4971-56-6

Basic information

• Product Name: TETRONIC ACID
• Synonyms: TIMTEC-BB SBB008561;TETRONIC ACID;TETRAHYDROFURAN-2,4-DIONE;4-HYDROXY-5(H)FURAN-2-ONE;Butanoic acid, 4-hydroxy-3-oxo-, gamma-lactone;2,4(3H,5H)-Furandione;2,4(3H,5H)-Furandione~4-Hydroxy-2(5H)-furanone~Tetrahydrofuran-2,4-dione;beta-oxo-gamma-butyrolactone
• CAS NO: 4971-56-6
• Molecular Formula: C₄H₄O₃
• Molecular Weight: 100.07
• EINECS: 225-617-4
• Mol File: 4971-56-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 139-140°C (dec.)
• Boiling Point: 324.3 °C at 760 mmHg
• Flash Point: 151.1 °C
• Appearance: /
• Density: 1.375 g/cm³
• Vapor Pressure: 0.000248mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 10.67±0.20(Predicted)
• CAS DataBase Reference: TETRONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TETRONIC ACID(4971-56-6)
• EPA Substance Registry System: TETRONIC ACID(4971-56-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• Hazardous Substances Data: 4971-56-6(Hazardous Substances Data)

Usage

Application

Tetronic acid is a crystalline enolic lactone C4H4O3 that has acidic properties and is the parent compound of acidic compounds obtained by the fermenting action of a mold (Penicillium charlesii) from spoiled corn. Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde. In organic synthesis, it is used as a precursor for other substituted and ring-fused furans and butenolides. It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes spirodiclofen and spiromesifen.

Uses

Tetronic Acid can be used for insecticides.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 7007, 1991 DOI: 10.1021/jo00025a012

InChI:InChI=1/C4H4O3/c5-3-1-4(6)7-2-3/h1-2H2

Synthetic route

ethyl (2-chloroaceto)acetate (638-07-3) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With potassium acetate; acetic acid at 80 - 90℃; for 12h;	45%

3-bromo-furan-2,4-dione (1192-50-3) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With sodium carbonate Behandeln mit Natriumamalgam unter Einleiten von Kohlendioxyd und anschliessend Behandeln mit Schwefelsaeure;
With sodium carbonate anschliessend Hydrierung an Palladium/Kohle;

3-bromo-furan-2,4-dione (1192-50-3) → tetrahydrofuran-2,4-dione (4971-56-6) + [3,3']bifuryl-2,4,2',4'-tetraone (167644-70-4)

Conditions	Yield
With sodium amalgam

ethanol (64-17-5) + 2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane → tetrahydrofuran-2,4-dione (4971-56-6) + acetone (67-64-1)

2,4-dioxo-tetrahydro-furan-3-carboxylic acid ethyl ester (36717-62-1) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With sodium hydroxide Ansaeuern mit wss. Salzsaeure;

4-(phenylamino)furan-2(5H)-one (22273-65-0) → tetrahydrofuran-2,4-dione (4971-56-6) + aniline (62-53-3)

Conditions	Yield
With water at 25℃; Rate constant; Mechanism;

4-oxo-2-imino-tetrahydrofuran-carboxylic acid-(3) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With sulfuric acid

2,4-dioxo-tetrahydro-furan-3-carboxylic acid methyl ester + aqueous-methanolic NaOH-solution → tetrahydrofuran-2,4-dione (4971-56-6)

barium salt of/the/ tetronic acid α-carboxylic acid → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With sulfuric acid

bromoacetic acid methyl ester (96-32-2) + magnesium compound of bromoacetic acid benzyl ester → tetrahydrofuran-2,4-dione (4971-56-6)

3-bromo-3-chloro-furan-2,4-dione + sodium amalgam → tetrahydrofuran-2,4-dione (4971-56-6)

tetronic acid α-carboxylic acid methyl ester → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With sodium hydroxide

hydrogenchloride (7647-01-0) + furan-2,4-dione-4-oxime → tetrahydrofuran-2,4-dione (4971-56-6) + hydroxylamine (7803-49-8)

4-hydroxy-2-iodo-acetoacetic acid-lactone + acidified potassium iodide solution → tetrahydrofuran-2,4-dione (4971-56-6) + iodine (7553-56-2)

hydrogenchloride (7647-01-0) + 4-hydroxy-3-phenylimino-butyric acid-lactone (63464-79-9) → tetrahydrofuran-2,4-dione (4971-56-6) + aniline (62-53-3)

hydrogenchloride (7647-01-0) + furan-2,4-dione-4-phenylhydrazone (114187-91-6) → tetrahydrofuran-2,4-dione (4971-56-6) + phenylhydrazine (100-63-0)

