Product Name

  • Name

    3-Hydroxy-2-methyl-4H-pyran-4-one

  • EINECS 204-271-8
  • CAS No. 118-71-8
  • Article Data49
  • CAS DataBase
  • Density 1.348 g/cm3
  • Solubility 1.2 g/100 mL (25 °C) in water
  • Melting Point 160-164 °C(lit.)
  • Formula C6H6O3
  • Boiling Point 284.7 °C at 760 mmHg
  • Molecular Weight 126.112
  • Flash Point 127.32 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 26-37/39
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 118-71-8 (3-Hydroxy-2-methyl-4H-pyran-4-one)
  • Hazard Symbols HarmfulXn
  • Synonyms 4H-Pyran-4-one,3-hydroxy-2-methyl-;2-Methyl-3-hydroxy-4-pyranone;2-Methyl-3-hydroxy-4-pyrone;2-Methyl-3-hydroxypyran-4-one;2-Methyl-3-hydroxypyrone;3-Hydroxy-2-methyl-1,4-pyrone;3-Hydroxy-2-methyl-4-pyranone;3-Hydroxy-2-methyl-4H-pyran-4-one;3-Hydroxy-2-methyl-g-pyrone;E 636;Larixic acid;Larixin (plant growth regulator);Larixinic acid;NSC 2829;NSC 404458;Palatone;Veltol;3-Hydroxy-2-methyl-4H-pyran-4-on;Maltol;
  • PSA 50.44000
  • LogP 0.65380

Synthetic route

methyl maltol barium

methyl maltol barium

A

Maltol
118-71-8

Maltol

B

barium sulfate

barium sulfate

Conditions
ConditionsYield
With sodium sulfate In water at 26℃; for 3h; Temperature; Time; Concentration;A 88.5%
B 99.8%
C15H26O3Si
1198597-46-4

C15H26O3Si

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With potassium acetate In water; N,N-dimethyl-formamide at 25℃; for 20h;92%
3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one
152547-41-6

3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 8h; Inert atmosphere;90%
C6H8O4

C6H8O4

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With sodium hydroxide In water at -5 - 30℃; pH=2 - 3;80.5%
1-(2-furyl)ethanol
4208-64-4

1-(2-furyl)ethanol

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With tert-butylhypochlorite In acetic acid 1.) 25 deg C, 2 h, 2.) 90 deg C, 4 h;75%
With chlorine In methanol; water 1.) -5 deg C; 2.) 90-95 deg C, 3.5 h;71%
With chlorine In methanol; water at 90 - 95℃; for 3.5h; Rearrangement;71%
4,6-dimethoxy-2-methyl-2H-pyran-3(6H)-one
63493-69-6

4,6-dimethoxy-2-methyl-2H-pyran-3(6H)-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With sulfuric acid at 25℃; for 0.333333h;74%
2-(1-hydroxyethyl)-2,3,5-trimethoxy-2,5-dihydrofuran
67171-01-1

2-(1-hydroxyethyl)-2,3,5-trimethoxy-2,5-dihydrofuran

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With sulfuric acid at 25℃; for 4h;67%
In sulfuric acid67%
Multi-step reaction with 2 steps
1: 77 percent / formic acid / methanol / 0.17 h / 20 °C
2: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C
View Scheme
trans-4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one
72690-06-3

trans-4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With acetic acid for 1.5h; Heating;66%
4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one
66212-70-2

4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With acetic acid65%
6-methoxy-2-methyl-2H-pyran-3(6H)-one
41728-10-3

6-methoxy-2-methyl-2H-pyran-3(6H)-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With chlorine In acetic acid 1.) 10 deg C, 30 min; 2.) reflux 1.5 h;56%
With sodium hydroxide; chlorine In water; acetic acid56%
Multi-step reaction with 2 steps
1: Cl2, triethylamine / CH2Cl2 / 1.) -10 deg C, 30 min; 2.) 10 deg C, 25 min
2: 66 percent / acetic acid / 1.5 h / Heating
View Scheme
1-(2-furyl)ethanol
4208-64-4

