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MilliporeSigma

K3125

Sigma-Aldrich

Kojic acid

≥98.5% (HPLC), powder, tyrosinase inhibitor

Sinónimos:

2-Hydroxymethyl-5-hydroxy-γ-pyrone, 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone

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About This Item

Fórmula empírica (notación de Hill):
C6H6O4
Número de CAS:
Peso molecular:
142.11
Beilstein/REAXYS Number:
120895
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

product name

Kojic acid,

assay

≥98.5% (HPLC)

form

powder

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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Application

Kojic acid has been used:
  • as an inhibitor of tyrosinase in guinea pigs pigmented hyperopic (PH)
  • as a reference inhibitor standard for screening tyrosinase inhibition
  • as a positive control for inhibition of tyrosinase in B16F10 melanoma cells

Biochem/physiol Actions

Kojic acid is derived from some fungal species such as, Aspergillus, Acetobacter and Penicillium.. It halts melanin synthesis by inhibiting tyrosinase enzyme. It is used in the preparation of skin whitening cosmetics. However, kojic acid usage is minimal in cosmetics, as it induces skin irritation by its unstability and cytotoxic nature during long storage. It is an antioxidant and elicits radioprotective effects on chelating with manganese and zinc.
Tyrosinase inhibitor.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

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Ka-Heng Lee et al.
European journal of medicinal chemistry, 44(8), 3195-3200 (2009-04-11)
A series of 46 curcumin related diarylpentanoid analogues were synthesized and evaluated for their anti-inflammatory, antioxidant and anti-tyrosinase activities. Among these compounds 2, 13 and 33 exhibited potent NO inhibitory effect on IFN-gamma/LPS-activated RAW 264.7 cells as compared to L-NAME
Effects of the Tyrosinase-Dependent Dopaminergic System on Refractive Error Development in Guinea Pigs
Jiang L, et al.
Investigative Ophthalmology & Visual Science, 59(11), 4631-4638 (2018)
Traditional herbal prescription LASAP-C inhibits melanin synthesis in B16F10 melanoma cells and zebrafish
Kim MK, et al.
BMC Complementary and Alternative Medicine, 16(1), 223-223 (2016)
Synthesis, biological activities and molecular docking studies of some novel 2, 4, 5-trisubstituted-1, 2, 4-triazole-3-one derivatives as potent tyrosinase inhibitors
Akin S, et al.
Journal of Molecular Structure, 1175(11), 280-286 (2019)
Wei Yi et al.
European journal of medicinal chemistry, 46(9), 4330-4335 (2011-07-23)
Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the

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