| Record Information |
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| Version | 2.0 |
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| Creation Date | 2010-05-21 16:18:59 UTC |
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| Update Date | 2014-12-24 20:26:31 UTC |
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| Accession Number | T3D3769 |
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| Identification |
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| Common Name | Kojic acid |
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| Class | Small Molecule |
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| Description | Kojic acid is a synthetic intermediate for production of food additives.
Kojic acid has been shown to exhibit anti-neoplastic function (4). |
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| Compound Type | - Ester
- Food Toxin
- Fungal Toxin
- Industrial/Workplace Toxin
- Metabolite
- Mycotoxin
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one | | 2-Hydroxymethyl-5-hydroxy-gamma-pyrone | | 5-Hydroxy-2-(hydroxymethyl)-4-pyrone | | 5-Hydroxy-2-(hydroxymethyl)-4H-Pyran-4-one | | 5-Hydroxy-2-(hydroxymethyl)pyran-4-one | | 5-Hydroxy-2-hydroxymethyl-4-pyrone | | 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone | | Acido kojico | | KOJ | | Kojate | | Pyran-4-one, 5-hydroxy-2-(hydroxymethyl) |
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| Chemical Formula | C6H6O4 |
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| Average Molecular Mass | 142.109 g/mol |
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| Monoisotopic Mass | 142.027 g/mol |
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| CAS Registry Number | 501-30-4 |
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| IUPAC Name | 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one |
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| Traditional Name | kojic acid |
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| SMILES | OCC1=CC(=O)C(O)=CO1 |
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| InChI Identifier | InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 |
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| InChI Key | InChIKey=BEJNERDRQOWKJM-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Pyrans |
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| Sub Class | Pyranones and derivatives |
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| Direct Parent | Pyranones and derivatives |
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| Alternative Parents | |
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| Substituents | - Pyranone
- Heteroaromatic compound
- Cyclic ketone
- Oxacycle
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aromatic alcohol
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | |
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| Physical Properties |
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| State | Solid |
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| Appearance | Tan powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 161°C | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | -0.64 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-00di-3950000000-d1e6f5b2e47ac5626c5f | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-05p6-9300000000-704def65872ec878b268 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00ko-9500000000-8c8ed21581e5ce62d657 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00dj-0972200000-d2e1134bffb7759fab36 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00dj-1940000000-7a8f18adc19d5275d098 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-3950000000-d1e6f5b2e47ac5626c5f | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03kc-6900000000-d96f98a42148a6e47233 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00di-9650000000-945de47e75f8ec9b9eaf | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0900000000-7497f496112e599fe169 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-001i-9200000000-79391fb0052779fa15a9 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0900000000-b4f5c76df606bee2639b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-1900000000-8c591424fe1f23b4f463 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9300000000-2f1a2b3413e8f032697f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-a3e3f8a5e8ce22a6cba3 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-2900000000-4f881cf1625489e94838 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9000000000-82a828b03c7d45e6515f | JSpectraViewer | | MS | Mass Spectrum (Electron Ionization) | splash10-00kf-9400000000-15508d600420b309e528 | JSpectraViewer | MoNA |
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| Toxicity Profile |
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| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (3) |
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| Mechanism of Toxicity | Kojic 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) |
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| Metabolism | Kojic acid is absorbed by the gastrointestinal tract, enters the circulation, and is probably metabolized similar to hexoses. (1) |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (7) |
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| Uses/Sources | Kojic 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) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Animals 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) |
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| Symptoms | Sensitive individuals may develop contact dermatitis. (1) |
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| Treatment | Not Available |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB01759 |
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| HMDB ID | HMDB32923 |
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| PubChem Compound ID | 3840 |
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| ChEMBL ID | Not Available |
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| ChemSpider ID | 3708 |
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| KEGG ID | C14516 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 34805 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | KOJ |
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| ACToR ID | Not Available |
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| Wikipedia Link | Kojic_acid |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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| General References | - Burdock GA, Soni MG, Carabin IG: Evaluation of health aspects of kojic acid in food. Regul Toxicol Pharmacol. 2001 Feb;33(1):80-101. [11259181 ]
- Noh JM, Kwak SY, Seo HS, Seo JH, Kim BG, Lee YS: Kojic acid-amino acid conjugates as tyrosinase inhibitors. Bioorg Med Chem Lett. 2009 Oct 1;19(19):5586-9. doi: 10.1016/j.bmcl.2009.08.041. Epub 2009 Aug 14. [19700313 ]
- Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- 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. [10466431 ]
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- Wikipedia. Kojic acid. Last Updated 14 May 2010. [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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| Down-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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