54839-86-0

Basic information

• Product Name: 2-(chloromethyl)-5-hydroxy-4H-pyran-4-one
• Synonyms: 2-chloromethyl-5-hydroxy-4-pyranone; 2-Chloromethyl-5-hydroxy-4-pyrone; 4H-Pyran-4-one, 2- (chloromethyl)-5-hydroxy-; 4H-pyran-4-one, 2-(chloromethyl)-5-hydroxy-; 7559-81-1
• CAS NO: 54839-86-0
• Molecular Formula: C₆H₅ClO₃
• Molecular Weight: 160.5551
• Mol File: 54839-86-0.mol

Chemical Properties

• Boiling Point: 321.9°C at 760 mmHg
• Flash Point: 148.5°C
• Density: 1.514g/cm³
• Vapor Pressure: 2.3E-05mmHg at 25°C
• Refractive Index: 1.576
• 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(54839-86-0)
• EPA Substance Registry System: 2-(chloromethyl)-5-hydroxy-4H-pyran-4-one(54839-86-0)

Safety Data

• Hazardous Substances Data: 54839-86-0(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 115049-92-8 2-(ethylcarbamimidoylmercapto-methyl)-5-hydroxy-pyran-4-one; hydrochloride 
• 96583-19-6 5-benzoyloxy-2-chloromethyl-pyran-4-one 
• 103049-23-6 2,5-dibenzoyl-3-benzoyloxy-6-chloromethyl-pyran-4-one 
• 108989-45-3 5-hydroxy-2-(methylcarbamimidoylmercapto-methyl)-pyran-4-one; hydrochloride 
• 100954-98-1 2-chloromethyl-5-trans-cinnamoyloxy-pyran-4-one 
• 733731-21-0 1,6-dimethyl-3-hydroxypyridin-4(1H)-one-2-carboxy-(N-3'-pyridyl)-amide 
• 1617517-28-8 6-(benzenesulfonylamino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methylamide 
• 1617516-52-5 2-(azidomethyl)-5-(benzyloxy)-4H-pyran-4-one 
• 60923-15-1 2-(aminomethyl)-5-(benzyloxy)-4H-pyran-4-one 
• 1617516-79-6 N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzenesulfonamide 
• 1617516-80-9 N-((5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl)benzenesulfonamide 
• 1617516-81-0 N-(5-hydroxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide 
• 1617516-82-1 N-(5-benzyloxy-6-hydroxymethyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide 
• 1617516-83-2 N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide 

Relevant articles and documents

A new salicylic acid-derivatized kojic acid vanadyl complex: Synthesis, characterization and anti-diabetic therapeutic potential

The molecular mechanisms of vanadium toxicity suggest that incorporation of antioxidant groups in the structure of vanadium complexes could be a preferable strategy in designing novel hypoglycemic vanadium complexes with proper efficacy and safety. By con

Mannich base derivatives of 3-hydroxy-6-methyl-4H-pyran-4-one with antimicrobial activity

A series of 3-hydroxy-6-methyl-2-[(substitutedpiperidine-1-yl)methyl]-4H- pyran-4-one structured compounds were synthesized by reacting 5-hydroxy-2-methyl-4H-pyran-4-one with suitable piperidine derivatives using Mannich reaction conditions. Antibacterial activities of the compounds for E. coli ATCC 25922, S. paratyphi ATCC BAA-1250, S. flexneri ATCC 12022, E. gergoviae ATCC 33426, and M. smegmatis ATCC 14468 were assessed in vitro by the broth dilution method for determination of minimum inhibitory concentration (MIC). In addition, their inhibitory effects over DNA gyrase enzyme were evaluated using a DNA gyrase supercoiling assay. All the synthesized compounds showed a MIC value of either 8 or 16 μg/mL for M. smegmatis, whereas minimum to moderate activity was achieved for the others. Those tested in the supercoiling assay had at best a very mild inhibition of the enzyme. This series deserves further attention for testing over Mycobacterium species and topoisomerase II inhibition to develop new lead drugs to treat non-tuberculous mycobacterial infections. TUBITAK.

Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

Abstract Organometallic complexes with (thio)pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio)pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay.

