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Chemical Compound Review

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

Synonyms: CHEMBL287556, NSC-1942, CCRIS 4131, kojic acid, acido kojico, ...
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Disease relevance of kojic acid


High impact information on kojic acid

  • Measurements of lactate dehydrogenase release during reperfusion showed a protective pattern similar to that found for heart contractile function, although 50 microM kojic acid also showed a significantly lower lactate dehydrogenase release during the first 10 minutes of reperfusion [6].
  • The most potent aurone was found to be the naturally occurring 4,6,4'-trihydroxyaurone which induces 75% inhibition at 0.1 mM concentration and is highly effective when compared to kojic acid, one of the best tyrosinase inhibitors known so far (the latter is completely inactive at such concentrations) [7].
  • The crystal structures of the copper-dependent Aspergillus japonicus quercetin 2,3-dioxygenase (2,3QD) complexed with the inhibitors diethyldithiocarbamate (DDC) and kojic acid (KOJ) are reported at 1.70 and 2.15 A resolution, respectively [8].
  • In order to examine whether kojic acid (KA) exerts a promoting effect on thyroid carcinogenesis, male F344 rats were initiated with N-bis(2-hydroxypropyl)nitrosamine (BHP; 2800 mg/kg body wt, single s.c. injection) and, starting 1 week later, received pulverized basal diet containing 2 or 0% KA for 12 weeks [9].
  • Promoting effects of kojic acid due to serum TSH elevation resulting from reduced serum thyroid hormone levels on development of thyroid proliferative lesions in rats initiated with N-bis(2-hydroxypropyl)nitrosamine [9].

Chemical compound and disease context of kojic acid

  • RESULTS: Complete regression of diffuse melasma was observed in 6 of 20 patients (30%), a partial regression in 12 of 20 patients (60%), and no regression in 2 of 20 patients (10%) treated with 50% glycolic acid and 10% kojic acid [10].
  • METHODS: Forty Chinese women with epidermal melasma were treated with 2% kojic acid in a gel containing 10% glycolic acid and 2% hydroquinone on one half of the face [4].
  • A minimal amount of 12.5 micrograms kojic acid or 1.25 micrograms patulin was detectable by means of pigment suppression with isolated mutants of Serratia marcescens, whereas the wild type of this strain was insensitive [11].
  • Kojic acid, isopropylcatechol, N-acetyl-4-cysteaminylphenol, and flavonoid extracts are other compounds that have been investigated for their ability to produce hypopigmentation, but their efficacy, safety, or trial design indicates that the interventions would need further study before they could be recommended [12].
  • Chemical peels are useful to treat melasma: trichloroacetic acid, Jessner's solution, Unna's paste, alpha-hydroxy acid preparations, kojic acid, and salicyclic acid, alone or in various combinations have shown good results [13].

Biological context of kojic acid


Anatomical context of kojic acid


Associations of kojic acid with other chemical compounds


Gene context of kojic acid


Analytical, diagnostic and therapeutic context of kojic acid

  • We found significant protection of contractile function (apex displacement) during reperfusion with 50 microM L1 and 20 microM (+)-cyanidanol-3 (p less than 0.01, n = 6), whereas no protection was found with 50 microM kojic acid (n = 6) [6].
  • Kojic acid, a fungal metabolic product, has been used as a skin-depigmenting agent in skin care products marketed in Japan. Iron in the skin is known to be involved in wrinkling as a result of chronic photodamage [20].
  • We now evaluated the anti-wrinkling activity of kojic acid by using hairless mice exposed to chronic solar-simulating ultraviolet (UV) irradiation as model animal [20].
  • Simultaneous determination of magnesium L-ascorbyl-2-phosphate and kojic acid in cosmetic bleaching products by using a microbore column and ion-pair liquid chromatography [31].
  • Induction of thyroid tumours in (C57BL/6N x C3H/N)F1 mice by oral administration of kojic acid [32].


