Methyl oleanonate

Base Information

• Chemical Name: Methyl oleanonate
• CAS No.: 1721-58-0
• Molecular Formula: C31H48O3
• Molecular Weight: 468.72
• DSSTox Substance ID: DTXSID201316509
• Nikkaji Number: J109.352E
• Metabolomics Workbench ID: 123753
• ChEMBL ID: CHEMBL1631518
• Mol file: 1721-58-0.mol

Synonyms:Methyl oleanonate;1721-58-0;CHEMBL1631518;3-Oxoolean-12-en-28-oic acid methyl ester;3-Oxo-olean-12-en-28-oic acid methyl ester;SCHEMBL16152971;DTXSID201316509;HY-N7624;BDBM50456758;AKOS040763800;MS-28660;CS-0134812;3-Oxo-18beta-olean-12-en-28-oic acid methyl ester

Chemical Property of Methyl oleanonate

Chemical Property:

• PSA: 43.37000
• LogP: 7.53020
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 468.36034539
• Heavy Atom Count: 34
• Complexity: 942

Purity/Quality:

98.5% ^*data from raw suppliers

Methyloleanonate 99.49% ^*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(=O)C5(C)C)C)C)C2C1)C)C(=O)OC)C
• Isomeric SMILES: C[C@]12CCC(=O)C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)OC)C)C)(C)C

Technology Process of Methyl oleanonate

There total 20 articles about Methyl oleanonate 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Oleanonsaeure (17990-42-0) → methyl 3-oxooleanolate (1721-58-0)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃;

DOI:10.1016/j.bioorg.2019.103054

Reference yield: 99.0%

oleanolic acid methyl ester (1724-17-0,73584-64-2) → methyl 3-oxooleanolate (1721-58-0)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1248/cpb.48.1681

Reference yield: 96.0%

oleanolic acid methyl ester (1724-17-0,73584-64-2) → 3-Oxoolean-12-en-28-saeure-methylester (1721-58-0)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In diethyl ether; acetone; at 10 ℃; for 0.0833333h;

DOI:10.1002/ardp.19823151006

upstream raw materials:

diazomethane

Oleanonsaeure

oleanolic acid methyl ester

dimethyl sulfate

Downstream raw materials:

methyl 3-hydroxyolean-12-en-28-oate

3,28-dihydroxyolean-12-ene

methyl maslinate

methyl corosolate

Refernces

• 1、 Gubaidullin, Rinat R.,Khalitova, Rezeda R.,Galimshina, Zulfiya R.,Spivak, Anna Yu. "Synthesis of novel [3,2-b] furan-fused pentacyclic triterpenoids via gold - Catalyzed intramolecular heterocyclization of 2-alkynyl-3-oxotriterpene acids". . p. 1888 - 1899. Retrieved 2018.
• 2、 Heise, Niels,Hoenke, Sophie,Simon, Vivienne,Deigner, Hans-Peter,Al-Harrasi, Ahmed,Csuk, René. "Type and position of linkage govern the cytotoxicity of oleanolic acid rhodamine B hybrids". . . Retrieved 2021.
• 3、 Nasini,G.,Piozzi,F.. "-". . p. 514. Retrieved 1981.
• 4、 Krajka-Ku?niak, Violetta,Bednarczyk-Cwynar, Barbara,Paluszczak, Jaros?aw,Szaefer, Hanna,Naro?na, Maria,Zaprutko, Lucjusz,Baer-Dubowska, Wanda. "Oleanolic acid oxime derivatives and their conjugates with aspirin modulate the NF-κB-mediated transcription in HepG2 hepatoma cells". . . Retrieved 2019.
• 5、 Raghuvanshi, Dushyant Singh,Verma, Narsingh,Singh, Shilpi,Luqman, Suaib,Chand Gupta, Amit,Bawankule, Dnyaneshwar U.,Tandon, Sudeep,Nagar, Abhishek,Kumar, Yogesh,Khan, Feroz. "Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents". . p. 16782 - 16794. Retrieved 2018.
• 6、 Leal, Ana S.,Wang, Rui,Salvador, Jorge A. R.,Jing, Yongkui. "Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells". . p. 1726 - 1738. Retrieved 2013.
• 7、 Pawe?czyk, Anna,Olender, Dorota,Sowa-Kasprzak, Katarzyna,Zaprutko, Lucjusz. "Hybrid compounds strategy in the synthesis of oleanolic acid skeleton-NSAID derivatives". . . Retrieved 2016.
• 8、 Ma,Nakamura,Hattori. "Chemical modification of oleanene type triterpenes and their inhibitory activity against HIV-1 protease dimerization". . p. 1681 - 1688. Retrieved 2000.
• 9、 Fontana, Gianfranco,Bruno, Maurizio,Notarbartolo, Monica,Labbozzetta, Manuela,Poma, Paola,Spinella, Alberto,Rosselli, Sergio. "Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement". . . Retrieved 2019/06/19.