88495-48-1

Usage

Structure

Contains a furanone ring and a hydroxymethyl group

Occurrence

Found in the essential oil of bourbon vanilla

Aroma

Sweet, fruity

Usage

Used as a flavoring agent in food and beverages

Potential properties

Anti-quorum sensing, antimicrobial

Upstream product

• 85701-08-2 (R)-4-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 70767-37-2 6-methyl-heptanoyl chloride 
• 80656-71-9 (S)-(+)-3-hydroxymethyl-4-butanolide 
• 80656-72-0 (R)-(-)-3-trimethylsilyloxymethyl-4-butanolide 
• 5352-72-7 (+)-(R)-5-oxotetrahydro-3-furancarboxylic acid 
• 1653-40-3 6-methylheptanol 
• 119614-32-3 6-methylhept-5-en-2-yn-1-ol 
• 934248-96-1 C₁₄H₂₂O₅ 
• 143724-42-9 (rel)-(1S/1R,3S)-(tetrahydro-1-methoxyfuran-3-yl)methanol 
• 36679-81-9 4-hydroxymethyl-1,2,3,4-tetrahydrofuran-2-one 
• 42927-61-7 methyl 5-methoxy-3-tetrahydrofuran-3-carboxylate 
• 870-63-3 prenyl bromide 
• 158522-70-4 Acetic acid 4-acetoxymethyl-3-(6-methyl-heptanoyl)-furan-2-yl ester 
• 158522-71-5 Acetic acid 2-hydroxy-4-(6-methyl-heptanoyl)-5-oxo-2,5-dihydro-furan-3-ylmethyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF OPTICALLY ACTIVE FORMS OF A-FACTOR, THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS IN INACTIVE MUTANTS OF STREPTOMYCES GRISEUS

The absolute configuration at C-3 of A-factor, 2-(6-methylheptanoyl)-3-hydroxymethyl-4-butanolide 1a, was determined to be S by synthesizing both enantiomers of it from paraconic acid. (3S)-A-factor was 2.5 times more active than the (3R)-isomer as the inducer of streptomycin biosynthesis in inactive mutants of Streptomyces griseus.

Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus

We report a concise synthesis of A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification-Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β- unsaturated carbonyl compound using sodium cyanoborohydride.

Regioselective synthesis of hydroxy butenolides: A convenient synthesis of A-factor

An elegant approach for the regioselective preparation of hydroxy butenolide by the oxidation of 2-ethoxyfuran with MnO2-HCl is described.

A Synthesis of 3-Hydroxymethyl-2-(6-methylheptanoyl)-4-butanolide (A-Factor)

The A-Factor was conveniently synthesized from 3-furoic acid via the Birch reduction.