23-Hydroxybetulinic acid

Base Information

• Chemical Name: 23-Hydroxybetulinic acid
• CAS No.: 85999-40-2
• Molecular Formula: C30H48O4
• Molecular Weight: 472.709
• Mol file: 85999-40-2.mol

Synonyms:Lup-20(29)-en-28-oic acid,3,23-dihydroxy-,(3a,4R)-;23-Hydroxybetulinic acid;3β,23-Dihydroxylup-20(29)-en-28-oic acid;

Chemical Property of 23-Hydroxybetulinic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 585.787 °C at 760 mmHg
• PKA: 4.60±0.70(Predicted)
• Flash Point: 322.11 °C
• PSA: 77.76000
• Density: 1.106 g/cm³
• LogP: 6.06190
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Heated), Pyridine (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

23-HydroxybetulinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 23-hydroxy Betulinic acid is a triterpenoid that has been found in P. chinensis and has anticancer activity. It inhibits proliferation of K562, B16, and HeLa cells (IC50s = 39.9, 78.5, and 80 μM, respectively), as well as human umbilical vein endothelial cells (HUVECs; IC50 = 94.8 μM). It halts the cell cycle at the S phase and induces apoptosis in K562 cells in a concentration-dependent manner with a loss of the mitochondrial membrane potential and an increase in Bax and cytochrome C protein levels.
• Uses: 23-Hydroxybetulinic Acid is a potential cytoxic agent in the treatment of cancer. Apoptotic effect. Antiproliferative.

Technology Process of 23-Hydroxybetulinic acid

There total 18 articles about 23-Hydroxybetulinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

benzyl 3-oxo-23-hydroxy-lup-20(29)-en-28-oic acid (136684-40-7) → 23-hydroxybetulinic acid (85999-40-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h;

DOI:10.3184/174751912X13332875186150

Reference yield: 85.0%

DA001 (129724-84-1) → 23-hydroxybetulinic acid (85999-40-2)

Guidance literature:

With hydrogenchloride; methanol; water; at 35 ℃; for 96h;

Reference yield: 70.0%

benzyl 3,23-dihydroxy-lup-20(29)-en-28-oate (1215746-83-0) → 23-hydroxybetulinic acid (85999-40-2)

Guidance literature:

benzyl 3,23-dihydroxy-lup-20⁽²⁹⁾-en-28-oate; With tert-butyldimethylsilane; palladium diacetate; triethylamine; In 1,2-dichloro-ethane; at 60 ℃; for 2.5h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201407016

upstream raw materials:

chinensioside A

DA₀₀₁

benzyl 3-oxo-23-hydroxy-lup-20⁽²⁹⁾-en-28-oic acid

benzyl 3-hydroxyimino-lup-20⁽²⁹⁾-en-28-oate

Downstream raw materials:

benzyl 3-oxo-23-hydroxy-lup-20⁽²⁹⁾-en-28-oic acid

3,23-diacetoxylup-20⁽²⁹⁾-en-28-oic acid

acetic acid 8-acetoxymethyl-3a-chlorocarbonyl-1-isopropenyl-5a,5b,8,11a-tetramethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester

9-acetoxy-8-acetoxymethyl-1-isopropenyl-5a,5b,8,11a-tetramethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid allyl ester