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D5564

Sigma-Aldrich

7,8-Dihydroxycoumarin

≥97%, powder

Synonym(s):

Daphnetin, Daphnetol, Ruixiangsu

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About This Item

Empirical Formula (Hill Notation):
C9H6O4
CAS Number:
486-35-1
Molecular Weight:
178.14
EC Number:
207-632-8
MDL number:
MFCD00016977
UNSPSC Code:
12352200
PubChem Substance ID:
24278375
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥97%

form

powder

solubility

ethanol: 5 mg/mL

storage temp.

room temp

SMILES string

Oc1ccc2C=CC(=O)Oc2c1O

InChI

1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H

InChI key

ATEFPOUAMCWAQS-UHFFFAOYSA-N

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Biochem/physiol Actions

7,8-Dihydroxycoumarinan is an inhibitor of protein kinases. It is an active lactone present in plants such as Daphne Korean Nakai, and Thymelaeaceae Daphne. It serves as as analgesic, antiviral and antibacterial agent. 7,8-Dihydroxycoumarinan is found to induce tumor apoptosis via a number of signalling pathways. Thus, it is believed to exhibit antitumor effects. 7,8-Dihydroxycoumarinan might also be useful in treating lung carcinoma. It is also known to be used in treating coagulation disorders and rheumatoid arthritis. 7,8-Dihydroxycoumarinan is known to induce neurite growth and lengthen neuronal survival. It helps in clearing substances inducing necrosis, maintains water-electrolytes balance and energy metabolism. 7,8-Dihydroxycoumarinan is involved in the generation of neurotrophic factor and helps in restoring neuron function.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Neurotrophic effects of 7,8-dihydroxycoumarin in primary cultured rat cortical neurons
Yan L, et al.
Experimental and Therapeutic Medicine, 28(5), 493?498-493?498 (2012)
7, 8-Dihydroxycoumarin inhibits A549 human lung adenocarcinoma cell proliferation by inducing apoptosis via suppression of AktNF-kappaB signaling
Wang Y, et al.
Experimental and Therapeutic Medicine, 5(6), 1770-1774 (2013)
Y Z Yang et al.
The American journal of tropical medicine and hygiene, 46(1), 15-20 (1992-01-01)
Daphnetin is a dihydroxycoumarin that is being used in China for the treatment of coagulation disorders. It is also a chelator and an antioxidant. In vitro, daphnetin causes a 50% inhibition (IC50) of 3H-hypoxanthine incorporation by Plasmodium falciparum at concentrations
7, 8-dihydroxycoumarin may promote sciatic nerve regeneration by suppressing NF-kappaB expression in mice
Du JS, et al.
Molecular Medicine Reports, 8(5), 1525-1530 (2013)
E B Yang et al.
Biochemical and biophysical research communications, 260(3), 682-685 (1999-07-15)
Protein kinases play key roles in the control of cell proliferation, differentiation and metabolism. In this work, we studied the effect of coumarin and its derivatives, including daphnetin, esculin, 2-OH-coumarin, 4-OH-coumarin and 7-OH-coumarin, on the activity of protein kinases. It
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