2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane + alkalies → tetrahydrofuran-2,4-dione (4971-56-6) + acetone (67-64-1)

2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane + alkaline earth carbonates → tetrahydrofuran-2,4-dione (4971-56-6) + acetone (67-64-1)

3-bromo-furan-2,4-dione (1192-50-3) + sodium amalgam → tetrahydrofuran-2,4-dione (4971-56-6) + anhydrotetronic acid

sulfuric acid (7664-93-9) + 2-imino-4-oxo-tetrahydro-furan-3-carboxylic acid → tetrahydrofuran-2,4-dione (4971-56-6) + tetronic acid α-carboxylic acid

4-bromoethyl acetoacetate (13176-46-0) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With potassium acetate; acetic acid In dichloromethane at 80 - 85℃; for 5h;

ethyl 4-(tert-butoxy)-3-oxobutanoate (67354-35-2) → tetrahydrofuran-2,4-dione (4971-56-6)

Conditions	Yield
With hydrogenchloride In acetic acid at 20 - 30℃; for 1h;
With hydrogenchloride; acetic acid at 20℃; for 3h;

tetrahydrofuran-2,4-dione (4971-56-6) + (2-nitroethenyl)benzene (102-96-5) → 3-(2-nitro-1-phenylethyl)furan-2,4(3H,5H)-dione

Conditions	Yield
at 20℃; Michael addition; Neat (no solvent); Grinding; optical yield given as %de; diastereoselective reaction;	99%

tetrahydrofuran-2,4-dione (4971-56-6) + p-toluenesulfonyl chloride (98-59-9) → 4-(p-toluenesulfonyloxy)-2(5H)-furanone (471931-08-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one (18940-21-1) + 4-chlorobenzaldehyde (104-88-1) → 9-(4-chloro-phenyl)-6,6-dimethyl-4-phenyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4-b]quinoline-1,8-dione

Conditions	Yield
With acetic acid at 100℃; for 0.133333h; microwave irradiation;	98%
In acetic acid at 100℃; for 0.133333h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) + 4-fluorobenzaldehyde (459-57-4) → C26H24FNO3

Conditions	Yield
In acetic acid at 100℃; for 0.116667h; microwave irradiation;	98%

3-(cyclopropylamino)-5,5-dimethylcyclohex-2-enone + tetrahydrofuran-2,4-dione (4971-56-6) + 4-fluorobenzaldehyde (459-57-4) → C22H22FNO3

Conditions	Yield
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 4-bromo-benzaldehyde (1122-91-4) + naphthalen-2-ylamine (91-59-8) → C21H14BrNO2

Conditions	Yield
In water at 100℃; for 0.116667h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + benzaldehyde (100-52-7) + p-toluidine (106-49-0) → C18H15NO2

Conditions	Yield
In water at 100℃; for 0.0666667h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + terephthalaldehyde, (623-27-8) → 1,4-bis(3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one-4-yl)benzene

Conditions	Yield
With ethylene glycol at 100℃; for 0.0125h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + Isophthalaldehyde (626-19-7) → 1,3-bis(3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one-4-yl)benzene

Conditions	Yield
With ethylene glycol at 100℃; for 0.0125h; microwave irradiation;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + 4-chlorobenzaldehyde (104-88-1) → 4-(4-chlorophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one (1049682-27-0)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 25h;	98%
In water at 100℃; for 0.0333333h; microwave irradiation;	96%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	96%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + 4-nitrobenzaldehdye (555-16-8) → 4-(4-nitrophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one (1049682-33-8)

Conditions	Yield
In water at 100℃; for 0.0333333h; microwave irradiation;	98%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 3h;	87%
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 30h;	80%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + 4-bromo-benzaldehyde (1122-91-4) → 4-(4-bromophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one (1049682-29-2)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	98%
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 20h;	97%
In water at 100℃; for 0.0166667h; microwave irradiation;	95%

tetrahydrofuran-2,4-dione (4971-56-6) + 1-Phenyl-3-methyl-5-aminopyrazole (1131-18-6) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3-methyl-4-(3,4-dimethoxyphenyl)-1-phenyl-1H-furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one (1173933-04-4)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 9h;	98%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	91%

tetrahydrofuran-2,4-dione (4971-56-6) + 4-bromo-aniline (106-40-1) → 4-((4-bromophenyl)amino)furan-2(5H)-one (1100695-03-1)

