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

Name
2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one
EINECS
CAS No. 28564-83-2
Article Data24
CAS DataBase
Density 1.482 g/cm³
Solubility
Melting Point
Formula C₆H₈O₄
Boiling Point 281.1 °C at 760 mmHg
Molecular Weight 144.127
Flash Point 121.7 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

Conditions	Yield
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

Conditions	Yield
In ethanol; water; acetic acid at 75℃; for 20h; Heating;	A 21% B 8.8% C 20%

...Expand

: 59-23-4
D-Galactose

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
10 days of incubation under physiological pH and temperature; Yield given. Yields of byproduct given;

...Expand

: 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

Conditions	Yield
at 250℃; for 0.25h; Product distribution;

...Expand

: 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

Conditions	Yield
at 250℃; for 0.25h; Product distribution;

...Expand

: 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

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

...Expand

: 470-23-5, 470-24-6, 10247-46-8, 10489-79-9, 35673-97-3, 36441-90-4, 36441-92-6, 36468-68-5, 37500-17-7, 40461-86-7, 40461-87-8, 41579-20-8, 41846-98-4, 41846-99-5, 41847-00-1, 41847-01-2, 41847-02-3, 41847-03-4, 41847-04-5, 41847-05-6, 41847-06-7, 41847-51-2, 41847-52-3, 42744-42-3
D-fructose

: 107-95-9
3-amino propanoic acid

A: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

B: 19872-46-9
2,3-Dihydro-3,4-dihydroxy-5-acetylfuran

Conditions

Conditions	Yield
at 150℃; for 0.0333333h;	A n/a B 0.5 mg

...Expand

: 2280-44-6
D-Glucose

A: 98-00-0
(2-furyl)methyl alcohol

B: 1192-79-6
formyl-2 methyl-5 pyrrole

C: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

D: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

E: 1072-83-9
2-Acetylpyrrole

Conditions

Conditions	Yield
With L-Lysine hydrochloride; sodium hydrogencarbonate In water at 75℃; for 24h; Product distribution; pH 6.5; other times;

...Expand

: 1-<(2'-carboxy)pyrrolidinyl>-1-deoxy-D-fructose

A: 97073-15-9
3-(1'-pyrrolidinyl)-2-butanone

B: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C: 33527-93-4
1-(pyrrolidin-1-yl)butan-1-one

D: 54151-38-1
1-(1'-pyrrolidinyl)-2-propanone

E: 97073-14-8
1-(1'-pyrrolidinyl)-2-butanone

F: 2-hydroxy-1-(1'-pyrrolidinyl)-1-buten-3-one

Conditions

Conditions	Yield
at 250℃; for 0.00555556h; Product distribution; var. temp., var. time, also D-glucose/proline;

...Expand

: 492-62-6
alpha-D-glucopyranose

: 64-19-7
acetic acid

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With piperidine 1.) C2H5OH, reflux, 1.5 h, 2.) C2H5OH, 90 deg C, 22 h; Yield given. Multistep reaction;

: (R)-3,4,5,6-Tetrahydroxy-1-morpholin-4-yl-hexan-2-one

A: 110-91-8
morpholine

B: 6704-35-4
3-morpholinoacetone

C: 51060-15-2
1,2-(N'N'-dimorpholino)-1-propene

D: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

E: 64-19-7
acetic acid

F: 2-hydroxy-1-(N-morpholino)-1-buten-3-one

Conditions

Conditions	Yield
With other Amadori compounds at 250℃; for 20h; Mechanism;	A 32.6 % Chromat. B 10.1 % Chromat. C 1.9 % Chromat. D 1.9 % Chromat. E 21.6 % Chromat. F 10.1 % Chromat.

...Expand

: N-β-D-glucopyranosyl-3-chloro-4-methylaniline

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With potassium disulphite Mechanism; Irradiation; degradation in watermelon bait;

: 2280-44-6
D-Glucose

: 56-40-6
glycine

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 17678-20-5
4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

C: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

D: 2-acetyl-6-hydroxy-7-(hydroxymethyl)-1,5,6,7-tetrahydro-4H-azepinone

Conditions

Conditions	Yield
In water for 2h; Heating; pH 5;

...Expand

: 50-99-7
D-glucose

A: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

B: 1073-96-7
5-hydroxymaltol

Conditions

Conditions	Yield
Stage #1: D-glucose With piperidine In ethanol for 2h; Condensation; Heating; Stage #2: With mercaptoacetic acid In ethanol for 24h; Elimination; Heating; Title compound not separated from byproducts;

: 50-99-7
D-glucose

A: 17678-20-5
4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

B: 3658-77-3
furaneol

C: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With glycine In water for 4h; Maillard reaction; Heating;	A n/a B n/a C 7.1 mg

