23504-03-2

Basic information

• Product Name: 4-isopropylresorcinol
• Synonyms: 4-isopropylresorcinol;4-Isopropylbenzene-1,3-diol;4-(1-Methylethyl)-1,3-benzenediol;Einecs 245-703-5;4-Isopropylresorcinol, 1,3-Dihydroxy-4-(prop-2-yl)benzene;1,3-Benzenediol, 4-(1-Methylethyl)-;4-propan-2-ylbenzene-1,3-diol
• CAS NO: 23504-03-2
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19038
• EINECS: 245-703-5
• Mol File: 23504-03-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 278.1 °C at 760 mmHg
• Flash Point: 133.8 °C
• Appearance: Off white or white powder
• Density: 1.116 g/cm³
• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.03±0.18(Predicted)
• CAS DataBase Reference: 4-isopropylresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-isopropylresorcinol(23504-03-2)
• EPA Substance Registry System: 4-isopropylresorcinol(23504-03-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 23504-03-2(Hazardous Substances Data)

Usage

Description

4-Isopropylresorcinol, also known as 4-Isopropylbenzene-1,3-diol, is an organic compound with the molecular formula C10H14O2. It is a white crystalline solid that is soluble in water and has a molecular weight of 166.22 g/mol. It is derived from resorcinol, a naturally occurring phenolic compound, by the addition of an isopropyl group to the benzene ring. 4-Isopropylresorcinol exhibits various biological activities, making it a potential candidate for pharmaceutical and chemical applications.

Uses

Used in Pharmaceutical Industry:
4-Isopropylresorcinol is used as a reagent in the synthesis of 3,5-disubstituted-4-alkynylisoxazolales, which are heat shock protein 90 (HSP90) inhibitors. HSP90 is a molecular chaperone that plays a crucial role in the stabilization and activation of various client proteins involved in cell survival, growth, and differentiation. Inhibition of HSP90 has been shown to have potential therapeutic benefits in the treatment of various human cancer cell lines, including lung, breast, and pancreatic cancers.
In addition to its use as a reagent in the synthesis of HSP90 inhibitors, 4-isopropylresorcinol itself has been reported to exhibit anti-inflammatory, antimicrobial, and antioxidant properties. These properties make it a potential candidate for the development of new drugs and therapeutic agents for various diseases and conditions.
Used in Chemical Industry:
4-Isopropylresorcinol can also be used as an intermediate in the synthesis of various organic compounds and polymers. Its unique structure and functional groups make it a versatile building block for the development of new materials with specific properties and applications.

InChI:InChI=1/C9H12O2/c1-6(2)8-4-3-7(10)5-9(8)11/h3-6,10-11H,1-2H3

Upstream product

• 17736-45-7 2,4-dimethoxy-1-(prop-1-en-2-yl)benzene 
• 67-63-0 isopropyl alcohol 
• 108-46-3 recorcinol 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 747414-16-0 (((4-(prop-1-en-2-yl)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 
• 24416-78-2 7-(benzyloxy)-4-methyl-2H-chromen-2-one 
• 1360813-23-5 C₁₆H₁₆O₂ 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 96826-27-6 2-(2,4-dimethoxyphenyl)propan-2-ol 
• 7051-14-1 1-isopropyl-2,4-dimethyloxybenzene 

Downstream Products

• 65239-68-1 1-(2,4-Dihydroxy-5-isopropyl-phenyl)-2,2,2-trifluoro-ethanone 
• 909870-97-9 4-bromo-6-isopropyl-benzene-1,3-diol 
• 65240-35-9 1-{3-[2,6-Dihydroxy-3-isopropyl-5-(2,2,2-trifluoro-acetyl)-benzyl]-2,4-dihydroxy-5-isopropyl-phenyl}-2,2,2-trifluoro-ethanone 
• 747414-17-1 1-(2,4-dihydroxy-5-isopropylphenyl)ethan-1-one 
• 958888-27-2 5-isopropyl-2,4-dihydroxy benzaldehyde 
• 1046490-81-6 2,4-dihydroxy-5-isopropylbenzenecarbodithioic acid 
• 1046490-85-0 N-(2,3-dihydro-1H-inden-5-yl)-2,4-dihydroxy-5-isopropylbenzothioamide 
• 1350472-35-3 1,3-bisphosphonooxy-4-isopropylbenzene 
• 1350472-38-6 1,3-bis(dibenzylphosphonooxy)-4-isopropylbenzene 

