Xanthoxylin

Base Information

• Chemical Name: Xanthoxylin
• CAS No.: 90-24-4
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• Hs Code.: 29145090
• European Community (EC) Number: 201-978-3
• NSC Number: 17392
• UNII: Z8RSY5TZPA
• DSSTox Substance ID: DTXSID10237981
• Nikkaji Number: J4.315J
• Wikipedia: Brevifolin
• Wikidata: Q18210424
• Metabolomics Workbench ID: 43956
• ChEMBL ID: CHEMBL450288
• Mol file: 90-24-4.mol

Synonyms:2-hydroxy-4,6-dimethoxyacetophenone;brevifolin;xanthoxylin;xanthoxyline

Chemical Property of Xanthoxylin

Chemical Property:

• Vapor Pressure: 1.57E-05mmHg at 25°C
• Melting Point: 80-84 °C(lit.)
• Refractive Index: 1.527
• Boiling Point: 355.1 °C at 760 mmHg
• PKA: 9.41±0.15(Predicted)
• Flash Point: 141.2 °C
• PSA: 55.76000
• Density: 1.172g/cm³
• LogP: 1.61200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in hot methanol.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 204

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Hydroxy-4,6-dimethoxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=C(C=C(C=C1OC)OC)O
• Uses: 1-(2-Hydroxy-4,6-dimethylphenyl)-ethanone was investigated for its properties as an antibacterial agent and urease inhibitory effects. 2'-Hydroxy-4',6'-dimethoxyacetophenone is a chemical with potential antibacterial agent effects and urease inhibitory effects as well as synthesis applications.

Technology Process of Xanthoxylin

There total 49 articles about Xanthoxylin 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: 98.0%

1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → 2-hydroxy-4,6-dimethoxyacetophenone (90-24-4)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

Reference yield: 97.0%

dimethyl sulfate (77-78-1) + 2,4,6-trihydroxyacetophenone monohydrate (249278-28-2) → 2-hydroxy-4,6-dimethoxyacetophenone (90-24-4)

Guidance literature:

With potassium carbonate; In acetone; Reflux;

DOI:10.1016/j.tet.2017.05.022

Reference yield: 94.4%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → 2-hydroxy-4,6-dimethoxyacetophenone (90-24-4)

Guidance literature:

With potassium carbonate; dimethyl sulfate; In acetone;

upstream raw materials:

diazomethane

2,4,6-trihydroxyacetophenone

3,5-dimethoxyphenol

acetic anhydride

Downstream raw materials:

4',6'-dimethoxy-2'-(4-nitrobenzoyloxy)acetophenone

(E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one

2-hydroxy-4,6-dimethoxyacetophenone monoacetate

1,1′-(2-hydroxy-4,6-dimethoxy-1,3-phenylene)bis(ethan-1-one)

Refernces

• 1、 Bansal, Yogita,Kaur, Sukhvir. "Dual inhibitors of Interleukin-6 and acetylcholinesterase for treatment of Alzheimer's disease: Design, docking, synthesis and biological evaluation". . . Retrieved 2021/11/13.
• 2、 Luo, Si-Yuan,Tang, Zhuo-Ya,Li, Qingjiang,Weng, Jiang,Yin, Sheng,Tang, Gui-Hua. "Total Synthesis of Mulberry Diels-Alder-Type Adducts Kuwanons G and H". . p. 4786 - 4793. Retrieved 2021/04/06.