486-35-1 Usage
Description
7,8-Dihydroxycoumarin is a naturally occurring coumarin derivative with potential anti-inflammatory and protective properties, particularly for those suffering from lung injury. It is a primary reference substance with assigned absolute purity, considering chromatographic purity, water, residual solvents, and inorganic impurities. The exact purity value can be found on the certificate provided by PhytoLab GmbH & Co. KG.
Uses
Used in Pharmaceutical Industry:
7,8-Dihydroxycoumarin is used as an active pharmaceutical ingredient for its anti-inflammatory and protective properties, particularly in the treatment of lung injury. Its pharmacological effects are attributed to its natural origin as a coumarin derivative, which provides a promising foundation for further research and development in the pharmaceutical sector.
Used in Traditional Chinese Medicine (TCM):
In TCM, 7,8-Dihydroxycoumarin is used as a component in medicines for the treatment of injuries. Its warming and relaxing properties make it suitable for warming the spleen and stomach, as well as promoting circulation and relaxing muscles and joints. This application takes advantage of the compound's natural properties and its traditional use in herbal medicine.
Physical Properties:
7,8-Dihydroxycoumarin appears as a white or off-white powder, which is odorless and tasteless. It has the following solubility properties: slightly soluble in methanol (equilibrium solubility of 485.4 μg/mL), slightly soluble in ethanol (equilibrium solubility of 230.06 μg/mL), and insoluble in water (equilibrium solubility of 176.7 μg/mL). The melting point of 7,8-Dihydroxycoumarin is between 262–264°C.
History
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.
Indications
This product is contained in national standards for chemical drugs, mainly used in
Buerger’s disease, occlusive vascular disease, and coronary heart disease.
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.
Pharmacology
Daphnetin pharmacological effect mainly includes: 1. Improvement of the cardiovascular system function； 2. Effects on the central nervous system.
Daphnetin also acts on the NF-k B and NFAT signal pathway and results in immune inhibition; it is also used for the treatment of malaria parasite and Pneumocystis carinii infection by chelating to Fe2 + or by acting on ribonucleotide reductase; daphnetin shows bacteriostatic effects on gold grapes, Escherichia coli, Shigella’s blessing, and Pseudomonas aeruginosa by inhibiting succinic acid oxidase in mitochondria in bacteria; daphnetin reduces the incidences of diarrhea in model mice by inhibiting mice gastrointestinal propulsive movement and has a stronger toxic effect on several important aphids .
Plasma protein binding of Daphetin is low. The urinary excretion is higher. The distribution volume is relatively larger. Both of metabolism and excretion are rapid. Drug elimination is mainly through the kidney with a half-life of only 15 min. The tissue distributions after intravenous injection and oral administration are equal. Daphnetin may distribute in the brain through the blood-brain barrier. The metabolites have poor stability and low oral bioavailability. People have studied the metabolic pathways and metabolic product. Daphnetin may be the substrates of MRP2 and BCRP transporters, and thus intestinal absorption is affected; in the plasma of rats, the main metabolite are 7-O and 8-O glucoside substitution products which are mediated by UT1A6 and UT1A9. The anti-inflammatory activity of the metabolites is dependent on daphnetin-7-methyl ether.
Clinical Use
It has been verified by a large number of clinical cases that oral daphnetin capsule
can significantly improve thromboangiitis obliterans; oral daphnetin has a better
curative effect than intramuscular injection of Changbai daphne in patients with
angina pectoris due to coronary heart disease. Daphnetin shows an obvious analgesic sedative effect on surgical and nonsurgical pain-relieved patients after intravenous drip or injection of daphnetin; oral daphnetin capsule shows significant
therapeutic effects on rheumatoid arthritis.There are no reports about serious adverse reactions. Two cases of whole-body
red itch were reported. It sometimes has mild gastrointestinal reaction when continuously used.
Purification Methods
Crystallise it from aqueous EtOH. It can be sublimed. [Beilstein 18/3 V 202.].
Check Digit Verification of cas no
The CAS Registry Mumber 486-35-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 486-35:
(5*4)+(4*8)+(3*6)+(2*3)+(1*5)=81
81 % 10 = 1
So 486-35-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H
486-35-1Relevant articles and documents
Coumarins from the bark of Daphne marginata
Zhang, Wei,Shen, Yunheng,Liu, Runhui,Zhang, Chuan,Chen, Haisheng,Fu, Peng,Shan, Lei,Zhang, Weidong
, p. 317 - 318 (2007)
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Sato,Hasegawa
, p. 2367,2372 (1971)
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Antagonistic activity of hydroxycoumarin-based antioxidants as possible singlet oxygen precursor photosensitizers
Guerrero, Tomás,Vázquez-Ortega, Fernanda,Lagunes, Irene,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo,Medina, Manuel E.,Trigos, ángel
, (2021/05/10)
Coumarins are phenolic-type compounds with efficient antioxidant activity due to their ability to scavenge reactive oxygen species. Nevertheless, their ability to behave as photosensitizers capable of generating reactive oxygen species, such as singlet oxygen, has been less studied. In this work, the photosensitizing ability of seven hydroxycoumarins was evaluated through the photooxidation of ergosterol by quantifying the conversion of ergosterol into ergosterol peroxide. In our experimental conditions, we found that almost every tested antioxidant coumarin promotes the peroxidation of ergosterol. The results suggest that the hydroxycoumarins exhibit potential photosensitizing activity by promoting singlet oxygen generation by a Type II photochemical mechanism. Density functional theory (DFT) calculations were also performed to obtain further insight into the chemical reactivity of tested compounds; the observed tendency in the group of antioxidant coumarins to promote the reaction was their hardness due to the principle of maximum hardness. To evaluate our conclusion, we performed the reaction using a highly polarizable coumarin as a photosensitizer, which resulted in an increased photosensitizing capacity supported with DFT calculations, which reinforces our analysis. Finally, we found that hydroxycoumarins can be potentially pro-oxidants since some of them can act as photosensitizers and generate singlet oxygen in the presence of UV–Vis light, a characteristic that must be considered when these compounds are used as antioxidants.
Tumor diagnosis and treatment fluorescent probe for targeting tumor Wolburg effect
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Paragraph 0048-0053, (2020/11/02)
The invention discloses a tumor diagnosis and treatment fluorescent probe for targeting tumor Warburg effect, and the structure of the fluorescent probe is shown as a formula (I). The fluorescent probe can be directly used in a cell line to analyze and detect the expression degree of tumor cell GLUT1 protein, so as to complete the screening of tumor cells. Meanwhile, tumor cell proliferation is inhibited by directly blocking the GLUT1 channel to inhibit intake of sugar nutritional ingredients by tumors. And an effective means and a useful tool are provided for early screening and diagnosis oftumors, development of new anti-tumor drugs and the like.
Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements
Pardo-Casta?o, Camilo,García, Andrés C.,Benavides, Paola,Bola?os, Gustavo
, p. 3799 - 3810 (2019/09/30)
Collinin is a derivative of coumarin that has shown remarkable potential against cancer, tuberculosis, periodontitis, and other prevalent diseases, and is usually extracted from plants of the Rutaceae family at a very low yield. In this work, collinin and a position-isomer herein called isocollinin were synthesized at different scales (from 1 to 50 g of precursor) by a route consisting of two parallel and two sequential chemical reactions. The isomers were characterized by 1H NMR, 13C NMR, nuclear Overhauser enhancement spectroscopy NMR, melting temperature, and melting enthalpy. For each isomer, the Hansen solubility parameters and the radius of its solubility sphere were experimentally determined by solubility tests in 15 common solvents and two solvent blends. The solubility of each isomer in pressurized CO2 was determined at 30 and 50 °C from 72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique, which was validated with the anthracene-CO2 system. The solubility of both isomers in CO2 increased with pressure in the range of temperatures and pressures considered, but that of collinin exhibited an asymptotic behavior around 80.8 and 104.8 bar, at 30 and 50 °C, respectively.
