Evoxanthine

Base Information

• Chemical Name: Evoxanthine
• CAS No.: 477-82-7
• Molecular Formula: C₁₆H₁₃NO₄
• Molecular Weight: 283.284
• NSC Number: 407812
• DSSTox Substance ID: DTXSID00324839
• Nikkaji Number: J12.553I
• Wikidata: Q82084768
• Mol file: 477-82-7.mol

Synonyms:EVOXANTHINE;477-82-7;NSC407812;11-methoxy-5-methyl-[1,3]dioxolo[4,5-b]acridin-10-one;MLS003373786;11-Methoxy-5-methyl-[1,3]dioxolo[4,5-b]acridin-10(5H)-one;11-methoxy-5-methyl-1,3-dioxolo[4,5-b]acridin-10(5H)-one;1,3-Dioxolo[4,5-b]acridin-10(5H)-one, 11-methoxy-5-methyl-;DTXSID00324839;NSC-407812;SMR002048583;1,5-b]acridin-10(5H)-one, 11-methoxy-5-methyl-;11-Methoxy-5-methyl[1,3]dioxolo[4,5-b]acridin-10(5H)-one #;11-METHOXY-5-METHYL-2H,5H,10H-[1,3]DIOXOLO[4,5-B]ACRIDIN-10-ONE

Chemical Property of Evoxanthine

Chemical Property:

• Vapor Pressure: 3.53E-10mmHg at 25°C
• Boiling Point: 501.3°C at 760 mmHg
• Flash Point: 257°C
• PSA: 49.69000
• Density: 1.356g/cm³
• LogP: 2.42900
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 283.08445790
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

Evoxanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C(=O)C3=C(C4=C(C=C31)OCO4)OC
• Description: Evoxanthine is an alkaloid that has been found in O. renieri and has antimalarial and anticancer activities. It is active against P. falciparum with an IC50 value of 67.6 μg/ml. Evoxanthine decreases proliferation of nine sensitive and drug-resistant cancer cell lines (IC50s = 6.11-80.99 μM).

Technology Process of Evoxanthine

There total 17 articles about Evoxanthine 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: 61.0%

4-Methoxy-6-(methyl-phenyl-amino)-benzo[1,3]dioxole-5-carboxylic acid dimethylamide (83060-91-7) → evoxanthine (477-82-7)

Guidance literature:

With formic acid; for 60h; Heating;

DOI:10.1021/ja00384a064

Reference yield: 28.0%

11-Methoxy-5-methyl-8,9-dihydro-5H-[1,3]dioxolo[4,5-b]acridin-10-one (124347-02-0) → evoxanthine (477-82-7)

Guidance literature:

palladium on activated charcoal; In xylene; for 1h; Heating;

Reference yield:

4-methoxy-benzo[1,3]dioxole (1817-95-4) → evoxanthine (477-82-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) phosphorus oxychloride / 1.) RT, 30 min, 2.) 100 deg C, 2 h

2: 98 percent / sodium chlorite, dibasic sodium phosphate, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / Ambient temperature

3: 85 percent / nitric acid / 0.17 h / 0 °C

4: 95 percent / hydrogen / platinum oxide / 2 h / 2068.6 Torr

5: 78 percent / sodium hydroxide / toluene / 0 °C

6: 88 percent / sodium hydride / N,N-dimethyl-acetamide / 1.) RT, 12 h, 2.) 30 min

7: diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C, 90 min, 2.) RT, 90 min

8: 28 percent / palladium-on-charcoal / xylene / 1 h / Heating

With sodium hydroxide; sodium chlorite; disodium hydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; hydrogen; nitric acid; sodium hydride; diisopropylamine; trichlorophosphate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; hexane; N,N-dimethyl acetamide; water; toluene; xylene; tert-butyl alcohol;

upstream raw materials:

norevoxanthine

methyl iodide

11-bromo-11,11a-dimethoxy-5-methyl-11,11a-dihydro-5H-[1,3]dioxolo[4,5-b]acridin-10-one

11-Methoxy-5-methyl-8,9-dihydro-5H-[1,3]dioxolo[4,5-b]acridin-10-one

Downstream raw materials:

Norevoxanthin

Refernces

• 1、 Iwao, M.,Reed, J. N.,Snieckus, V.. "Directed Metalation of Tertiary Benzamides. Ortho N-Aryl Amination and Synthesis of Acridones". . p. 5531 - 5533. Retrieved 2007/10/02.