Relevant articles and documents

Design and Synthesis of Hsp90 Inhibitors with B-Raf and PDHK1 Multi-Target Activity

The design of multi-target ligands has become an innovative approach for the identification of effective therapeutic treatments against complex diseases, such as cancer. Recent studies have demonstrated that the combined inhibition of Hsp90 and B-Raf provides synergistic effects against several types of cancers. Moreover, it has been reported that PDHK1, which presents an ATP-binding pocket similar to that of Hsp90, plays an important role in tumor initiation, maintenance and progression, participating also to the senescence process induced by B-Raf oncogenic proteins. Based on these premises, the simultaneous inhibition of these targets may provide several benefits for the treatment of cancer. In this work, we set up a design strategy including the assembly and integration of molecular fragments known to be important for binding to the Hsp90, PDHK1 and B-Raf targets, aided by molecular docking for the selection of a set of compounds potentially able to exert Hsp90-B-Raf-PDHK1 multi-target activities. The designed compounds were synthesized and experimentally validated in vitro. According to the in vitro assays, compounds 4 a, 4 d and 4 e potently inhibited Hsp90 and moderately inhibited the PDHK1 kinase. Finally, molecular dynamics simulations were performed to provide further insights into the structural basis of their multi-target activity.

Radiosynthesis, biological evaluation and preliminary microPET study of 18F-labeled 5-resorcinolic triazolone derivative based on ganetespib targeting HSP90

Heat-shock protein 90 (HSP90) is a molecular chaperone that activates oncogenic transformation in several solid tumors, including lung and breast cancers. Ganetespib, a most promising candidate among several HSP90 inhibitors under clinical trials, has entered Phase III clinical trials for cancer therapy. Despite numerous evidences validating HSP90 as a target of anticancer, there are few studies on PET agents targeting oncogenic HSP90. In this study, we synthesized and biologically evaluated a novel 18F-labeled 5-resorcinolic triazolone derivative (1, [18F]PTP-Ganetespib) based on ganetespib. [18F]PTP-Ganetespib was labeled by click chemistry of Ganetespib-PEG-Alkyne (10) and [18F]PEG-N3 (11) with 37.3 ± 5.11% of radiochemical yield and 99.7 ± 0.09% of radiochemical purity. [18F]PTP-Ganetespib showed proper LogP (0.96 ± 0.06) and good stability in human serum over 97% for 2 h. [18F]PTP-Ganetespib showed high uptakes in breast cancer cells containing triple negative breast cancer (TNBC) MDA-MB-231 and Her2-negative MCF-7 cells, which are target breast cancer cell lines of HSP90 inhibitor, ganetespib, as an anticancer. Blocking of HSP90 by the pretreatment of ganetespib exhibited significantly decreased accumulation of [18F]PTP-Ganetespib in MDA-MB-231 and MCF-7 cells, indicating the specific binding of [18F]PTP-Ganetespib to MDA-MB-231 and MCF-7 cells with high HSP90 expression. In the biodistribution and microPET imaging studies, the initial uptake into tumor was weaker than in other thoracic and abdominal organs, but [18F]PTP-Ganetespib was retained relatively longer in the tumor than other organs. The uptake of [18F]PTP-Ganetespib in tumors was not sufficient for further development as a tumor-specific PET imaging agent by itself, but this preliminary PET imaging study of [18F]PTP-Ganetespib can be basis for developing new PET imaging agents based on HSP90 inhibitor, ganetespib.

Heat shock protein inhibitor and preparation method and application thereof

The present invention discloses a heat shock protein inhibitor and a preparation method and an application thereof, and belongs to the technical field of medicinal chemistry. The heat shock protein inhibitor has the structure features of a formula I. The compound can inhibit activity of the heat shock protein 90, and then can be used for preparing anti-tumor drugs.