60890

Sigma-Aldrich

Kojic acid

purum, ≥98.0% (HPLC)

Synonym(s):
2-Hydroxymethyl-5-hydroxy-γ-pyrone, 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone
Empirical Formula (Hill Notation):
C6H6O4
CAS Number:
Molecular Weight:
142.11
Beilstein/REAXYS Number:
120895
EC Number:
MDL number:
PubChem Substance ID:

grade

purum

assay

≥98.0% (HPLC)

mp

152-155 °C (lit.)

SMILES string

OCC1=CC(=O)C(O)=CO1

InChI

1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2

InChI key

BEJNERDRQOWKJM-UHFFFAOYSA-N

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Biochem/physiol Actions

Tyrosinase inhibitor.

Certificate of Analysis

Certificate of Origin

Ya-Li Wang et al.
Journal of analytical methods in chemistry, 2018, 2141389-2141389 (2018-06-05)
Tyrosinase (TYR) is a rate-limiting enzyme in the synthesis of melanin, while direct TYR inhibitors are a class of important clinical antimelanoma drugs. This study established a spectrum-effect relationship analysis method and high-performance liquid chromatography-mass spectrometry (LC-MS) analysis method to...
G A Burdock et al.
Regulatory toxicology and pharmacology : RTP, 33(1), 80-101 (2001-03-22)
Kojic acid is a fungal metabolite commonly produced by many species of Aspergillus, Acetobacter, and Penicillium. The Aspergillus flavus group has traditionally been used in the production of a number of foods, including miso (soybean paste), shoyu (soy sauce), and...
Jun-Cheol Cho et al.
Bioorganic & medicinal chemistry letters, 22(12), 4159-4162 (2012-05-15)
We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results...
Jun-Cheol Cho et al.
Bioorganic & medicinal chemistry letters, 22(5), 2004-2007 (2012-02-15)
We synthesized cinnamate derivatives of kojic acid for use as depigmenting agents by various esterification methods. The cinnamate of 5-position of kojic acid (6) was obtained by EDC coupling, DCC coupling, acid chloride, and mixed anhydride methods. To obtain the...
Ahmad Firdaus B Lajis et al.
Journal of biomedicine & biotechnology, 2012, 952452-952452 (2012-10-24)
The depigmenting effect of kojic acid esters synthesized by the esterification of kojic acid using Rhizomucor miehei immobilized lipase was investigated in B16F1 melanoma cells. The depigmenting effect of kojic acid and kojic acid esters was evaluated by the inhibitory...

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