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
• General Description: Oleanolic acid is a naturally occurring triterpenoid compound identified in *Betula ermanii*, alongside other triterpenes, lignans, and phenolic derivatives. It is structurally characterized as a pentacyclic triterpene with a hydroxyl group at the C-3 position and a carboxylic acid at C-28, contributing to its bioactive properties. Oleanic acid is part of the broader phytochemical profile of *Betula* species, which are traditionally valued for their medicinal and cosmetic applications.

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:

Oleanolsaeuremethylester-acetat

Oleanonsaeure

oleanolic acid methyl ester

1,2,7-trimethylnaphthalene

Refernces

Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii

10.1248/cpb.43.1937

The research focused on the chemical evaluation of Betula species in Japan, specifically the constituents of Betula ermanii. The purpose of the study was to identify and characterize the chemical compounds present in different parts of the tree, including the fresh leaves, outer bark, inner bark, and root bark. The research concluded that the tree contained a variety of dammarane-type triterpenes, lignans, triterpenes, phenolics, and caffeoyl esters. Some of the key chemicals identified were 20(S),24(R)-epoxydammaran-3,11x,25-triol and its derivatives, betulin, betulin 3-caffeate, oleanolic acid, and various lignans such as (+)-lyoniresinol and (-)-lyoniresinol. The study also reported several new compounds, including 2, 3, 4, 6, 19, and 21, which were dammarane-type glycosides isolated for the first time from the leaves of Betula species. This comprehensive analysis of Betula ermanii's chemical constituents contributes to the understanding of its potential medicinal value, building on the known traditional uses of other Betula species in medicine and cosmetics.