Product Name

  • Name

    Kojic acid

  • EINECS 207-922-4
  • CAS No. 501-30-4
  • Article Data18
  • CAS DataBase
  • Density 1.542 g/cm3
  • Solubility Soluble in water
  • Melting Point 152-155 °C
  • Formula C6H6O4
  • Boiling Point 401.7 °C at 760 mmHg
  • Molecular Weight 142.111
  • Flash Point 179.9 °C
  • Transport Information
  • Appearance Tan powder
  • Safety 22-24/25-36/37-36
  • Risk Codes 40-68
  • Molecular Structure Molecular Structure of 501-30-4 (Kojic acid)
  • Hazard Symbols HarmfulXn
  • Synonyms Kojic acid(whitening agent in cosmetic);3-O-Ethyl ascorbic acid;5-Hydroxy-2-hydroxymethyl-4H-4-pyranone;4H-Pyran-4-one,5-hydroxy-2-(hydroxymethyl)-;5-Hydroxy-2-hydroxymethyl-4-pyrone;5-Hydroxy-2-(hydroxymethyl)-4-pyrone;5-18-02-00516 (Beilstein Handbook Reference);5-hydroxy-2-(hydroxymethyl)pyran-4-one;5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one;2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one;4H-Pyran-4-one, 5-hydroxy-2- (hydroxymethyl)-;
  • PSA 70.67000
  • LogP -0.16230

Synthetic route

5-acetoxy-2-acetoxymethyl-4H-pyran-4-one
26209-93-8

5-acetoxy-2-acetoxymethyl-4H-pyran-4-one

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With sodium methylate In methanol for 1h;95%
With methanol; ammonia
chlorokojic acid
7559-81-1

chlorokojic acid

acetone
67-64-1

acetone

A

allomaltol
644-46-2

allomaltol

B

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

C

iodokojic acid
16065-34-2

iodokojic acid

D

iodoacetone
3019-04-3

iodoacetone

Conditions
ConditionsYield
With sodium iodide at 45℃; for 24h; Substitution;A n/a
B n/a
C 78%
D n/a
5-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)-2-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)-4H-pyran-4-one

5-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)-2-(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)-4H-pyran-4-one

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With silica gel In methanol at 60℃; for 3h; Inert atmosphere;70%
2-keto-D-glucose

2-keto-D-glucose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: 2-keto-D-glucose With sodium acetate; acetic anhydride In N,N-dimethyl-formamide for 23h;
Stage #2: With sodium methylate In methanol for 1h;
20%
D-xylose
58-86-6

D-xylose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With Aspergillus oryzae Bei der Vergaerung;
D-sorbitol
50-70-4

D-sorbitol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
durch Aspergillus oryzae;
D-galactitol
608-66-2

D-galactitol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
bei der Einw.von Aspergillus oryzae;
L-arabinose
5328-37-0

L-arabinose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With Aspergillus oryzae Bei der Vergaerung;
glycerol
56-81-5

glycerol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With aspergillus glaucus Bei der Vergaerung;
bei der Einw.von Aspergillus glaucus;
D-xylose
58-86-6

D-xylose

aspergillus flavus

aspergillus flavus

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

D-glucose
50-99-7

D-glucose

aspergillus flavus

aspergillus flavus

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

D-myo-inositol
87-89-8

D-myo-inositol

aspergillus oryzae

aspergillus oryzae

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

5‑benzyloxy‑4H‑pyran‑4‑one‑2‑ylmethyl adamantan‑1‑ylacetate

5‑benzyloxy‑4H‑pyran‑4‑one‑2‑ylmethyl adamantan‑1‑ylacetate

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen under 258.776 Torr; for 0.166667h;
comenic acid
499-78-5

comenic acid

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: neat (no solvent) / 30 °C / Inert atmosphere; Schlenk technique; Glovebox
2: silica gel / methanol / 3 h / 60 °C / Inert atmosphere
View Scheme
D-Glucose
2280-44-6

D-Glucose

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ammonium hydroxide / 0.75 h / pH 6 / Enzymatic reaction
2.1: sodium acetate; acetic anhydride / N,N-dimethyl-formamide / 23 h
2.2: 1 h
View Scheme
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

5-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyran-4-one
5443-45-8

5-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyran-4-one

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h;100%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

chlorokojic acid
7559-81-1

chlorokojic acid

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 0.166667h;100%
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane for 3h; Inert atmosphere; chemoselective reaction;100%
With thionyl chloride at 20℃; for 3h;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate
2169-68-8

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate

ethyl 2-amino-4-(4-chlorophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

ethyl 2-amino-4-(4-chlorophenyl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

2-amino-4-(phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(phenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Product distribution; Heating; reaction with arylmethylenemalonitrile derivatives;99%
With piperidine In ethanol for 0.166667h; Heating;99%
With β‐cyclodextrin In water at 70℃; for 1h; Reagent/catalyst; Green chemistry;96%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
In water at 100℃; Michael Addition; Microwave irradiation; Sealed tube; Green chemistry;96%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate
2017-87-0

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate

ethyl 2-amino-6-(hydroxymethyl)-4-(4-methoxyphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

ethyl 2-amino-6-(hydroxymethyl)-4-(4-methoxyphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;99%
With piperidine In ethanol for 4h; Cycloaddition; Heating;28%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

benzyl bromide
100-39-0

benzyl bromide

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one
15771-06-9

5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 80℃;99%
With potassium carbonate In ethanol; water for 2h; Reflux;98%
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h;90%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

vinyl acetate
108-05-4

vinyl acetate

7-O-acetylkojic acid
25552-08-3

7-O-acetylkojic acid

Conditions
ConditionsYield
novozyme 435 In acetonitrile at 50℃; Enzymatic reaction;99%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

2,2',2''-triaminotriethylamine
4097-89-6

2,2',2''-triaminotriethylamine

6,6',6"-(((nitrilotris(ethane-2,1-diyl))tris(azanediyl))tris(methylene))tris(3-hydroxy-4H-pyran-4-one)

6,6',6"-(((nitrilotris(ethane-2,1-diyl))tris(azanediyl))tris(methylene))tris(3-hydroxy-4H-pyran-4-one)

Conditions
ConditionsYield
In ethanol; chloroform at 20℃; for 1h;98.5%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone
118708-61-5

5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;98%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Reflux;90%
dichloro(benzene)ruthenium(II) dimer
37366-09-9

dichloro(benzene)ruthenium(II) dimer

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

(η6-C6H6)RuCl(5-hydroxy-2-(hydroxymethyl)-4-pyrone)
1204169-40-3

(η6-C6H6)RuCl(5-hydroxy-2-(hydroxymethyl)-4-pyrone)

Conditions
ConditionsYield
With NaOMe In methanol byproducts: NaCl; kojic acid and NaOMe in dry MeOH stirred for 10 min; Ru complex added, stirred for 5 h; rotary evapd. to dryness; taken in CH2Cl2; soln. filtered, concd. to 3 ml, then Et2O excess added; left for 2 h at room temp.; ppt. collected, washed with Et2O; dried in vac.;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

malononitrile
109-77-3

malononitrile

2-amino-6-(hydroxymethyl)-8-oxo-4-m-tolyl-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
876710-04-2

2-amino-6-(hydroxymethyl)-8-oxo-4-m-tolyl-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene immobilized on silica In neat (no solvent) at 20℃; for 0.05h;98%
In water at 50℃; for 0.0833333h; Sonication;97%
With nanozeolite clinoptilolite In water at 95℃; for 0.333333h; Green chemistry;95%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-fluorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
797028-50-3

2-amino-4-(4-fluorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.1h; Sonication;98%
With nanozeolite clinoptilolite In water at 95℃; for 0.25h; Green chemistry;96%
With nano-silica sulfuric acid In water for 0.416667h; Reflux; Green chemistry;95%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
625376-09-2

2-amino-4-(pyridine-3-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.0833333h; Sonication;98%
With Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 In ethanol for 0.833333h; Reflux; Green chemistry;85%
furfural
98-01-1

furfural

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(furan-2-yl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
873570-71-9

2-amino-4-(furan-2-yl)-6-(hydroxymethyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.0833333h; Sonication;98%
With nanozeolite clinoptilolite In water at 95℃; for 0.333333h; Green chemistry;97%
With β‐cyclodextrin In water at 70℃; for 1h; Green chemistry;93%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

2-amino-4-(4-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With nanozeolite clinoptilolite In water at 95℃; for 0.3h; Green chemistry;98%
With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 In ethanol; water at 20℃; for 0.133333h; Sonication;98%
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.666667h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;97%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-methylphenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

2-amino-4-(4-methylphenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

Conditions
ConditionsYield
With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 In ethanol; water at 20℃; for 0.133333h; Sonication;98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene immobilized on silica In neat (no solvent) at 20℃; for 0.05h;97%
With ferrocene functionalized ionic liquid supported on silica coated Fe3O4 magnetic nanoparticles In ethanol; water at 25℃; for 0.166667h; Catalytic behavior; Solvent; Sonication;95%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

