Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6O4 |
| Molecular Weight | 142.1094 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=CC(=O)C(O)=CO1
InChI
InChIKey=BEJNERDRQOWKJM-UHFFFAOYSA-N
InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
| Molecular Formula | C6H6O4 |
| Molecular Weight | 142.1094 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_148.pdf and http://www.ncbi.nlm.nih.gov/pubmed/21049734
Curator's Comment: Description was created based on several sources, including
http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_148.pdf and http://www.ncbi.nlm.nih.gov/pubmed/21049734
Kojic acid was first discovered in Japan in 1907. Kojic acid is a chelation agent produced by several species of fungi, especially Aspergillus oryzae, which has the Japanese common name koji. Kojic acid is a by-product in the fermentation process of malting rice, for use in the manufacturing of sake, the Japanese rice wine. 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. It forms a bright red complex with ferric ions. Kojic acid may be used on cut fruits to prevent oxidative browning, in seafood to preserve pink and red colors, and in cosmetics. In skin care products, kojic acid functions primarily as a skin-lightening agent. It is a potent tyrosinase inhibitor. It penetrates the upper skin layers and inhibits the production of epidermal melanin. As an example of the latter, it is used to treat skin diseases like melasma. Kojic acid also has antibacterial and antifungal properties. The cocrystals of kojic acid with quercetin were found to have two times better cytotoxic activity to human cervical cancer cells (HeLa) and human colon cancer cells (Caco-2) in comparison with quercetin itself.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Absence of liver tumor-initiating activity of kojic acid in mice. | 2006-05 |
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| Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase. | 2006-04-15 |
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| Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure-activity relationship. | 2006-02-15 |
|
| Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression. | 2006-02 |
|
| Tetraketones: a new class of tyrosinase inhibitors. | 2006-01-15 |
|
| Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes. | 2006-01-12 |
|
| 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. | 2005-11-30 |
|
| Identifying 6,7,4'-trihydroxyisoflavone as a potent tyrosinase inhibitor. | 2005-10 |
|
| DeoxyArbutin: a novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency. | 2005-08 |
|
| Procyanidin trimers to pentamers fractionated from apple inhibit melanogenesis in B16 mouse melanoma cells. | 2005-07-27 |
|
| The entrapment of kojic oleate in bilayer vesicles. | 2005-07-14 |
|
| Taxonomic comparison of three different groups of aflatoxin producers and a new efficient producer of aflatoxin B1, sterigmatocystin and 3-O-methylsterigmatocystin, Aspergillus rambellii sp. nov. | 2005-07 |
|
| Potent inhibitory effects of N-aryl S-alkylthiocarbamate derivatives on the dopa oxidase activity of mushroom tyrosinase. | 2005-07 |
|
| Tyrosinase inhibition studies of diterpenoid alkaloids and their derivatives: structure-activity relationships. | 2005-07 |
|
| Evaluation of liver and peripheral blood micronucleus assays with 9 chemicals using young rats. A study by the Collaborative Study Group for the Micronucleus Test (CSGMT)/Japanese Environmental Mutagen Society (JEMS)-Mammalian Mutagenicity Study Group (MMS). | 2005-06-06 |
|
| Allergic contact dermatitis due to kojic acid. | 2005-06 |
|
| Repeated-batch production of kojic acid in a cell-retention fermenter using Aspergillus oryzae M3B9. | 2005-06 |
|
| Inhibition of tyrosinase activity by N,N-unsubstituted selenourea derivatives. | 2005-05 |
|
| Myrothenones A and B, cyclopentenone derivatives with tyrosinase inhibitory activity from the marine-derived fungus Myrothecium sp. | 2005-04 |
|
| Fungal populations and mycotoxins in silage in Assiut and Sohag governorates in Egypt, with a special reference to characteristic Aspergilli toxins. | 2005-02 |
|
| Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica. | 2005-01 |
|
| Topical methimazole as a new treatment for postinflammatory hyperpigmentation: report of the first case. | 2005 |
|
| Probing the interaction of kojic acid antibiotics with iron(III) chloride by using electrospray tandem mass spectrometry. | 2005 |
|
| Spotlight turns on cosmetics for Asian skin. | 2004-12-23 |
|
| Tyrosinase inhibitors isolated from the edible brown alga Ecklonia stolonifera. | 2004-12 |
|
| Piperlonguminine from Piper longum with inhibitory effects on alpha-melanocyte-stimulating hormone-induced melanogenesis in melanoma B16 cells. | 2004-12 |
|
| Tyrosinase inhibitors from Rhododendron collettianum and their structure-activity relationship (SAR) studies. | 2004-12 |
|
| Utilizing combination therapy to optimize melasma outcomes. | 2004-11-24 |
|
| [Simultaneous determination of magnesium L-ascorbyl-2-phosphate, arbutin and kojic acid in cosmetics by reversed-phase high performance liquid chromatography]. | 2004-11 |
|
| Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1. | 2004-11 |
|
| Prenylated flavonoids as tyrosinase inhibitors. | 2004-11 |
|
| Enhancement of hepatocarcinogenesis by kojic acid in rat two-stage models after initiation with N-bis(2-hydroxypropyl)nitrosamine or N-diethylnitrosamine. | 2004-09 |
|
| Topical agents used in the management of hyperpigmentation. | 2004-08-31 |
|
| Combining induced mutation and protoplasting for strain improvement of Aspergillus oryzae for kojic acid production. | 2004-07 |
|
| Solid-phase synthesis of kojic acid-tripeptides and their tyrosinase inhibitory activity, storage stability, and toxicity. | 2004-06-07 |
|
| Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines. | 2004-05-27 |
|
| Production of toxic metabolites in Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei: justification of mycotoxin testing in food grade enzyme preparations derived from the three fungi. | 2004-04 |
|
| Effects of kojic acid on oxidative damage and on iron and trace element level in iron-overloaded mice and rats. | 2004-03 |
|
| Kojic acid and its derivatives: history and present state of art. | 2004-03 |
|
| (-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production. | 2004-03 |
|
| Tetrapetalone A, a novel lipoxygenase inhibitor from Streptomyces sp. | 2004-01 |
|
| Morphology and biochemical activity of rat liver golgi complexes after pretreatment with bis(kojato)oxovanadium(IV) or kojic acid alone. | 2004 |
|
| Enzymatic synthesis of structured lipids. | 2004 |
|
| Optimal management of recalcitrant disorders of hyperpigmentation in dark-skinned patients. | 2004 |
|
| Management of dyschromias in ethnic skin. | 2004 |
|
| Photostability of naturally occurring whitening agents in cosmetic microemulsions. | 2003-07-29 |
|
| Functional glucosylation of kojic acid and daidzein with the Eucalyptus membrane-associated UDP-glucosyltransferase reaction system. | 2001 |
|
| Kojic acid production in an airlift bioreactor using partially hydrolyzed raw corn starch. | 2001 |
|
| Improvement of production of Kojic acid by a mutant strain Aspergillus oryzae, MK107-39. | 2001 |
Patents
| Substance Class |
Chemical
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admin
on
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Mon Mar 31 18:15:50 GMT 2025
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admin
on
Mon Mar 31 18:15:50 GMT 2025
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| Record UNII |
6K23F1TT52
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| Record Status |
Validated (UNII)
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100000088735
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207-922-4
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SUB23403
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6K23F1TT52
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m6635
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43572
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1426451
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DTXSID2040236
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3977
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C011890
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DB01759
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501-30-4
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KOJIC ACID
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