Oleocanthal

Base Information

• Chemical Name: Oleocanthal
• CAS No.: 289030-99-5
• Deprecated CAS: 1246025-97-7
• Molecular Formula: C17H20O5
• Molecular Weight: 304.343
• UNII: AC7QO6038O
• ChEMBL ID: CHEMBL2172394
• DSSTox Substance ID: DTXSID40183104
• NSC Number: 752227
• Pharos Ligand ID: PBA4X8A6AHZF
• Wikidata: Q402613
• Wikipedia: Oleocanthal
• Mol file: 289030-99-5.mol

Synonyms:deacetoxy-oleuropein aglycone;oleocanthal

Chemical Property of Oleocanthal

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• PSA: 80.67000
• LogP: 2.21840
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 304.13107373
• Heavy Atom Count: 22
• Complexity: 394

Purity/Quality:

99%, ^*data from raw suppliers

Oleocanthal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C=O)C(CC=O)CC(=O)OCCC1=CC=C(C=C1)O
• Isomeric SMILES: C/C=C(/C=O)\[C@@H](CC=O)CC(=O)OCCC1=CC=C(C=C1)O
• Uses: Oleocanthal is a compound of olive oil with potential use as anti-inflammatory and chemotherapeutic agents.

Technology Process of Oleocanthal

There total 20 articles about Oleocanthal 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: 76.0%

(4S,E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-2-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylic acid → Oleocanthal (289030-99-5)

Guidance literature:

With b-glucosidase; sodium acetate; acetic acid; at 37 ℃; for 3h; pH=5; Enzymatic reaction;

Reference yield: 75.0%

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester (869476-96-0) → Oleocanthal (289030-99-5)

Guidance literature:

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester; With hydrogenchloride; In acetonitrile;

With sodium iodite; In acetonitrile;

Reference yield: 45.0%

[(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester (944340-53-8) → Oleocanthal (289030-99-5)

Guidance literature:

With sodium periodate; In dichloromethane; at 0 ℃; for 1.25h;

upstream raw materials:

[(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester

((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid

Downstream raw materials:

C₁₉H₂₆N₂O₅

(3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Refernces

• 1、 Sarikaki, Georgia,Christoforidou, Nikoleta,Gaboriaud-Kolar, Nicolas,Smith, Amos B.,Kostakis, Ioannis K.,Skaltsounis, Alexios-Leandros. "Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves". . p. 1735 - 1739. Retrieved 2020/06/08.
• 2、 -. "USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS". Page/Page column 16-17. . Retrieved 2009/04/24.