Ursolic acid acetate Chemical Properties

Melting point:

279-280 °C

Boiling point:

567.6±50.0 °C(Predicted)

Density 

1.09±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

4.67±0.70(Predicted)

color 

White to off-white

Ursolic acid acetate Usage And Synthesis

Uses

Ursolic acid acetate (Acetylursolic acid), isolated from the aerial roots of Ficus microcarpa, exhibits cytotoxicity against KB cells with IC50 of 8.4 μM[1].

Definition

ChEBI: Acetylursolic acid is a triterpenoid.

Synthesis

Acetylation of ursolic acid (5.00 g, 10.96 mmol) with acetic anhydride (2.60 mL, 26.00 mmol) in pyridine (80 mL) was carried out by adding triethylamine (3.00 mL, 21.68 mmol) and a catalytic amount of DMAP for a 12 h reaction at 25°C. The reaction was carried out by aqueous post-treatment. Upon completion of the reaction, an aqueous post-treatment and purification by silica gel column chromatography (SiO2, eluent: hexane/ethyl acetate, 8:2) afforded the target compound 14 (5.30 g, 97% yield) as a colorless solid. Thin layer chromatography (TLC) showed Rf = 0.71 (SiO2, eluent: hexane/ethyl acetate, 7:3). The melting point of the compound is 235-238°C (literature value:[8] 242-244°C). Specific optical rotation [α]D = +64.89° (c = 0.86, CHCl3) (literature value:[8] [α]D = +71.2° (c = 1.0, CHCl3)). Mass spectra (ESI, MeOH) showed m/z = 499.1 (15%, [M + H]+), 521.3 (30%, [M + Na]+), 1019.3 (100%, [2M + Na]+).

References

[1] Chiang YM, et al. Cytotoxic triterpenes from the aerial roots of Ficus microcarpa. Phytochemistry. 2005 Feb;66(4):495-501. DOI:10.1016/j.phytochem.2004.12.026

Ursolic acid acetate(7372-30-7)Related Product Information

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• Triacetin
• Arbutin
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• Benzyl acetate
• Vinyl acetate
• Ethyl 2-(Chlorosulfonyl)acetate
• Terpinyl acetate
• INDOPHENOL ACETATE
• POLY(VINYL ACETATE)
• Sodium triacetoxyborohydride
• Sodium acetate
• Ursolic acid
• Cellulose acetate
• Benzyloxyacetyl chloride
• Ethyl acetate
• Butyl acetate
• 4-Acetoxystyrene