| Identification | Back Directory | [Name]
Oleanolic acid 3-acetate | [CAS]
4339-72-4 | [Synonyms]
product/154638
3-O-Acetyloleanolicaci
Oleanolic acid acetate
3-O-Acetylolealic acid
oleanolic acid 3-acetate
3-O-Acetyloleanolic acid
3β-Acetoxyolean-12-en-28-oic acid
3β-Acetyloxyolean-12-en-28-oic acid
3beta-3-Acetoxyolean-12-en-28-oic acid
(3β)- 3-(acetyloxy)- olean-12-en-28-oic acid
Olean-12-en-28-oic acid, 3-(acetyloxy)-, (3β)-
(3beta)- 3-(acetyloxy)- olean-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 | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C32H50O4 | [MDL Number]
MFCD09752429 | [MOL File]
4339-72-4.mol | [Molecular Weight]
498.74 |
| Chemical Properties | Back Directory | [Melting point ]
265-268 °C | [Boiling point ]
564.4±50.0 °C(Predicted) | [density ]
1.10 | [storage temp. ]
Sealed in dry,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| |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [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 |
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