Daphnetin

Daphnetin is a chemical compound with the molecular formula C₉H₆O₄. It has been isolated from plants of the genus Daphne.^[2][3] It has also been found in Matricaria chamomilla (chamomile).^[4]

Quick facts Names, Identifiers ...

Daphnetin

Names
IUPAC name 7,8-Dihydroxy-2H-chromen-2-one
Other names 7,8-Dihydroxycoumarin
Identifiers
CAS Number	486-35-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17313
ChEMBL	ChEMBL244948
ChemSpider	4444191
ECHA InfoCard	100.006.939
EC Number	207-632-8
KEGG	C03093
PubChem CID	5280569
UNII	XC84571RD2
CompTox Dashboard (EPA)	DTXSID00197560
InChI InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H Key: ATEFPOUAMCWAQS-UHFFFAOYSA-N
SMILES C1=CC(=C(C2=C1C=CC(=O)O2)O)O
Properties
Chemical formula	C9H6O4
Molar mass	178.143 g·mol−1
Melting point	256 °C (493 °F; 529 K)[1]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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It a crystalline solid with a melting point of 256 °C.^[1] It is soluble in boiling water.^[1]

Daphnetin can undergo enzymatic glycosylation to yield its 7-O-glucoside which is called daphnin (daphnetin 7-β-D-glucopyranoside). The reaction is catalyzed by the enzyme O-dihydroxy coumarin 7-O-glucosyltransferase.^[5][6]

Daphnetin shows several neuroprotective and anti-inflammatory effects on the inhibition of the TLR4/NF-κB mediated inflammatory signaling pathway. They also could inhibit the IKKs/IkBa/NF-κB, AKT, and the Src/FAK/ERK1/2 multi-target medication signaling pathway for anti-angiogenesis and cancer.^[7]

Daphnetin has been reported to be a strong sensitizer, which means that this compound and its glycosidic derivatives (e.g. daphnin) can be a cause of allergic reactions.^[4]