept-2-ene-7-carbonyl chloride, 3,6-dimethyl-, [1S-(1alpha,6alpha,7alpha)]- (9CI)
5-Chlorosalicylic aldehyde
diazenedicarboxylic acid bis(N'-methylpiperazide)
Carbamic acid, N-[1-(hydroxymethyl)-2-phenylethyl]-, phenylmethyl ester
丙炔酸叔丁酯
2-THIENYL IODIDE
Isocaproyl chloride
2,5-二氯-4,6-二甲基烟酰胺
5-三氟甲基嘧啶-2,4-二醇
Bicyclo[4.1.0]hept-2-ene-7-carbonyl chloride, 3,6-dimethyl-, [1S-(1alpha,6alpha,7alpha)]- (9CI)
5-Chlorosalicylic aldehyde
diazenedicarboxylic acid bis(N'-methylpiperazide)
Carbamic acid, N-[1-(hydroxymethyl)-2-phenylethyl]-, phenylmethyl ester
丙炔酸叔丁酯
2-THIENYL IODIDE
Isocaproyl chloride
2,5-二氯-4,6-二甲基烟酰胺