79338-84-4

Basic information

• Product Name: 3,5-Dihydroxy-4-isopropylstilbene
• Synonyms: 3,5-Dihydroxy-4-isopropylstilbene;(E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol;2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol;3,5-Dihydroxy-4-isopropyl-trans-stilbene
• CAS NO: 79338-84-4
• Molecular Formula: C₁₇H₁₈O₂
• Molecular Weight: 254.32362
• EINECS: 1312995-182-4
• Mol File: 79338-84-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 431.8°C at 760 mmHg
• Flash Point: 204.2°C
• Appearance: /
• Density: 1.158
• Vapor Pressure: 4.62E-08mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.86±0.15(Predicted)
• CAS DataBase Reference: 3,5-Dihydroxy-4-isopropylstilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dihydroxy-4-isopropylstilbene(79338-84-4)
• EPA Substance Registry System: 3,5-Dihydroxy-4-isopropylstilbene(79338-84-4)

Safety Data

• Hazardous Substances Data: 79338-84-4(Hazardous Substances Data)

Usage

Description

3,5-Dihydroxy-4-isopropylstilbene, also known as Tapinarof, is a small molecule stilbene compound originally isolated from the metabolite of photorhabdus iuminescence, a soil nematode (Heterorhabditis sp.), and has been synthesized artificially.

Uses

Used in Dermatological Applications:
3,5-Dihydroxy-4-isopropylstilbene is used as a therapeutic agent for the treatment of psoriasis and atopic dermatitis. Clinical trials conducted abroad have shown that Benzenemod cream, containing Tapinarof, 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.

Biological activity

Tapinarof(GSK2894512) is a natural agonist of aryl hydrocarbon receptor (AhR) that induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. Benvitimod induces apoptosis in CD4+ T cells in a dose-dependent manner with an IC50 value of 5.2 μM.

InChI:InChI=1/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+

Upstream product

• 344396-18-5 4-isopropyl-3,5-dimethoxy-benzyl alcohol 
• 115781-08-3 3,5-dihydroxy-4-isopropyl stilbene 
• 1622988-14-0 (Z)-3,5-dihydroxy-4-isopropylstilbene 
• 4670-09-1 2-(3,5-dihydroxyphenyl)acetic acid 
• 344396-19-6 3,5-dimethoxy-4-(1-methylethyl)benzaldehyde 
• 122-03-2 (4-isopropylbenzaldehyde) 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 2323519-79-3 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]-1,3-cyclohexanedione 
• 25108-61-6 1,3-dimethoxy-2-(1-methylethenyl)benzene 
• 16929-70-7 1,3-dimethoxy-2-(1-hydroxy-1-methylethyl)benzene 
• 16700-61-1 1,3-dimethoxy-2-(1-methylethyl)benzene 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 141509-20-8 (E)-1,3-dimethoxy-2-(1-methylethyl)-5-(2-phenylethenyl)benzene 

Downstream Products

• 344396-15-2 3,5-Di-chloroacetoxy-4-isopropyl-trans-stilbene 

Relevant articles and documents

Preparation method of benzenediol bioactive substance

The invention discloses a preparation method of a benzenediol bioactive substance, and belongs to the technical field of organic synthesis. The method comprises the following steps: reacting 4-isopropyl-3, 5-dimethoxybenzyl alcohol with triethyl phosphite

PROCESS FOR PREPARING TAPINAROF

The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from

Facile synthesis of cyclohexanediones and dialkylresorcinols - Bioactive natural products from entomopathogenic bacteria

A synthesis for the recently identified, widespread bacterial natural product classes of dialkylresorcinols and cyclohexanediones was developed. The synthesis route is similar to the biosynthesis route in that the formation of the cyclohexanedione ring results from two parts, as exemplified by the synthesis of the multifunctional isopropylstilbenes identified in Photorhabdus luminescens. Testing of these compounds revealed good bioactivity against Trypanosoma brucei rhodesiense and T. cruzi, the causative agents of sleeping sickness and Chagas disease, respectively.