1-(2-furyl)ethanol

A

Maltol
118-71-8

Maltol

B

potassium bromide

potassium bromide

Conditions
ConditionsYield
With sodium bromide; chlorine In tetrahydrofuran; waterA 55%
B n/a
4-bromo-6-hydroxy-2-methyl-2H-pyran-3(6H)-one
66187-06-2

4-bromo-6-hydroxy-2-methyl-2H-pyran-3(6H)-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
In phosphoric acid34%
6-ethoxy-4,5-epoxy-3-oxo-2-methyltetrahydropyran
60546-72-7

6-ethoxy-4,5-epoxy-3-oxo-2-methyltetrahydropyran

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
In water9.5%
methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose
2592-53-2

methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranoside-4-ulose

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1h; Ambient temperature;60 mg
3-(β-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one
20847-13-6

3-(β-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With hydrogenchloride6 mg
With almond β-glucosidase at 37℃; for 1h; pH=7.5; aq. buffer; Enzymatic reaction;
3-(β-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one
20847-13-6

3-(β-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one

A

Maltol
118-71-8

Maltol

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;
soyasaponin βg
553664-53-2

soyasaponin βg

A

Maltol
118-71-8

Maltol

B

soyasaponin I
51330-27-9

soyasaponin I

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 4℃;A 4.4 mg
B 57.4 mg
4-(α-D-glocopyranosyloxy)-2-hydroxy-2-methyl-2H-pyran-3(6H)-one
95263-68-6

4-(α-D-glocopyranosyloxy)-2-hydroxy-2-methyl-2H-pyran-3(6H)-one

A

Maltol
118-71-8

Maltol

B

β-D-glucose
492-61-5

β-D-glucose

Conditions
ConditionsYield
enzymic hydrolysis;
1-(N-L-triptophanyl)-1-deoxy-D-fructose
87251-66-9

1-(N-L-triptophanyl)-1-deoxy-D-fructose

A

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

5-hydroxymethyl-2-furfuraldehyde

B

Maltol
118-71-8

Maltol

C

isomaltol
3420-59-5

isomaltol

D

α-carboline
244-76-8

α-carboline

E

L-Tryptophan
73-22-3

L-Tryptophan

Conditions
ConditionsYield
In water at 95℃; under 750.06 - 450036 Torr; Rate constant; Product distribution; various pressure; ΔV*;
thymidine diphosphate 4-keto-6-deoxy-α-D-glucose
16752-71-9

thymidine diphosphate 4-keto-6-deoxy-α-D-glucose

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With potassium phosphate buffer for 0.333333h; pH=3.6; Decomposition;
cellulose

cellulose

A

Maltol
118-71-8

Maltol

B

2-hydroxy-3-methylcyclopent-2-en-1-one
80-71-7

2-hydroxy-3-methylcyclopent-2-en-1-one

C

levoglucosan
498-07-7

levoglucosan

Conditions
ConditionsYield
With air at 400 - 450℃; Oxidation; Formation of xenobiotics;
Eucalyptus grandis wood

Eucalyptus grandis wood

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
Decomposition; Formation of xenobiotics; pyrolysis;
trichloro-acetic acid 2-methyl-4-oxo-4H-pyran-3-yl ester

trichloro-acetic acid 2-methyl-4-oxo-4H-pyran-3-yl ester

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With lithium perchlorate; potassium carbonate In acetonitrile for 1.5h; Electrolysis; Hg cathode, Pt anode, -1.0 V (vs SCE);
isomaltol O-methyl ether
3420-58-4

isomaltol O-methyl ether

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / NaHCO3, Br2 / methanol / 1.) -30 deg C; 2.) room temp., 2 h
2: 100 percent / NaBH4 / methanol / 15 - 25 °C
3: 67 percent / H2SO4 / 4 h / 25 °C
View Scheme
Multi-step reaction with 4 steps
1: 75 percent / NaHCO3, Br2 / methanol / 1.) -30 deg C; 2.) room temp., 2 h
2: 100 percent / NaBH4 / methanol / 15 - 25 °C
3: 77 percent / formic acid / methanol / 0.17 h / 20 °C
4: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C
View Scheme
2-acetyl-2,3,5-trimethoxy-2,5-dihydrofuran
67171-02-2

