50607-35-7

Basic information

• Product Name: 3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one
• Synonyms: 3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one
• CAS NO: 50607-35-7
• Molecular Formula: C₈H₁₀O₃
• Molecular Weight: 154.16
• Mol File: 50607-35-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one(50607-35-7)
• EPA Substance Registry System: 3-Ethyl-4-hydroxy-6-methyl-2H-pyran-2-one(50607-35-7)

Safety Data

• Hazardous Substances Data: 50607-35-7(Hazardous Substances Data)

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 113689-79-5 methyl 2-ethyl-3,5-dioxohexanoate 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 143456-22-8 2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 

Downstream Products

• 82420-03-9 3,3’-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one) 
• 82420-00-6 3,3'-<(4-Chlorphenyl)-methylen>-bis-(4-hydroxy-6-methyl-2H-pyran-2-on) 

Relevant articles and documents

Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs

Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50?=?0.04–3.8?μg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50?=?223–304?μg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.

A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2- pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551.

REDUCTION OF α-PYRONE DERIVATIVES WITH BORANE-METHYLSULFIDE COMPLEX

Selective reduction of the 5-carbomethoxy- and the 5-carboethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a-11, 19) to yield the 5-hydroxymethyl derivatives (12-18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex.Additionally, red