Betulonicacid

Betulonicacid Property

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

Safety Statements 

24/25

HS Code 

29389090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P234Keep only in original container.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P370+P378In case of fire: Use … for extinction.

P390Absorb spillage to prevent material damage.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

Betulonicacid Chemical Properties,Usage,Production

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