4-chloro-3-nitro-benzaldehyde
16588-34-4

4-chloro-3-nitro-benzaldehyde

2-amino-4-(4-chloro-3-nitrophenyl)-6-hydroxymethyl-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile
1613234-40-4

2-amino-4-(4-chloro-3-nitrophenyl)-6-hydroxymethyl-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
With nano-silica sulfuric acid In water for 0.2h; Reflux; Green chemistry;98%
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.5h; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-4-(4-cyanophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile
1613234-41-5

2-amino-4-(4-cyanophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran3-carbonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.583333h; Green chemistry;98%
With nano-silica sulfuric acid In water for 0.25h; Reflux; Green chemistry;94%
With Ca9.5Mg0.5(PO4)5.5(SiO4)0.5F1.5 In ethanol for 0.25h; Reflux; Green chemistry;92%
With β‐cyclodextrin In water at 70℃; for 1h; Green chemistry;90%
With lipase from Aspergillus niger In ethanol; water at 20℃; for 3.5h; Enzymatic reaction;90%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

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

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

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 24h;98%
With potassium modified alumina catalysts (CAT3) In 1,4-dioxane; water at 20℃; for 24h; Aldol Condensation; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

1-naphthaldehyde
66-77-3

1-naphthaldehyde

malononitrile
109-77-3

malononitrile

2‑amino‑6‑hydroxymethyl‑4‑(naphthalen‑1‑yl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

2‑amino‑6‑hydroxymethyl‑4‑(naphthalen‑1‑yl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

Conditions
ConditionsYield
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.5h; Green chemistry;98%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

2‑amino‑6‑(hydroxymethyl)‑4‑(4‑nitrophenyl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

2‑amino‑6‑(hydroxymethyl)‑4‑(4‑nitrophenyl)‑8‑oxo‑4,8‑dihydropyrano[3,2‑b]pyran‑3‑carbonitrile

Conditions
ConditionsYield
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.333333h; Green chemistry;98%
With sulfonic acid functionalized MCM-41 In water at 90℃; for 0.583333h; Green chemistry;98%
With C5H6NO3S(1+)*F6P(1-) In neat (no solvent) at 90℃; for 0.25h; Reagent/catalyst;92%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

formaldehyd
50-00-0

formaldehyd

1-(4-fluorophenylmethyl)piperazine
70931-28-1

1-(4-fluorophenylmethyl)piperazine

2-((4-(4-fluorobenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

2-((4-(4-fluorobenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
In methanol at 20℃; Mannich Aminomethylation;98%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

2-Amino-6-methylpyridine
1824-81-3

2-Amino-6-methylpyridine

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

C18H17N3O4

C18H17N3O4

Conditions
ConditionsYield
With hyper-cross-linked β-cyclodextrin nanosponge In ethanol for 0.25h; Solvent; Time; Mannich Aminomethylation; Reflux;98%
piperazine
110-85-0

piperazine

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

formaldehyd
50-00-0

formaldehyd

6,6'-(piperazine-1,4-diylbis(methylene))bis(5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one)

6,6'-(piperazine-1,4-diylbis(methylene))bis(5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one)

Conditions
ConditionsYield
Stage #1: piperazine; formaldehyd In ethanol at 20℃; for 0.5h;
Stage #2: 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one In ethanol for 5h;
97%
1) EtOH, H2O, 30 min, 2) EtOH, H2O, room temperature, 1 h; Yield given. Multistep reaction;
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

4-(trifluoromethylthio)benzaldehyde
4021-50-5

4-(trifluoromethylthio)benzaldehyde

malononitrile
109-77-3

malononitrile

6-amino-7-cyano-2-hydroxymethyl-8-[(4-trifluoromethylthio)phenyl]-4,8-dihydropyrano[3,2-b]pyran-4-one

6-amino-7-cyano-2-hydroxymethyl-8-[(4-trifluoromethylthio)phenyl]-4,8-dihydropyrano[3,2-b]pyran-4-one

Conditions
ConditionsYield
With triethylamine In ethanol for 0.25h; Heating;97%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

propionic acid anhydride
123-62-6

propionic acid anhydride

2-propionyloxymethyl-4H-pyran-4-on-5-yl propionate
1092474-58-2

2-propionyloxymethyl-4H-pyran-4-on-5-yl propionate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;97%
indole
120-72-9

indole

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

benzaldehyde
100-52-7

benzaldehyde

2-((1H-indol-3-yl)(phenyl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one
1261077-99-9

