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Betulonicacid

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CAS:4481-62-3
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CAS:4481-62-3
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  • CAS:4481-62-3
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  • Purity: 99.70%
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  • CAS:4481-62-3
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  • CAS:4481-62-3
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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 Structure
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
pka4.62±0.70(Predicted)
color White to Off-White
InChIKeySLJTWDNVZKIDAU-SVAFSPIFSA-N
SMILESC1(=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
MSDS Information
Betulonicacid Usage And Synthesis
Chemical PropertiesBetulin 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.
DefinitionChEBI: Betulonic acid is a triterpenoid. It has a role as an anticoronaviral agent.
Synthesis
Betulinic acid

472-15-1

Betulonicacid

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 50Plasmodium; 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 materialsBETULIN DIACETATE-->Betulin-->Betulone-->betulonic aldehyde-->Betulinic acid-->Acetone-->Dichloromethane-->EDTA methidiumpropylamide
Preparation ProductsBetulinic acid
Tag: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

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