ChemicalBook CAS DataBase List Oleanolic acid

Oleanolic acid synthesis

4synthesis methods

Product Name:Oleanolic acid
CAS Number:508-02-1
Molecular formula:C30H48O3
Molecular Weight:456.7

Olean-12-en-28-oic acid, 3-[(O-β-D-xylopyranosyl-(1→3)-O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl)oxy]-, O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, (3β)-

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508-02-1
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Yield:508-02-1 3.5 mg

Reaction Conditions:

with hydrogenchloride in chloroform;water; for 6 h;Reflux;

Steps:

Two-phase acid hydrolysis and determination of aglycones of 1-5:

General procedure: Due to the less quantity of saponins 1, 2 and 4, their mixture (15mg) was carried out in a solution of 10% hydrochloric acid (50mL) and CHCl₃ (25mL) under reflux for 6h. After cooling, the CHCl₃ layer was washed with H₂O (3×2mL) and concentrated in vacuo. The residue was chromatographed on Sephadex LH-20 using MeOH as eluent to yield the glycone (siaresinolic acid, 2.8mg). This compound was identified by ESIMS and NMR. The aglycones of 3 and 5 were obtained using the same method (oleanolic acid, 3.5mg for 3 and hederagenin, 4.2mg for 5). The identification date of these aglycones see Supplementary data.

References:

Wang, Xiao-Yang;Gao, Hui;Zhang, Wei;Li, Yuan;Cheng, Guang;Sun, Xiao-Li;Tang, Hai-Feng [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 20,p. 5714 - 5720]