32323-44-7

Upstream product

• 123-76-2 levulinic acid 
• 1775-46-8 3,5-dibromolevulinic acid 
• 62557-43-1 3-bromolevulinic acid 
• 14594-23-1 5-bromolaevulinic acid 

Downstream Products

• 539-88-8 4-oxopentanoic acid ethyl ester 
• 676556-23-3 5-[(E)-1-Bromo-3-phenyl-prop-2-en-(Z)-ylidene]-5H-furan-2-one 
• 676556-25-5 (Z)-5-(1-bromo-1-phenylmethylene)-2(5H)-furanone 
• 1218769-65-3 (Z)-5-(phenylthiophene-3-ylmethylene)furan-2-(5H)-one 
• 158071-59-1 5-[(E)-3-Phenyl-prop-2-en-(E)-ylidene]-5H-furan-2-one 
• 158071-58-0 (5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one 
• 35304-87-1 (E)-4-benzylidene-2-butenolide 
• 35304-86-0 (Z)-5-phenyl-2,4-pentadien-4-olide 

Relevant academic research and scientific papers

METHYLENE FURANONE DERIVATIVES AND USE OF SAID DERIVATIVES AS A PHOTOPROTECTING OR ANTIOXIDANT OR DEPIGMENTATION AGENT IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS

The present invention relates to novel methylene furanone derivatives as well as the use thereof as a protective, antioxidant, or depigmentation agent in cosmetic or dermatological compositions. The invention also relates to a method for preparing said derivatives involving a Suzuki-Miyaura coupling reaction from corresponding dibromofuranone derivatives. The invention also relates to a method of preparation involving a coupling reaction of 2-methoxy-furan derivatives with a ketone followed by dehydration.

Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)- furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi

A library of 25 1′-unsubstituted and 1′-bromo or 1′-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm format

Stereoselective syntheses of dihydroxerulin and xerulinic acid, anti-hypocholesterolemic dyes from the fungus Xerula melanotricha

The title compounds 2 and 3, which are inhibitors of the biosynthesis of cholesterol, were synthesized in a convergent and perfectly stereoselective manner. In the key step, bromobutenolide 6 (obtained from levulinic acid in two steps) was coupled with either of the novel bis(stannanes) trans,cis, -trans-35 or trans,trans,trans-35 [each accessible from 3-(tributylstannyl)allyl alcohol (17) in four steps], giving γ-alkylidenebutenolide trans,trans,trans-32. This compound was coupled with iododiyne 42 or the bromoenediynoate 44 leading to dihydroxerulin (2) and to the (trimethylsilylethyl)ester 45 of xerulinic acid, respectively. Deprotection of the latter provided totally synthetic xerulinic acid (3) for the first time.

A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides

γ-(Dibromomethylene)butenolide (2) and β-bromo-γ- (bromomethylene)butenolide (Z-5), both of which obtained from dibromolevulinic acid (6) in a single step, underwent Pd-catalyzed couplings with phenyl- or styryltributylstannane giving mono-bromobutenolides with excellent stereo- and regiocontrol. A second Stille coupling or the reduction with Zn dust led to bromine-free γ-alkylidenebutenolides as single stereoisomers.

Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones

A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.