Conditions	Yield
In acetonitrile for 0.666667h; Solvent; Temperature; Microwave irradiation; Reflux;	98%
In 1,4-dioxane at 20℃;

tetrahydrofuran-2,4-dione (4971-56-6) + 3-Aminocrotononitrile (1118-61-2) + 3-Chlorobenzaldehyde (587-04-2) + phenylhydrazine (100-63-0) → C21H16ClN3O2 (1016225-37-8)

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: m-Chlorobenzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-Aminocrotononitrile (1118-61-2) + 4-nitrobenzaldehdye (555-16-8) + phenylhydrazine (100-63-0) → C21H16N4O4 (1016225-38-9)

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-nitrobenzaldehdye at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-Aminocrotononitrile (1118-61-2) + benzaldehyde (100-52-7) + phenylhydrazine (100-63-0) → C21H17N3O2 (1190990-97-6)

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: benzaldehyde at 70℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Ionic liquid; Green chemistry;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-Aminocrotononitrile (1118-61-2) + 4-methyl-benzaldehyde (104-87-0) + phenylhydrazine (100-63-0) → C22H19N3O2 (1016225-30-1)

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-methyl-benzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-Aminocrotononitrile (1118-61-2) + 4-hydroxy-benzaldehyde (123-08-0) + phenylhydrazine (100-63-0) → C21H17N3O3 (1016225-32-3)

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-hydroxy-benzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + (2-amino-5-chlorophenyl)(phenyl)methanol (1159372-20-9) → C17H12ClNO2 (867068-08-4)

Conditions	Yield
With zinc(II) chloride In toluene for 0.333333h; Microwave irradiation; Sealed tube; Heating;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 1,1-diethyl (2R,3S)-2-formyl-3-phenylcyclopropane-1,1-dicarboxylate (1023303-72-1) → diethyl (2R,3S)-2-((4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)methyl)-3-phenylcyclopropane-1,1-dicarboxylate

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In dichloromethane at 25℃; for 0.5h; diastereoselective reaction;	98%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) + 3-nitro-benzaldehyde (99-61-6) → 6,6-dimethyl-9-(3-nitro-phenyl)-4-p-tolyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4-b]quinoline-1,8-dione

Conditions	Yield
With acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%

tetrahydrofuran-2,4-dione (4971-56-6) + 2-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)acetic acid (882-07-5) + 3-nitro-benzaldehyde (99-61-6) → [6,6-dimethyl-9-(3-nitro-phenyl)-1,8-dioxo-3,5,6,7,8,9-hexahydro-1H-furo[3,4-b]quinolin-4-yl]-acetic acid

Conditions	Yield
With acetic acid at 100℃; for 0.116667h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.116667h; microwave irradiation;	97%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) + 4-methoxy-benzaldehyde (123-11-5) → 9-(4-methoxyphenyl)-6,6-dimethyl-4-p-tolyl-5,6,7,9-tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-dione

Conditions	Yield
With acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 2h;	94%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) + benzaldehyde (100-52-7) → C26H25NO3

Conditions	Yield
In acetic acid at 100℃; for 0.133333h; microwave irradiation;	97%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-(p-tolylamino)cyclohex-2-en-1-one (36646-74-9) + 4-bromo-benzaldehyde (1122-91-4) → C24H20BrNO3

Conditions	Yield
In acetic acid at 100℃; for 0.0666667h; microwave irradiation;	97%

tetrahydrofuran-2,4-dione (4971-56-6) + 4-bromo-benzaldehyde (1122-91-4) + aniline (62-53-3) → C17H12BrNO2

Conditions	Yield
In water at 100℃; for 0.0833333h; microwave irradiation;	97%

tetrahydrofuran-2,4-dione (4971-56-6) + 3-nitro-benzaldehyde (99-61-6) + p-toluidine (106-49-0) → 7-methyl-9-(3-nitrophenyl)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one

Conditions	Yield
In water at 100℃; for 0.116667h; microwave irradiation;	97%

thiophene-2-carbaldehyde (98-03-3) + tetrahydrofuran-2,4-dione (4971-56-6) + 1-amino-naphthalene (134-32-7) → C19H13NO2S

Conditions	Yield
In water at 100℃; for 0.1h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 0.5h; regioselective reaction;	93%

tetrahydrofuran-2,4-dione (4971-56-6) + 4-chlorobenzaldehyde (104-88-1) + 1-amino-naphthalene (134-32-7) → C21H14ClNO2

Conditions	Yield
In water at 100℃; for 0.0666667h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 1h; regioselective reaction;	92%

