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520-45-6

Basic Information
CAS No.: 520-45-6
Name: Dehydroacetic acid
Article Data: 73
Molecular Structure:
Molecular Structure of 520-45-6 (Dehydroacetic acid)
Formula: C8H8O4
Molecular Weight: 168.149
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;
EINECS: 208-293-9
Density: 1.264 g/cm3
Melting Point: 111-113 °C(lit.)
Boiling Point: 332.6 °C at 760 mmHg
Flash Point: 150.5 °C
Solubility: 500mg/L at 25℃
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 22
PSA: 60.44000
LogP: 0.22130
Synthetic route
5394-63-8

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

520-45-6

Dehydracetic acid

Conditions
ConditionsYield
at 350℃; under 3.8 Torr;80%
93279-40-4

1-ethoxybutyn-3-one

A

74-85-1

ethene

B

520-45-6

Dehydracetic acid

Conditions
ConditionsYield
In tetrachloromethane at 90 - 95℃; for 1h;A n/a
B 77%
2911-22-0

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

520-45-6

Dehydracetic acid

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

acetic acid

520-45-6

Dehydracetic acid

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

1,1,2,2-tetramethoxyethylene

5394-63-8

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

A

93279-41-5

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

B

520-45-6

Dehydracetic acid

Conditions
ConditionsYield
In xylene for 0.666667h; Heating;A 38%
B n/a
5394-63-8

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

93-91-4

1-phenylbutan-1,3-dione

A

13838-60-3

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

B

520-45-6

Dehydracetic acid

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

acetic acid

71-43-2

benzene

A

520-45-6

Dehydracetic acid

B

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%
60-27-5

Creatinine

75-36-5

acetyl chloride

A

19036-49-8

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

B

520-45-6

Dehydracetic acid

Conditions
ConditionsYield
A 25%
B 10%
674-82-8

4-methyleneoxetan-2-one

A

520-45-6

Dehydracetic acid

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%
69814-59-1

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

108-24-7

acetic anhydride

A

20127-81-5

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

B

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
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Chemistry


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

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.

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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

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 .