Benzyl oleanolate

Base Information

• Chemical Name: Benzyl oleanolate
• CAS No.: 303114-51-4
• Molecular Formula: C37H54O3
• Molecular Weight: 546.834
• ChEMBL ID: CHEMBL445301
• DSSTox Substance ID: DTXSID201249988
• Nikkaji Number: J1.973.642C
• Mol file: 303114-51-4.mol

Synonyms:benzyl oleanolate;303114-51-4;CHEMBL445301;benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate;OA-Bn;28-benzyloleonolic acid;SCHEMBL9888531;DTXSID201249988;BDBM50246619;Phenylmethyl (3beta)-3-hydroxyolean-12-en-28-oate;(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-benzyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate;benzyl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10- hydroxy-2,2,6a,6b,9,9,12a-heptamethyl- 1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b- tetradecahydropicene-4a-carboxylate (Compound 4)

Chemical Property of Benzyl oleanolate

Chemical Property:

• Boiling Point: 604.224 °C at 760 mmHg
• Flash Point: 217.48 °C
• PSA: 46.53000
• Density: 1.098 g/cm³
• LogP: 8.89240
• XLogP3: 9.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 546.40729558
• Heavy Atom Count: 40
• Complexity: 1030

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

BENZYL-OLEANOLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)OCC6=CC=CC=C6)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)OCC6=CC=CC=C6)C)C)(C)C)O

Technology Process of Benzyl oleanolate

There total 11 articles about Benzyl oleanolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Oleanolic acid (508-02-1) + benzyl bromide (100-39-0) → oleanolic acid benzyl ester (303114-51-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2006.05.086

Reference yield: 95.1%

Oleanolic acid (508-02-1) + benzyl chloride (100-44-7) → oleanolic acid benzyl ester (303114-51-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.bmcl.2006.03.009

Reference yield: 94.0%

→ oleanolic acid benzyl ester (303114-51-4)

Guidance literature:

upstream raw materials:

Oleanolic acid

phenyldiazomethane

benzyl chloride

benzyl bromide

Downstream raw materials:

benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside

benzyl 3-O-(2-chloroethoxycarbonyl)-3β-hydroxyolean-12-en-28-oate

benzyl 3-O-(tert-butyldiphenylsilyl)oleanolate

C₄₀H₅₈O₄

Refernces

• 1、 Chu, Fuhao,Zhang, Wenxi,Guo, Wenbo,Wang, Zhaoyi,Yang, Yuqin,Zhang, Xinyu,Fang, Kang,Yan, Mengmeng,Wang, Penglong,Lei, Haimin. "Oleanolic acid-amino acids derivatives: Design, synthesis, and hepatoprotective evaluation in vitro and in vivo". . . Retrieved 2018.
• 2、 -. "Pentacyclic triterpenoid TGR5 receptor stimulant, preparation method and application thereof". Paragraph 0123; 0329-0331. . Retrieved 2021/04/26.
• 3、 Zhong, Ye,Li, Hui-ning,Zhou, Lin,Su, Hua-sheng,Cheng, Mao-sheng,Liu, Yang. "Synthesis and antitumor activity evaluation of oleanolic acid saponins bearing an acetylated L-arabinose moiety". . . Retrieved 2021/04/19.