Lup-20(29)-ene-3,28-diol, (3β)-
betulin
CAS: 473-98-3
Molecular Formula: C30H50O2
Lup-20(29)-ene-3,28-diol, (3β)- - Names and Identifiers
| Name | betulin |
| Synonyms | betulin Betuline Betulinol BETULIN(P) BETULIN hplc betula camphor Betulinic alcohol lup-20(29)-ene-3,28-diol 3b,28-Dihydroxylup-20(29)-ene Lup-20(29)-ene-3,28-diol, (3β)- (3beta)-lup-20(29)-ene-3,28-diol (3beta,5xi,9xi,18xi)-lup-20(29)-ene-3,28-diol (3beta,5xi,9xi,13xi,14xi,18xi,19xi)-lup-20(29)-ene-3,28-diol |
| CAS | 473-98-3 |
| EINECS | 207-475-5 |
| InChI | InChI=1/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22?,23?,24-,25?,27-,28+,29+,30+/m0/s1 |
| InChIKey | FVWJYYTZTCVBKE-ROUWMTJPSA-N |
Lup-20(29)-ene-3,28-diol, (3β)- - Physico-chemical Properties
| Molecular Formula | C30H50O2 |
| Molar Mass | 442.72 |
| Density | 0.9882 (rough estimate) |
| Melting Point | 256-257°C(lit.) |
| Boling Point | 493.26°C (rough estimate) |
| Specific Rotation(α) | D15 +20° (c = 2 in pyridine) |
| Flash Point | 210.9°C |
| Solubility | Soluble in ethanol, chloroform and benzene, slightly soluble in cold water, petroleum ether, etc. |
| Vapor Presure | 4.32E-13mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | Pale Brown to Beige |
| Merck | 14,1189 |
| pKa | 15.10±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.5045 (estimate) |
| MDL | MFCD00016802 |
| Physical and Chemical Properties | Melting Point 256-257°C. |
Lup-20(29)-ene-3,28-diol, (3β)- - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R68/20/21/22 - R68 - Possible risk of irreversible effects |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | OK5755000 |
| HS Code | 29181985 |
Lup-20(29)-ene-3,28-diol, (3β)- - Reference
| Reference Show more | 1. Jiang Yang Sun, Fei Fei, Yan Yaguang, et al. Effects of carbon monoxide on cell growth and triterpenoid accumulation in suspension cultures of Betula platyphylla [J]. Chinese herbal medicine 2019 v.50;No.650(15):170-175. 2. Liu Lu, Ren Yanhong, Zhang Jie, et al. Protective effects of betulin on adriamycin-induced cardiac damage in rats [J]. Journal of Toxicology, 2017, 06(v.31):47-50 54. 3. Ji Xin, Liu Xiaoqian, Gao Lu, Xiao Suping, Liang obanhua, Li Chun, Wang Zhiming. Qualitative and Quantitative Analysis of triterpenoids in fructus Ligustri Lucidi [J]. Chinese Journal of Traditional Chinese Medicine, 2021,46(05):1168-1178. 4. 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. 5. [IF = 3.978] Hongfei Yu et al."The effect of triterpenoid saponins on pancreatic lipase in vitro: Activity, conformation, kinetics, thermodynamics and morphology."Biochem Eng J. 2017 Sep;125:1 6. [IF=6.023] Li Ren et al."Anti-inflammatory action of betulin and its potential as a dissociated glucocorticoid receptor modulator."Food Chem Toxicol. 2021 Nov;157:112539 |
Lup-20(29)-ene-3,28-diol, (3β)- - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| birch bark extract | betulin (Betulin), also known as betulin, betulin, betulin, is a kind of triterpene extracted from birch bark. The use of compounds in bark is unknown, but they can be used as betulinic acid (carboxylic acid group substituted alcohol group) and other compounds with more biological functions The precursor. |
| extraction method | currently, the way to obtain betulin is mainly through direct extraction, mainly through solvent reflux extraction method and recrystallization purification method, specifically: 1. betulin is extracted with ethanol solution, heated and refluxed for about 5 hours, the extract is decompressed and distilled, then recrystallized with ethanol for 2-3 times to obtain a crude betulin product. 2. the crude product is recrystallized with methanol/chloroform (1:1), and 80g of crude product requires about 300mL of methanol and chloroform solution; Let stand overnight and filter to obtain white needle-like betulin solid. 3. ultrasonic treatment of the extract was designed for 20min during reflux, and the extraction rate and product purity of betulin were improved by destroying the bark tissue. 4. the optimal extraction conditions of supercritical CO2 fluid are as follows: the dosage of modifier is 115 mL/g birch bark powder; The extraction pressure is 20MPa; The extraction temperature is 55 ℃; The flow rate of liquid CO2 is 10kg/h. |
| identification method | HPLC determination conditions of betulin: ▼ ▲ separation component chromatographic column stationary phase mobile phase flow rate (ml/min) detection wavelength (nm) column temperature betulin (10 μl injection) C18(150 × 2)mm 5 μ acetonitrile/water = 30:700.227030 ℃ |
| physiological effects of betulin | 1. betulin and its derivatives as biological agents show great potential in the treatment of HIV and cancer. it works by interfering with the latter stage of the virus life cycle and is related to the entry and growth of the virus. 2. Effective anti-tumor drugs directly cause certain types of tumor cells to initiate self-destructing apoptosis procedures, and can slow down the growth of several types of tumor cells. 3. It can reduce diet-induced obesity, reduce lipid content in serum and tissues, and improve insulin sensitivity. 4. They have mild anti-inflammatory properties at higher concentrations, and their anti-inflammatory properties are mainly due to inhibition of non-neural gene pathways. 5. Betulin can inhibit the maturation of sterol regulatory element binding proteins (SBERPs) in vivo, thus reducing the biosynthesis of cholesterol and fatty acids. 6. In addition, it also has the activities of inhibiting protein dissolution in hair fibers, improving damaged hair luster, promoting hair growth, etc. It can be used in food, cosmetics, medicine and other industries. |
| store | cool and dry, away from light and high temperature. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: anti-inflammatory, anti-viral, inhibit protein dissolution in hair fibers, improve damaged hair luster, promote hair growth and other activities. it has anti-inflammatory, anti-virus, inhibiting protein dissolution in hair fibers, improving damaged hair luster, promoting hair growth and other activities, and can be used in food, cosmetics, medicine and other industries. |
Last Update：2024-04-09 19:05:12
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