Product Name

  • Name

    Dehydroacetic acid

  • EINECS 208-293-9
  • CAS No. 520-45-6
  • Article Data73
  • CAS DataBase
  • Density 1.264 g/cm3
  • Solubility 500mg/L at 25℃
  • Melting Point 111-113 °C(lit.)
  • Formula C8H8O4
  • Boiling Point 332.6 °C at 760 mmHg
  • Molecular Weight 168.149
  • Flash Point 150.5 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 22
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 520-45-6 (Dehydroacetic acid)
  • Hazard Symbols HarmfulXn
  • Synonyms 3-Acetyl-6-methyl-1-oxacyclohex-5-ene-2,4-dione;3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione;3-Acetyl-6-methyldihydropyrandione-2,4;3-Acetyl-6-methylpyran-2,4(3H)-dione;Aceticacid, dehydro-;Biocide 470F;DHAA;DHS;Dehydracetic acid;Methylacetopyronone;
  • PSA 60.44000
  • LogP 0.22130

Synthetic route

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
at 350℃; under 3.8 Torr;80%
1-ethoxybutyn-3-one
93279-40-4

1-ethoxybutyn-3-one

A

ethene
74-85-1

ethene

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
In tetrachloromethane at 90 - 95℃; for 1h;A n/a
B 77%
6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
2911-22-0

6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydride In tetrahydrofuran; paraffin for 1h; Heating;60%
acetic acid
64-19-7

acetic acid

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 20℃; for 6h;42%
1,1,2,2-tetramethoxyethylene
1069-12-1

1,1,2,2-tetramethoxyethylene

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

A

2,3-dihydro-2,2,3,3-tetramethoxy-6-methyl-4H-pyran-4-one
93279-41-5

2,3-dihydro-2,2,3,3-tetramethoxy-6-methyl-4H-pyran-4-one

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
In xylene for 0.666667h; Heating;A 38%
B n/a
2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

1-phenylbutan-1,3-dione
93-91-4

1-phenylbutan-1,3-dione

A

3-benzoyl-2,6-dimethyl-4-pyrone
13838-60-3

3-benzoyl-2,6-dimethyl-4-pyrone

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
at 120 - 130℃; for 4h;A 36%
B 0.49 g
acetic acid
64-19-7

acetic acid

benzene
71-43-2

benzene

A

Dehydracetic acid
520-45-6

Dehydracetic acid

B

1-phenylbutan-1,3-dione
93-91-4

1-phenylbutan-1,3-dione

Conditions
ConditionsYield
Stage #1: acetic acid; benzene With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;
Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;
A 36%
B 18%
Creatinine
60-27-5

Creatinine

acetyl chloride
75-36-5

acetyl chloride

A

N-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)acetamide
19036-49-8

N-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)acetamide

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
A 25%
B 10%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

A

Dehydracetic acid
520-45-6

Dehydracetic acid

C12H12O6

C12H12O6

C12H12O6

C12H12O6

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 4h; Ambient temperature;A n/a
B 15.6%
C 22.4%
2-methylene-4,4,5,5-tetramethyl-1,3-dioxolane
69814-59-1

2-methylene-4,4,5,5-tetramethyl-1,3-dioxolane

acetic anhydride
108-24-7

acetic anhydride

A

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
20127-81-5

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With dmap; water 1) 80 - 90 deg C, 2h, 2) 2h; Yield given. Multistep reaction;A 15%
B n/a
With dmap; water 1) 80 - 90 deg C, 2h, 2) 2h; Yield given. Multistep reaction;A n/a
B 0.07 g
acetylketene
691-45-2

acetylketene

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
at 20℃;12%
2-amino-1H-imidazol-4(5H)-one
503-86-6

2-amino-1H-imidazol-4(5H)-one

acetyl chloride
75-36-5

acetyl chloride

A

1-acetylhydantoin
25046-23-5

1-acetylhydantoin

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
A 9%
B 10%
acetyl chloride
75-36-5

acetyl chloride

A

1-acetylhydantoin
25046-23-5

1-acetylhydantoin

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
A 9%
B 10%
2-amino-5-phenyl-4-oxazolinone
2152-34-3

2-amino-5-phenyl-4-oxazolinone

acetyl chloride
75-36-5

acetyl chloride

A

Dehydracetic acid
520-45-6

Dehydracetic acid

B

2-acetamido-5-phenyl-4-oxazolinone
15381-90-5

2-acetamido-5-phenyl-4-oxazolinone

Conditions
ConditionsYield
With triethylamine In benzene from 0-5 deg C to boiling point;A 10%
B 5%
With triethylamine In benzene for 5h; from 0-5 deg C to biling point;A 10%
B 5%
1,4-dioxane
123-91-1

1,4-dioxane

pyridine
110-86-1

pyridine

Ketene
463-51-4

Ketene

A

2-methyl-10a,11-dihydro-pyrano[2,3-b]quinolizine-4,5-dione
1744-69-0

2-methyl-10a,11-dihydro-pyrano[2,3-b]quinolizine-4,5-dione

B

Dehydracetic acid
520-45-6

Dehydracetic acid

pyridine
110-86-1

pyridine

4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

acetylacetone
123-54-6

acetylacetone

Dehydracetic acid
520-45-6

Dehydracetic acid

pyridine
110-86-1

pyridine

Ketene
463-51-4

Ketene

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
es erfolgt Polymerisation;
pyridine
110-86-1

pyridine

6-methyl-pyran-2,4-dione
541-98-0

6-methyl-pyran-2,4-dione

Dehydracetic acid
520-45-6

Dehydracetic acid

pyridine
110-86-1

pyridine

acetyl chloride
75-36-5

acetyl chloride

Dehydracetic acid
520-45-6

Dehydracetic acid

4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

diethyl ether
60-29-7

diethyl ether

phenylmagnesium bromide

phenylmagnesium bromide

A

1,1-diphenylethanol
599-67-7

1,1-diphenylethanol

B

acetophenone
98-86-2

acetophenone

C

Dehydracetic acid
520-45-6

Dehydracetic acid

4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

toluene
108-88-3

toluene

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With 4-methyl-morpholine; pyridine; triethylamine Reagens 4: Natriumaethylat oder Natriumbutylat;
With basicene catalysts
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

benzene
71-43-2

benzene

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With basicene catalysts
With 4-methyl-morpholine; pyridine; triethylamine Reagens 4: Natriumaethylat oder Natriumbutylat;
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

A

3,9-Diacetyl-4,5,10-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2,8-dion
13444-23-0

3,9-Diacetyl-4,5,10-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2,8-dion

B

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With sodium phenoxide; benzene
6-methyl-pyran-2,4-dione
541-98-0

6-methyl-pyran-2,4-dione

sodium acetate
127-09-3

sodium acetate

Dehydracetic acid
520-45-6

Dehydracetic acid

6-methyl-pyran-2,4-dione
541-98-0

6-methyl-pyran-2,4-dione

acetyl chloride
75-36-5

acetyl chloride

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With aluminium trichloride; nitrobenzene
carbon suboxide
504-64-3

carbon suboxide

methylmagnesium iodide

methylmagnesium iodide

A

1,3,5-triacetyl-2,4,6-trihydroxybenzene
2161-87-7

1,3,5-triacetyl-2,4,6-trihydroxybenzene

B

Dehydracetic acid
520-45-6

Dehydracetic acid

S-ethyl acetothioacetate
3075-23-8

S-ethyl acetothioacetate

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
beim Erhitzen im Vakuum;
isoamyl acetoacetate
2308-18-1

isoamyl acetoacetate

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
bei der Destillation;
bei der Destillation unter gewoehnlichem Druck;
3-acetoxy-crotonic acid ethyl ester
29214-62-8

3-acetoxy-crotonic acid ethyl ester

A

ethyl acetoacetate
141-97-9

ethyl acetoacetate

B

ethyl acetate
141-78-6

ethyl acetate

C

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
at 233℃;
1,6-dimethyl-1,3,4,6-tetraoxohexane
1114-91-6