Upstream product

• 1192-50-3 3-bromo-furan-2,4-dione 
• 36717-62-1 2,4-dioxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 22273-65-0 4-(phenylamino)furan-2(5H)-one 
• 96-32-2 bromoacetic acid methyl ester 
• 7647-01-0 hydrogenchloride 
• 114187-91-6 furan-2,4-dione-4-phenylhydrazone 
• 7664-93-9 sulfuric acid 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 13176-46-0 4-bromoethyl acetoacetate 
• 63464-79-9 4-hydroxy-3-phenylimino-butyric acid-lactone 
• 64-17-5 ethanol 
• 67354-35-2 ethyl 4-(tert-butoxy)-3-oxobutanoate 

Downstream Products

• 69556-70-3 4-methoxy-5H-furan-2-one 
• 114380-48-2 4-[6-(3,4,5-trimethoxy-benzoyl)-benzo[1,3]dioxol-5-ylimino]-dihydro-furan-2-one 
• 79126-76-4 furan-2,3,4-trione-3-phenylhydrazone 
• 104179-53-5 4-(2-acetyl-phenylimino)-dihydro-furan-2-one 
• 21053-89-4 4-benzoyloxy-5H-furan-2-one 
• 4945-38-4 2-hydroxymethylquinoline-3-carboxylic acid lactone 
• 63464-79-9 4-hydroxy-3-phenylimino-butyric acid-lactone 
• 114187-91-6 furan-2,4-dione-4-phenylhydrazone 
• 101600-77-5 4-(2-benzoyl-phenylimino)-dihydro-furan-2-one 
• 725203-12-3 furan-2,3,4-trione-3-oxime 
• 857619-02-4 4-hydroxy-2-nitro-acetoacetic acid-lactone 
• 85422-51-1 5-(4,5-Dihydro-2,4-dioxo-3(2H)-furanylidene)-2,4,6-(1H,3H,5H)-pyrimidinetrione 
• 134079-93-9 2-amino-4-(2-chlorophenyl)-5,7-dihydro-5-oxo-4H-furo[3,4-b]pyran-3-carbonitrile 
• 134079-95-1 2-Amino-4-methyl-5-oxo-4-phenyl-5,7-dihydro-4H-furo[3,4-b]pyran-3-carbonitrile 

Relevant articles and documents

Synthesis and Antifungal Activity of Novel Furan-2,4-dione Derivatives Containing Substituted Phenylhydrazine Moiety

A series of novel 3-(2-(substituted phenyl)hydrazinylmethylidene)furan-2,4(3H,5H)-diones were designed and synthesized with ethyl 4-chloroacetoacetate as the starting material. Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, EI-MS and elemental analysis. Bioassay data demonstrated that these compounds exhibited remarkable antifungal activity against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici. Compound 3-(2-(4-bromophenyl)hydrazinylmethylidene)furan-2,4(3H,5H)-dione (5g) had excellent bioactivity against Botrytis cinerea with an EC50 value of 0.18 μg/mL - markedly lower than the 0.24 μg/mL of the commercial fungicide procymidone. The result revealed that introducing the halogenated phenylhydrazine at the 3-position of furan-2,4(3H, 5H)-dione was an effective way to design new tetronic acid derivatives as new fungicides. A series of novel furan-2,4-dione derivatives containing a substituted phenylhydrazine moiety were designed and synthesized. These compounds exhibited remarkable antifungal activity against Fusarium graminearum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici. Compound 5g showed significantly better bioactivity than the control fungicides.

Synthesis, characterization, antifungal evaluation and 3D-QSAR study of phenylhydrazine substituted tetronic acid derivatives

A series of 3-(1-(2-(substituted phenyl)hydrazinyl)alkylidene)furan-2,4(3H, 5H)-diones were designed and prepared using two synthetic routes. Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, MS, elemental analysis and single-crystal X-ray diffraction. Their bioactivity was evaluated against Botrytis cinerea in vitro. Most target compounds exhibited remarkable antifungal activity. Two compounds 7f and 7h were highly effective and their EC50 values were 0.241 μg/mL and 0.167 μg/mL, respectively, close to that of the control drug procymidone. 3D-QSAR studies of CoMFA and CoMSIA were carried out. Models with good predictive ability were generated with the cross validated q2 values for CoMFA and CoMSIA being 0.565 and 0.823. Conventional r2 values were 0.983 and 0.945, respectively. The results provided a practical tool for guiding the design and synthesis of novel and more potent tetronic acid derivatives containing substituted phenylhydrazine moiety.

Methods of inhibiting the advanced glycosylation of proteins using tetramic and tetronic acids and compositions therefor

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises substituted or unsubstituted tetramic and tetronic acids capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.