Kojic acid (CHEM002736)

Record Information
Version1.0
Creation Date2010-05-21 16:18:59 UTC
Update Date2026-05-14 17:15:16 UTC
Accession NumberCHEM002736
Identification
Common NameKojic acid
ClassSmall Molecule
Description
Kojic acid is a synthetic intermediate for production of food additives. Kojic acid has been shown to exhibit anti-neoplastic function (4).
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Food Toxin
  • Fungal Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • PFAS
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Hydroxy-2-(hydroxymethyl)-4-pyroneChEBI
5-Hydroxy-2-hydroxymethyl-4-pyroneChEBI
Acido kojicoChEBI
KojisaeureChEBI
KojateGenerator
2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-oneHMDB
2-Hydroxymethyl-5-hydroxy-gamma-pyroneHMDB
5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-oneHMDB
5-Hydroxy-2-(hydroxymethyl)pyran-4-oneHMDB
5-Hydroxy-2-hydroxymethyl-4H-4-pyranoneHMDB
KOJHMDB
Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)HMDB
Kojyl-appaMeSH, HMDB
5-((3-Aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4H-pyran-4-oneMeSH, HMDB
Chemical FormulaC6H6O4
Average Molecular Mass142.109 g/mol
Monoisotopic Mass142.027 g/mol
CAS Registry Number501-30-4
IUPAC Name5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
Traditional Namekojic acid
SMILESOCC1=CC(=O)C(O)=CO1
InChI IdentifierInChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
InChI KeyBEJNERDRQOWKJM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Cyclic ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceTan powder.
Experimental Properties
PropertyValue
Melting Point161°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility92.3 g/LALOGPS
logP-1ALOGPS
logP-0.5ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)9.3ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.27 m³·mol⁻¹ChemAxon
Polarizability12.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
Mechanism of ToxicityKojic acid acts as a competitive and reversible inhibitor of animal and plant polyphenol oxidases (tyrosinases), xanthine oxidase, and D- and some L-amino acid oxidases. Inhibition of tyrosinases prevents melanosis, while inhibition of the oxidases prevents metabolism of certain amino acids. Kojic acid also reversibly affects thyroid function by inhibiting iodine uptake, leading to decreases in thyroid hormones T3 and T4 and increases in thyroid-stimulating hormone (TSH). Increased TSH from pituitary gland in turn stimulates thyroid hyperplasia. (1, 2)
MetabolismKojic acid is absorbed by the gastrointestinal tract, enters the circulation, and is probably metabolized similar to hexoses. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (5)
Uses/SourcesKojic acid is a chelation agent and mycotoxin produced by several species of Aspergillus, Acetobacter, and Penicillium fungi, especially Aspergillus oryzae, which has the Japanese common name koji. Kojic acid is a by-product in the fermentation process of malting rice, and is used in the manufacturing of numerous foods, including miso, soy sauce, and sake. Kojic acid is a mild inhibitor of the formation of pigment in plant and animal tissues, and is used in food and cosmetics to preserve or change colors of substances, such as in skin-lightening or bleaching formulas. It is also used as a food additive for preventing enzymatic browning and in seafood to preserve pink and red colors. Kojic acid also has antibacterial and antifungal properties and is used in skin diseases like melasma. (6, 1)
Minimum Risk LevelNot Available
Health EffectsAnimals studies have shown that kojic acid increases the occurrence of thyroid cancer and thyroid adenomas, though it is not known whether this is also true in humans. (1)
SymptomsSensitive individuals may develop contact dermatitis. (1)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB01759
HMDB IDHMDB0032923
FooDB IDFDB010906
Phenol Explorer IDNot Available
KNApSAcK IDC00041026
BiGG IDNot Available
BioCyc IDKOJIC-ACID
METLIN IDNot Available
PDB IDKOJ
Wikipedia LinkKojic_acid
Chemspider ID3708
ChEBI ID43572
PubChem Compound ID3840
Kegg Compound IDC14516
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11534762
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1348188
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15039076
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16198580
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18083129
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19471877
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20943172
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23683589
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24116376
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7714722
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8987542
13. Novotny L, Rauko P, Abdel-Hamid M, Vachalkova A: Kojic acid--a new leading molecule for a preparation of compounds with an anti-neoplastic potential. Neoplasma. 1999;46(2):89-92.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.