2-acetyl-2,3,5-trimethoxy-2,5-dihydrofuran

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / NaBH4 / methanol / 15 - 25 °C
2: 67 percent / H2SO4 / 4 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH4 / methanol / 15 - 25 °C
2: 77 percent / formic acid / methanol / 0.17 h / 20 °C
3: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C
View Scheme
2-methoxy-3,4-dichloro-6-methyl tetrahydropyran-5-one
71280-24-5

2-methoxy-3,4-dichloro-6-methyl tetrahydropyran-5-one

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With sodium hydroxide In sulfuric acid
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
In tetrahydrofuran; BrCl; water
1-(2-furyl)ethanol
4208-64-4

1-(2-furyl)ethanol

A

Maltol
118-71-8

Maltol

B

3-hydroxy-2-methyl-γ -pyrone (maltol)

3-hydroxy-2-methyl-γ -pyrone (maltol)

Conditions
ConditionsYield
In tetrahydrofuran; water; chlorine
2-(1-hydroxyethyl)-3-methoxy furan

2-(1-hydroxyethyl)-3-methoxy furan

Maltol
118-71-8

Maltol

Conditions
ConditionsYield
With chlorine In methanol; water
Maltol
118-71-8

Maltol

benzyl bromide
100-39-0

benzyl bromide

3-O-benzylmaltol
61049-69-2

3-O-benzylmaltol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.25h; Inert atmosphere;100%
Stage #1: Maltol; benzyl bromide In N,N-dimethyl-formamide at 80℃; for 0.25h;
Stage #2: With potassium carbonate In N,N-dimethyl-formamide for 1h;
100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;100%
Maltol
118-71-8

Maltol

benzyl chloride
100-44-7

benzyl chloride

3-O-benzylmaltol
61049-69-2

3-O-benzylmaltol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 5h; Reflux;99.4%
With potassium carbonate In methanol for 1h; Reflux;98%
With sodium hydroxide In methanol Heating / reflux;95%
Maltol
118-71-8

Maltol

methyl iodide
74-88-4

methyl iodide

3-methoxy-2-methyl-4-pyrone
4780-14-7

3-methoxy-2-methyl-4-pyrone

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Reflux;99.4%
With potassium carbonate In acetone for 6h; Reflux;99%
With potassium carbonate In acetone for 3h; Reflux;99.4%
Maltol
118-71-8

Maltol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one
152547-41-6

3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;99%
With 1H-imidazole In dichloromethane at 23℃; for 2h; Inert atmosphere;99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;98%
Maltol
118-71-8

Maltol

[ReOCl3(PPh3)2]

[ReOCl3(PPh3)2]

[ReOCl2(3-hydroxy-2-methyl-4H-pyran-4-one(1-))(PPh3)]

[ReOCl2(3-hydroxy-2-methyl-4H-pyran-4-one(1-))(PPh3)]

Conditions
ConditionsYield
In dichloromethane suspn. Ru colmplex and maltol in CH2Cl2 was refluxed for 4 h; soln. was kept at -15°C for 7 days, ppt. was filtered off, washedwith n-hexane and dried in vacuo; elem. anal.;99%
Maltol
118-71-8

Maltol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

C22H24O3Si

C22H24O3Si

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 23℃; for 1.5h; Inert atmosphere;99%
Maltol
118-71-8

Maltol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

3-((4-methoxybenzyl)oxy)-2-methyl-4H-pyran-4-one

3-((4-methoxybenzyl)oxy)-2-methyl-4H-pyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;99%
With potassium carbonate In acetone for 6h; Reflux;97%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h;65%
Maltol
118-71-8

