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28564-83-2

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28564-83-2 Usage

Uses

2,3-Dihydro-3,5-dihydroxy-6-methyl-4-pyrone is a new DNA strand-breaking substance. It induced DNA strand breaking in a dose- and time-dependent manner. It was active to break DNA strands at pH 7.4 and 9.4. It is a characteristic volatile product of the Maillard reaction

Check Digit Verification of cas no

The CAS Registry Mumber 28564-83-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,5,6 and 4 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 28564-83:
(7*2)+(6*8)+(5*5)+(4*6)+(3*4)+(2*8)+(1*3)=142
142 % 10 = 2
So 28564-83-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O4/c1-3-5(8)6(9)4(7)2-10-3/h4,7-8H,2H2,1H3

28564-83-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 4H-PYRAN-4-ONE,2,3-DIHYDRO-3,5-DIHYDROXY-6-METHYL-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:28564-83-2 SDS

28564-83-2Synthetic route

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

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

2,3-dihydro-3,5-dihydroxy-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%
piperidine
110-89-4

piperidine

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

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

A

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

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

B

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

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

C

piperidino-hexose-reductone
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%
D-Galactose
59-23-4

D-Galactose

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
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%
D-glucose
50-99-7

D-glucose

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
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;
D-Mannose
3458-28-4

D-Mannose

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
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%
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

2,2-dimethylpropylamine
5813-64-9

2,2-dimethylpropylamine

A

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

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

B

2-acetyl-neopentylpyrrole
114853-23-5

2-acetyl-neopentylpyrrole

C

2-(2-hydroxyacetyl)-1-neopentylpyrrole
114853-24-6

2-(2-hydroxyacetyl)-1-neopentylpyrrole

D

5-hydroxymethyl-1-neopentylpyrrole-2-carbaldehyde
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;
1-deoxy-1-(N-methylanilino)-D-fructose
71143-97-0

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

A

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

(2-furyl)methyl alcohol

B

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

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

C

ethanol
64-17-5

ethanol

D

acetic acid
64-19-7

acetic acid

E

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

F

N-methylaniline
100-61-8

N-methylaniline

Conditions
ConditionsYield
at 250℃; for 0.25h; Product distribution;
1-deoxy-1-dibenzylamino-D-fructose
69712-22-7

1-deoxy-1-dibenzylamino-D-fructose

A

1-benzyl-1H-pyrrole
2051-97-0

1-benzyl-1H-pyrrole

B

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

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

C

N-methyldibenzylamine
102-05-6

N-methyldibenzylamine

D

benzaldehyde
100-52-7

benzaldehyde

E

acetic acid
64-19-7

acetic acid

F

dibenzylamine
103-49-1

dibenzylamine

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

D-glucose

glycine
56-40-6

glycine

A

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

(2-furyl)methyl alcohol

B

2,5-Dimethylpyrrole
625-84-3

2,5-Dimethylpyrrole

C

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

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

D

2-Acetylpyrrole
1072-83-9

2-Acetylpyrrole

E

acetic acid
64-19-7

acetic acid

F

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
In water at 95℃; for 2h; Product distribution; other reaction time, other temperature;
D-Glucose
2280-44-6

D-Glucose

A

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

(2-furyl)methyl alcohol

B

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

formyl-2 methyl-5 pyrrole

C

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

5-hydroxymethyl-2-furfuraldehyde

D

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

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

E

2-Acetylpyrrole
1072-83-9

2-Acetylpyrrole

Conditions
ConditionsYield
With L-Lysine hydrochloride; sodium hydrogencarbonate In water at 75℃; for 24h; Product distribution; pH 6.5; other times;
1-<(2'-carboxy)pyrrolidinyl>-1-deoxy-D-fructose

