Betulonicacid CAS 4481-62-3
Betulonicacid Basic information
| Product Name: | Betulonicacid |
| Synonyms: | Betulinonic acid;LiquidaMba;Betulonic acid;Liquidambaric acid;(+)-Betulonic acid, 98%, from Liquidambar formosana Hance;Liquidambaric acid 4481-62-3;Betunolic acid;Lup-20(29)-en-28-oic acid, 3-oxo- |
| CAS: | 4481-62-3 |
| MF: | C30H46O3 |
| MW: | 454.68 |
| EINECS: | |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract |
| Mol File: | 4481-62-3.mol |
Betulonicacid Chemical Properties
| Melting point | 253 °C |
| Boiling point | 548.1±33.0 °C(Predicted) |
| density | 1.061±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| form | Solid |
| pka | 4.62±0.70(Predicted) |
| color | White to Off-White |
| Major Application | food and beverages |
| InChIKey | SLJTWDNVZKIDAU-SVAFSPIFSA-N |
| SMILES | C1(=O)[C@@]([C@]2([C@](C)(CC1)[C@]1([H])[C@@]([C@]3([C@@](CC1)([H])[C@@]1([C@@](CC[C@H]1C(C)=C)(C(O)=O)CC3)[H])C)(C)CC2)[H])(C)C |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | WGK 3 |
| HS Code | 29389090 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Betulin ketoacetic acid in the form of a white crystalline powder is a pentacyclic triterpenoid widely distributed in a variety of plants, and its content in the bark of Betula alba ranges from 0.25 to 2% (in dry form). |
| Uses | (+)-Betulonic Acid shows potent cytotoxic activities against PC3, MGC-803, Bcap-37, and MCF-7 cell lines. |
| Definition | ChEBI: Betulonic acid is a triterpenoid. It has a role as an anticoronaviral agent. |
| Synthesis | 472-15-1 4481-62-3 General procedure for the synthesis of 3-oxo-lupin-20(29)-en-28-oic acid from betulinic acid:1. preparation of Jones' reagent: chromium trioxide (CrO3, 26.72 g) was dissolved in concentrated sulfuric acid (H2SO4, 23 ml) and the solution was subsequently diluted to 100 ml with water.2. Reaction process: Betulinic acid (BA, 500 mg, 1.09 mmol) was dissolved in a solvent mixture of dichloromethane (CH2Cl2, 12 ml) and acetone (12 ml), and Jones reagent (1 ml) was added slowly after cooling.3. Reaction control: the reaction mixture was stirred at room temperature for 15 min followed by addition of methanol (MeOH, 5 ml) to terminate the reaction. After continued stirring for 10 minutes, the reaction mixture was diluted by adding dichloromethane (CH2Cl2, 20 ml).4. Post-treatment: The organic layer was washed sequentially with water and saturated sodium chloride (NaCl) solution, dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum.5. Purification: the crude product was recrystallized three times in methanol (MeOH) to give 3-oxo lupin-20(29)-en-28-oic acid (462 mg, 93% yield) as a white solid. |
| IC 50 | Plasmodium; HSV-1 |
| References | [1] Phytochemistry, 1998, vol. 49, # 3, p. 709 - 717 [2] Journal of Asian Natural Products Research, 2014, vol. 16, # 1, p. 34 - 42 [3] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 759 - 762 [4] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3122 - 3134 [5] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 240 - 248 |
Betulonicacid Preparation Products And Raw materials
| Raw materials | BETULIN DIACETATE-->Betulin-->Betulone-->betulonic aldehyde-->Betulinic acid-->Acetone-->Dichloromethane-->EDTA methidiumpropylamide |
| Preparation Products | Betulinic acid |
