Oleanonic acid

Base Information

• Chemical Name: Oleanonic acid
• CAS No.: 17990-42-0
• Deprecated CAS: 6785-78-0
• Molecular Formula: C30H46O3
• Molecular Weight: 454.693
• ChEMBL ID: CHEMBL470029
• DSSTox Substance ID: DTXSID90939279
• Metabolomics Workbench ID: 137282
• Nikkaji Number: J38.666I
• Wikidata: Q72498846
• Mol file: 17990-42-0.mol

Synonyms:oleanonic acid

Chemical Property of Oleanonic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 190 °C
• Refractive Index: 1.552
• Boiling Point: 551.704 °C at 760 mmHg
• PKA: 4.65±0.70(Predicted)
• Flash Point: 301.52 °C
• PSA: 54.37000
• Density: 1.099 g/cm³
• LogP: 7.44180
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 454.34469533
• Heavy Atom Count: 33
• Complexity: 927

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Oxo-olean-12-en-28-oic acid ^*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)O)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)O)C)C)(C)C
• Uses: Oleanonic Acid, is a derivative of Oleanolic Acid (O521000), which has been evaluated in vitro for their growth inhibition against human hepatocellular carcinoma cell line (HepG2) and colon cancer cell line, and thus used as antitumor agents.

Technology Process of Oleanonic acid

There total 15 articles about Oleanonic acid 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: 99.0%

Oleanolic acid (508-02-1) → Oleanonsaeure (17990-42-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 99.0%

oleanolic acid (508-02-1,6880-10-0,25499-90-5) → (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4-a-carboxylic acid (17990-42-0,73522-35-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

Reference yield: 93.0%

3-epioleanolic acid (25499-90-5) → Oleanonsaeure (17990-42-0)

Guidance literature:

With dipyridinium dichromate; acetic anhydride; In dichloromethane; Reflux;

DOI:10.3390/molecules18033615

upstream raw materials:

oleanolic acid

oleanolic acid

Oleanolic acid

3-oxoolean-12-en-28-al

Downstream raw materials:

methyl 3-oxooleanolate

2-hydroximino-3-oxo-oleanolic acid

olean-12-en-4-hydroxy-3,28-dioic acid

isoxazolo[4,5-b]olean-12-en-28-oic acid

Refernces

• 1、 Wu, Panpan,He, Hao,Ma, Hang,Tu, Borong,Li, Jiahao,Guo, Shengzhu,Chen, Silin,Cao, Nana,Zheng, Wende,Tang, Xiaowen,Li, Dongli,Xu, Xuetao,Zheng, Xi,Sheng, Zhaojun,David Hong, Weiqian,Zhang, Kun. "Oleanolic acid indole derivatives as novel α-glucosidase inhibitors: Synthesis, biological evaluation, and mechanistic analysis". . . Retrieved 2021.
• 2、 Hu, Jun,Wu, Jindan,Ju, Yong. "Methyl 1,2-shift rearrangement on c-ring and decarboxylation at C28 of oleanolic acid derivatives". . p. 133 - 136. Retrieved 2014.
• 3、 Ruzicka,van der Sluys-Veer. "-". . p. 1371,1382. Retrieved 1938.
• 4、 Wang, Wei-Wei,Xu, Shao-Hua,Zhao, Ya-Zheng,Zhang, Chao,Zhang, Yuan-Yuan,Yu, Bo-Yang,Zhang, Jian. "Microbial hydroxylation and glycosylation of pentacyclic triterpenes as inhibitors on tissue factor procoagulant activity". . p. 1026 - 1030. Retrieved 2017.
• 5、 Honda, Tadashi,Padegimas, Eric M.,David, Emilie,Sundararajan, Chitra,Liby, Karen T.,Williams, Charlotte,Sporn, Michael B.,Visnick, Melean. "2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent". . p. 2275 - 2278. Retrieved 2010.
• 6、 Hida, Takemasa,Fukui, Yuuki,Kawata, Kyozo,Kabaki, Mikio,Masui, Toshiaki,Fumoto, Masataka,Nogusa, Hideo. "Practical application of oxidation using a novel Na2WO 4-H2O2 system under neutral conditions for scale-up manufacturing of 12α-Hydroxy-3-oxooleanano-28,13-lactone: Key intermediate of endothelin a receptor antagonist S-0139". . p. 289 - 294. Retrieved 2010.
• 7、 He, Hao,Li, Huifang,Akanji, Toyosi,Niu, Shengli,Luo, Zhujun,Li, Dongli,Seeram, Navindra P.,Wu, Panpan,Ma, Hang. "Synthesis and biological evaluations of oleanolic acid indole derivatives as hyaluronidase inhibitors with enhanced skin permeability". . p. 1665 - 1678. Retrieved 2021.
• 8、 Zimmermann. "-". . . Retrieved 1936.
• 9、 Meng, Yan-Qiu,Zhao, Yu-Wei,Kuai, Zhen-Yu,Liu, Li-Wei,Li, Wei. "Synthesis and antitumor activity evaluation of novel oleanolic acid derivatives". . p. 1000 - 1010. Retrieved 2017.
• 10、 Kashiwada, Yoshiki,Wang, Hui-Kang,Nagao, Tsuneatsu,Kitanaka, Susumu,Yasuda, Ichiro,Fujioka, Toshihiro,Yamagishi, Takashi,Cosentino, L. Mark,Kozuka, Mutsuo,Okabe, Hikaru,Ikeshiro, Yasumasa,Hu, Chang-Qi,Yeh, Eric,Lee, Kuo-Hsiung. "Anti-AIDS agents, 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids". . p. 1090 - 1095. Retrieved 1998.