3,5-Dihydroxy-4-isopropylstilbene

Base Information

• Chemical Name: 3,5-Dihydroxy-4-isopropylstilbene
• CAS No.: 79338-84-4
• Molecular Formula: C17H18 O2
• Molecular Weight: 254.329
• European Community (EC) Number: 838-014-1
• UNII: 84HW7D0V04
• DSSTox Substance ID: DTXSID301045262
• Nikkaji Number: J478.929F,J936.093J
• Wikipedia: Benvitimod
• Wikidata: Q4634086,Q76386711
• NCI Thesaurus Code: C152511
• RXCUI: 2602286
• Pharos Ligand ID: CWFD8WKL4TMF
• Metabolomics Workbench ID: 99721
• ChEMBL ID: CHEMBL259571
• Mol file: 79338-84-4.mol

Synonyms:2-isopropyl-5-(2-phenylethenyl)benzene-1,3-diol;3,5-DH4IS;3,5-dihydroxy-4-isopropylstilbene;5-(2-phenylethenyl)-2-isopropyl-1,3-benzenediol;benvitimod;GSK2894512;tapinarof;WBI-1001

Chemical Property of 3,5-Dihydroxy-4-isopropylstilbene

Chemical Property:

• Vapor Pressure: 4.62E-08mmHg at 25°C
• Boiling Point: 431.8°C at 760 mmHg
• PKA: 9.86±0.15(Predicted)
• Flash Point: 204.2°C
• PSA: 40.46000
• Density: 1.158
• LogP: 4.39160
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 254.130679813
• Heavy Atom Count: 19
• Complexity: 280

Purity/Quality:

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

Tapinarof(Benvitimod;GSK2894512) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C=C(C=C1O)C=CC2=CC=CC=C2)O
• Isomeric SMILES: CC(C)C1=C(C=C(C=C1O)/C=C/C2=CC=CC=C2)O
• Recent ClinicalTrials: Tapinarof for the Treatment of Plaque Psoriasis in Adults (3001)
• Description: Tapinarof is a small molecule stilbene compound,?with a chemical name of?3,5-Dihydroxy-4-isopropylstilbene,which was originally isolated from the metabolite of photorhabdus iuminescence, a soil nematode (Heterorhabditis sp.), and has been synthesized artificially.
• Uses: Clinically, tapinarof was first used in the treatment of psoriasis and atopic dermatitis. Clinical trials conducted abroad have shown that Benzenemod cream has good efficacy and safety on atopic dermatitis and psoriasis. In China, as a class 1.1 new drug, Benzenemod cream has undergone phase I-II clinical trials, and the results show that it has good efficacy and safety for plaque psoriasis.

Technology Process of 3,5-Dihydroxy-4-isopropylstilbene

There total 22 articles about 3,5-Dihydroxy-4-isopropylstilbene 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: 92.3%

O,O-diethyl benzylphosphonate (1080-32-6) + 3,5-diacetyloxy-4-isopropylbenzaldehyde3,5-diacetyloxy-4-isopropylbenzaldehyde → CST (79338-84-4,1622988-14-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 50 - 60 ℃; for 2h; Inert atmosphere; Large scale;

Reference yield: 89.0%

(Z)-2-(3,5-dihydroxy-4-isopropylphenyl)-3-phenylacrylic acid → CST (79338-84-4,1622988-14-0)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; at 190 ℃; for 6h; Reagent/catalyst;

Reference yield: 87.0%

(E)-1,3-dimethoxy-2-(1-methylethyl)-5-(2-phenylethenyl)benzene (141509-20-8) → CST (79338-84-4,1622988-14-0)

Guidance literature:

With borontribromide methylsulfide; In 1,2-dichloro-ethane; for 24h; Heating;

DOI:10.1021/jo00040a063

upstream raw materials:

(E)-1,3-dimethoxy-2-(1-methylethyl)-5-(2-phenylethenyl)benzene

2,6-dimethoxyacetophenone

1,3-dimethoxy-2-(1-methylethyl)benzene

1,3-dimethoxy-2-(1-hydroxy-1-methylethyl)benzene

Downstream raw materials:

3,5-Di-chloroacetoxy-4-isopropyl-trans-stilbene

Refernces

• 1、 -. "Synthesis method of (E)-3,5-dihydroxy-4-isopropyl stilbene". . . Retrieved 2021/01/29.
• 2、 -. "Method for preparing 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol". Paragraph 0012; 0036; 0037. . Retrieved 2017/04/25.