4940-10-7

Basic information

• Product Name: 2-(1-Hydroxyethyl)-3-hydroxy-pyran-4(1H)-one
• Synonyms: 2-(1-Hydroxyethyl)-3-hydroxy-pyran-4(1H)-one
• CAS NO: 4940-10-7
• Molecular Weight: 156.138
• Mol File: 4940-10-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(1-Hydroxyethyl)-3-hydroxy-pyran-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-Hydroxyethyl)-3-hydroxy-pyran-4(1H)-one(4940-10-7)
• EPA Substance Registry System: 2-(1-Hydroxyethyl)-3-hydroxy-pyran-4(1H)-one(4940-10-7)

Safety Data

• Hazardous Substances Data: 4940-10-7(Hazardous Substances Data)

Upstream product

• 496-63-9 3-hydroxy-pyran-4-one 
• 75-07-0 acetaldehyde 
• 74425-84-6 4-Bromo-6-methoxy-2H-pyran-3(6H)-one 
• 60249-17-4 6-methoxy-2H-pyran-3(6H)-one 
• 19969-71-2 2,5-dimethoxy-2-hydroxymethyl-2,5-dihydrofuran 
• 98-00-0 (2-furyl)methyl alcohol 

Downstream Products

• 216579-23-6 8-oxo-4,8-dihydro-4-methyl-2-phenyl-4H-pyrano[3,2-d]-m-dioxin 

Relevant articles and documents

Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents

3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class.

Synthesis, physicochemical characterization, and biological evaluation of 2-(1'-hydroxyalkyl-3-hydroxypyridin-4-ones: Novel iron chelators with enhanced pFe3+ values

The synthesis of a range of 2-(1'-hydroxyalkyl)-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pK(a) values of the ligands and the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of a 1'-hydroxyalkyl group at the 2-position leads to a significant improvement in the pFe3+ values. Such an effect was found to be greater with the hydroxyethyl substituent than with the hydroxy-methyl substituent, particularly in the cases of 1-ethyl-2(1'-hydroxyethyl)-3- hydroxypyridin-4-one (pFe3+ = 21.4) and 1,6-dimethyl-2-(1'-hydroxyethyl)3- hydroxypyridin-4-one (pFe3+ = 21.5) where an enhancement on pFe3+ values in the region of two orders of magnitude is observed, as compared with Deferiprone (1,2-dimethyl-3-hydroxypyridin-4-one) (pFe3+ = 19.4). The ability of these novel 3-hydroxypyridin-4-ones to facilitate the iron excretion in bile was investigated using a [59Fe] ferritin-loaded rat model. Chelators and prodrug chelators possessing high pFe3+ values show great promise in their ability to remove iron under in vivo conditions.