7559-81-1

Basic information

• Product Name: (2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE
• Synonyms: 2-(chloromethyl)-5-hydroxy-4h-pyran-4-on;(2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE;CHLOROKOJIC ACID;4H-Pyran-4-one, 2-(chloromethyl)-5-hydroxy-;Nsc10216;2-(chloromethyl)-5-hydroxypyran-4-one
• CAS NO: 7559-81-1
• Molecular Formula: C₆H₅ClO₃
• Molecular Weight: 160.56
• Mol File: 7559-81-1.mol
• Article Data: 96

Chemical Properties

• Melting Point: 164-165°C
• Boiling Point: 321.9°Cat760mmHg
• Flash Point: 148.5°C
• Appearance: /
• Density: 1.514g/cm³
• Vapor Pressure: 2.3E-05mmHg at 25°C
• Refractive Index: 1.576
• PKA: 7.80±0.10(Predicted)
• CAS DataBase Reference: (2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE(7559-81-1)
• EPA Substance Registry System: (2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE(7559-81-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 7559-81-1(Hazardous Substances Data)

Usage

Uses

2-?(Chloromethyl)?-?5-?hydroxy-4H-?pyran-?4-?one is an intermediate in synthesizing Allo Maltol (A546700), the esters of 5-hydroxy-2-methyl-4H-pyran-4-one are used as novel tyrosinase inhibitors for skin-lightening cosmetic compositions.

InChI:InChI=1/C6H5ClO3/c7-2-4-1-5(8)6(9)3-10-4/h1,3,9H,2H2

Upstream product

• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 7719-09-7 thionyl chloride 

Downstream Products

• 200335-54-2 2-[5-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-4H-pyran-2-ylmethyl]-2-(2-methyl-allyl)-malonic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 200335-55-3 2-[5-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-4H-pyran-2-ylmethyl]-2-(2-methyl-allyl)-malonic acid bis-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester 
• 2298-99-9 2,6-dimethyl-3-hydroxy-4H-pyran-4-one 
• 22639-18-5 2-(1-Hydroxyethyl)-3-hydroxy-6-methyl-pyran-4(1H)-one 
• 120902-14-9 5-hydroxy-2-(chloromethyl)-4H-pyran-4-onyl triphenyl phosphorane 
• 877635-22-8 C₁₇H₁₂N₂O₄S 
• 877635-31-9 C₁₈H₁₄N₂O₄S 
• 877635-49-9 C₁₈H₁₄N₂O₅S 
• 877635-55-7 C₁₉H₁₆N₂O₅S 
• 877635-58-0 C₂₀H₁₈N₂O₅S 
• 877635-62-6 C₂₁H₂₀N₂O₅S 
• 877635-40-0 C₂₁H₂₀N₂O₄S 
• 877636-24-3 C₁₇H₁₁FN₂O₄S 
• 877637-63-3 C₁₉H₁₇N₃O₆S₂ 

Relevant articles and documents

Synthesis, solution studies and DFT investigation of a tripodal ligand with 3-hydroxypyran-4-one scaffold

Hydroxypyranones form very stable complexes and possess varied uses in medical applications. They are promising chelators for treating iron overload diseases as they form stable complexes with Fe3+. A novel tripodal ligand tris[(5-hydroxy-4-oxo

Bis-maltol-polyamine family: structural modifications at strategic positions. Synthesis, coordination and antineoplastic activity of two new ligands

Two new maltol-based ligands are presented,L1(N,N′-bis((3-hydroxy-6-methyl-4-pyron-2-yl)methyl)-N,N′-dimethylethylenediamine) andL2(N,N′-bis((3-hydroxy-6-hydroxymethyl-4-pyron-2-yl)methyl)-N,N′-dimethylethylenediamine). They were strategically designed by inserting a methyl or hydroxymethyl function at C6, to study the previously hypothesized involvement of that ring position in the anticancer properties and the peculiar metal coordination ability in aqueous solution already shown by this family of ligands. Solid state and solution studies revealed differences neither in the molecular conformation or crystal packing nor in the acid-base behavior compared with the precursor Malten. The introduced substituent groups seem to affect instead both the degradation time (ca.4-5 h forL1andL2vs.10 h for Malten) and the binding properties towards Cu(ii), Zn(ii) and Co(ii), log?Kvalues being the highest forL1within the series of the diamino-bis-maltol ligands. The introduction of -CH2OH at C6 is sufficient to impair the biological activity of the compound and is coherent with the hypothesized mechanism of action.

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.