Oleanolic Acid

Base Information

• Chemical Name: Oleanolic Acid
• CAS No.: 508-02-1
• Deprecated CAS: 2088830-42-4
• Molecular Formula: C30H48O3
• Molecular Weight: 456.709
• Hs Code.: 29181990
• European Community (EC) Number: 208-081-6
• NSC Number: 114945
• UNII: 6SMK8R7TGJ
• DSSTox Substance ID: DTXSID50858790
• Nikkaji Number: J6.235I
• Wikipedia: Oleanolic_acid
• Wikidata: Q418628
• RXCUI: 1426254
• Pharos Ligand ID: 83HPFHGUH6N7
• Metabolomics Workbench ID: 28743
• ChEMBL ID: CHEMBL168
• Mol file: 508-02-1.mol

Synonyms:Hederins;Oleanane Triterpenes;Oleanol;Oleanolic Acid;Triterpenes, Oleanane

Chemical Property of Oleanolic Acid

Chemical Property:

• Appearance/Colour: light yellow
• Vapor Pressure: 1.47E-14mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.557
• Boiling Point: 553.5 °C at 760 mmHg
• PKA: 2.52(at 25℃)
• Flash Point: 302.6 °C
• PSA: 57.53000
• Density: 1.1 g/cm³
• LogP: 7.23360
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Very Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 885

Purity/Quality:

98% ^*data from raw suppliers

Oleanolic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-60-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)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)O)C)C)(C)C)O
• Recent ClinicalTrials: Bioavailability of Oleanolic Acid Formulated as Functional Olive Oil
• Recent NIPH Clinical Trials: The effect of grape-derived pomace on improving oral environment
• Description: Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid with the formula of C30H48O3. It was found in the non-glyceride fraction of olive pomace oil and is widely distributed in food and plants where it exists as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be linked to one or more sugar chains. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. Oleanolic acid and its derivatives possess several promising pharmacological activities, such as hepatoprotective effects, and anti-inflammatory, antioxidant, or anticancer activities.
• Uses: Oleanolic acid is a triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. It can Inhibits secretory phospholipase A2 that is mainly used for the treatment of acute jaundiced hepatitis with remarkable efficacy, and also has good effect on chronic hepatitis.?
• Indications: Oleanolic acid is included in the Pharmacopoeia of the People's Republic of China (Part 2, volume 3), the British Pharmacopoeia (2017), and the European Pharmacopoeia (8.7th ed.). It is mainly used for the adjuvant treatment of acute infectious icteric hepatitis and acute and chronic hepatitis. It also can be utilized in psoriasis, rheumatoid arthritis, nephritic edema, ascites, stomach with turbid, metrorrhagia, bruises, carbuncle, soreness and weakness of the waist and knees, fetal irritability and so on.
• Clinical Use: It is reported that contrast with Western medicine, the 60~90?mg/d oleanolic acid tablets supplemented with vitamin B can treat acute and chronic hepatitis, with effective rates of 94.4% and 69.81%, respectively, in clinical results. It has been listed on the drug manual as adjuvant therapy for acute and chronic hepatitis.

Technology Process of Oleanolic Acid

There total 219 articles about Oleanolic 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:

3β-O-palmitoyl-28-[3'-palmitoyl-β-D-glucopyranosyl]-olean-12-en-28-oic acid (1393711-53-9) → β-D-glucose (492-61-5) + Oleanolic acid (508-02-1) + 1-hexadecylcarboxylic acid (57-10-3)

Guidance literature:

With methanol; potassium hydroxide; for 4h; Reflux;

DOI:10.1016/j.phytol.2011.06.004

Reference yield:

stipuleanosides R1 → β-D-glucose (492-61-5) + D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + α-L-arabinofuranoside (38029-69-5) + oleanolic acid (508-02-1,6880-10-0,25499-90-5)

Guidance literature:

With β-glucuronidase; acetate buffer; at 37 ℃; hydrolysis; other enzyme (glycyrrhizinic acid hydrolase);

Reference yield:

3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-28-O-[β-D-glucopyranosyl-(1→6)-[β-D-fucopyranosyl-(1→2)]-β-D-glucopyranosyl]oleanolic acid → D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + Oleanolic acid (508-02-1)

Guidance literature:

With hydrogenchloride; water; at 85 ℃; for 2h;

DOI:10.1016/j.fitote.2015.12.012

upstream raw materials:

sodium ethanolate

methanol

oleanolic acid methyl ester

sodium acetate

Downstream raw materials:

oleanolic acid methyl ester

diphenylmethyl oleanolate

(4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-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

oleanane

Refernces

• 1、 Tripathi, R. D.,Tiwari, K. P.. "GENICULATIN, A TRITERPENOID SAPONIN FROM EUPHORBIA GENICULATA". . p. 2163 - 2166. Retrieved 1980.
• 2、 Zhang, Zhizhen,Koike, Kazuo,Jia, Zhonghua,Nikaido, Tamotsu,Guo, Dean,Zheng, Junhua. "Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis". . p. 740 - 745. Retrieved 1999.
• 3、 Shah, Bhahwal Ali,Chib, Renu,Gupta, Pankaj,Sethi, Vijay Kumar,Koul, Surrinder,Andotra, Samar Singh,Nargotra, Amit,Sharma, Sujata,Pandey, Anjali,Bani, Sarang,Purnima, Basant,Taneja, Subhash Chandra. "Saponins as novel TNF-α inhibitors: Isolation of saponins and a nor-pseudoguaianolide from Parthenium hysterophorus". . p. 3230 - 3235. Retrieved 2009.
• 4、 Carvalho,Seita. "A new oleanolic acid derivative from Securinega tinctoria". . p. 369 - 372. Retrieved 1993.
• 5、 Kemertelidze, E. P.,Gvazava, L. N.,Alaniya, M. D.,Kikoladze, V. S.. "TRITERPENE GLYCOSIDES OF THE LEAVES OF Digitalis ciliata". . p. 212 - 215. Retrieved 1991.
• 6、 Marquina,Maldonado,Garduno-Ramirez,Aranda,Villarreal,Navarro,Bye,Delgado,Alvarez. "Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens". . p. 93 - 97. Retrieved 2001.
• 7、 Apsamatova et al.. "". . . Retrieved 1979.
• 8、 Zhang, Zhizhen,Koike, Kazuo,Jia, Zhonghua,Nikaido, Tamotsu,Guo, Dean,Zheng, Junhua. "Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis". . p. 388 - 393. Retrieved 1999.
• 9、 Tian, Jun,Wu, Feng-E,Qiu, Ming-Hua,Nie, Rui-Lin. "TWO TRITERPENOID SAPONINS FROM PTEROCEPHALUS BRETSCHNEIDRI". . p. 1539 - 1542. Retrieved 1993.
• 10、 Barbosa, Lara F.,Mathias, Leda,Braz-Filho, Raimundo,Vieira, Ivo J. Curcino. "Chemical constituents from Aspidosperma illustre (Apocynaceae)". . p. 1434 - 1438. Retrieved 2010.