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

A

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

3-(1'-pyrrolidinyl)-2-butanone

B

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

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

C

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

1-(pyrrolidin-1-yl)butan-1-one

D

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

1-(1'-pyrrolidinyl)-2-propanone

E

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

1-(1'-pyrrolidinyl)-2-butanone

F

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

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

Conditions
ConditionsYield
at 250℃; for 0.00555556h; Product distribution; var. temp., var. time, also D-glucose/proline;
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

acetic acid
64-19-7

acetic acid

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

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

Conditions
ConditionsYield
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

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

A

morpholine
110-91-8

morpholine

B

3-morpholinoacetone
6704-35-4

3-morpholinoacetone

C

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

1,2-(N'N'-dimorpholino)-1-propene

D

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

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

E

acetic acid
64-19-7

acetic acid

F

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

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

Conditions
ConditionsYield
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.
N-β-D-glucopyranosyl-3-chloro-4-methylaniline

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

A

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

5-hydroxymethyl-2-furfuraldehyde

B

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

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

Conditions
ConditionsYield
With potassium disulphite Mechanism; Irradiation; degradation in watermelon bait;
D-Glucose
2280-44-6

D-Glucose

glycine
56-40-6

glycine

A

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

5-hydroxymethyl-2-furfuraldehyde

B

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

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

C

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

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

Conditions
ConditionsYield
In water for 2h; Heating; pH 5;
D-glucose
50-99-7

D-glucose

A

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

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

B

5-hydroxymaltol
1073-96-7

5-hydroxymaltol

Conditions
ConditionsYield
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;
D-glucose
50-99-7

D-glucose

A

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

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

B

furaneol
3658-77-3

furaneol

C

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

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

Conditions
ConditionsYield
With glycine In water for 4h; Maillard reaction; Heating;A n/a
B n/a
C 7.1 mg
D-Glucose
2280-44-6

D-Glucose

bovine serum albumin

bovine serum albumin

A

furaneol
3658-77-3

furaneol

B

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

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

C

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

4-hydroxy-5-methyl-3[2H]-furanone

Conditions
ConditionsYield
In phosphate buffer; water at 37℃; for 2191.5h; pH=7.4; Maillard reaction;
1-deoxy-2,3-D-erythro-hexo-2,3-diulose

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

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

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

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

C

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

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

F

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

1-hydroxy-butane-2,3-dione

G

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

3,4-dihydroxy-2-oxobutanal

H

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

4-hydroxy-2-oxobutanal

I

acetic acid
64-19-7

acetic acid

J

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

Conditions
ConditionsYield
With L-alanin; diethylenetriaminopentaacetic acid at 37℃; Mechanism; Kinetics; Temperature; Reagent/catalyst; Maillard reaction; aq. phosphate buffer; Inert atmosphere;
1-deoxy-2,3-D-erythro-hexo-2,3-diulose

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

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

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

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

C

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

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

D

erythrulose
40031-31-0

erythrulose

E

glyceric acid
473-81-4

glyceric acid

F

acetaldehyde
75-07-0

acetaldehyde

G

Glycolaldehyde
141-46-8

Glycolaldehyde

H

Glyceraldehyde
56-82-6

Glyceraldehyde

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

D-glucose

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

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

Conditions
ConditionsYield
Stage #1: D-glucose With piperidine In ethanol Reflux; Inert atmosphere;
Stage #2: With acetic acid In ethanol Heating; Inert atmosphere;
D-maltose
69-79-4

D-maltose

A

furfural
98-01-1

furfural

B

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

1-(2-furyl)-1-ethanone

C

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

5-hydroxymethyl-2-furfuraldehyde

D

Maltol
118-71-8

Maltol

E

D-Fructose
57-48-7

D-Fructose

F

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

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

G

D-glucose
50-99-7

D-glucose

K

1-deoxymaltosone

1-deoxymaltosone

L

3-deoxymaltosone

3-deoxymaltosone

M

3-deoxypentos-2-ulose

3-deoxypentos-2-ulose

N

1,4-dideoxyhexosulose

1,4-dideoxyhexosulose

Conditions
ConditionsYield
With L-alanin In water at 130℃; for 5h; pH=5.0; Time; Sealed tube;
D-maltose
69-79-4

