57543-59-6

Basic information

• Product Name: 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID
• Synonyms: 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID
• CAS NO: 57543-59-6
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.19
• Mol File: 57543-59-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 237-240°C
• Boiling Point: 364.2°C at 760 mmHg
• Flash Point: 145.8°C
• Appearance: /
• Density: 1.331g/cm³
• Vapor Pressure: 6.05E-06mmHg at 25°C
• Refractive Index: 1.592
• PKA: 3.75±0.20(Predicted)
• CAS DataBase Reference: 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID(57543-59-6)
• EPA Substance Registry System: 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID(57543-59-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 57543-59-6(Hazardous Substances Data)

Usage

General Description

8-Methoxy-2H-chromene-3-carboxylic acid is a chemical compound with the molecular formula C12H10O5. It is a derivative of chromene, which is a bicyclic compound containing both a benzene ring and a furan ring. 8-METHOXY-2H-CHROMENE-3-CARBOXYLIC ACID contains a methoxy group (CH3O-) at the 8-position, and a carboxylic acid group (-COOH) at the 3-position of the chromene ring. It is used in pharmaceutical research as a potential drug candidate due to its biological activities, such as anti-inflammatory and anti-cancer properties. It is also used as an intermediate in the synthesis of other organic compounds. Additionally, this compound has potential applications in the field of agrochemicals and materials science.

InChI:InChI=1/C11H10O4/c1-14-9-4-2-3-7-5-8(11(12)13)6-15-10(7)9/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 548756-56-5 tert-butyl 3-hydroxy-3-(2-hydroxy-3-methoxyphenyl)-2-methylenenpropanoate 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 83823-29-4 8-Methoxy-2H-chromene-3-carboxylic acid amide 
• 57543-69-8 8‐methoxy‐2H‐chromene‐3‐carbonitrile 

Downstream Products

• 1069518-54-2 benzyl-(8-methoxy-chroman-3-yl)-amine 
• 1026839-64-4 Dibenzyl-((R)-8-methoxy-chroman-3-yl)-amine 

Relevant articles and documents

6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine Agonists with Autoreceptor Selectivity

The dopamine agonist profiles of 3,4-duhydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and 8-ol (4 and 5, respectively) were examined.Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand propylnorapomorphine than for those labeled with the dopamine antagonist ligand haloperidol.Both compounds attenuated the simulation of brain dopamine synthesis caused by γ-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats.This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones

The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.

Design and synthesis of chiral 2H-chromene-N-imidazolo-amino acid conjugates as aldose reductase inhibitors

Aldose reductase (ALR2) inhibitors provide a viable mode to fight against diabetic complications. ALR2 exhibit plasticity in the active site vicinities and possible shifts in the nearby two supporting alpha helices. Therefore, a novel series of amino acid conjugates of chromene-3-imidazoles (13–15) were designed and synthesized based on natural isoflavonoids. The compounds were identified on the basis of spectral (1H NMR,13C NMR and MS) data and tested in vitro for ALR2 inhibitory activity with an IC50value ranges from 0.031 ± 0.082 μM to 4.29 ± 0.55 μM. Our in silico and biochemical studies confirmed that 15e has the best inhibition activity among the synthesized compounds with a high selective index against the Aldehyde reductase (ALR1). Supplementation of 15e to STZ induced rats decreased the blood glucose levels and delayed the progression of cataract in a dose-dependent manner. The present study thus provides novel series of compounds with a promising inhibitor to prevent or delay the cataract progression.