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

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

HS Code 

29389090

Betulonicacid Usage And Synthesis

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

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(4481-62-3)Related Product Information

• Terrestrosin K
• roburic acid
• Pachymic acid
• LiquidaMbaric lactone
• Poricoic acid A(F)
• Terrestrosin D
• Carboxyatractyloside
• ALLEOSIDE A
• Nalidixic acid
• 4,4'-Carbonyldiphthalic acid
• Betulinic acid
• Betulinicaldehyde
• Betulin
• LUPENONE
• Betulonicacid
• Betulonicacidmethylester
• LUP-20(29)-ENE
• 6-HEPTYLDECAHYDRONAPHTHALENE-2-CARBOXYLIC ACID