An allomaltol derivative triggers distinct death pathways in luminal a and triple-negative breast cancer subtypes

Breast cancer is the most common cancer in women that shows a predisposition to metastasize to the distant organs. Kojic acid is a natural fungal metabolite exhibiting various biological activities. Compounds derived from kojic acid have been extensively studied and proved to demonstrate anti-neoplastic features on different cancer types. In the present study, allomaltol-structural analog of kojic acid and its seven derivatives including four novel compounds, have been synthesized, characterized and their possible impact on breast cancer cell viability was investigated. It was discovered that compound 5, bearing 3,4-dichlorobenzyl piperazine moiety, could decrease the viability of both MCF-7 and MDA-MB-231 cell lines distinctively. To ascertain the death mechanism, cells were subjected to different tests following the application of IC50 concentration of compound 5. Data obtained from lactate dehydrogenase activity and gene expression assays pointed out that necrosis had taken place predominantly in MDA-MB-231. On the other hand, in MCF-7 cells, the p53 apoptotic pathway was activated by overexpression of the pro-apoptotic TP53 and Bax genes and suppression of the anti-apoptotic Mdm-2 and Bcl-2 genes. Furthermore, Bax/Blc-2 ratio was escalated by 3.5 fold in the study group compared to the control. Compound 5 did not provoke drug resistance in MCF-7 cells since the Mdr-1 gene expression, drug efflux, and H2O2 content remained unaltered. As for MDA-MB-231 cells, only a 1.4 fold increase in the Mdr-1 gene expression was detected. These results indicate the advantage of the allomaltol derivative over the chemotherapeutic agents conventionally used for breast cancer treatment that can be highly toxic and mostly lead to drug resistance. Thus, this specific allomaltol derivative offers an alternative therapeutic approach for breast cancer which needs further investigation.

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

Kojyl cinnamate esters are peroxisome proliferator-activated receptor α/γ dual agonists

Adiponectin is an adipocytokine with insulin-sensitizing, anti-inflammatory, anti-atherosclerotic, and anti-aging properties. Compounds with the ability to promote adiponectin secretion are of interest for the development of anti-aging drugs to improve skin-aging phenotypes. In the phenotypic assay to measure adiponectin secretion during adipogenesis in human adipose tissue-derived mesenchymal stem cells (hAT-MSCs), kojyl cinnamate ester derivatives increased adiponectin secretion. A target identification study showed that the kojyl cinnamate ester derivatives competitively bound to peroxisome proliferator-activated receptor α/γ (PPARα/γ). The upregulation of adiponectin production induced by kojyl cinnamate ester derivatives was significantly correlated with PPARα and PPARγ binding activities. Kojyl cinnamate ester derivatives significantly increased the transcription of genes encoding cholesterol and fatty acid synthesizing enzymes in hAT-MSCs. Notably, the kojyl cinnamate esters upregulated the gene transcription of lipid metabolic enzymes in human epidermal keratinocytes, which are important in the integrity of skin permeability barrier. In addition, the kojyl cinnamate esters that function as PPARα/γ dual modulators inhibited ultraviolet B irradiation-induced inflammation in human epidermal keratinocytes. Therefore, kojyl cinnamate ester derivatives are a novel class of PPARα/γ dual agonists with the potential to improve skin-aging phenotypes.

Synthesis, characterization, and antimicrobial activity of kojic acid grafted chitosan oligosaccharide

A novel water-soluble chitosan oligosaccharide (COS) derivative, chitosan oligosaccharide/kojic acid grafts assigned as COS/KA, was prepared by using the selective partial alkylation of N-benzylidene COS and chlorokojic acid in the presence of dimethyl sulfoxide (DMSO) and pyridine (Py). The derivative was characterized by UV-vis spectroscopy, FTIR, 1H NMR, TGA, SEM, and XRD techniques, which showed that the alkylation reaction took place at the C-6 and C-3 positions of COS. The results showed that the degree of substitution (DS) for COS/KA was from 0.38 to 1.21, and the product exhibited an excellent solubility in organic solvents and distilled water. The antibacterial results indicated that the antibacterial activity of COS/KA was strengthened relative to COS with the increase of DS for Staphylococcus aureus, Escherichia coli, Aspergillus niger and Saccharomyces cerevisiae. These findings provide important supports for developing new antibacterial agents and expand the scope of application of COS in the food industry.

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.

The clean and mild synthesis, crystal structure, and intra-molecular hydrogen bond study of substituted new 4,8-dihydropyrano[3,2-b]-pyrans containing chlorokojic acid moiety

A safe, green and convenient process was developed for the synthesis of a novel group of 4,8-dihydropyrano[3,2-b]-pyrans by dialkyl acetylenedicarboxylates and alkyl isocyanides being trapped by chlorokojic acid in good to excellent yields at ambient temperature. Characterization of all structures was carried out by FT-IR and 1H and 13C NMR spectrometers, and two compounds were analyzed using X-ray diffraction technique. Crystal structures showed an intramolecular hydrogen bond and stacking of the dimeric (RS) molecules with the unit cell along the a-axis.

Optimization of O3-acyl kojic acid derivatives as potent and selective human neutrophil elastase inhibitors

Human neutrophil elastase (HNE) is an attractive target for treating chronic and acute inflammatory lung diseases. An optimization campaign of the kojic acid scaffold to develop new potent HNE inhibitors is reported. O 3-Pivaloyl derivatives we