1,6-dimethyl-1,3,4,6-tetraoxohexane

Dehydracetic acid
520-45-6

Dehydracetic acid

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid
Dehydracetic acid
520-45-6

Dehydracetic acid

2,6-dimethylpyridin-4-ol
13603-44-6

2,6-dimethylpyridin-4-ol

Conditions
ConditionsYield
With ammonia In water at 120℃; for 0.333333h; Microwave irradiation;100%
With ammonia In water at 120℃; for 0.333333h; Microwave irradiation;100%
With ammonia In water at 120℃; for 0.333333h; microwave irradiation;100%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Dehydracetic acid
520-45-6

Dehydracetic acid

C11H13NO4

C11H13NO4

Conditions
ConditionsYield
In tert-butyl methyl ether at 20℃; for 8h;100%
zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

Dehydracetic acid
520-45-6

Dehydracetic acid

diaqua-bis(3-acetyl-3,4-dihydro-6-methyl-2,4-dioxo-2H-pyranato)zinc

diaqua-bis(3-acetyl-3,4-dihydro-6-methyl-2,4-dioxo-2H-pyranato)zinc

Conditions
ConditionsYield
In ethanol; water 40-50°C, 3-4 h; pptn. on cooling, ppt. filtration off, washing (ethanol, ether), vaccum drying (over silica gel); elem. anal.;98%
Dehydracetic acid
520-45-6

Dehydracetic acid

3-acetyl-5,6-dihydro-4-hydroxy-6-methyl-2-pyrone
18781-80-1

3-acetyl-5,6-dihydro-4-hydroxy-6-methyl-2-pyrone

Conditions
ConditionsYield
With pyridine; hydrogen; palladium on activated charcoal In benzene under 3102.9 Torr; for 40h; Ambient temperature;95%
thiosemicarbazide
79-19-6

thiosemicarbazide

Dehydracetic acid
520-45-6

Dehydracetic acid

dehydroacetic acid thiosemicarbazone

dehydroacetic acid thiosemicarbazone

Conditions
ConditionsYield
In ethanol for 2h; Heating;95%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-[(2E)-(4-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449494-00-1

(2Z)-2-[(2E)-(4-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;95%
2-aminopyridine
504-29-0

2-aminopyridine

Dehydracetic acid
520-45-6

Dehydracetic acid

C13H12N2O3

C13H12N2O3

Conditions
ConditionsYield
In ethanol for 4h; Reflux;95%
copper diacetate
142-71-2

copper diacetate

Dehydracetic acid
520-45-6

Dehydracetic acid

bis(3-acetyl-3,4-dihydro-6-methyl-2,4-dioxo-2H-pyranato)copper(II)

bis(3-acetyl-3,4-dihydro-6-methyl-2,4-dioxo-2H-pyranato)copper(II)

Conditions
ConditionsYield
In ethanol; water 40-50°C, 3-4 h; pptn. on cooling, ppt. filtration off, washing (ethanol, ether), vaccum drying (over silica gel); elem. anal.;94%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-nitrobenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one
1449493-89-3

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-nitrobenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;94%
methanol
67-56-1

methanol

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

Dehydracetic acid
520-45-6

Dehydracetic acid

[Mn(dehydroacetic acid (1-))2(CH3OH)2]*0.25H2O

[Mn(dehydroacetic acid (1-))2(CH3OH)2]*0.25H2O

Conditions
ConditionsYield
In methanol mixt. Mn(OAc)2*4H2O and ligand in MeOH was refluxed for 5 h; solid was filtered, washed with MeOH, dried under vac. overnight; elem. anal.;93%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-[(2E)-(3-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449493-93-9

(2Z)-2-[(2E)-(3-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;93%
methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

Dehydracetic acid
520-45-6

Dehydracetic acid

N-[1-(6-Methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]-L-phenylalanine methyl ester

N-[1-(6-Methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]-L-phenylalanine methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating;92%
N-butylamine
109-73-9

