D5564

7,8-Dihydroxycoumarin

Name: 7,8-Dihydroxycoumarin
Brand: SIGMA

≥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

Key Documents

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biological source

synthetic (organic)

Quality Level

200

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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Bioactive Small Molecule Inhibitors

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Show Differences

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This Item	A6733	T4080	SML0273
Sigma-Aldrich D5564 7,8-Dihydroxycoumarin	Sigma-Aldrich A6733 Auranofin	Sigma-Aldrich T4080 6, 2′, 4′-trimethoxyflavone	Sigma-Aldrich SML0273 VAS2870
assay ≥97%	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥97% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. room temp	storage temp. room temp	storage temp. room temp
solubility ethanol: 5 mg/mL	solubility DMSO: ≥5 mg/mL	solubility DMSO: >5 mg/mL	solubility DMSO: ≥5 mg/mL
biological source synthetic (organic)	biological source -	biological source -	biological source -

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,[1] and Thymelaeaceae Daphne.[2] 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.[1] 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.[3] 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.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000469678

0000461099

0000367121

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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)

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)

Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor.

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

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)

Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase.

Gregory J Finn et al.

Biochemical pharmacology, 67(9), 1779-1788 (2004-04-15)

Daphnetin has been shown to be a potent in vitro anti-proliferative agent to the human renal cell carcinoma (RCC) cell line, A-498. In the present study, we investigated its effects on mitogen-activated protein kinase (MAPK) signalling along with cell cycle

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