D-maltose

A

furfural
98-01-1

furfural

B

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

1-(2-furyl)-1-ethanone

C

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

5-hydroxymethyl-2-furfuraldehyde

D

Maltol
118-71-8

Maltol

E

isomaltol
3420-59-5

isomaltol

F

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

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

G

D-glucose
50-99-7

D-glucose

J

1-deoxymaltosone

1-deoxymaltosone

K

3-deoxymaltosone

3-deoxymaltosone

L

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

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

M

3-deoxypentos-2-ulose

3-deoxypentos-2-ulose

N

1,4-dideoxyhexosulose

1,4-dideoxyhexosulose

Conditions
ConditionsYield
With L-lysine In water at 130℃; for 5h; pH=5.0; Sealed tube;
D-maltose
69-79-4

D-maltose

A

furfural
98-01-1

furfural

B

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

1-(2-furyl)-1-ethanone

C

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

5-hydroxymethyl-2-furfuraldehyde

D

Maltol
118-71-8

Maltol

E

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

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

F

D-glucose
50-99-7

D-glucose

I

1-deoxymaltosone

1-deoxymaltosone

J

3-deoxymaltosone

3-deoxymaltosone

K

3-deoxypentos-2-ulose

3-deoxypentos-2-ulose

Conditions
ConditionsYield
With L-proline In water at 130℃; for 5h; pH=5.0; Sealed tube;
D-glucose
50-99-7

D-glucose

A

furfural
98-01-1

furfural

B

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

5-hydroxymethyl-2-furfuraldehyde

C

D-Fructose
57-48-7

D-Fructose

D

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

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

H

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

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

I

3-deoxypentos-2-ulose

3-deoxypentos-2-ulose

J

1,4-dideoxyhexosulose

1,4-dideoxyhexosulose

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

2-methyl-4-oxo-4H-pyran-3-yl acetate

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

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

Conditions
ConditionsYield
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
Maltol
118-71-8

Maltol

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

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

Conditions
ConditionsYield
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
dihydromaltol acetate
38877-20-2

dihydromaltol acetate

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

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

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

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

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

DDMP-5-BoC

DDMP-5-BoC

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 3h;95%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

propionic acid anhydride
123-62-6

propionic acid anhydride

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

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

Conditions
ConditionsYield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;94.75%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

isopentanoyl chloride
108-12-3

isopentanoyl chloride

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

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

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;94.51%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

C15H14O5

C15H14O5

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;94.51%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

isobutyryl chloride
79-30-1

isobutyryl chloride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;94.39%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

C22H38O5

C22H38O5

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;94.39%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;94.35%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; for 10h; Inert atmosphere;94.3%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

phenylacetyl chloride
103-80-0

phenylacetyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; for 10h; Inert atmosphere;93.29%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;93.28%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

benzoyl chloride
98-88-4

benzoyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;92.33%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

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

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

Conditions
ConditionsYield
With pyridine In toluene at 5 - 20℃; for 8h; Inert atmosphere;92.29%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

palmitic anhydride
623-65-4

palmitic anhydride

C22H38O5

C22H38O5

Conditions
ConditionsYield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;92.29%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

3-Methylbenzoyl chloride
1711-06-4

3-Methylbenzoyl chloride

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

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

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 8h; Inert atmosphere;92.24%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

propionyl chloride
79-03-8

propionyl chloride

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

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

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;91.5%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

Isovaleric anhydride
1468-39-9

Isovaleric anhydride

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

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

Conditions
ConditionsYield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;91.45%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

cinnamic anhydride
21947-71-7

cinnamic anhydride

C15H14O5

C15H14O5

Conditions
ConditionsYield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;91.45%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

benzyl chloroformate
501-53-1

benzyl chloroformate

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere;91%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

isobutyryl chloride
79-30-1

isobutyryl chloride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;90.85%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;89.69%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

n-valeryl chloride
638-29-9

n-valeryl chloride

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

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

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;88.94%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

isopentanoyl chloride
108-12-3

isopentanoyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃; for 6h;88.78%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

benzoic acid anhydride
93-97-0

benzoic acid anhydride

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

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

Conditions
ConditionsYield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;88.49%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

