7,8-Dihydroxycoumarin

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-pyr

7,8-dihydroxycoumarin is a hydroxycoumarin.

Daphnetin, mainly extracted from Yu Ruixiang Changbai Daphne (Daphne Korean Nakai), Daphne giraldii Nitsche bark, and root bark, is the main efficacy component of the plants D.tangutica Maxim and D.retttsa Hemsl. Changbai daphnes has the pharmacological effects of warming the spleen and stomach, relaxing the muscles and joints, and promoting circulation. In TCM, it’s commonly used as medicines for treatment of injuries. Because Changbai daphne is a pungent and warm natured herbal medicine, it was used to warm the spleen and stomach by dispelling cold.

Derived from Daphne Korean Nakai

Changbai daphne, a Chinese traditional medicine in clinic, is mainly used for treatment of coronary heart disease, rheumatoid arthritis, thromboangiitis obliterans, etc. Changbai daphne belongs to the first-class protective plants in Jilin province in China, and the rarity restricted the drug development. Scientists tried to find the effective components of Changbai daphne. In 1977, scientists of phytochemistry research group in the Traditional Chinese Medicine research laboratory from Jilin institute of Chinese medicine first successfully isolated the crystalline monomer– daphnetin– from the plant. Pharmacological results show that the pharmacological activities of this crystal are equal to Changbai daphne, which suggested the crystal is the main active ingredient . Through the condensation reaction experiment using equimolecular pyrogallic acid, malic acid, and twice the amount of sulfuric acid, under heating reaction, scientists successfully got pale yellow needle daphnetin crystals. From then on artificially synthesized daphnetin has been successfully implemented . A large-scale industrial production can be acquired. The followup researches on the metabolism and pharmacological activity of daphnetin were carried out. In 2009, the State Food and Drug Administration of China approved daphnetin capsule to be used in the clinical.

General procedure: An open reaction vessel containing a mixture of the phenol (1.0 mmol), propiolic acid (1.1 mmol), and Yb(OTf)General procedure: The appropriate o-hydroxybenzaldehyde (1 mmol) and ethyl(triphenylphosphoranylidene) acetate(1.2 mmol) were dissolved in N, N-diethylaniline (1.5 mL) and the resulting mixture was stirred under aN2 atmosphere and reflux for 15 min. The solvent was removed under reduced pressure (1 mmHg, 52 °C) and the resulting brown oil was purified by column chromatography (petroleum ether-ethylacetate, 3:1).

Daphnetin is a natural coumarin derivative providing anti-inflammatory and protective properties to those suffering from lung injury.

Molecular Weight:178.14
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:178.02660867
Monoisotopic Mass:178.02660867
Topological Polar Surface Area:66.8
Heavy Atom Count:13
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes