4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol

Base Information

• Chemical Name: 4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol
• CAS No.: 4339-71-3
• Molecular Formula: C14H12 O4
• Molecular Weight: 244.247
• DSSTox Substance ID: DTXSID20860062
• Wikidata: Q27164196
• Metabolomics Workbench ID: 125891
• ChEMBL ID: CHEMBL1972346
• Mol file: 4339-71-3.mol

Synonyms:3'-hydroxyresveratol;3,3',4',5-tetrahydroxystilbene;3,3',4,5'-tetrahydroxy stilbene;3,3',4,5'-tetrahydroxystilbene;3,5,3',4'-tetrahydroxy-stilbene;3,5,3',4'-tetrahydroxy-trans-stilbene;3,5,3',4'-tetrahydroxystilbene;astringinin;demethyl isorhapontigenin;piceatannol;piceatanol;RSVL-1

Chemical Property of 4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol

Chemical Property:

• Melting Point: 229 °C (decomp)
• Boiling Point: 507.3°Cat760mmHg
• PKA: 9.30±0.10(Predicted)
• Flash Point: 252.2°C
• PSA: 80.92000
• Density: 1.468g/cm³
• LogP: 2.67940
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 244.07355886
• Heavy Atom Count: 18
• Complexity: 282

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O

Technology Process of 4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol

There total 4 articles about 4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol 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: 64.3%

cis-trans-3,3',4',5-tetramethoxystilbene (20767-18-4) → piceatannol (4339-71-3,106325-86-4)

Guidance literature:

With aluminum (III) chloride; triethylamine; In chlorobenzene; at 50 - 85 ℃; for 4h; Temperature;

Reference yield:

3,5-dimethoxybenzylchloride (6652-32-0) → piceatannol (4339-71-3,106325-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N-dimethyl-formamide / 4.5 h / Reflux

2.1: sodium methylate / methanol / 2 h / 5 - 10 °C

2.2: 3 h / 20 °C

3.1: triethylamine; aluminum (III) chloride / chlorobenzene / 4 h / 50 - 85 °C

With aluminum (III) chloride; sodium methylate; triethylamine; In methanol; N,N-dimethyl-formamide; chlorobenzene;

Reference yield:

3,5-dimethoxybenzyl alcohol (705-76-0) → piceatannol (4339-71-3,106325-86-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trichlorophosphate / methanol / 2 h / Reflux

2.1: N,N-dimethyl-formamide / 4.5 h / Reflux

3.1: sodium methylate / methanol / 2 h / 5 - 10 °C

3.2: 3 h / 20 °C

4.1: triethylamine; aluminum (III) chloride / chlorobenzene / 4 h / 50 - 85 °C

With aluminum (III) chloride; sodium methylate; triethylamine; trichlorophosphate; In methanol; N,N-dimethyl-formamide; chlorobenzene;

upstream raw materials:

3,5-dimethoxybenzylchloride

3,5-dimethoxybenzyl alcohol

cis-trans-3,3',4',5-tetramethoxystilbene

Downstream raw materials:

3,4,3',5'-tetrakis-benzoyloxy-stilbene

Dihydropiceatannol

cis-trans-3,3',4',5-tetramethoxystilbene

Refernces