Maltol

p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

3-((4-methoxybenzyl)oxy)-2-methyl-4H-pyran-4-one

3-((4-methoxybenzyl)oxy)-2-methyl-4H-pyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 6h; Reflux;99%
Maltol
118-71-8

Maltol

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
at 90℃; for 6h;98%
With acetic acid at 80℃; for 18h; Inert atmosphere;84%
With sodium acetate In chloroform at 125℃; under 2250.2 Torr; for 0.25h; Irradiation;75%
at 80℃; for 6h;
Maltol
118-71-8

Maltol

[(hydrotris(3,5-phenylmethylpyrazolyl)borato)CoCl]

[(hydrotris(3,5-phenylmethylpyrazolyl)borato)CoCl]

[(hydrotris(3,5-phenylmethylpyrazolyl)borato)Co(maltolato)]

[(hydrotris(3,5-phenylmethylpyrazolyl)borato)Co(maltolato)]

Conditions
ConditionsYield
With (C2H5)3N In methanol; dichloromethane (C2H5)3N added to a soln. of Co complex, a soln. of ligand in MeOH added, stirred at room temp. under N2; evapd. (vac.), dissolved in C6H6, filtered, crystd. by diffusion of the soln. with pentane; elem. anal.;98%
Maltol
118-71-8

Maltol

vanadium(V) oxytriisopropoxide
5588-84-1

vanadium(V) oxytriisopropoxide

(malt)2V(V)(O)(O(i)Pr)
117624-61-0, 891865-72-8

(malt)2V(V)(O)(O(i)Pr)

Conditions
ConditionsYield
In acetonitrile at -20 - 20℃;98%
Maltol
118-71-8

Maltol

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
In ethanol at 100℃; for 6h; Temperature;97.02%
Maltol
118-71-8

Maltol

silver nitrate

silver nitrate

silver(I) 3-hydroxy-2-methyl-γ-pyranoate
620591-69-7

silver(I) 3-hydroxy-2-methyl-γ-pyranoate

Conditions
ConditionsYield
With triethylamine In ethanol; triethylamine; acetonitrile byproducts: NEt3*HNO3; a soln. of γ-pyranone in Et3N and EtOH were added dropwise under N2 to a soln. of AgNO3 in MeCN-EtOH in the dark at 25°C, the mixt.was stirred for 2 h; filtd., ppt. was washed with cold EtOH, filtrate evapd. under vac.; elem. anal.;97%
Maltol
118-71-8

Maltol

oxalic acid
144-62-7

oxalic acid

3-hydroxy-2-methyl-4-pyrone/oxalic acid 1:1 cocrystals

3-hydroxy-2-methyl-4-pyrone/oxalic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;97%
Maltol
118-71-8

Maltol

salicylic acid
69-72-7

salicylic acid

3-hydroxy-2-methyl-4-pyrone/salicylic acid 1:1 cocrystals
1325228-62-3

3-hydroxy-2-methyl-4-pyrone/salicylic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;97%
Maltol
118-71-8

Maltol

4-methoxy-phenyl-sulphonyl chloride
98-68-0

4-methoxy-phenyl-sulphonyl chloride

C13H12O6S

C13H12O6S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.166667h;97%
Maltol
118-71-8

Maltol

oxotribromobis(triphenylphosphine)rhenium(V)
18703-07-6, 74741-94-9, 162117-95-5

oxotribromobis(triphenylphosphine)rhenium(V)

[ReOBr2(3-hydroxy-2-methyl-4H-pyran-4-one(1-))(PPh3)]

[ReOBr2(3-hydroxy-2-methyl-4H-pyran-4-one(1-))(PPh3)]

Conditions
ConditionsYield
In dichloromethane suspn. Ru colmplex and maltol in CH2Cl2 was refluxed for 4 h; soln. was kept at -15°C for 7 days, ppt. was filtered off, washedwith n-hexane and dried in vacuo; elem. anal.;96%
Maltol
118-71-8