N-butylamine

Dehydracetic acid
520-45-6

Dehydracetic acid

3-[1-(Butylamino)ethylidene]-6-methyl-3,4-dihydro-2H-pyran-2,4-dione

3-[1-(Butylamino)ethylidene]-6-methyl-3,4-dihydro-2H-pyran-2,4-dione

Conditions
ConditionsYield
In benzene for 2h; Condensation; Isomerization; Heating;92%
pyridine
110-86-1

pyridine

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

Dehydracetic acid
520-45-6

Dehydracetic acid

(C5H5N)2(C8H7O4)2Zn

(C5H5N)2(C8H7O4)2Zn

Conditions
ConditionsYield
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.;92%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-[ (2E)-(4-bromobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449494-02-3

(2Z)-2-[ (2E)-(4-bromobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;92%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-[(2E)-(4-fluorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449493-91-7

(2Z)-2-[(2E)-(4-fluorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;91%
4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol
82-54-2

4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol

Dehydracetic acid
520-45-6

Dehydracetic acid

3-acetyl-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6-methyl-2H-pyran-2,4(3H)-dione

3-acetyl-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6-methyl-2H-pyran-2,4(3H)-dione

Conditions
ConditionsYield
In methanol at 25℃; diastereoselective reaction;91%
methanol
67-56-1

methanol

Dehydracetic acid
520-45-6

Dehydracetic acid

3,5-dioxohexanoic acid methyl ester
29736-80-9

3,5-dioxohexanoic acid methyl ester

Conditions
ConditionsYield
With magnesium at 85℃;90%
With magnesium for 16h; Reflux;81%
With magnesium for 10h; Heating;80%
With magnesium methanolate for 8h; Heating;75%
L-tyrosine methyl ester HCl
3417-91-2

L-tyrosine methyl ester HCl

Dehydracetic acid
520-45-6

Dehydracetic acid

N-[1-(6-Methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]-L-tyrosine methyl ester

N-[1-(6-Methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]-L-tyrosine methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating;90%
tryptamine hydochloride
343-94-2

tryptamine hydochloride

Dehydracetic acid
520-45-6

Dehydracetic acid

3-(1-[2-(3-indolyl)ethylamino]ethylidene)-6-methyl-2,4-pyrandione

3-(1-[2-(3-indolyl)ethylamino]ethylidene)-6-methyl-2,4-pyrandione

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol for 4h; Heating;90%
3-Methylpyridine
108-99-6

3-Methylpyridine

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

Dehydracetic acid
520-45-6

Dehydracetic acid

(C5H4NCH3)2(C8H7O4)2Zn

(C5H4NCH3)2(C8H7O4)2Zn

Conditions
ConditionsYield
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.;90%
N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2,3-dihydro-3-hydroxy-2-[(2E)-(3-methoxybenzylidene)hydrazinylidene]-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449493-95-1

(2Z)-2,3-dihydro-3-hydroxy-2-[(2E)-(3-methoxybenzylidene)hydrazinylidene]-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;90%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-methylbenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one
1449494-05-6

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-methylbenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;90%
benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

Dehydracetic acid
520-45-6

Dehydracetic acid

H2dha-bhz

H2dha-bhz

Conditions
ConditionsYield
In methanol for 4h; Reflux;90%
Dehydracetic acid
520-45-6

Dehydracetic acid

3-Ethyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
255852-63-2

3-Ethyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride In tetrahydrofuran89%
With triethylsilane; lithium perchlorate; trifluoroacetic acid Reduction;83%
With methanol; platinum Hydrogenation;
picoline
108-89-4

picoline

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

Dehydracetic acid
520-45-6

Dehydracetic acid

(C5H4NCH3)2(C8H7O4)2Zn

(C5H4NCH3)2(C8H7O4)2Zn

Conditions
ConditionsYield
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.;89%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-{[ (2E)-(pyridin-4-yl)methylidene]hydrazinylidene}-4H-furo[3,2-c]pyran-4-one
1449493-99-5

