| Identification | Back Directory | [Name]
Ursolic acid acetate | [CAS]
7372-30-7 | [Synonyms]
Aids070315
Aids-070315
Acetylursolicaci
3-Acetylursolic acid
URSOLIC ACID ACETATE
3β-(Acetyloxy)urs-12-en-28-oic acid
(3β)-3-(Acetyloxy)-urs-12-en-28-oic acid
URSOLIC ACID ACETATE (ACETYLURSOLIC ACID)
(3beta)-3-(Acetyloxy)-urs-12-en-28-oic acid
Urs-12-en-28-oic acid, 3-(acetyloxy)-, (3β)-
Urs-12-en-28-oic acid, 3-(acetyloxy)-, (3beta)-
(1S,2R,6aS,6aS,6bR,8aS,12aS)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid | [Molecular Formula]
C32H50O4 | [MDL Number]
MFCD09752431 | [MOL File]
7372-30-7.mol | [Molecular Weight]
498.74 |
| Chemical Properties | Back Directory | [Melting point ]
279-280 °C | [Boiling point ]
567.6±50.0 °C(Predicted) | [density ]
1.09±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,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 |
| Hazard Information | Back Directory | [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 |
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