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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:41 UTC
Update Date2018-03-12 22:10:43 UTC
HMDB IDHMDB0032923
Secondary Accession Numbers
  • HMDB32923
Metabolite Identification
Common NameKojic acid
DescriptionKojic acid, also known as acido kojico or kojisaeure, 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. Kojic acid exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). Within the cell, kojic acid is primarily located in the cytoplasm. Kojic acid can be biosynthesized from 4H-pyran. Kojic acid is a potentially toxic compound.
Structure
Thumb
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
5-((3-Aminopropyl)phosphinooxy)-2-(hydroxymethyl)-4H-pyran-4-oneMeSH
Chemical FormulaC6H6O4
Average Molecular Weight142.1094
Monoisotopic Molecular Weight142.02660868
IUPAC Name5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
Traditional Namekojic acid
CAS Registry Number501-30-4
SMILES
OCC1=CC(=O)C(O)=CO1
InChI Identifier
InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
InChI KeyBEJNERDRQOWKJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyranones and derivatives. These 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.64Not 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-3950000000-d1e6f5b2e47ac5626c5fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05p6-9300000000-704def65872ec878b268View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ko-9500000000-8c8ed21581e5ce62d657View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dj-0972200000-d2e1134bffb7759fab36View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-1940000000-7a8f18adc19d5275d098View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3950000000-d1e6f5b2e47ac5626c5fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03kc-6900000000-d96f98a42148a6e47233View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9650000000-945de47e75f8ec9b9eafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0900000000-7497f496112e599fe169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-9200000000-79391fb0052779fa15a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b4f5c76df606bee2639bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-8c591424fe1f23b4f463View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9300000000-2f1a2b3413e8f032697fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-a3e3f8a5e8ce22a6cba3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-2900000000-4f881cf1625489e94838View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-82a828b03c7d45e6515fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9400000000-15508d600420b309e528View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01759
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010906
KNApSAcK IDC00041026
Chemspider ID3708
KEGG Compound IDC14516
BioCyc IDKOJIC-ACID
BiGG IDNot Available
Wikipedia LinkKojic_acid
METLIN IDNot Available
PubChem Compound3840
PDB IDKOJ
ChEBI ID43572
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:10466431 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .