1,3-Acetonedicarboxylic acid supplier

Name
1,3-Acetonedicarboxylic acid
EINECS 208-797-9
CAS No. 542-05-2
Article Data61
CAS DataBase
Density 1.499 g/cm³
Solubility Soluble in water
Melting Point 133 °C (dec.)(lit.)
Formula C₅ H₆O₅
Boiling Point 408.4 °C at 760 mmHg
Molecular Weight 146.1
Flash Point 214.9 °C
Transport Information
Appearance 44-36/37/38
Safety 22-24/25-37/39-26
Risk Codes 44-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Glutaricacid, 3-oxo- (8CI);Glutaric acid, b-oxo- (4CI);1,3-Dicarboxyacetone;3-Ketoglutaric acid;3-Oxoglutaric acid;3-Oxopentanedioic acid;Acetone-1,3-dicarboxylic acid;s-Acetonedicarboxylic acid;b-Ketoglutaric acid;b-Oxoglutaric acid;3-oxopentanedioic acid;
PSA 91.67000
LogP -0.49510

Synthetic route

: 152294-13-8
2-methoxypropane-1,3-dicarboxylic acid

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
Stage #1: 2-methoxypropane-1,3-dicarboxylic acid With sodium nitrate; lead(IV) tetraacetate at 36℃; for 2.5h; Stage #2: With zinc(II) oxalate at 36℃; for 2h; Temperature;	98.2%

: 77-92-9
citric acid

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid at -3 - 30℃; for 7h;	93.1%
With potassium bromate; hydrogenchloride; water Rate constant; Thermodynamic data; kobs vs. substrate concentration at 35 deg C and vs. HCl concentration at 40 deg C; ΔH(excit), ΔS(excit) (temp.-range 30-45 deg C);
With potassium bromate; cerium (IV) sulfate In water at 26℃; oscillatory reaction, effect of the storing time;

: 3-amino-3-amido-glutaric acid

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With aluminum oxide; hypochlorous acid phenyl ester; sodium chloride In 5,5-dimethyl-1,3-cyclohexadiene at 6 - 55℃; for 4.5h; Temperature;	91%

: 53798-96-2
1,5-dimethyl citrate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid

: 115996-74-2
2-hydroxypropane-1,2,3-tricarboxylic acid

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid 1 h 20 deg C, then 3 h 50 deg C;

: 105-50-0
diethyl 1,3-acetonedicarboxylate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With potassium bromate; sulfuric acid; cerous nitrate at 25 - 35℃; Thermodynamic data; activation energy, dual frequency oscillating reaction;

: 77-92-9
citric acid

A: 64-18-6
formic acid

B: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With cerium (IV) sulfate; phosphoric acid In water at 25℃; Kinetics; Mechanism; Thermodynamic data; CH3COOH, other neutral salts and temperatures, ΔE(activ.);

: 77-92-9
citric acid

A: 542-05-2
acetonedicarboxylic acid

B: 124-38-9
carbon dioxide

Conditions

Conditions	Yield
With ruthenium trichloride; perchloric acid; bromate salt; sulfuric acid; mercury(II) diacetate In water at 19.9 - 39.9℃; Rate constant;
With potassium bromate; perchloric acid; mercury(II) diacetate In acetic acid at 29.84℃; Kinetics; Further Variations:; Reagents;

: 7664-93-9
sulfuric acid

: 77-92-9
citric acid

: 542-05-2
acetonedicarboxylic acid

: 7664-93-9
sulfuric acid

: 77-92-9
citric acid

KMnO4: KMnO4

: 542-05-2
acetonedicarboxylic acid

...Expand

: 77-92-9
citric acid

Mn2O3+H2O: Mn2O3+H2O

: 542-05-2
acetonedicarboxylic acid

: 77-92-9
citric acid

potassium permanganate: potassium permanganate

A: 542-05-2
acetonedicarboxylic acid

B: 124-38-9
carbon dioxide

...Expand

: 77-92-9
citric acid

acid: acid

A: 542-05-2
acetonedicarboxylic acid

B: 64-19-7
acetic acid

Conditions

Conditions	Yield
bei der Einw.von Aspergillus niger;

