1664-27-3

Basic information

• Product Name: 4,5-DIMETHOXYCATECHOL
• Synonyms: 1,2-DIHYDROXY-4,5-DIMETHOXYBENZENE;4,5-DIMETHOXYCATECHOL;4,5-DiMethoxybenzene-1,2-diol
• CAS NO: 1664-27-3
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.16
• Mol File: 1664-27-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 354.1 °C at 760 mmHg
• Flash Point: 168 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 1.68E-05mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,5-DIMETHOXYCATECHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIMETHOXYCATECHOL(1664-27-3)
• EPA Substance Registry System: 4,5-DIMETHOXYCATECHOL(1664-27-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1664-27-3(Hazardous Substances Data)

Usage

General Description

4,5-Dimethoxycatechol is a chemical compound with the molecular formula C8H10O4. It is a catechol derivative, which is a type of organic compound that contains two adjacent hydroxyl groups attached to a benzene ring. 4,5-Dimethoxycatechol is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and organic compounds. It has also been studied for its potential antioxidant and anti-inflammatory properties, as well as its ability to inhibit the growth of certain microorganisms. Additionally, 4,5-Dimethoxycatechol has been investigated for its role in the synthesis of natural products and as a reagent in organic chemistry reactions. Overall, this compound has a wide range of potential applications in various fields of science and industry.

InChI:InChI=1/C8H10O4/c1-11-7-3-5(9)6(10)4-8(7)12-2/h3-4,9-10H,1-2H3

Upstream product

• 21086-65-7 4,5-dimethoxy-1,2-benzoquinone 
• 583-63-1 ortoquinone 
• 124-41-4 sodium methylate 
• 586-77-6 4-bromo-N,N-dimethylaniline 

Downstream Products

• 69305-40-4 5,6-dimethoxy-2',2',3',4',4'-pentamethyl-2-phenyl-2λ⁵-spiro[benzo[1,3,2]dioxaphosphole-2,1'-phosphetane] 
• 1312700-61-0 4,5-dimethoxy-1,2-ethoxyethoxyethoxydiol 
• 1312700-62-1 4,5-dimethoxy-1,2-ethoxyethoxyethoxyditosylate 
• 75080-61-4 2-Ethoxy-5-methoxy-1,4-benzoquinone 
• 388120-01-2 (1R,2R,4aS)-trans-decahydro-1α[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2α,4aβ-trimethyl-5-methylene-naphthalene 
• 388120-48-7 4,5-Dimethoxy-3-((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone 
• 388120-02-3 (1R,2R,4aS)-trans-decahydro-1α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2α,4aβ,5-tetramethyl-naphthalene 
• 259194-86-0 4,5-Dimethoxy-3-((1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone 
• 388120-11-4 4,5-Dimethoxy-3-((1R,2R,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone 
• 388120-04-5 [1-R-(1β,2β,4aβ,8aα)-3-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)-methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione 
• 388120-03-4 [1-R-(1β,2β,4aβ,8aα)-3-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)-methyl]-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione 
• 259194-83-7 (4aS,5S,8aS)-5,8a-Dimethyl-6-methylene-5-(2,3,5,6-tetramethoxy-benzyl)-octahydro-naphthalen-1-one 

Relevant articles and documents

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Total synthesis and biological evaluation of the nakijiquinones

The Her-2/Neu receptor tyrosine kinase is vastly overexpressed in about 30% of primary breast, ovary, and gastric carcinomas. The nakijiquinones are the only naturally occurring inhibitors of this important oncogene, and structural analogues of the nakijiquinones may display inhibitory properties toward other receptor tyrosine kinases involved in cell signaling and proliferation. Here, we describe the first enantioselective synthesis of the nakijiquinones. Key elements of the synthesis are (i) the reductive alkylation of a Wieland - Mieschertype enone with a tetramethoxyaryl bromide, (ii) the oxidative conversion of the aryl ring into a p-quinoid system, (iii) the regioselective saponification of one of the two vinylogous esters incorporated therein, and (iv) the selective introduction of different amino acids via nucleophilic conversion of the remaining vinylogous ester into the corresponding vinylogous amide. The correct stereochemistry and substitution patterns are completed by conversion of two keto groups into a methyl group and an endocyclic olefin via olefination/reduction and olefination/isomerization sequences, respectively. This synthesis route also gave access to analogues of nakijiquinone C with inverted configuration at C-2 or with an exocyclic instead of an endocyclic double bond. Investigation of the kinase-inhibiting properties of the synthesized derivatives revealed that the C-2 epimer 30 of nakijiquinone C is a potent and selective inhibitor of the KDR receptor, a receptor tyrosine kinase involved in tumor angiogenesis. Molecular modeling studies based on the crystal structure of KDR and a model of the ATP binding site built from a crystal structure of FGF-R revealed an insight into the structural basis for the difference in activity between the natural product nakijiquinone C and the C-2 epimer 30.