Oleanolic acid 3-acetate Chemical Properties

Melting point:

265-268 °C

Boiling point:

564.4±50.0 °C(Predicted)

Density 

1.10

storage temp. 

2-8°C

solubility 

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

form 

Powder

pka

4.63±0.70(Predicted)

color 

White to off-white

InChIKey

RIXNFYQZWDGQAE-VQHLFADXNA-N

SMILES

[C@@]12(C)CC[C@]3(CCC(C)(C)C[C@@]3([H])C1=CC[C@]1([H])[C@@]3([C@]([H])(C(C)(C)[C@H](CC3)OC(C)=O)CC[C@@]21C)C)C(O)=O |&1:0,4,11,16,18,19,24,33,r|

Oleanolic acid 3-acetate Usage And Synthesis

Uses

3-O-Acetyloleanolic acid (3AOA), an oleanolic acid derivative isolated from the seeds of Vigna sinensis K., induces in cancer and also exhibits anti-angiogenesis activity[1].

Synthesis

In a 25 mL dry Schlenk flask, oleanolic acid (2.0 mmol, 1.00 eq.) was dissolved in 10 mL of anhydrous pyridine, followed by the addition of ethanoic anhydride (2.50 eq.). The reaction mixture was slowly warmed to room temperature (rt) and stirred overnight. Upon completion of the reaction, the mixture was washed several times with water and the organic phase was extracted with ethyl acetate. The organic phases were combined and dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give pure (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13. 14b-octadecahydroperylene-4a(2H)-carboxylic acid in >99% yield, which was directly used in the next step of the reaction.

References

[1] Yoo KH, et al. 3-O-acetyloleanolic acid induces apoptosis in human colon carcinoma HCT-116 cells. Phytother Res. 2012 Oct;26(10):1541-6. DOI:10.1002/ptr.4616
[2] Hwang-Bo J, et al. 3-O-Acetyloleanolic acid inhibits VEGF-A-induced lymphangiogenesis and lymph node metastasis in an oral cancer sentinel lymph node animal model. BMC Cancer. 2018 Jul 5;18(1):714. DOI:10.1186/s12885-018-4630-0

Oleanolic acid 3-acetate(4339-72-4)Related Product Information

• Benzyl acetate
• Triacetin
• Amyl acetate
• Sodium acetate
• Tocopheryl acetate
• Glatiramer acetate
• Vinyl acetate
• POLY(VINYL ACETATE)
• Ethyl 2-(Chlorosulfonyl)acetate
• Oleanolic acid
• Ethyl acetate
• Folic acid
• Stearic acid
• Citric acid
• Ascoric Acid
• ACETATE
• (3beta)-3-[[(2E)-3-(4-Chlorophenyl)-1-oxo-2-propenyl]oxy]-olean-12-en-28-oic acid
• 3-beta-Hydroxy-olean-12-en-28-oic acid butyrate