  1. Oxyresveratrol and hydroxystilbene compounds. Inhibitory effect on tyrosinase and mechanism of action. Kim, Y.M., Yun, J., Lee, C.K., Lee, H., Min, K.R., Kim, Y. J. Biol. Chem. (2002) [Pubmed]
  2. Changes in thyroid function during development of thyroid hyperplasia induced by kojic acid in F344 rats. Fujimoto, N., Onodera, H., Mitsumori, K., Tamura, T., Maruyama, S., Ito, A. Carcinogenesis (1999) [Pubmed]
  3. Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression. Kim, K.S., Kim, J.A., Eom, S.Y., Lee, S.H., Min, K.R., Kim, Y. Pigment Cell Res. (2006) [Pubmed]
  4. Treatment of melasma using kojic acid in a gel containing hydroquinone and glycolic acid. Lim, J.T. Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.]. (1999) [Pubmed]
  5. The individual and combined toxicity of kojic acid and aflatoxin in broiler chickens. Giroir, L.E., Huff, W.E., Kubena, L.F., Harvey, R.B., Elissalde, M.H., Witzel, D.A., Yersin, A.G., Ivie, G.W. Poult. Sci. (1991) [Pubmed]
  6. Prevention of postischemic cardiac injury by the orally active iron chelator 1,2-dimethyl-3-hydroxy-4-pyridone (L1) and the antioxidant (+)-cyanidanol-3. van der Kraaij, A.M., van Eijk, H.G., Koster, J.F. Circulation (1989) [Pubmed]
  7. Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes. Okombi, S., Rival, D., Bonnet, S., Mariotte, A.M., Perrier, E., Boumendjel, A. J. Med. Chem. (2006) [Pubmed]
  8. Functional analysis of the copper-dependent quercetin 2,3-dioxygenase. 1. Ligand-induced coordination changes probed by X-ray crystallography: inhibition, ordering effect, and mechanistic insights. Steiner, R.A., Kooter, I.M., Dijkstra, B.W. Biochemistry (2002) [Pubmed]
  9. Promoting effects of kojic acid due to serum TSH elevation resulting from reduced serum thyroid hormone levels on development of thyroid proliferative lesions in rats initiated with N-bis(2-hydroxypropyl)nitrosamine. Mitsumori, K., Onodera, H., Takahashi, M., Funakoshi, T., Tamura, T., Yasuhara, K., Takegawa, K., Takahashi, M. Carcinogenesis (1999) [Pubmed]
  10. The use of chemical peelings in the treatment of different cutaneous hyperpigmentations. Cotellessa, C., Peris, K., Onorati, M.T., Fargnoli, M.C., Chimenti, S. Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.]. (1999) [Pubmed]
  11. Development of sensitive bacterial tests, exemplified by two mycotoxins. Lenz, P., Süssmuth, R., Seibel, E. Toxicology (1986) [Pubmed]
  12. The treatment of melasma: a review of clinical trials. Gupta, A.K., Gover, M.D., Nouri, K., Taylor, S. J. Am. Acad. Dermatol. (2006) [Pubmed]
  13. Management of facial hyperpigmentation. Pérez-Bernal, A., Muñoz-Pérez, M.A., Camacho, F. American journal of clinical dermatology. (2000) [Pubmed]
  14. Inhibitors of mammalian melanocyte tyrosinase: in vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors. Curto, E.V., Kwong, C., Hermersdörfer, H., Glatt, H., Santis, C., Virador, V., Hearing, V.J., Dooley, T.P. Biochem. Pharmacol. (1999) [Pubmed]
  15. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. Battaini, G., Monzani, E., Casella, L., Santagostini, L., Pagliarin, R. J. Biol. Inorg. Chem. (2000) [Pubmed]
  16. N-acetyl-L-tyrosine (NAT) as a substrate for mushroom tyrosinase. Kahn, V., Ben-Shalom, N. Pigment Cell Res. (1998) [Pubmed]
  17. Mutagenicity to Salmonella typhimurium of some Aspergillus and Penicillium mycotoxins. Wehner, F.C., Thiel, P.G., van Rensburg, S.J., Demasius, I.P. Mutat. Res. (1978) [Pubmed]