...Expand

: 2280-44-6
D-Glucose

bovine serum albumin: bovine serum albumin

A: 3658-77-3
furaneol

B: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C: 19322-27-1
4-hydroxy-5-methyl-3[2H]-furanone

Conditions

Conditions	Yield
In phosphate buffer; water at 37℃; for 2191.5h; pH=7.4; Maillard reaction;

...Expand

: 1-deoxy-2,3-D-erythro-hexo-2,3-diulose

A: 849585-22-4
LACTIC ACID

B: 17678-20-5
4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

C: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

D: 533-50-6, 35007-64-8, 40031-31-0, 496-55-9
D-erythrulose

E: 473-81-4, 600-19-1, 6000-40-4, 28305-26-2
D-glyceric acid

F: 114794-47-7
1-hydroxy-butane-2,3-dione

G: 25691-81-0
3,4-dihydroxy-2-oxobutanal

H: 28119-61-1
4-hydroxy-2-oxobutanal

I: 64-19-7
acetic acid

J: 116-09-6
hydroxy-2-propanone

Conditions

Conditions	Yield
With L-alanin; diethylenetriaminopentaacetic acid at 37℃; Mechanism; Kinetics; Temperature; Reagent/catalyst; Maillard reaction; aq. phosphate buffer; Inert atmosphere;

...Expand

: 1-deoxy-2,3-D-erythro-hexo-2,3-diulose

A: 849585-22-4
LACTIC ACID

B: 17678-20-5
4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

C: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

D: 40031-31-0
erythrulose

E: 473-81-4
glyceric acid

F: 75-07-0
acetaldehyde

G: 141-46-8
Glycolaldehyde

H: 56-82-6
Glyceraldehyde

Conditions

Conditions	Yield
With L-alanin at 50℃; for 48h; pH=7.4; aq. phosphate buffer; in air;

...Expand

: D-glucose

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
Stage #1: D-glucose With piperidine In ethanol Reflux; Inert atmosphere; Stage #2: With acetic acid In ethanol Heating; Inert atmosphere;

: 69-79-4
D-maltose

A: 98-01-1
furfural

B: 1192-62-7
1-(2-furyl)-1-ethanone

C: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

D: 118-71-8
Maltol

E: 57-48-7
D-Fructose

F: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

G: 50-99-7
D-glucose

H: 643-71-0, 25990-59-4, 26187-86-0, 26345-59-5, 49865-02-3, 54142-77-7, 81844-97-5, 81844-98-6, 81845-00-3, 89576-70-5, 90457-64-0, 1854-25-7
D-glucosone

I: 4084-27-9, 30382-30-0, 50455-94-2, 82399-12-0, 4134-97-8
3-deoxygalactosone

J: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

K: 1-deoxymaltosone

L: 3-deoxymaltosone

M: 3-deoxypentos-2-ulose

N: 1,4-dideoxyhexosulose

Conditions

Conditions	Yield
With L-alanin In water at 130℃; for 5h; pH=5.0; Time; Sealed tube;

...Expand

: 69-79-4
D-maltose

A: 98-01-1
furfural

B: 1192-62-7
1-(2-furyl)-1-ethanone

C: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

D: 118-71-8
Maltol

E: 3420-59-5
isomaltol

F: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

G: 50-99-7
D-glucose

H: 4084-27-9, 30382-30-0, 50455-94-2, 82399-12-0, 4134-97-8
3-deoxygalactosone

I: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

J: 1-deoxymaltosone

K: 3-deoxymaltosone

L: 1-deoxy-2,3-D-erythro-hexo-2,3-diulose

M: 3-deoxypentos-2-ulose

N: 1,4-dideoxyhexosulose

Conditions

Conditions	Yield
With L-lysine In water at 130℃; for 5h; pH=5.0; Sealed tube;

...Expand

: 69-79-4
D-maltose

A: 98-01-1
furfural

B: 1192-62-7
1-(2-furyl)-1-ethanone

C: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

D: 118-71-8
Maltol

E: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

F: 50-99-7
D-glucose

G: 4084-27-9, 30382-30-0, 50455-94-2, 82399-12-0, 4134-97-8
3-deoxygalactosone

H: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

I: 1-deoxymaltosone

J: 3-deoxymaltosone

K: 3-deoxypentos-2-ulose

Conditions

Conditions	Yield
With L-proline In water at 130℃; for 5h; pH=5.0; Sealed tube;

...Expand

: 50-99-7
D-glucose

A: 98-01-1
furfural

B: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

C: 57-48-7
D-Fructose

D: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

E: 643-71-0, 25990-59-4, 26187-86-0, 26345-59-5, 49865-02-3, 54142-77-7, 81844-97-5, 81844-98-6, 81845-00-3, 89576-70-5, 90457-64-0, 1854-25-7
D-glucosone