Cinnamoyl chloride
102-92-1

Cinnamoyl chloride

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

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

Conditions
ConditionsYield
With triethylamine In chloroform at -5 - 20℃; for 10h; Inert atmosphere;87.6%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;87.28%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

propionyl chloride
79-03-8

propionyl chloride

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

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

Conditions
ConditionsYield
With N,N-diisopropylmethylamine In chloroform at 0 - 20℃; for 6h; Inert atmosphere;87.11%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

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

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

Conditions
ConditionsYield
With pyridine In toluene at -5 - 20℃; for 8h; Inert atmosphere;86.44%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

propionic acid anhydride
123-62-6

propionic acid anhydride

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

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

Conditions
ConditionsYield
With triethylamine In acetonitrile at -5 - 20℃; for 8h; Inert atmosphere;84.96%
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one
28564-83-2

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

2-phenylethyl chloroformate
57913-41-4

2-phenylethyl chloroformate

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

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

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

28564-83-2Relevant articles and documents

Degradation of 3-Chloro-p-toluidine Hydrochloride in Watermelon Bait. Identification and Chemical Characterization of Novel N-Glucoside and Oxopropanimine

Tawara, Jeanne N.,Johnston, John J.,Goodall, Margaret J.

, p. 3983 - 3988 (1996)

Stability of the avicide 3-chloro-p-toluidine hydrochloride (CPTH) in watermelon bait was assessed. When exposed to light, the presence of CPTH accelerated nonenzymic browning (Maillard) reactions and degradation of the watermelon matrix. The addition of potassium metabisulfite appeared to hinder bait degradation. These experiments resulted in the identification and chemical characterization of two novel CPTH derivatives: N-β-D-glucopyranosyl-3-chloro-4-methylaniline and N-(3-chloro4-methylphenyl)-2-oxopropanimine.

Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4: H -pyran-4-one to scavenge free radicals

Bai, Bing,Cai, Lili,Chen, Zhifei,Fu, Yufeng,Liu, Qiang,Ma, Yuping,Sun, Zhitao,Wang, Qingfu,Xi, Gaolei,Zhao, Zhiwei

, p. 34456 - 34461 (2021/12/02)

It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.

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

-

, (2020/02/14)

The invention relates to a synthesis method of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, which creatively uses maltose as an initial raw material to synthesize the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. The synthesis method comprises: firstly, generating maltol acetate through acetylation; secondly, carrying out catalytic hydrogenation to obtain dihydromaltol acetate; adding asilylation reagent again to synthesize a dihydromaltol acetate silyl enol ether compound; increasing reaction activity of 5-position methylene and introducing hydroxy to the 5-position through peroxidation to obtain 5-hydroxy-dihydromaltol acetate; and performing a deacetylation reaction to obtain the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one that is a target compound. According to the technical scheme, the five-step reaction process is simple, the yield is higher than 80%, the purity of the final product reaches 98% or above, large-scale production can be conducted, and the method has a wide application prospect.

Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds

Kanzler, Clemens,Haase, Paul T.,Schestkowa, Helena,Kroh, Lothar W.

, p. 7829 - 7837 (2016/10/31)

It is well established that a wide range of reductones is formed in the course of the Maillard reaction and that these substances contribute to the oxidative stability of food. The aim of this study was to analyze 12 important heterocyclic intermediates with and without reductone structure as well as structurally related substances under equal conditions to compare their antioxidant properties in detail. For this purpose, five methods were selected including photometrical methods such as the trolox equivalent antioxidant capacity assay and an electron paramagnetic resonance spectroscopic method. Reductones with furan-3-one structure and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one were reducing in all assays, whereas isomaltol and maltol did not react in assays based on the reduction of metal ions because of their complexing abilities. The introduction of protecting groups to the free hydroxyl functions of selected reductones could nearly eliminate their reducing abilities. In addition, the oxidation products of the different reductive heterocycles were compared after treatment with iodine. Mainly short-chained organic acids such as lactic, glycolic, and glyceric acid are formed as result of the degradation, which indicates 1,3-dicarbonyl cleavage reactions of corresponding tricarbonyl compounds as intermediates of the oxidation.

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