26209-93-8

Basic information

• Product Name: 6-[(acetyloxy)methyl]-4-oxo-4H-pyran-3-yl acetate
• Synonyms: 4H-Pyran-4-one, 5- (acetyloxy)-2-[(acetyloxy)methyl]-; 4H-pyran-4-one, 5-(acetyloxy)-2-[(acetyloxy)methyl]-; 4H-Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-, diacetate; 6-(Acetoxymethyl)-4-oxo-4H-pyran-3-yl acetate
• CAS NO: 26209-93-8
• Molecular Formula: C₁₀H₁₀O₆
• Molecular Weight: 226.1828
• Mol File: 26209-93-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 378.8°C at 760 mmHg
• Flash Point: 170.8°C
• Density: 1.31g/cm³
• Vapor Pressure: 6.14E-06mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 6-[(acetyloxy)methyl]-4-oxo-4H-pyran-3-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(acetyloxy)methyl]-4-oxo-4H-pyran-3-yl acetate(26209-93-8)
• EPA Substance Registry System: 6-[(acetyloxy)methyl]-4-oxo-4H-pyran-3-yl acetate(26209-93-8)

Safety Data

• Hazardous Substances Data: 26209-93-8(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 108-24-7 acetic anhydride 
• 73322-37-9 1,3,4,6-Tetra-O-acetyl-β-D-arabino-hexopyranos-2-ulose monohydrate 
• 75-36-5 acetyl chloride 
• 5605-82-3 3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride 
• 73322-43-7 1,3,4,6-Tetra-O-acetyl-β-D-lyxo-hexopyranos-2-ulose 
• 73322-44-8 1,3,4,6-Tetra-O-acetyl-α-D-lyxo-hexopyranos-2-ulose monohydrate 
• 73322-38-0 1,3,4,6-Tetra-O-acetyl-α-D-arabino-hexopyranos-2-ulose monohydrate 
• 98-88-4 benzoyl chloride 
• 41107-22-6 (2R,3R)‐3,5‐diacetoxy‐2‐(acetoxymethyl)‐2,3‐dihydro‐4H‐pyran‐4‐one 
• 87236-45-1 4-nitrophenyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 
• 13036-15-2 1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 33886-26-9 5-Benzoyloxy-2-benzoyloxymethyl-4H-pyran-4-on 
• 25552-08-3 7-O-acetylkojic acid 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 33777-44-5 2-acetoxymethyl-5-benzoyloxy-pyran-4-one 
• 102665-16-7 3-acetoxy-6-acetoxymethyl-2,5-dibenzoyl-pyran-4-one 

Relevant articles and documents

The issue of misidentification of kojic acid with flufuran in aspergillus flavus

In the course of investigations on the complex phenomenon of bee decline, Aspergillus flavus was isolated from the haemocoel of worker bees. Observations on the metabolomic profile of this strain showed kojic acid to be the dominant product in cultures on Czapek-Dox broth. However, an accurate review of papers documenting secondary metabolite production in A. flavus also showed that an isomer of kojic acid, identified as 5-(hydroxymethyl)-furan-3-carboxylic acid and named flufuran is reported from this species. The spectroscopic data of kojic acid were almost identical to those reported in the literature for flufuran. This motivated a comparative study of commercial kojic acid and 5-(hydroxymethyl)-furan-3-carboxylic acid, highlighting some differences, for example in the 13C-NMR and UV spectra for the two compounds, indicating that misidentification of the kojic acid as 5-(hydroxymethyl)-furan-3-carboxylic acid has occurred in the past.

Chemo-enzymatic three-step conversion of glucose to kojic acid

Kojic acid is an important biomolecule, currently produced by fermentation and having a wide range of potential applications. A faster and more direct chemical route could open the door for its large-scale production and wider utilization in biorefineries. Here we describe an efficient method for the preparation of kojic acid from d-glucose via glucosone by a three-step chemo-enzymatic route.

Sugar Enolones, XII. Peroxidation of Pyranose-derived Enol Esters: An Efficacious Synthesis of Peracetylhexosuloses and their Conversion into γ-Pyrones via 3,2-Enolones

Pyranose-derived 1,2-enol acetates of type 4 readily react with 3-chloroperbenzoic acid in ether to an anomeric mixture of glycos-2-uloses 6, as is demonstrated by the conversions 7 -> 11/12, 18 -> 19/20 and 21 -> 22.Structural and configurational assignm