  18. Delayed ERK activation by ceramide reduces melanin synthesis in human melanocytes. Kim, D.S., Kim, S.Y., Chung, J.H., Kim, K.H., Eun, H.C., Park, K.C. Cell. Signal. (2002) [Pubmed]
  19. Arbutin increases the pigmentation of cultured human melanocytes through mechanisms other than the induction of tyrosinase activity. Nakajima, M., Shinoda, I., Fukuwatari, Y., Hayasawa, H. Pigment Cell Res. (1998) [Pubmed]
  20. Prevention of the photodamage in the hairless mouse dorsal skin by kojic acid as an iron chelator. Mitani, H., Koshiishi, I., Sumita, T., Imanari, T. Eur. J. Pharmacol. (2001) [Pubmed]
  21. Kojic acid scavenges free radicals while potentiating leukocyte functions including free radical generation. Niwa, Y., Akamatsu, H. Inflammation (1991) [Pubmed]
  22. Mycotoxin production and evolutionary relationships among species of Aspergillus section Clavati. Varga, J., Rigó, K., Molnár, J., Tóth, B., Szencz, S., Téren, J., Kozakiewicz, Z. Antonie Van Leeuwenhoek (2003) [Pubmed]
  23. Probing the interaction of kojic acid antibiotics with iron(III) chloride by using electrospray tandem mass spectrometry. Sudhir, P.R., Wu, H.F., Zhou, Z.C. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
  24. Four psychrotolerant species with high chemical diversity consistently producing cycloaspeptide A, Penicillium jamesonlandense sp. nov., Penicillium ribium sp. nov., Penicillium soppii and Penicillium lanosum. Frisvad, J.C., Larsen, T.O., Dalsgaard, P.W., Seifert, K.A., Louis-Seize, G., Lyhne, E.K., Jarvis, B.B., Fettinger, J.C., Overy, D.P. Int. J. Syst. Evol. Microbiol. (2006) [Pubmed]
  25. Prenylated flavonoids from the roots of Sophora flavescens with tyrosinase inhibitory activity. Son, J.K., Park, J.S., Kim, J.A., Kim, Y., Chung, S.R., Lee, S.H. Planta Med. (2003) [Pubmed]
  26. Sphingosylphosphorylcholine-induced ERK activation inhibits melanin synthesis in human melanocytes. Kim, D.S., Park, S.H., Kwon, S.B., Park, E.S., Huh, C.H., Youn, S.W., Park, K.C. Pigment Cell Res. (2006) [Pubmed]
  27. Ultrastructural localization of D-amino acid oxidase in microperoxisomes of the rat nervous system. Arnold, G., Liscum, L., Holtzman, E. J. Histochem. Cytochem. (1979) [Pubmed]
  28. The inhibitory components from Artocarpus incisus on melanin biosynthesis. Shimizu, K., Kondo, R., Sakai, K., Lee, S.H., Sato, H. Planta Med. (1998) [Pubmed]
  29. Hepatocellular tumor induction in heterozygous p53-deficient CBA mice by a 26-week dietary administration of kojic acid. Takizawa, T., Mitsumori, K., Tamura, T., Nasu, M., Ueda, M., Imai, T., Hirose, M. Toxicol. Sci. (2003) [Pubmed]
  30. Examination of 1,5-anhydro-D-fructose and the enolone ascopyrone P, metabolites of the anhydrofructose pathway of glycogen and starch degradation, for their possible application in fruits, vegetables, and beverages as antibrowning agents. Yuan, Y., Mo, S., Cao, R., Westh, B.C., Yu, S. J. Agric. Food Chem. (2005) [Pubmed]
  31. Simultaneous determination of magnesium L-ascorbyl-2-phosphate and kojic acid in cosmetic bleaching products by using a microbore column and ion-pair liquid chromatography. Shih, Y. Journal of AOAC International. (2001) [Pubmed]
  32. Induction of thyroid tumours in (C57BL/6N x C3H/N)F1 mice by oral administration of kojic acid. Fujimoto, N., Watanabe, H., Nakatani, T., Roy, G., Ito, A. Food Chem. Toxicol. (1998) [Pubmed]
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