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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
Pricing and availability is not currently available.

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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Show Differences

1 of 4

This Item
A6733T4080SML0273
7,8-Dihydroxycoumarin ≥97%, powder

D5564

7,8-Dihydroxycoumarin

Auranofin ≥98% (HPLC)

A6733

Auranofin

6, 2′, 4′-trimethoxyflavone ≥98% (HPLC)

T4080

6, 2′, 4′-trimethoxyflavone

VAS2870 ≥97% (HPLC)

SML0273

VAS2870

form

powder

form

powder

form

powder

form

powder

assay

≥97%

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000367121
0000303974
0000303974
0000367121
0000299401

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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)
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
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)
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