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591-11-7

Basic Information
CAS No.: 591-11-7
Name: BETA-ANGELICA LACTONE
Article Data: 75
Molecular Structure:
Molecular Structure of 591-11-7 (BETA-ANGELICA LACTONE)
Formula: C5H6 O2
Molecular Weight: 98.1014
Synonyms: 2-Pentenoicacid, 4-hydroxy-, g-lactone (6CI,7CI); 2-Oxo-5-methyl-2,5-dihydrofuran; 2-Penten-4-olide;4-Hydroxy-2-pentenoic acid g-lactone; 4-Hydroxypent-2-enoic acid lactone; 4-Methyl-2-buten-4-olide;5-Methyl-2(5H)-furanone; 5-Methyl-5H-furan-2-one; NSC 655; D1-Angelica lactone; a,b-Angelica lactone; b-Angelica lactone; g-Methyl-Da,b-butenolide
Density: 1.095g/cm3
Melting Point: <-17 °C
Boiling Point: 210°C at 760 mmHg
Flash Point: 78.9°C
Safety: Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.
PSA: 26.30000
LogP: 0.48790
Synthetic route
1617-32-9

(E)-3-pentenoic acid

591-11-7

5-methyl-5H-furan-2-one

Conditions
ConditionsYield
Stage #1: (E)-3-pentenoic acid With Oxalyl bromide; dimethyl sulfoxide In dichloromethane at -10 - 20℃; for 1.16667h; Inert atmosphere;
Stage #2: With potassium carbonate In dichloromethane-d2; water at 20℃; for 5h; Inert atmosphere;
93%
Stage #1: (E)-3-pentenoic acid With oxalyl dichloride; 1,1'-sulfinylbisbenzene In dichloromethane at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: With 18-crown-6 ether; potassium carbonate In dichloromethane at -78 - 20℃; for 5h; Reagent/catalyst; Inert atmosphere;
85%
Stage #1: (E)-3-pentenoic acid With oxalyl dichloride; 1,1'-sulfinylbisbenzene In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: With 18-crown-6 ether; potassium carbonate In dichloromethane at 20℃; for 5h; Inert atmosphere;
85%
With (M*,3aS*,3a'S*)-3,3',3a',4,4',5,5'-octahydro-3,3,3',3'-tetraisopropyl-6,6'-spirobi[6H-cyclopent[c]isoxazole]; palladium diacetate; p-benzoquinone In dichloromethane at 30℃; for 24h; Inert atmosphere;71%
201230-82-2

carbon monoxide

74785-04-9

(2R*,3Z)-4-Iodo-3-buten-2-ol

591-11-7

5-methyl-5H-furan-2-one

Conditions
ConditionsYield
With potassium carbonate; hydrazine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 35℃; under 2280 Torr; for 72h;95%
5204-64-8

3-pentenoic acid

591-11-7

5-methyl-5H-furan-2-one

Conditions
ConditionsYield
Stage #1: 3-pentenoic acid With Oxalyl bromide; dimethyl sulfoxide In dichloromethane at -10 - 20℃; Inert atmosphere;
Stage #2: With sodium hydroxide In dichloromethane; water for 5h; Reagent/catalyst;
93%
123-76-2

levulinic acid

A

591-11-7

5-methyl-5H-furan-2-one

B

591-12-8

5-methyl-2-furanone

C

10008-73-8

5-methylenedihydrofuran-2-one

Conditions
ConditionsYield
With silylated SiO2 catalyst In water at 250℃; under 760.051 Torr; for 0.8h; Reagent/catalyst; Inert atmosphere; Flow reactor;
123-76-2

levulinic acid

A

591-11-7

5-methyl-5H-furan-2-one

B

591-12-8

5-methyl-2-furanone

Conditions
ConditionsYield
With H-ZSM5/SiO2 at 129.84℃; under 75.0075 Torr; Reagent/catalyst; Temperature;A 33%
B 64%
bei der Destillation;
With montmorillonite K 10 at 165℃; under 50 Torr; Overall yield = 92 %; Overall yield = 15.6 g;
123-76-2

levulinic acid

591-11-7

5-methyl-5H-furan-2-one

Conditions
ConditionsYield
bei der Destillation; Behandeln mit einer konz. Kaliumcarbonatloesung;
Multi-step reaction with 2 steps
1: 60 percent / H3PO4 / Heating
2: 43 percent / Et3N / benzene / 15 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: H3PO4
2: 79 percent / Et3N / 4 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: phosphoric acid / 175 °C
2: triethylamine / ethanol / 12 h
View Scheme
Stage #1: levulinic acid under 50 Torr;
Stage #2: With triethylamine at 80℃;
539-88-8

4-oxopentanoic acid ethyl ester

A

591-11-7

5-methyl-5H-furan-2-one

B

108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With formic acid; UN-No2881 ex. Kataleuna at 275℃;A 7%
B 30%
591-12-8

5-methyl-2-furanone

591-11-7

5-methyl-5H-furan-2-one

Conditions
ConditionsYield
With triethylamine at 100℃; for 4h;79%
With triethylamine In toluene at 60℃; for 6h;60%
With triethylamine at 75℃; for 2h;55%
98-00-0

(2-furyl)methyl alcohol

67-56-1

methanol

A

591-11-7

5-methyl-5H-furan-2-one

B

591-12-8

5-methyl-2-furanone

C

624-45-3

levulinic acid methyl ester

D

13679-46-4

2-(methoxymethyl)furan

Conditions
ConditionsYield
With zeolite H-beta at 110℃; for 1.5h; Autoclave;A n/a
B n/a
C 10.1 %Chromat.
D 18.3 %Chromat.
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Chemistry

Molecular Formula: C5H6O2
Molar mass: 98.0999 g/mol
EINECS: 209-700-2
Density: 1.095 g/cm3
Flash Point: 78.9 °C
Index of Refraction: 1.459
Boiling Point: 210 °C at 760 mmHg
Vapour Pressure: 0.197 mmHg at 25°C
Structure of 5-Methyl-2(5H)-furanone (591-11-7):

XLogP3-AA: 0.6
H-Bond Donor: 0
H-Bond Acceptor: 2
Systematic Name of 5-Methyl-2(5H)-furanone (591-11-7): 5-Methyl-5H-furan-2-one 
SMILES: O=C\1OC(/C=C/1)C 
InChI: InChI=1/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3 
InChIKey: BGLUXFNVVSVEET-UHFFFAOYAU 
Std. InChI: InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3 
Std. InChIKey: BGLUXFNVVSVEET-UHFFFAOYSA-N

Toxicity Data With Reference

1.    

ipr-mus LD50:750 mg/kg

    APTOA6    Acta Pharmacologica et Toxicologica. 2 (1946),109.
2.    

orl-cat LDLo:500 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 36 (1929),355.

Safety Profile

Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Specification

 5-Methyl-2(5H)-furanone (591-11-7) also can be called Angelica lactone ; 2(5H)-furanone, 5-methyl- ; .DELTA.1-Angelica lactone ; .alpha.,.beta.-Angelica lactone ; 4-Hydroxy-2-pentenoic Acid g-Lactone ;and ; 4-Hydroxy-2-pentenoic acid .gamma.-lactone .