Kojic acid

Kojic acid
Names
Preferred IUPAC name
5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
Other names
Kojic acid, 5-Hydroxy-2-(hydroxymethyl)-4-pyrone, 2-hydroxymethyl-5-hydroxy-γ-pyrone
Identifiers
3D model (JSmol)
120895
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.203 Edit this at Wikidata
EC Number
  • 207-922-4
3620
KEGG
RTECS number
  • UQ0875000
UNII
  • InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 checkY
    Key: BEJNERDRQOWKJM-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
  • O=C1/C=C(\O/C=C1/O)CO
Properties
C6H6O4
Molar mass 142.110 g·mol−1
Appearance white
Melting point 152 to 155 °C (306 to 311 °F; 425 to 428 K)
Slight
Acidity (pKa) 9.40[1]
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H351
P201, P280, P308+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Kojic acid is an organic compound with the formula HOCH2C5H2O2OH. It is a derivative of 4-pyrone that functions in nature as a chelation agent produced by several species of fungi, especially Aspergillus oryzae, which has the Japanese common name koji.[2][3][4] Kojic acid is a by-product in the fermentation process of malting rice, for use in the manufacturing of sake, the Japanese rice wine.[2] It 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.[5] It forms a bright red complex with ferric ions.[6]

  1. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  2. ^ a b Bentley, R. (2006). "From miso, sake and shoyu to cosmetics: a century of science for kojic acid". Nat. Prod. Rep. 23 (6): 1046–1062. doi:10.1039/b603758p. PMID 17119644.
  3. ^ Yabuta T (1924). "The constitution of kojic acid, a γ-pyrone derivative formed by Aspergillus oryzae from carbohydrates". Journal of the Chemical Society. 125: 575–587. doi:10.1039/ct9242500575.
  4. ^ Parvez, Shoukat; Kang, Moonkyu; Chung, Hwan-Suck; Cho, Chongwoon; Hong, Moo-Chang; Shin, Min-Kyu; Bae, Hyunsu (2006). "Survey and mechanism of skin depigmenting and lightening agents". Phytotherapy Research. 20 (11): 921–34. doi:10.1002/ptr.1954. PMID 16841367. S2CID 22156361.
  5. ^ "Kojic acid and enzymatic browning]". Food and Agriculture Organization of the United Nations. 2000. Archived from the original on 2008-03-04.
  6. ^ Nurchi, Valeria M.; Lachowicz, Joanna I.; Crisponi, Guido; Murgia, Sergio; Arca, Massimiliano; Pintus, Anna; Gans, Peter; Niclos-Gutierrez, Juan; Domínguez-Martín, Alicia; Castineiras, Alfonso; Remelli, Maurizio (2011-05-27). "Kojic acid derivatives as powerful chelators for iron(III) and aluminium(III)". Dalton Transactions. 40 (22): 5984–5998. doi:10.1039/C1DT00005E. ISSN 1477-9234. PMID 21552634.