Daphnetin

Names

[ CAS No. ]:
486-35-1

[ Name ]:
Daphnetin

[Synonym ]:
Daphnetin
7,8-Dihydroxychromen-2-one
7,8-Dihydroxycoumarin
7,8-dihydroxy-coumarin
2H-1-Benzopyran-2-one, 7,8-dihydroxy-
EINECS 207-632-8
7,8-Dihydroxy-2H-chromen-2-one
7,8-Dihydroxy-2H-1-benzopyran-2-one
MFCD00016977
TCMDC-125839

Biological Activity

[Description]:

Daphnetin (7,8-dihydroxycoumarin), one coumarin derivative isolated from plants of the Genus Daphne, is a protein kinase inhibitor, with IC50s of 7.67 μM, 9.33 μM and 25.01 μM for EGFR, PKA and PKC in vitro, respectively[1][2]. Daphnetin (7,8-dihydroxycoumarin) is a secondary metabolite of plants used in folk medicine to counter inflammatory and allergic diseases, also has been clinically used in the treatment of coagulation disorders, rheumatoid arthritis with anti-malarian and anti-pyretic properties[3].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Signaling Pathways >> JAK/STAT Signaling >> EGFR

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> PKA

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR

Signaling Pathways >> Stem Cell/Wnt >> PKA

Research Areas >> Inflammation/Immunology

Signaling Pathways >> TGF-beta/Smad >> PKC

[Target]

EGFR:7.67 μM (IC50)

PKA:9.33 μM (IC50)

PKC:25.01 μM (IC50)

[References]

[1]. Yang EB, et al. Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor. Biochem Biophys Res Commun. 1999 Jul 14;260(3):682-5.

[2]. Lv H, et al. Daphnetin-mediated Nrf2 antioxidant signaling pathways ameliorate tert-butyl hydroperoxide (t-BHP)-induced mitochondrial dysfunction and cell death. Free Radic Biol Med. 2017 May;106:38-52.

[3]. Jiménez-Orozco FA, et al. Differential effects of esculetin and daphnetin on in vitro cell proliferation and in vivo estrogenicity. Eur J Pharmacol. 2011 Oct 1;668(1-2):35-41.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
430.4±45.0 °C at 760 mmHg

[ Melting Point ]:
265-268°C (dec.)

[ Molecular Formula ]:
C₉H₆O₄

[ Molecular Weight ]:
178.14

[ Flash Point ]:
184.5±22.2 °C

[ Exact Mass ]:
178.026611

[ PSA ]:
70.67000

[ LogP ]:
0.77

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.689

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN6382600

CHEMICAL NAME :: Coumarin, 7,8-dihydroxy-

CAS REGISTRY NUMBER :: 486-35-1

BEILSTEIN REFERENCE NO. :: 0009372

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C9-H6-O4

MOLECULAR WEIGHT :: 178.15

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5370 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 22,87,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 429 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 22,87,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 375 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 22,87,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
GN6382600

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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