Kojic acid

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Kojic acid
KojicAcid.svg
Names
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
501-30-4 YesY
ChEBI CHEBI:43572 N
ChEMBL ChEMBL287556 YesY
ChemSpider 3708 YesY
DrugBank DB01759 N
EC number 207-922-4
Jmol-3D images Image
KEGG C14516 YesY
PubChem 3840
RTECS number UQ0875000
UNII 6K23F1TT52 YesY
Properties
C6H6O4
Molar mass 142.11 g/mol
Appearance white
Melting point 152 to 155 °C (306 to 311 °F; 425 to 428 K)
Slight
Acidity (pKa) 9.40[1]
Hazards
R-phrases R36/37/38
S-phrases S22, S24/25
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Kojic acid is a chelation agent produced by several species of fungi, especially Aspergillus oryzae, which has the Japanese common name koji.[2][3] 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.[4] It forms a bright red complex with ferric ions.

Biosynthesis[edit]

13C-Labeling studies have revealed at least two pathways to kojic acid. In the usual route, dehydratase enzymes convert glucose to kojic acid. Pentoses are also viable precursors in which case dihydroxyacetone is invoked as an intermediate.[2]

Applications[edit]

Kojic acid may be used on cut fruits to prevent oxidative browning, in seafood to preserve pink and red colors, and in cosmetics to lighten skin. As an example of the latter, it is used to treat skin diseases like melasma.[5] Kojic acid also has antibacterial and antifungal properties.[citation needed] 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[6]

Protective effects from radiation-induced damage[edit]

Kojic acid appears to possess marked protective (radioresistance) effects from radiation-induced damage. It increased the 30 day survival rate of mice after exposed to a lethal dose of gamma radiation and had significant radioprotective effects on the hematopoietic system, the immune system and DNA of mice exposed to a 4 Gy sublethal dose of radiation. Pretreatment with Kojic acid has been shown to protect Chinese hamster ovary cells against ionizing radiation-induced damage. Dogs pretreated with kojic acid after whole-body exposure to a lethal dose of 3 Gy gamma radiation had a 51 day survival rate of 66.7% versus the dogs in the 3 Gy irradiation only group, which all died within 16 days of postirradiation.[7]

References[edit]

  1. ^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
  2. ^ a b c Bentley, R. (2006). "From miso, sake and shoyu to cosmetics: a century of science for kojic acid". Nat. Prod. Rep. 23: 1046–1062. 
  3. ^ Yabuta T (1924). "The constitution of kojic acid, a gamma-pyrone derivative formed by Aspergillus oryzae from carbohydrates". Journal of the Chemical Society 125: 575–587. doi:10.1039/ct9242500575. 
  4. ^ Kojic acid and enzymatic browning
  5. ^ Melasma, American Academy of Dermatology
  6. ^ Veverka, M., Dubaj, T., Gallovič, J., Jorík, V., Veverková, E., Danihelová, M., & Šimon, P. (2015). Cocrystals of quercetin: synthesis, characterization, and screening of biological activity. Monatshefte für Chemie-Chemical Monthly,146(1), 99-109 doi:10.1007/s00706-014-1314-6
  7. ^ Wang, Kai; Li, Peng-Fei; Han, Chun-Guang; Du, Li; Liu, Chao; Hu, Ming; Lian, Shi-Jie; Liu, Yong-Xue (2014). "Protective Effects of Kojic Acid on the Periphery Blood and Survival of Beagle Dogs after Exposure to a Lethal Dose of Gamma Radiation". Radiation Research 182 (6): 666–673. doi:10.1667/RR13823.1. 

External links[edit]