68732-99-0

Basic information

• Product Name: 4H-Pyran-4-one, 2,3-dihydro-5-hydroxy-2-(hydroxymethyl)-, (2S)-
• Synonyms: 4H-Pyran-4-one, 2,3-dihydro-5-hydroxy-2-(hydroxymethyl)-, (2S)-
• CAS NO: 68732-99-0
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.13
• Mol File: 68732-99-0.mol

Chemical Properties

• Melting Point: 92-94 °C
• Boiling Point: 287.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.429±0.06 g/cm3(Predicted)
• PKA: 9.18±0.40(Predicted)
• CAS DataBase Reference: 4H-Pyran-4-one, 2,3-dihydro-5-hydroxy-2-(hydroxymethyl)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Pyran-4-one, 2,3-dihydro-5-hydroxy-2-(hydroxymethyl)-, (2S)-(68732-99-0)
• EPA Substance Registry System: 4H-Pyran-4-one, 2,3-dihydro-5-hydroxy-2-(hydroxymethyl)-, (2S)-(68732-99-0)

Safety Data

• Hazardous Substances Data: 68732-99-0(Hazardous Substances Data)

Upstream product

• 68733-00-6 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose 
• 88851-59-6 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose oxime 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 297768-00-4 3,4,6-tri-O-acetyl-1,5-anhydro-D-arabino-hex-2-ulose 
• 75414-43-6 1,5-D-anhydrofructose 
• 211800-60-1 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose 

Relevant articles and documents

A new chemical synthesis of Ascopyrone P from 1,5-anhydro-d-fructose

The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-d-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-d-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-d-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).

Ascopyrone P: Chemical synthesis from D-glucose

The pyranone, 1,5-anhydro-4-deoxy-D-glycero-hex-l-en-3-ulose (1) (ascopyrone P), has been synthesised in eight steps from D-glucose. The key steps were deacetylation of 3,6-di-O-acetyl-1,5-anhydro-D-glycero-hex-3-en-2-ulose (8) to give isomers and hydrate