(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-{[ (2E)-(pyridin-4-yl)methylidene]hydrazinylidene}-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;89%
benzaldehyde
100-52-7

benzaldehyde

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-[(2E)-benzylidenehydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449494-04-5

(2Z)-2-[(2E)-benzylidenehydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;89%
L-valine methylester hydrochloride
6306-52-1

L-valine methylester hydrochloride

Dehydracetic acid
520-45-6

Dehydracetic acid

methyl (S,E)-3-methyl-2-(1-(6-methyl-2,4-dioxo-2H-pyran-3(4H)-ylidene)ethylamino)butanoate

methyl (S,E)-3-methyl-2-(1-(6-methyl-2,4-dioxo-2H-pyran-3(4H)-ylidene)ethylamino)butanoate

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating;88%
furfural
98-01-1

furfural

N-isocyaniminotriphenylphosphorane
73789-56-7

N-isocyaniminotriphenylphosphorane

Dehydracetic acid
520-45-6

Dehydracetic acid

(2Z)-2-{[(2E)-(furan-2-yl)methylidene]hydrazinylidene}-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
1449493-97-3

(2Z)-2-{[(2E)-(furan-2-yl)methylidene]hydrazinylidene}-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;88%

Dehydroacetic acid Chemical Properties


IUPAC Name: 3-Acetyl-6-methylpyran-2,4-dione
Canonical SMILES: CC1=CC(=O)C(C(=O)O1)C(=O)C
InChI: InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
InChIKey: PGRHXDWITVMQBC-UHFFFAOYSA-N
Molecular formula: C8H8O4
Molecular Weight: 168.15
EINECS: 212-227-4
Melting point: 111-113 °C(lit.)
Boiling Point: 332.6 °C at 760 mmHg 
Flash Point: 150.6 °C 
Index of Refraction: 1.489 
Molar Refractivity: 38.43 cm
Molar Volume: 133 cm
Surface Tension: 41.9 dyne/cm 
Density: 1.264 g/cm3 
Enthalpy of Vaporization: 57.54 kJ/mol 
Vapour Pressure: 0.000144 mmHg at 25 °C 
storage temp.: 0-6 °C
Stability: Stable. Incompatible with oxidizing agents, bases, reducing agents.
Appearance: white to light yellow crystal powder
Classification Code of Methylacetopyronone (CAS NO.520-45-6): Agricultural Chemical; Fungicide, bactericide, wood preservativ ; Tumor data

Dehydroacetic acid Uses

  Methylacetopyronone (CAS NO.520-45-6) is a pyrone derivative used as a fungicide and bactericide. It is used to reduce pickle bloating as a preservative for squash and strawberries. The sodium salt, sodium dehydroacetate, is often used in place of dehydroacetic acid because of its greater solubility in water. Industrially, it is also used as a plasticizer in a variety of synthetic resins.

Dehydroacetic acid Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1186mg/kg (1186mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 98, 1950.
mouse LD50 oral 1330mg/kg (1330mg/kg)   Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 12, Pg. 520, 1971.
rabbit LDLo skin 5gm/kg (5000mg/kg)   Journal of the American College of Toxicology. Vol. 4(3), Pg. 123, 1985.
rat LD50 oral 500mg/kg (500mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.

Dehydroacetic acid Consensus Reports

Reported in EPA TSCA Inventory.

Dehydroacetic acid Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: HarmfulXn
Risk Statements:
R22:  Harmful if swallowed 
Safety Statements:
S22:  Do not breathe dust 
WGK Germany: 1
RTECS: UP8050000

Dehydroacetic acid Specification

 Methylacetopyronone (CAS NO.520-45-6), its Synonyms are 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl- ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione, ion(1-), ; Dehydroacetic Acid ; 3-Acety;-6-methylpyran-2,4(3H)-dione ; 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one ; 3-Acetyl-6-methyl-2,4-pyrandione ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione. enol form ; 3-Acetyl-6-methyldihydropyrandione-2,4 ; 2-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid, delta-lactone .

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