| Identification | Back Directory | [Name]
Betulonicacid | [CAS]
4481-62-3 | [Synonyms]
LiquidaMba
Betulonicaci
Betulonic acid
Betunolic acid
Betulinonic acid
Liquidambaric acid
Liquidambaric acid 4481-62-3
Lup-20(29)-en-28-oic acid, 3-oxo-
(+)-Betulonic acid, 98%, from Liquidambar formosana Hance | [Molecular Formula]
C30H46O3 | [MDL Number]
MFCD08459607 | [MOL File]
4481-62-3.mol | [Molecular Weight]
454.69 |
| Chemical Properties | Back Directory | [Melting point ]
253 °C | [Boiling point ]
548.1±33.0 °C(Predicted) | [density ]
1.061±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [Chemical Properties]
Betulinic acid is a white crystalline powder and is a pentacyclic triterpenoid compound widely distributed in many plants. Its content in birch bark is 0.25-2% (calculated on dry basis). | [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]
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 |
|
|