...Expand

: 7732-18-5
water

: 7705-08-0
iron(III) chloride

: 77-92-9
citric acid

Mn2(SO4)3: Mn2(SO4)3

A: 542-05-2
acetonedicarboxylic acid

B: 67-64-1
acetone

Conditions

Conditions	Yield
Reaktion des Trinatriumcitrats beim Belichten;

...Expand

: 7732-18-5
water

: 77-92-9
citric acid

Mn2(SO4)3: Mn2(SO4)3

K2SO4: K2SO4

A: 542-05-2
acetonedicarboxylic acid

B: 67-64-1
acetone

Conditions

Conditions	Yield
Reaktion des Trinatriumcitrats beim Belichten;

...Expand

: 77-92-9
citric acid

A: 542-05-2
acetonedicarboxylic acid

B CO2: CO2

Conditions

Conditions	Yield
With N-Bromosuccinimide; perchloric acid; mercury(II) diacetate; palladium dichloride at 35℃; Rate constant; Kinetics; Thermodynamic data; ΔE(a), ΔH(excit.), ΔS(excit.), ΔG(excit.);

: 77-92-9
citric acid

96 percent H2SO4: 96 percent H2SO4

A: 542-05-2
acetonedicarboxylic acid

B CO: CO

...Expand

ammonium citrate: ammonium citrate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With bacterium pyocyaneus

: 77-92-9
citric acid

ammonium citrate: ammonium citrate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With Aspergillus niger

citric acid-monohydrate: citric acid-monohydrate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid at -5℃;

sugar-lime: sugar-lime

: 542-05-2
acetonedicarboxylic acid

: 77-92-9
citric acid

A: 542-05-2
acetonedicarboxylic acid

B carbon monoxide; water: carbon monoxide; water

Conditions

Conditions	Yield
With sulfuric acid

: 53798-96-2
1,5-dimethyl citrate

absolute sulfuric acid: absolute sulfuric acid

A: 542-05-2
acetonedicarboxylic acid

B carbon monoxide: carbon monoxide

...Expand

: 861570-37-8
2,4-dibenzoyl-3-oxo-glutaric acid

alkalies: alkalies

A: 542-05-2
acetonedicarboxylic acid

B: 65-85-0
benzoic acid

...Expand

: 7664-93-9
sulfuric acid

: 77-92-9
citric acid

A: 542-05-2
acetonedicarboxylic acid

B CO: CO

Conditions

Conditions	Yield
wasserfreie Citronensaeure reagiert;

...Expand

: 56345-96-1
dimethyl 3-cyano-3-hydroxy-1,5-pentanedioate

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid 2: concentrated sulfuric acid; sodium nitrite 3: sulfuric acid monohydrate View Scheme

: citric acid β-amide-α,α'-dimethyl ester

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; sodium nitrite 2: sulfuric acid monohydrate View Scheme

: 51964-39-7
2-(sulfooxy)propane-1,2,3-tricarboxylic acid

: 542-05-2
acetonedicarboxylic acid

Conditions

Conditions	Yield
With phosphorus pentoxide for 4h;	64 g

: 542-05-2
acetonedicarboxylic acid

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 25299-40-5
1,5-bis(dimethylamino)-1,4-pentadien-3-one

Conditions

Conditions	Yield
at 70℃; for 1h;	100%

: 542-05-2
acetonedicarboxylic acid

: 100-46-9
benzylamine

: 28957-72-4
N-benzyltropinone

Conditions

Conditions	Yield
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride In water at 0℃; for 0.333333h; Stage #2: acetonedicarboxylic acid; benzylamine With sodium hydroxide; disodium hydrogenphosphate In water for 2h; pH=1 - ~ 4.5;	100%
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride In water at 0℃; for 0.333333h; Stage #2: acetonedicarboxylic acid; benzylamine With sodium hydroxide; disodium hydrogenphosphate In water pH=4 - 5; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride In water for 0.333333h; Stage #2: acetonedicarboxylic acid; benzylamine With hydrogenchloride; sodium hydroxide; disodium hydrogenphosphate In water pH=4.5; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride; water for 1h; Heating / reflux; Stage #2: acetonedicarboxylic acid; benzylamine With sodium acetate In water at 0 - 50℃; for 6h; Stage #3: With sodium hydroxide In water
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride In water at 20℃; for 0.5h; Stage #2: acetonedicarboxylic acid; benzylamine With hydrogenchloride; sodium hydroxide; disodium hydrogenphosphate In water at 20℃; pH=4 - 5; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;

