Evodol

Base Information

• Chemical Name: Evodol
• CAS No.: 22318-10-1
• Deprecated CAS: 128242-19-3,989-95-7
• Molecular Formula: C₂₆H₂₈O₉
• Molecular Weight: 484.503
• DSSTox Substance ID: DTXSID60904237
• Wikidata: Q72478010
• Mol file: 22318-10-1.mol

Synonyms:Evodol;22318-10-1;LIMONIN DIOSPHENOL;Glaucin C;(1R,2R,7S,13R,14R,16S,19S,20S)-19-(furan-3-yl)-11-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docos-10-ene-5,12,17-trione;(4aS,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-7-hydroxy-6,6,8a,12a-tetramethyl-4,4a,9a,12,12a,13,14,14a-octahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione;DTXSID60904237;HY-N2621;AKOS037514644;NSC 314322;XL161810;CS-0023027;11H,13H-Oxireno(d)pyrano(4',3':3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)-4a,8,8a,9,10,10a,14,14a-octahydro-3-hydroxy-2,2,4a,8a-tetramethyl-, (4aR-(4aalpha,4bR*,5abeta,8beta,8abeta,10abeta,10bR*,14abeta))-

Chemical Property of Evodol

Chemical Property:

• Melting Point: 281 °C
• Boiling Point: 736.2oC at 760 mmHg
• PKA: 8.59±0.70(Predicted)
• Flash Point: 399oC
• PSA: 124.80000
• Density: 1.47g/cm3
• LogP: 2.94320
• Storage Temp.: ?20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 1
• Exact Mass: 484.17333247
• Heavy Atom Count: 35
• Complexity: 1110

Purity/Quality:

95%-98% ^*data from raw suppliers

Evodol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)O)C
• Isomeric SMILES: C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C(=C6[C@@]37COC(=O)C[C@@H]7OC6(C)C)O)C
• Uses: Evodol is a liminoid constituent of Euodia rutaecarpa var. bodinieri and is an inhibitor of NO production in lipopolysaccharide-?activated RAW264.7 machrophages.

Technology Process of Evodol

There total 5 articles about Evodol 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:

Limonin (1180-71-8,42867-83-4) → evodol (22318-10-1)

Guidance literature:

With potassium tert-butylate; oxygen; In tert-butyl alcohol; for 2h; hydrogenetion apparatus;

DOI:10.1246/bcsj.60.2503

Reference yield:

rutaevine (33237-37-5) → evodol (22318-10-1)

Guidance literature:

With methanol; pyridinium chlorochromate; Yield given. Multistep reaction; 1.) CH₂Cl₂, RT, overnight; 2.) CH₂Cl₂, 1 h;

DOI:10.1246/bcsj.60.2503

Reference yield:

6α-acetoxy-5-epilimonin (115458-72-5) → evodol (22318-10-1)

Guidance literature:

With methanol; potassium hydrogencarbonate;

upstream raw materials:

rutaevine

6α-acetoxy-5-epilimonin

Limonin

Refernces

• 1、 Sugimoto, Tohru,Ueno, Akira,Kadota, Shigetoshi,Cui, Chengbin,Kikuchi, Tohru. "NEW 5β-H LIMONOIDS FROM EVODIA RUTAECARPA BENTHAM". . p. 1237 - 1240. Retrieved 2007/10/02.