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| | Oleanolic acid 3-acetate Basic information |
| Product Name: | Oleanolic acid 3-acetate | | Synonyms: | oleanolic acid 3-acetate;(3beta)- 3-(acetyloxy)- olean-12-en-28-oic acid;3β-Acetoxyolean-12-en-28-oic acid;3β-Acetyloxyolean-12-en-28-oic acid;(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid;(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid;3-O-Acetylolealic acid;(3β)- 3-(acetyloxy)- olean-12-en-28-oic acid | | CAS: | 4339-72-4 | | MF: | C32H50O4 | | MW: | 498.74 | | EINECS: | 2017-001-1 | | Product Categories: | Pentacyclic triterpenes | | Mol File: | 4339-72-4.mol |  |
| | 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 Preparation Products And Raw materials |
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