: 542-05-2
acetonedicarboxylic acid

: 95-54-5
1,2-diamino-benzene

: 24107-34-4
2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepine

Conditions

Conditions	Yield
With hydrogenchloride In chloroform at 20℃; for 8h;	97%
With PPA; acrylic acid for 3h; Ambient temperature;	94%

: 542-05-2
acetonedicarboxylic acid

: 10521-08-1
pyran-2,4,6-trione

Conditions

Conditions	Yield
With acetic anhydride at 0℃; for 3h;	95.3%
With acetic anhydride at 0℃; for 15h;	93%
With acetic anhydride; acetic acid at 0 - 10℃; for 3h;	86%

: 71-23-8
propan-1-ol

: 542-05-2
acetonedicarboxylic acid

: 53630-64-1
dipropyl 1,3-acetonedicarboxylate

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;	93%
With hydrogenchloride at 0℃;	85%
With fuming sulphuric acid; citric acid
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
Steglich Esterification;

: 542-05-2
acetonedicarboxylic acid

: 108-46-3
recorcinol

: 6950-82-9
2-(7-hydroxy-2-oxochromen-4-yl)acetic acid

Conditions

Conditions	Yield
With sulfuric acid In water at 20℃; for 4h;	91%
With sulfuric acid In water at 0 - 20℃;	70%
With sulfuric acid	64%

: 542-05-2
acetonedicarboxylic acid

: 111-30-8
Glutaraldehyde

: 100-46-9
benzylamine

: 2291-58-9
9-benzyl-9-azabicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
Stage #1: acetonedicarboxylic acid; Glutaraldehyde; benzylamine With sodium phosphate dibasic dodecahydrate In water at 20℃; for 24h; Cooling with ice; Stage #2: With hydrogenchloride In water at 50℃; for 2h; pH=3; pH-value; Temperature; Reagent/catalyst;	91%
With hydrogenchloride In water at 60℃;	69%
Stage #1: acetonedicarboxylic acid; Glutaraldehyde; benzylamine In water at 20℃; Stage #2: With acetic acid In water at 20℃;	61%

...Expand

: 4894-26-2
3,4-dihydro-β-carboline

: 542-05-2
acetonedicarboxylic acid

: 80884-85-1
α-<1,2,3,4-tetrahydro-β-carbolinyl-(1)>acetoacetic acid

Conditions

Conditions	Yield
In methanol; water for 1h;	90%

: 542-05-2
acetonedicarboxylic acid

: 638-37-9
butanedial

: 100-46-9
benzylamine

: 28957-72-4
N-benzyltropinone

Conditions

Conditions	Yield
Stage #1: acetonedicarboxylic acid; butanedial; benzylamine With sodium acetate In water at 3 - 50℃; for 7.75h; Stage #2: With hydrogenchloride In water at 20 - 25℃;	90%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 931-53-3
Cyclohexyl isocyanide

: 1187-42-4, 18514-52-8, 20344-79-0
1,1-diamino-2,2-ethenedicarbonitrile

: 5-(cyclohexylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions

Conditions	Yield
In water at 20℃; for 1h;	90%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 38336-04-8
O-benzylethanolamine

: 34160-24-2
2,5-dimethoxytetrahydrofuran

: 1428580-80-6
8-(2-(benzyloxy)-ethyl)-8-azabicyclo[3.2.1]octan-3-one

Conditions

Conditions	Yield
Stage #1: 2,5-dimethoxytetrahydrofuran With hydrogenchloride In water at 0 - 80℃; Inert atmosphere; Stage #2: acetonedicarboxylic acid; O-benzylethanolamine With hydrogenchloride; sodium acetate In water at 5 - 45℃; pH=4.6 - 5.3;	90%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 111-30-8
Glutaraldehyde