F: 4084-27-9, 30382-30-0, 50455-94-2, 82399-12-0, 4134-97-8
3-deoxygalactosone

G: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

H: 1-deoxy-2,3-D-erythro-hexo-2,3-diulose

I: 3-deoxypentos-2-ulose

J: 1,4-dideoxyhexosulose

Conditions

Conditions	Yield
With L-alanin In water at 130℃; for 5h; pH=5.0; Time; Sealed tube;	A n/a B n/a C Ca. 5 %Chromat. D n/a E n/a F n/a G n/a H n/a I n/a J n/a

...Expand

: 28787-36-2
2-methyl-4-oxo-4H-pyran-3-yl acetate

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: palladium on activated charcoal; hydrogen / ethyl acetate / 8 h / 760.05 Torr 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -70 °C 2.2: 0.5 h 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 0.5 h 4.1: sodium methylate; methanol / 10 h / 20 °C View Scheme

: 118-71-8
Maltol

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ethanol / 6 h / 100 °C 2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 8 h / 760.05 Torr 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -70 °C 3.2: 0.5 h 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 0.5 h 5.1: sodium methylate; methanol / 10 h / 20 °C View Scheme

: 38877-20-2
dihydromaltol acetate

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -70 °C 1.2: 0.5 h 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 2.2: 0.5 h 3.1: sodium methylate; methanol / 10 h / 20 °C View Scheme

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 24424-99-5
di-tert-butyl dicarbonate

: DDMP-5-BoC

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 3h;	95%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 123-62-6
propionic acid anhydride

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

Conditions

Conditions	Yield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;	94.75%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 108-12-3
isopentanoyl chloride

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

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;	94.51%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 102-92-1
Cinnamoyl chloride

: C15H14O5

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;	94.51%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 79-30-1
isobutyryl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	94.39%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 112-67-4
n-hexadecanoyl chloride

: C22H38O5

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	94.39%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;	94.35%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 21615-34-9
2-Methoxybenzoyl chloride

: 2,3-dihydro-(3,5-di(o-methoxybenzoyloxy))-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 10h; Inert atmosphere;	94.3%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 103-80-0
phenylacetyl chloride

: 2,3-dihydro-(3,5-di(phenylacetoxy))-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 10h; Inert atmosphere;	93.29%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 75-36-5
acetyl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	93.28%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	92.33%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 97-72-3
2-Methylpropionic anhydride

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

Conditions

Conditions	Yield
With pyridine In toluene at 5 - 20℃; for 8h; Inert atmosphere;	92.29%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 623-65-4
palmitic anhydride

: C22H38O5

Conditions

Conditions	Yield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;	92.29%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 1711-06-4
3-Methylbenzoyl chloride

: 2,3-dihydro-(3,5-di(m-methylbenzoyloxy))-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 8h; Inert atmosphere;	92.24%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 79-03-8
propionyl chloride

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

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;	91.5%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 1468-39-9
Isovaleric anhydride

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

Conditions

Conditions	Yield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;	91.45%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 21947-71-7
cinnamic anhydride

: C15H14O5

Conditions

Conditions	Yield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;	91.45%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 501-53-1
benzyl chloroformate

: benzyl 3-hydroxy-6-methyl-4-oxo-2,3-dihydro-4H-pyran-5-yl carbonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere;	91%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 79-30-1
isobutyryl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	90.85%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 75-36-5
acetyl chloride

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	89.69%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 638-29-9
n-valeryl chloride

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

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;	88.94%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 108-12-3
isopentanoyl chloride

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

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; for 6h;	88.78%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 93-97-0
benzoic acid anhydride

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

Conditions

Conditions	Yield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;	88.49%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 102-92-1
Cinnamoyl chloride

: 2,3-dihydro-(3,5-di(cinnamoyloxy))-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With triethylamine In chloroform at -5 - 20℃; for 10h; Inert atmosphere;	87.6%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;	87.28%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 79-03-8
propionyl chloride

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

Conditions

Conditions	Yield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;	87.11%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 97-72-3
2-Methylpropionic anhydride

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

Conditions

Conditions	Yield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;	86.44%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 123-62-6
propionic acid anhydride

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

Conditions

Conditions	Yield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;	84.96%

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

: 57913-41-4
2-phenylethyl chloroformate

: 3-hydroxy-6-methyl-4-oxo-3,4-dihydro-2H-pyran-5-yl 2-phenylethyl carbonate

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane at 60℃; for 6h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	84.9%

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

Product Name

2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one

Synthetic route

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

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