Maltol

malic acid
617-48-1

malic acid

3-hydroxy-2-methyl-4-pyrone/malic acid 1:1 cocrystals

3-hydroxy-2-methyl-4-pyrone/malic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;96%
Maltol
118-71-8

Maltol

benzenesulfonic acid
98-11-3

benzenesulfonic acid

3,4-dihydroxy-2-methylpyrylium benzenesulfonate

3,4-dihydroxy-2-methylpyrylium benzenesulfonate

Conditions
ConditionsYield
In methanol for 1h; Reflux;96%
Maltol
118-71-8

Maltol

3-hydroxy-2-methylpyrid-4-one
17184-19-9

3-hydroxy-2-methylpyrid-4-one

Conditions
ConditionsYield
Stage #1: Maltol With ammonium hydroxide at 40℃; for 2h;
Stage #2: With ammonium carbonate at 40℃; for 10h; Reagent/catalyst; Temperature; Reflux;
95.7%
With ammonia In water for 10h; Reflux;85%
With ammonia In water for 10h; Reflux;79%
Maltol
118-71-8

Maltol

3-O-benzylmaltol
61049-69-2

3-O-benzylmaltol

Conditions
ConditionsYield
by a literature procedure;95%
Maltol
118-71-8

Maltol

ferric trimaltol

ferric trimaltol

Conditions
ConditionsYield
Stage #1: Maltol With sodium hydroxide In water pH=11.6 - 13.5;
Stage #2: With iron(III) chloride In water pH=7.1; Product distribution / selectivity;
95%
With ferric citrate; sodium carbonate In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity;
With iron(II) gluconate; potassium hydroxide In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity; Heating / reflux;
With sodium hydroxide; sodium iron(II) citrate In water Product distribution / selectivity;
With sodium hydroxide; sodium ferric citrate In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity;
Maltol
118-71-8

Maltol

bis(3-hydroxy-2-methyl-4-pyronato)tin(II)
130294-04-1

bis(3-hydroxy-2-methyl-4-pyronato)tin(II)

Conditions
ConditionsYield
In toluene; acetonitrile Electrolysis; electrochemical oxidation of Sn (anode metal) in a CH3CN:toluene (1:1) soln. containing Et4NClO4 of 3-hydroxy-2-methyl-4-pyrone over a period of 1-2 h under N2; filtn., reducing of volume of soln., cooling, drying in vac., washing of yellow solid (EtOH), elem. anal.;95%
Maltol
118-71-8

Maltol

LACTIC ACID
849585-22-4

LACTIC ACID

3-hydroxy-2-methyl-4-pyrone/lactic acid 1:1 cocrystals
1325228-66-7

3-hydroxy-2-methyl-4-pyrone/lactic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;95%
Maltol
118-71-8

Maltol

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

3-hydroxy-4-methoxy-2-methylpyrylium trifluoromethanesulfonate

3-hydroxy-4-methoxy-2-methylpyrylium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane for 4h; Reflux; Inert atmosphere;95%
In dichloromethane for 4h; Reflux;54%
Maltol
118-71-8

Maltol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

3-Methoxymethoxy-2-methyl-pyran-4-one
181647-78-9

3-Methoxymethoxy-2-methyl-pyran-4-one

Conditions
ConditionsYield
With diisopropylamine Ambient temperature;94%
Maltol
118-71-8

Maltol

5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-methyl-3-(3,4,5-trimethoxy-benzyloxy)-pyran-4-one

2-methyl-3-(3,4,5-trimethoxy-benzyloxy)-pyran-4-one

Conditions
ConditionsYield
tetra(n-butyl)ammonium hydroxide In dichloromethane; water Etherification; Heating;94%
Stage #1: Maltol With tetra(n-butyl)ammonium hydroxide In water at 20℃; for 1h;
Stage #2: 5-(chloromethyl)-1,2,3-trimethoxybenzene In dichloromethane for 24h; Heating;
Maltol
118-71-8

