15771-06-9

Basic information

• Product Name: 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one
• Synonyms: 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one;2-(hydroxyMethyl)-5-(phenylMethoxy)-4H-Pyran-4-one;4H-Pyran-4-one, 2-(hydroxymethyl)-5-(phenylmethoxy)-
• CAS NO: 15771-06-9
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.234
• EINECS: 200-258-5
• Mol File: 15771-06-9.mol
• Article Data: 72

Chemical Properties

• Melting Point: Oil°
• Boiling Point: 488.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.83±0.10(Predicted)
• CAS DataBase Reference: 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one(15771-06-9)
• EPA Substance Registry System: 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one(15771-06-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 15771-06-9(Hazardous Substances Data)

Usage

Description

5-(Benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one is a chemical compound derived from Kojic Acid (K655080), characterized by its unique molecular structure that features a benzyloxy group and a hydroxymethyl group attached to a pyranone ring. 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one is known for its potential applications in various industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
5-(Benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one is used as a reagent for the synthesis of hydroxypyridinone-L-phenylalanine conjugates. These conjugates are considered potential tyrosinase inhibitors, which can be beneficial in the development of treatments for conditions related to excessive melanin production, such as hyperpigmentation or melasma.
Used in Cosmetic Industry:
As a derivative of Kojic Acid, 5-(Benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one may also find applications in the cosmetic industry, where tyrosinase inhibitors are often used to create skin-lightening or brightening products. The compound's ability to inhibit tyrosinase, an enzyme responsible for melanin production, makes it a valuable ingredient in formulations aimed at reducing the appearance of dark spots and uneven skin tone.

Upstream product

• 100-44-7 benzyl chloride 
• 89539-54-8 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 100-39-0 benzyl bromide 
• 7732-18-5 water 

Downstream Products

• 1258290-15-1 (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl 4-(3-(piperidin-1-yl)propoxy)benzoate 
• 1229937-22-7 (R)-3-(4,5-bis(benzyloxy)pyridin-2-yl)-4-(2,3-dihydroxypropyl)-1H-1,2,4-triazol-5(4H)-one 
• 1229937-09-0 5-(4,5-bis(benzyloxy)pyridin-2-yl)-1,3,4-oxadiazol-2(3H)-one 
• 112334-42-6 benzyl 4,5-bis(benzyloxy)picolinate 
• 40838-34-4 2-chloromethyl-5-methoxy-4H-pyran-4-one 
• 18234-41-8 5-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 
• 1219-33-6 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid 
• 1064077-22-0 (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 
• 107758-06-5 methyl 5-benzyloxy-4-oxo-4H-pyran-2-carboxylate 
• 59281-14-0 5-benzyloxy-4-hydroxy-2-hydroxymethylpyridine 
• 959676-13-2 3-benzyloxy-1-thiazolinoethyl-4(1H)-pyridone 
• 959327-48-1 3-benzyloxy-1-thiazolinomethyl-4(1H)-pyridone 
• 177943-50-9 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-5,6-O-isopropylidene-L-ascorbic acid 
• 177943-51-0 3-O-benzyl-2-O-(5-benzyloxy-4H-pyran-4-one-2-methyl)-L-ascorbic acid 

Relevant articles and documents

Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety

In an effort to synthesize more effective non-nucleoside reverse transcriptase inhibitors (NNRTIs) against the HIV-1 infection, a new series of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety were designed by molecular docking studies, prepared and characterized by spectroscopic techniques. All the synthesized compounds were in vitro evaluated for their inhibitory effect against the HIV-1 replication in the MT-4 cells. Results showed that none of these synthesized compounds displayed any specific anti HIV-1 activity. Surprisingly, these compounds showed high cytotoxicity against MT-4 cells with low selectivity index (50 = 1.3 μM and EC50 = 1.8 μM respectively).