: 9-azabicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
With ammonium hydroxide In water at 0 - 20℃; for 48h; Robinson-Schopf Reaction;	90%

: 542-05-2
acetonedicarboxylic acid

: 7159-96-8
ethyl N-(3-hydroxyphenyl)carbamate

: 343310-64-5
ethyl 2-(7-(ethoxycarbonylamino)-2-oxo-2H-chromen-4-yl)acetic acid

Conditions

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 8h;	89%
With 70percent H2SO4 at 20℃; for 8h; Pechmann reaction;	63%
With sulfuric acid at 0 - 20℃; Pechmann condensation;	41%

: 696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran

: 542-05-2
acetonedicarboxylic acid

: 100-46-9
benzylamine

: 28957-72-4
N-benzyltropinone

Conditions

Conditions	Yield
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride; water at 70℃; for 1h; Stage #2: acetonedicarboxylic acid; benzylamine With hydrogenchloride; sodium acetate In water at 0 - 20℃;	88%
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride In water at 80℃; for 2h; Stage #2: acetonedicarboxylic acid; benzylamine With hydrogenchloride; sodium acetate In water at 0 - 55℃; for 14h; Stage #3: With sodium hydroxide In water at 20℃;	72%
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran With hydrogenchloride; water for 1h; Reflux; Stage #2: acetonedicarboxylic acid; benzylamine With sodium acetate In water at 0 - 50℃; for 6h; Stage #3: With sodium hydroxide In water pH=12;	61%

...Expand

: 696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran

: 542-05-2
acetonedicarboxylic acid

: 106-40-1
4-bromo-aniline

: (1R,5S)-8-(4-bromophenyl)-8-azabicyclo[3.2.1]octan-3-one

Conditions

Conditions	Yield
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran; acetonedicarboxylic acid With 4-(1-(4-iodophenyl)azetidin-3-yl)morpholine In water at 20℃; for 0.5h; Stage #2: 4-bromo-aniline In methanol; water at 0℃; for 0.333333h;	88%
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran; acetonedicarboxylic acid With hydrogenchloride In water at 20℃; for 0.5h; Stage #2: 4-bromo-aniline In methanol; water at 0 - 20℃;	88%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 35162-34-6
N-methyl-3,4-dimethoxyaniline

: N1,N5-bis(3,4-dimethoxyphenyl)-N1,N5-dimethyl-3-oxopentanediamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	87%

: 77898-24-9
3-chloro-4-fluoro-N-methylaniline

: 542-05-2
acetonedicarboxylic acid

: N1,N5-bis(3-chloro-4-fluorophenyl)-N1,N5-dimethyl-3-oxopentanediamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	87%

: 542-05-2
acetonedicarboxylic acid

: 108-24-7
acetic anhydride

: 10521-08-1
pyran-2,4,6-trione

Conditions

Conditions	Yield
With acetic acid In toluene at 5 - 10℃;	87%

: 542-05-2
acetonedicarboxylic acid

A: 102526-10-3
1,1,1,3,3,5,5,5-octafluoropentane

B: 102526-11-4
fluoroanhydride of 3,3,5,5,5-pentafluoropentanoic acid

Conditions

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 20℃; for 12h; steel autoclave;	A 85% B n/a

: 542-05-2
acetonedicarboxylic acid

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 1187-42-4, 18514-52-8, 20344-79-0
1,1-diamino-2,2-ethenedicarbonitrile

: 5-(1,1-dimethylethylamino)-1,6-dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile

Conditions

Conditions	Yield
In water at 20℃; for 1h;	85%

...Expand

: 542-05-2
acetonedicarboxylic acid

: copper dichloride

: 3-ketoglutaric acid copper (II) salt

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water at 20℃; for 24h;	83%

: 542-05-2
acetonedicarboxylic acid

: silver nitrate

: silver acetonedicarboxylate

Conditions

Conditions	Yield
With hexan-1-amine for 0.5h; Cooling with ice;	82%

: 542-05-2
acetonedicarboxylic acid

: 108-24-7
acetic anhydride

: 66315-03-5
4-Hydroxy-3H-pyran-2,6-dione

Conditions

Conditions	Yield
With acetic acid at 8 - 20℃; for 3h;	80%

: 542-05-2
acetonedicarboxylic acid

: 66315-03-5
4-Hydroxy-3H-pyran-2,6-dione

Conditions

Conditions	Yield
With acetic anhydride; acetic acid at 8 - 20℃; for 3h;	80%

: 542-05-2
acetonedicarboxylic acid

: 14542-93-9
1,1,3,3-tetramethylbutane isonitrile

: 1187-42-4, 18514-52-8, 20344-79-0
1,1-diamino-2,2-ethenedicarbonitrile

: 1,6-dihydro-6,6-dimethyl-5-[(1,1,3,3-tetramethylbutyl)amino]pyrazine-2,3-dicarbonitrile

Conditions

Conditions	Yield
In water at 20℃; for 2h;	80%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 88333-03-3, 10340-91-7
Benzyl isocyanide

: 1187-42-4, 18514-52-8, 20344-79-0
1,1-diamino-2,2-ethenedicarbonitrile

: 1200592-28-4
1,6-dihydro-6,6-dimethyl-5-[(phenylmethyl)amino]pyrazine-2,3-dicarbonitrile

Conditions

Conditions	Yield
In water at 20℃; for 2h;	80%

...Expand

: 696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran

: 542-05-2
acetonedicarboxylic acid

: 3287-99-8, 39110-74-2
benzylamine hydrochloride

: 83393-23-1
8-benzyl-3-oxo-8-azabicyclo[3.2.1]octane hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; disodium hydrogenphosphate at 25 - 30℃;	80%

...Expand

1,3-Acetonedicarboxylic acid Chemical Properties

IUPAC Name: 3-Oxopentanedioic acid
Molecular Formula: C₅H₆O₅
Molecular Weight: 146.10 g/mol
Canonical SMILES: C(C(=O)CC(=O)O)C(=O)O
InChI: InChI=1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
EINECS: 208-797-9
Product Categories: Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; API intermediates
Water Solubility: soluble
Sensitive: Hygroscopic
XLogP3-AA: -0.7
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Tautomer Count: 5
Exact Mass; 146.021523
MonoIsotopic Mass: 146.021523
Topological Polar Surface Area: 91.7
Heavy Atom Count: 10
Complexity: 153
Molar Volume: 97.4 cm³
Polarizability: 11.24×10^-24cm³
Surface Tension: 67.9 dyne/cm
Density: 1.499 g/cm³
Flash Point: 214.9 °C
Enthalpy of Vaporization: 72.46 kJ/mol
Boiling Point: 408.4 °C at 760 mmHg
Storage temperature: 2-8 °C
Melting Point: 133 °C (dec.)(lit.)
Vapour Pressure of 1,3-Acetonedicarboxylic acid (CAS NO.542-05-2): 8.2E-08 mmHg at 25 °C

1,3-Acetonedicarboxylic acid Uses

1,3-Acetonedicarboxylic acid (CAS NO.542-05-2) may be used as a building block in organic chemistry.

1,3-Acetonedicarboxylic acid Production

Use citric acid as raw material, in the presence of concentrated sulphuric acid , 1,3-Acetonedicarboxylic acid (CAS NO.542-05-2) is obtain from de-formic acid .

1,3-Acetonedicarboxylic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 44-36/37/38
R44: Risk of explosion if heated under confinement.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26-36
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S37/39: Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany of 1,3-Acetonedicarboxylic acid (CAS NO.542-05-2): 3

1,3-Acetonedicarboxylic acid Specification

1,3-Acetonedicarboxylic acid (CAS NO.542-05-2), its Synonyms are 3-Ketoglutaric acid ; 3-Oxoglutaric acid ; 3-Oxopentanedioic acid ; Pentanedioic acid, 3-oxo- . It is white to off-white powder.

Product Name

1,3-Acetonedicarboxylic acid

Synthetic route

1,3-Acetonedicarboxylic acid Chemical Properties

1,3-Acetonedicarboxylic acid Uses

1,3-Acetonedicarboxylic acid Production

1,3-Acetonedicarboxylic acid Safety Profile

1,3-Acetonedicarboxylic acid Specification

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