2-((1H-indol-3-yl)(phenyl)methyl)-3-hydroxy-6-(hydroxymethyl)-4H-pyran-4-one

Conditions
ConditionsYield
Stage #1: 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one; benzaldehyde With FAU zeolite nanoparticles In neat (no solvent) at 110℃; for 0.166667h; Green chemistry;
Stage #2: indole In neat (no solvent) Temperature; Green chemistry;
97%
With Zn4O(BDC)3 supported on NiFe2O4 nanoparticles In neat (no solvent) at 110℃; for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Concentration;92%
With indium(III) chloride at 120℃; for 1.08333h; neat (no solvent);85%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

malononitrile
109-77-3

malononitrile

2-amino-4-(thiophen-2-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile
625376-15-0

2-amino-4-(thiophen-2-yl)-4,8-dihydro-6-(hydroxymethyl)-8-oxo-pyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
In water at 50℃; for 0.1h; Sonication;97%
With s-triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles In water at 100℃; for 0.416667h; Green chemistry;95%
With nanozeolite clinoptilolite In water at 95℃; for 0.3h; Green chemistry;92%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

indole-2,3-dione
91-56-5

indole-2,3-dione

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2'-amino-6'-(hydroxymethyl)-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate
884213-99-4

ethyl 2'-amino-6'-(hydroxymethyl)-2,8'-dioxo-8'H-spiro[indoline-3,4'-pyrano[3,2-b]pyran]-3'-carboxylate

Conditions
ConditionsYield
With N-doped graphene quantum dots modified with CuO (0D)/ZnO (1D) heterojunction In water for 0.25h;97%
With 1,4-diaza-bicyclo[2.2.2]octane In methanol at 60℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent;94%
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane for 0.583333h; Reflux;89%

Kojic acid Chemical Properties

Molecular Formula: C6H6O4
Molecular Weight: 142.11
EINECS: 207-922-4 
Index of Refraction: 1.606
Density: 1.542 g/cm3
Flash Point: 179.9 °C
Enthalpy of Vaporization: 75.44 kJ/mol
Boiling Point: 401.7 °C at 760 mmHg
Vapour Pressure: 4.01E-08 mmHg at 25 °C
Melting point: 152-155 °C
Water solubility: Soluble
Appearance: Tan powder
Structure of Kojic acid (CAS NO.501-30-4):
          
IUPAC Name: 5-Hydroxy-2-(hydroxymethyl)pyran-4-one
Product Category of Kojic acid (CAS NO.501-30-4): Heterocycles;Plant Oils, Toxins, Phenolic Acids & Derivatives

Kojic acid Uses

 Kojic acid (CAS NO.501-30-4) can be used in food and cosmetics to preserve or change colors of substances. On cut fruits it is used to prevent oxidative browning, in seafood to preserve pink and red colors, and in cosmetics to lighten skin.  

Kojic acid Toxicity Data With Reference

1.    

mmo-sat 1 mg/plate

    MUREAV    Mutation Research. 67 (1979),367.
2.    

mma-sat 4 mg/plate

    JTSCDR    Journal of Toxicological Sciences. 7 (1982),255.
3.    

ivn-rat LDLo:1000 mg/kg

    85ERAY    Antibiotics: Origin, Nature, and Properties. 3 (1978),1755.
4.    

orl-mus LDLo:4 g/kg

    NATUAS    Nature. 155 (1945),302.
5.    

ipr-mus LD50:250 mg/kg

    85GDA2    CRC Handbook of Antibiotic Compounds, Volumes 1-9. 5 (1981),393.
6.    

scu-mus LDLo:1500 mg/kg

    NATUAS    Nature. 155 (1945),302.
7.    

ivn-mus LDLo:1500 mg/kg

    NATUAS    Nature. 155 (1945),302.
8.    

ivn-dog LDLo:1000 mg/kg

    85ERAY    Antibiotics: Origin, Nature, and Properties. 3 (1978),1755.
9.    

ivn-rbt LDLo:1000 mg/kg

    85ERAY    Antibiotics: Origin, Nature, and Properties. 3 (1978),1755.


 

Kojic acid Consensus Reports

EPA Genetic Toxicology Program.

Kojic acid Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: HarmfulXn
Risk Statements: 
R40:Limited evidence of a carcinogenic effect
R68 :Possible risk of irreversible effects
Safety Statements:
S22:Do not breathe dust
S24/25:Avoid contact with skin and eyes
S36/37:Wear suitable protective clothing and gloves
S36 :Wear suitable protective clothing
WGK Germany: 3

Kojic acid Specification

 Kojic acid , its cas register number is 501-30-4. It also can be called 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one ; and 5-Hydroxy-2-hydroxymethyl-4-pyrone . It is a mild inhibitor of the formation of pigment in plant and animal tissues. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, Kojic acid (CAS NO.501-30-4) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide.

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