1184181-48-3

Basic information

• Product Name: 2,4-Dihydroxy-5-isopropylbenzoic acid
• Synonyms: 2,4-Dihydroxy-5-isopropylbenzoic acid
• CAS NO: 1184181-48-3
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.19988
• Mol File: 1184181-48-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 395.2±27.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: 2,4-Dihydroxy-5-isopropylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxy-5-isopropylbenzoic acid(1184181-48-3)
• EPA Substance Registry System: 2,4-Dihydroxy-5-isopropylbenzoic acid(1184181-48-3)

Safety Data

• Hazardous Substances Data: 1184181-48-3(Hazardous Substances Data)

Usage

General Description

2,4-Dihydroxy-5-isopropylbenzoic acid, also known as gentisic acid, is a naturally occurring organic compound found in plants such as grapes, strawberries, and raspberries. It is classified as a phenolic acid due to its structure, containing two hydroxyl groups. Gentisic acid has antioxidant properties and is believed to have potential health benefits, such as anti-inflammatory and anti-microbial effects. It is also used as a precursor in the synthesis of various pharmaceuticals and is being studied for its potential applications in the treatment of diseases such as cancer and diabetes. Additionally, it has shown promise in environmental and agricultural applications, particularly in the control of plant pathogens and as a potential natural alternative to synthetic pesticides.

Upstream product

• 89-86-1 4-hydroxysalicylic acid 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 943519-37-7 2,4-dihydroxy-5-isopropylbenzoic acid methyl ester 
• 124-38-9 carbon dioxide 
• 23504-03-2 2,4-dihydroxy-1-isopropylbenzene 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 96826-27-6 2-(2,4-dimethoxyphenyl)propan-2-ol 

Downstream Products

• 1584301-56-3 5-(2,4-dihydroxy-5-isopropylbenzoyl)-N-ethyl-4,5,6,7-tetrahydroisoxazole[4,5-c]pyridine-3-carboxamide 
• 1584301-48-3 ethyl 5-(2,4-dihydroxy-5-isopropylbenzoyl)-4,5,6,7-tetrahydroisoxazole[4,5-c]pyridine-3-carboxylate 
• 1584301-65-4 5-(2,4-diacetoxy-5-isopropylbenzoyl)-N-ethyl-4,5,6,7-tetrahydroisoxazole[4,5-c]pyridine-3-carboxamide 

Relevant articles and documents

Targeting the entry region of Hsp90's ATP binding pocket with a novel 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl amide

The molecular chaperone Hsp90 plays an important role in cancer cell survival and proliferation by regulating the maturation and stabilization of numerous oncogenic proteins. Due to its potential to simultaneously disable multiple signaling pathways, Hsp90 has emerged as an attractive therapeutic target for cancer treatment. In this study, the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors are described. Among the synthetic compounds, 6,7-dihydrothieno [3,2-c]pyridin-5(4H)-yl amide 19 exhibits a remarkable binding affinity to the N-terminus of Hsp90 in a fluorescence polarization (FP) binding assay (IC50= 50.3 nM). Furthermore, it effectively inhibits the proliferation of H1975 non-small cell lung cancer (NSCLC) and Skbr3 breast cancer cell lines with GI50values of 0.31 μM and 0.11 μM, respectively. Compound 19 induces the degradation of the Hsp90 client proteins including EGFR, Her2, Met, c-Raf, and Akt, and consequently promotes apoptotic cancer cell death. Compound 19 also inhibits the growth of H1975 xenografts in NOD-scid IL2R gammanullmice without any apparent body-weight loss. The immunohistologic evaluation indicates that compound 19 decreases the expression of Akt in xenograft tumor tissue via an inhibition of the Hsp90 chaperon function. Additionally, the cytochrome P450 assay indicates that compound 19 has no effect on the activities of five major P450 isoforms (IC50> 50 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between compound 19 and the substrate drugs of the five major P450 isoforms are not expected. Overall, compound 19 represents a new class of Hsp90 inhibitor with its 6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl-amide structure, and it has the therapeutic potential to overcome drug resistance in cancer chemotherapy.

Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base

The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.

Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors

Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone that is responsible for the stabilization and maturation of many oncogenic proteins. Therefore, Hsp90 has emerged as an attractive target in the field of cancer chemotherapy. In this study, we report the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors. In particular, compound 30f shows a significant Hsp90α inhibitory activity with IC50 value of 5.3 nM and an excellent growth inhibition with GI50 value of 0.42 μM against non-small cell lung cancer cells, H1975. Compound 30f effectively reduces the expression levels of Hsp90 client proteins including Her2, EGFR, Met, Akt, and c-Raf. Consequently, compound 30f promotes substantial cleavages of PARP, Caspase 3, and Caspase 8, indicating that 30f induces cancer cell death via apoptotic pathway. Moreover, cytochrome P450 assay indicates that compound 30f has weak inhibitory effect on the activities of five major P450 isoforms (IC50 > 5 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between 30f and the substrate drugs of the five major P450 isoforms are not expected. Compound 30f also inhibits the tumor growth in a mouse xenograft model bearing subcutaneous H1975 without noticeable abnormal behavior and body weight changes. The immunostaining and western immunoblot analysis of EGFR, Met, Akt in xenograft tissue sections of tumor further demonstrate a good agreement with the in vitro results.