4-Hydroxyderricin

Base Information

• Chemical Name: 4-Hydroxyderricin
• CAS No.: 55912-03-3
• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.403
• UNII: PF5YY4IV2O
• DSSTox Substance ID: DTXSID101316382
• Nikkaji Number: J361.087J,J2.788.475J
• Metabolomics Workbench ID: 26518
• ChEMBL ID: CHEMBL458094
• Mol file: 55912-03-3.mol

Synonyms:4-hydroxyderricin

Chemical Property of 4-Hydroxyderricin

Chemical Property:

• Vapor Pressure: 2.32E-12mmHg at 25°C
• Melting Point: 136.0-137.0 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 542°Cat760mmHg
• PKA: 7.83±0.40(Predicted)
• Flash Point: 190.8°C
• PSA: 66.76000
• Density: 1.181g/cm³
• LogP: 4.51120
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 338.15180918
• Heavy Atom Count: 25
• Complexity: 484

Purity/Quality:

≥98% ^*data from raw suppliers

4-Hydroxyderricin ≥96.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)C
• Isomeric SMILES: CC(=CCC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)OC)C

Technology Process of 4-Hydroxyderricin

There total 16 articles about 4-Hydroxyderricin 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: 99.0%

2'-hydroxyl-4'-methoxy-4-methoxymethoxy-3'-prenyl-chalcone (1092462-94-6) → 4-hydroxyderricin (54647-08-4,55912-03-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 30 ℃; for 24h;

DOI:10.1016/j.tetlet.2008.09.015

Reference yield: 65.0%

(E)-3-[4-ethoxymethoxyphenyl]-1-[2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)]prop-2-en-1-one → 4-hydroxyderricin (54647-08-4,55912-03-3)

Guidance literature:

With DOWEX resin; In methanol; at 20 ℃; for 4h;

DOI:10.5012/bkcs.2013.34.9.2815

Reference yield:

1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) → 4-hydroxyderricin (54647-08-4,55912-03-3)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone / 24 h / Reflux

2: sodium hydroxide / ethanol / 12 h / 0 - 20 °C

3: montmorillonite K₁₀ / dichloromethane / 1.5 h / 0 °C

4: toluene-4-sulfonic acid / methanol / 24 h / 30 °C

With potassium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In methanol; ethanol; dichloromethane; acetone; 2: Claisen-Schmidt condensation;

DOI:10.1016/j.tet.2011.04.104

upstream raw materials:

2'-hydroxyl-4'-methoxy-4-methoxymethoxy-3'-prenyl-chalcone

4'-methoxy-4-methoxymethoxy-2'-prenyloxychalcone

1-(2-hydroxy-4-methoxyphenyl)ethanone

1-(2-hydroxy-4-methoxy-3-(3-methyl-butyl-2-ene-1-yl)phenyl)ethanone

Downstream raw materials:

4'-methoxy-4.2'-diacetoxy-trans-chalcone

4-acetoxy-2'-hydroxy-3'-prenyl-4'-methoxychalcone

(E)-1-(2-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-4-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

xanthoangelol E

Refernces

• 1、 -. "Preparation method and application of natural product Xanthoangelol D and derivative thereof". Paragraph 0005; 0008. . Retrieved 2019/11/28.
• 2、 Sugamoto, Kazuhiro,Matsusita, Yoh-Ichi,Matsui, Kana,Kurogi, Chiaki,Matsui, Takanao. "Synthesis and antibacterial activity of chalcones bearing prenyl or geranyl groups from Angelica keiskei". experimental part. p. 5346 - 5359. Retrieved 2011/08/04.