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28564-83-2

Basic Information
CAS No.: 28564-83-2
Name: 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one
Article Data: 24
Molecular Structure:
Molecular Structure of 28564-83-2 (2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one)
Formula: C6H8O4
Molecular Weight: 144.127
Synonyms: 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(4H)-pyranone;2,3-Dihydro-3,5-dihydroxy-6-methyl-4-pyranone;2,3-Dihydro-3,5-dihydroxy-6-methyl-4-pyrone;2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one;3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one;3-Hydroxy-2,3-dihydromaltol;5,6-Dihydro-3,5-dihydroxy-2-methyl-4H-pyran-4-one;5-Hydroxy-5,6-dihydromaltol;Pyranone;
Density: 1.482 g/cm3
Boiling Point: 281.1 °C at 760 mmHg
Flash Point: 121.7 °C
PSA: 66.76000
LogP: -0.26390
Synthetic route

2,3-dihydro-3-hydroxy-5-acetoxy-6-methyl-4H-pyran-4-one

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions
ConditionsYield
With methanol; sodium methylate at 20℃; for 10h;97.22%
110-89-4

piperidine

1-deoxy-D-erythro-2,3-hexodiulose

A

17678-20-5

4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

B

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C

34421-11-9, 39994-32-6

piperidino-hexose-reductone

Conditions
ConditionsYield
In ethanol; water; acetic acid at 75℃; for 20h; Heating;A 21%
B 8.8%
C 20%
59-23-4

D-Galactose

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: D-Galactose With morpholine In ethanol at 60℃; for 3h;
Stage #2: With chloroacetic acid In ethanol at 75℃; for 30h;
20.3%
50-99-7

D-glucose

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: D-glucose With pyrrolidine In ethanol at 60℃; for 4h;
Stage #2: With acetic acid In ethanol at 75℃; for 40h;
16.5%
Stage #1: D-glucose With piperidine In ethanol at 90℃; for 1.5h;
Stage #2: With acetic acid In ethanol for 22h; Reflux;
7%
Stage #1: D-glucose With piperidine; acetic acid; triethylamine at 20 - 70℃;
Stage #2: With mercaptoacetic acid In ethanol at 75℃; for 20.6667h;
3458-28-4

D-Mannose

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: D-Mannose With diethylamine In ethanol at 60℃; for 2h;
Stage #2: With acetic acid In ethanol at 75℃; for 20h;
12.4%
492-62-6

alpha-D-glucopyranose

5813-64-9

2,2-dimethylpropylamine

A

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

B

114853-23-5

2-acetyl-neopentylpyrrole

C

114853-24-6

2-(2-hydroxyacetyl)-1-neopentylpyrrole

D

114853-25-7

5-hydroxymethyl-1-neopentylpyrrole-2-carbaldehyde

Conditions
ConditionsYield
10 days of incubation under physiological pH and temperature; Yield given. Yields of byproduct given;
71143-97-0

1-deoxy-1-(N-methylanilino)-D-fructose

A

98-00-0

(2-furyl)methyl alcohol

B

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C

64-17-5

ethanol

D

64-19-7

acetic acid

E

93-61-8

N-methyl-N-phenylformamide

F

100-61-8

N-methylaniline

Conditions
ConditionsYield
at 250℃; for 0.25h; Product distribution;
69712-22-7

1-deoxy-1-dibenzylamino-D-fructose

A

2051-97-0

1-benzyl-1H-pyrrole

B

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C

102-05-6

N-methyldibenzylamine

D

100-52-7

benzaldehyde

E

64-19-7

acetic acid

F

103-49-1

dibenzylamine

Conditions
ConditionsYield
at 250℃; for 0.25h; Product distribution;
50-99-7

D-glucose

56-40-6

glycine

A

98-00-0

(2-furyl)methyl alcohol

B

625-84-3

2,5-Dimethylpyrrole

C

28564-83-2

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

D

1072-83-9

2-Acetylpyrrole

E

64-19-7

acetic acid

F

802294-64-0

propionic acid

Conditions
ConditionsYield
In water at 95℃; for 2h; Product distribution; other reaction time, other temperature;
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Specification

The 4H-Pyran-4-one,2,3-dihydro-3,5-dihydroxy-6-methyl- is an organic compound with the formula C6H8O4. The IUPAC name of this chemical is 3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one. With the CAS registry number 28564-83-2, it is also named as Pyranone. The product's classification code is Mutation data.

Physical properties about 4H-Pyran-4-one,2,3-dihydro-3,5-dihydroxy-6-methyl- are: (1)ACD/LogP: -0.42; (2)ACD/LogD (pH 5.5): -0.42; (3)ACD/LogD (pH 7.4): -0.43; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 14; (7)ACD/KOC (pH 7.4): 13.82; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 44.76 Å2; (12)Index of Refraction: 1.578; (13)Molar Refractivity: 32.27 cm3; (14)Molar Volume: 97.2 cm3; (15)Polarizability: 12.79×10-24cm3; (16)Surface Tension: 67.1 dyne/cm; (17)Density: 1.482 g/cm3; (18)Flash Point: 121.7 °C; (19)Enthalpy of Vaporization: 60.34 kJ/mol; (20)Boiling Point: 281.1 °C at 760 mmHg; (21)Vapour Pressure: 0.000433 mmHg at 25°C.

Preparation: this chemical can be prepared by πperidine and 1-deoxy-D-erythro-2,3-hexodiulose. This reaction will need solvent ethanol, H2O and acetic acid. The reaction time is 20 hours by heating. The yield is about 20%.



Uses of 4H-Pyran-4-one,2,3-dihydro-3,5-dihydroxy-6-methyl-: it can be used to produce 5-hydroxy-2-methyl-4-propylamino-6H-pyran-3-one by heating. It will need reagent acetic acid and solvent tetrahydrofuran with reaction time of 20 min. The yield is about 42%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1C(/O)=C(\OCC1O)C
(2)InChI: InChI=1/C6H8O4/c1-3-5(8)6(9)4(7)2-10-3/h4,7-8H,2H2,1H3
(3)InChIKey: VOLMSPGWNYJHQQ-UHFFFAOYAV
(4)Std. InChI: InChI=1S/C6H8O4/c1-3-5(8)6(9)4(7)2-10-3/h4,7-8H,2H2,1H3
(5)Std. InChIKey: VOLMSPGWNYJHQQ-UHFFFAOYSA-N