Oleoside 11-methyl ester

Base Information

• Chemical Name: Oleoside 11-methyl ester
• CAS No.: 60539-23-3
• Molecular Formula: C17H24O11
• Molecular Weight: 404.371
• DSSTox Substance ID: DTXSID501313328
• Nikkaji Number: J1.537.983I,J510.902G
• Wikidata: Q105340954
• ChEMBL ID: CHEMBL4159745
• Mol file: 60539-23-3.mol

Synonyms:methyloleoside

Chemical Property of Oleoside 11-methyl ester

Chemical Property:

• PSA: 172.21000
• Density: 1.51±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: -1.74670
• XLogP3: -2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 404.13186158
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

≥98% ^*data from raw suppliers

11-Methyloleoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)O
• Isomeric SMILES: C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)O
• Uses: 11-Methyloleoside is a secoiridoid glucoside isolated from the seeds of Fraxinus excelsior that shows differential antiinflammatory activities in LPS-treated mouse macrophage and anticancer effects in human cancer cell. 11-Methyloleoside is also a useful synthetic intermediate in the synthesis of Ligustroside (L397960).

Technology Process of Oleoside 11-methyl ester

There total 5 articles about Oleoside 11-methyl ester 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: 90.0%

oleuropeine (32619-42-4) → 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (60539-23-3)

Guidance literature:

With sodium carbonate; at 20 ℃; for 3h; pH=11.5;

DOI:10.1021/jf991178b

Reference yield: 29.0%

Oleoside dimethyl ester (30164-95-5) → 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (60539-23-3) + (2S,4S,E)-4-(carboxymethyl)-3-ethylidene-2-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid (178600-68-5)

Guidance literature:

With sodium hydroxide; In water; for 48h; Ambient temperature;

DOI:10.1016/0031-9422(95)00211-O

Reference yield:

jasmoside → 4-carboxymethyl-5-ethylidene-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester (60539-23-3) + jasminin

Guidance literature:

With sodium hydroxide; water;

DOI:10.1016/S0031-9422(00)81120-6

upstream raw materials:

sambacolignoside

Oleoside dimethyl ester

oleuropeine

Downstream raw materials:

(2S,4S,E)-4-(carboxymethyl)-3-ethylidene-2-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

Refernces

• 1、 Samara, Pinelopi,Christoforidou, Nikoleta,Lemus, Christelle,Argyropoulou, Aikaterini,Ioannou, Kyriaki,Vougogiannopoulou, Konstantina,Aligiannis, Nektarios,Paronis, Efthimios,Gaboriaud-Kolar, Nicolas,Tsitsilonis, Ourania,Skaltsounis, Alexios-Leandros. "New semi-synthetic analogs of oleuropein show improved anticancer activity in?vitro and in?vivo". . p. 11 - 29. Retrieved 2017/05/29.
• 2、 Capozzi,Piperno,Uccella. "Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments". . p. 1623 - 1629. Retrieved 2007/10/03.