Molecular dynamics simulation and 3D-pharmacophore analysis of new quinoline-based analogues with dual potential against EGFR and VEGFR-2

Epidermal growth factor and vascular endothelial growth factor-2 are important targets of tyrosine kinase for the treatment of various cancerous diseases. Combination of inhibition of both targets to produce synergy in the signal pathway is a critical approach to identify novel tyrosine kinase inhibitors. In this study, a series of new compounds derived from the 4-aminoquinoline as dual inhibitors were synthesized. The obtained results of cytotoxicity assay against human carcinoma cell lines indicated 0.8 μM for 4c against A549 showing its high efficiency in comparison to erlotinib. Pharmacophore modeling as a structure-based method was investigated on dual inhibitors and 4c which was compared with co-crystallized in the active site of EGFR and VEGFR-2. They have shown the same binding orientation as vandetanib, erlotinib and sorafenib. Molecular dynamics simulation results approved that Met769, Lys721, Asp1046, and Lys868 are key residues in two binding sites for dual activity. Ala1050 and Pro968 were identified as new amino acid interaction sites for dual inhibition. 4c showed more favorable stability than vandetanib in VEGFR-2 receptor for a 50 ns dynamic simulation. The high correlation between essential pharmacophoric features of designed compounds and lead inhibitors interactions provided a deeper insight into the structural basis of 4-aminoquinoline inhibition.

Synthesis and biological evaluation of deferiprone-resveratrol hybrids as antioxidants, Aβ1–42aggregation inhibitors and metal-chelating agents for Alzheimer's disease

A series of deferiprone-resveratrol hybrids have been designed and synthesized as multitarget-directed ligands (MTDLs) through merging the chelating moiety 3-hydroxypyridin-4-one into the structure of resveratrol, a natural antioxidant agent and β-amyloid peptide (Aβ) aggregation inhibitor. The in?vitro biological evaluation revealed that most of these newly synthesized compounds exhibited good inhibitory activity against self-induced Aβ1–42aggregation, excellent antioxidant activity and potent metal chelating capability. Compounds 3i and 4f were identified as the most promising MTDLs with triple functions, possessing micromolar IC50values for Aβ1–42aggregation inhibition, greater 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS?+) scavenging activity than Trolox and similar pFe(III) values to that of deferiprone.

Synthesis of novel isoxazole derivatives bearing kojic acid moiety and evaluation of their antimicrobial activity

[Figure not available: see fulltext.] A novel series of 3,5-disubstituted isoxazoles bearing kojic acid moiety were synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction of terminal alkynes with nitrile oxide formed in situ from the corresponding hydroximoyl chloride. Structures of the synthesized compounds were characterized using spectroscopic analysis data. Antimicrobial activity of the isoxazole conjugates was determined as MIC values by broth microdilution method against different bacteria: Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhi, and fungi Candida kefyr. The obtained results revealed notable antibacterial and antifungal activities of the compounds.

ALA hybrid 3-hydroxypyridone derivative as well as preparation method and application thereof

The invention designs and synthesizes a novel anti-tumor active compound with iron chelating property and photosensitive activity based on the principles of reasonable drug design, drug-likeness and the like. The invention aims to provide a preparation me

Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity

Abstract: Pyran-4-one (maltol, kojic acid and chlorokojic acid 1) esters of adamantan-1-ylacetic acid were prepared through efficient synthetic routes in good yields and evaluated for their in vitro antiproliferative activity on four cancer cell lines: K562 (chronic myelogenous leukemia), HeLa (cervical cancer), Caco-2 (colorectal adenocarcinoma) and NCI-H358 (bronchioalveolar carcinoma). The results indicate that the presence and the position of the adamantyl acyl group or chlorine atom are the necessary requirement for antitumor activity of pyranone systems. Derivatives of kojic acid with either free (compounds 1 and 8) or acylated 5-OH group (compounds 2 and 9) have shown good-to-moderate activity (IC50 values ranging from 13.1 to 43.0?μM) on all cell lines. Adamantyl kojic acid derivative 5 with a free OH group on the position 2 showed activity only on the K562 cell line. It seems that removal of halogen or adamantyl unit from position 2 elicits antileukemic activity, as observed in compound 5. The positive influence of the adamantyl unit was also observed on a 3-OH acylated derivative of maltol I which was also selectively active on the same cell line. 5-O-benzylated adamantyl compounds 6 and 7 and unmodified starting pyranones were found to be inactive. Antibacterial activity of compounds was also evaluated on S. aureus ATCC 13709, M. catarrhalis ATCC 23246, E. faecalis ATCC29212 and E. coli TolC-Tn10, but no activity was observed (MIC values 128–256?μg/mL). Graphical abstract: [Figure not available: see fulltext.]