Maltol

methanesulfonic acid
75-75-2

methanesulfonic acid

3,4-dihydroxy-2-methylpyrylium methanesulfonate

3,4-dihydroxy-2-methylpyrylium methanesulfonate

Conditions
ConditionsYield
In methanol for 1h; Reflux;94%
Maltol
118-71-8

Maltol

glycolic Acid
79-14-1

glycolic Acid

3-hydroxy-2-methyl-4-pyrone/glycolic acid 1:1 cocrystals

3-hydroxy-2-methyl-4-pyrone/glycolic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;93%

3-Hydroxy-2-methyl-4-pyrone Specification

The 3-Hydroxy-2-methyl-4-pyrone, with the CAS registry number 118-71-8 and EINECS registry number 204-271-8, has the systematic name of 3-hydroxy-2-methyl-4H-pyran-4-one. It is a kind of White crystalline powder with a fragrant caramel-butterscotch odor, and belongs to following the proudct categories: Food & Feed Additives; Heterocycles; Food & Flavor Additives. It can be found in the bark of larch tree, in pine needles, and in roasted malt and so on.isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity. It is soluble in hot water, chloroform, and other polar solvents. And the molecular formula of this chemical is C6H6O3.

The physical properties of 3-Hydroxy-2-methyl-4-pyrone are as followings:
(1)ACD/LogP: 0.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.07; (4)ACD/LogD (pH 7.4): 0.029; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 25.982; (8)ACD/KOC (pH 7.4): 23.677; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.561; (14)Molar Refractivity: 30.292 cm3; (15)Molar Volume: 93.546 cm3; (16)Polarizability: 12.009×10-24cm3; (17)Surface Tension: 51.792 dyne/cm; (18)Density: 1.348 g/cm3; (19)Flash Point: 127.32 °C; (20)Enthalpy of Vaporization: 60.778 kJ/mol; (21)Boiling Point: 284.7 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation of 3-Hydroxy-2-methyl-4-pyrone:
 (1) It can be extracted from natural products, because it is a naturally occurring organic compound; (2)It can be prepared by pyromucic aldehyde; (3)Semi-synthesis: It can be prepared by kojic acid, and after a series of oxidation, decarboxylation, formaldehyde reaction, reduction, distillation and recrystallization, you can get the product.

Uses of 3-Hydroxy-2-methyl-4-pyrone:
 It is a fragrance molecule used in flavor enhancers and fragrances.usually used as a flavor enhancer. It is also used to impart a sweet aroma to fragrances because of its odor of cotton candy and caramel.

Safety Information of 3-Hydroxy-2-methyl-4-pyrone:
You should be cautious while dealing with 3-Hydroxy-2-methyl-4-pyrone. It irritates to eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1c(c(=O)cco1)O;
(2)InChI: InChI=1/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3;
(3)InChIKey: XPCTZQVDEJYUGT-UHFFFAOYAH.

The toxicity data of 3-Hydroxy-2-methyl-4-pyrone is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral 3720mg/kg (3720mg/kg)   Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.
guinea pig LD50 oral 1410mg/kg (1410mg/kg)   Dow Chemical Company Reports. Vol. -, Pg. -, 1967.
mouse LD16 intraperitoneal 1400mg/kg (1400mg/kg)   Russian Pharmacology and Toxicology Vol. 38, Pg. 213, 1975.
mouse LD50 oral 550mg/kg (550mg/kg)   FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 56, 1967.
mouse LD50 subcutaneous 820mg/kg (820mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1008, 1974.
rabbit LD skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 841, 1975.
rabbit LD50 oral 1620mg/kg (1620mg/kg)   Dow Chemical Company Reports. Vol. -, Pg. -, 1967.
rat LD50 oral 1410mg/kg (1410mg/kg)   FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 56, 1967.

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