6,7-Dihydroxycoumarin (Esculetin)

• CAT Number: R024829
• CAS Number: 305-01-1
• Molecular Formula: C9H6O4
• Molecular Weight: 178.143
• Purity: ≥95%
• Synonyms: Esculetin; 6,7-Dihydroxy-2-benzopyrone; 6,7-Dihydroxycoumarin; Aesculetin; Asculetine; Cichorigenin; Cichoriin Aglycon; Esculetol; Esculin Aglycon; NSC 26428
• Target: PI3K
• Storage: Room temperature
• IUPAC Name: 6,7-dihydroxychromen-2-one
• InChI: InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
• InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N
• SMILES: C1=CC(=O)OC2=CC(=C(C=C21)O)O

Esculetin is a natural plant phenolic that shares features of coumarins and catechols. It inhibits lipoxygenases (LOs), including 5-LO and 12-LO (ID50s = 4 and 2.5 µM, respectively). This action is likely due to its ability to bind iron, as it also inhibits other iron-containing enzymes, including the lysine-specific demethylase KDM5B. Like other coumarins, esculetin promotes TRAIL-induced apoptosis in cancer cells. Esculetin is also used as an antioxidant to reduce reactive oxygen species and modulate oxidant-sensitive enzymes. Esculetin, which can be derived from esculin by β-glucosidases, also has anti-fungal activities.