5691-70-3

Basic information

• Product Name: 2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE
• Synonyms: 2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE
• CAS NO: 5691-70-3
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• Mol File: 5691-70-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 179 °C (decomp)
• Boiling Point: 451.6°Cat760mmHg
• Flash Point: 226.9°C
• Appearance: /
• Density: 1.332g/cm³
• Vapor Pressure: 2.4E-08mmHg at 25°C
• Refractive Index: 1.641
• PKA: 2.70±0.30(Predicted)
• CAS DataBase Reference: 2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE(5691-70-3)
• EPA Substance Registry System: 2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE(5691-70-3)

Safety Data

• Hazardous Substances Data: 5691-70-3(Hazardous Substances Data)

Usage

General Description

2-HYDROXY-5-METHOXY-[1,4]BENZOQUINONE is a chemical compound with the molecular formula C7H6O4. It is a derivative of benzoquinone and is also known as juglone, found in the leaves, roots, and bark of many plants, including walnut trees. It is a yellow crystalline solid that is sparingly soluble in water. Juglone possesses allelopathic properties, meaning it can inhibit the growth of neighboring plants by disrupting their metabolic processes. It is also used in the production of dyes and pigments, as well as in organic synthesis reactions. Juglone has been studied for its potential medicinal uses, including anticancer and antimicrobial properties. However, it can also be toxic to humans and animals if ingested in large quantities.

InChI:InChI=1/C17H17NO4S/c1-21-11-8-6-10(7-9-11)15(19)18-16-14(17(20)22-2)12-4-3-5-13(12)23-16/h6-9H,3-5H2,1-2H3,(H,18,19)

Upstream product

• 74202-09-8 5-methoxybenzene-1,2,4-triol 
• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 151-10-0 1,3-Dimethoxybenzene 
• 115685-93-3 4-(1-Cyclopropyl-ethoxy)-5-methoxy-[1,2]benzoquinone 
• 115685-94-4 4-Methoxy-5-(1-phenyl-ethoxy)-[1,2]benzoquinone 
• 115685-92-2 4-(1-Cyclopropyl-nonyloxy)-5-methoxy-[1,2]benzoquinone 
• 213831-86-8 2-acetoxy-5-methoxy-[1,4]benzoquinone 
• 615-94-1 2,5-dihydroxy-1,4-benzoquinone 
• 16523-32-3 2,5-diacetoxy-1,4-benzoquinone 
• 173348-63-5 2-acetoxy-5-hydroxy-p-benzoquinone 
• 99814-64-9 4-methoxy-5-(4-methoxyphenoxy)cyclohexa-3,5-diene-1,2-dione 
• 150-76-5 4-methoxy-phenol 
• 186581-53-3 diazomethane 

Downstream Products

• 38475-42-2 2-methoxy-4,5-di-acetoxyphenyl acetate 
• 3117-03-1 2,5-dimethoxyquinone 
• 1360078-89-2 C₁₁H₁₅NO₄ 

Relevant articles and documents

Tyrosinase Model Systems Supported by Pyrazolylmethylpyridine Ligands: Electronic and Steric Factors Influencing the Catalytic Activity and Impact of Complex Equilibria in Solution

Two new copper(I) complexes supported by pyrazolylmethylpyridine (PMP) ligands are synthesized and investigated regarding their ability to catalyze the oxygenation of several monophenolic substrates. The PMP ligands containing a pyridine and a pyrazole donor group represent hybrids between dipyridylmethane (DPM) and bis(pyrazolyl)methane (BPM) ligands. The catalytic activity of the two new [Cu(MeCN)2PMP]PF6 complexes is found to be intermediate between that of catalytically inactive [Cu(MeCN)2DPM]PF6 and highly active [Cu(MeCN)2BPM]PF6, suggesting that the electronic properties of a multidentate ligand can be designed in a modular fashion. DFT calculations are used to explore the differences in reactivity between the two systems. Regarding the behavior of these complexes in solution, evidence for an equilibrium between homoleptic and heteroleptic forms is presented. The crystal structure of a dinuclear complex exhibiting two homoleptic CuII units bridged by a fluorido ligand is obtained, which might represent one of the decay products of PMP-type catalysts after prolonged reaction times.

Tyrosinase and catechol oxidase activity of copper(I) complexes supported by imidazole-based ligands: structure–reactivity correlations

Four new imidazole-based ligands, 4-((1H-imidazol-4-yl)methyl)-2-phenyl-4,5-dihydrooxyzole (LOL1), 4-((1H-imidazol-4-yl)methyl)-2-(tert-butyl)-4,5-dihydrooxyzole (LOL2), 4-((1H-imidazol-4-yl)methyl)-2-methyl-4,5-dihydrooxyzole (LOL3), and N-(2,2-dimethylpropylidene)-2-(1-trityl-1H-imidazol-4-yl-)ethyl amine (Limz1), have been synthesized. The corresponding copper(I) complexes [Cu(I)(LOL1)(CH3CN)]PF6 (CuLOL1), [Cu(I)(LOL2)(CH3CN)]PF6 (CuLOL2), [Cu(I)(LOL3)(CH3CN)]PF6 (CuLOL3), [Cu(I)(Limz1)(CH3CN)2]PF6 (CuLimz1) as well as the Cu(I) complex derived from the known ligand bis(1-methylimidazol-2-yl)methane (BIMZ), [Cu(I)(BIMZ)(CH3CN)]PF6 (CuBIMZ), are screened as catalysts for the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC-H2) to 3,5-di-tert-butylquinone (3,5-DTBQ). The primary reaction product of these oxidations is 3,5-di-tert-butylsemiquinone (3,5-DTBSQ) which slowly converts to 3,5-DTBQ. Saturation kinetic studies reveal a trend of catalytic activity in the order CuLOL3?≈?CuLOL1?>?CuBIMZ?>?CuLOL2?>?CuLimz1. Additionally, the catalytic activity of the copper(I) complexes towards the oxygenation of monophenols is investigated. As substrates 2,4-di-tert-butylphenol (2,4-DTBP-H), 3-tert-butylphenol (3-TBP-H), 4-methoxyphenol (4-MeOP-H), N-acetyl-l-tyrosine ethyl ester monohydrate (NATEE) and 8-hydroxyquinoline are employed. The oxygenation products are identified and characterized with the help of UV/Vis and NMR spectroscopy, mass spectrometry, and fluorescence measurements. Whereas the copper complexes with ligands containing combinations of imidazole and imine functions or two imidazole units (CuLimz1 and CuBIMZ) are found to exhibit catalytic tyrosinase activity, the systems with ligands containing oxazoline just mediate a stoichiometric conversion. Correlations between the structures of the complexes and their reactivities are discussed.

Preparation and structure-activity relationships of novel asterriquinone derivatives

Asterriquinone (ARQ, la) is an antitumor metabolite of Aspergillus terreus IFO 6123. To gain insight into the structure-activity relationships of ARQ, a series of chemically modified derivatives (1 - 6), the ARQ analogues (b - e) and the 2,5-dihydroxy-p-benzoquinone analogues (f - h), were prepared, and cytotoxic activity against mouse leukemia P388 cells investigated. Results indicated that: 1) at least one hydroxy group or acetoxy group in the p-benzoquinone moiety is important to exhibit cytotoxicity; 2) in the p-benzoquinone moiety, a single methoxy group and/or one acetoxy group substitution showed more potent cytotoxicity than when two hydroxy groups are substituted (1); 3) the indole ring is important for the cytotoxicity of ARQ analogues; 4) the 1,1-dimethyl-2-propenyl group in the indole ring is not important for the cytotoxic activity of ARQ.