fraxetin
6-methoxy-7,8-dihydroxycoumarin
Identification
| Name | fraxetin |
| IUPAC | 7,8-dihydroxy-6-methoxychromen-2-one |
| CAS Number | 574-84-5 |
| EINECS | 209-376-2 |
| FDA UNII | CD3GD44O3K |
| Molecular Formula | C10 H8 O5 |
| Molecular Weight | 208.16976000 |
| MDL Number | MFCD00006873 |
| Nikkaji Number | J11.539H |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 231.00 °C. @ 760.00 mm Hg |
| Boiling Point | 472.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 385.00 °F. TCC ( 196.00 °C. ) (est) |
| logP (o/w) | 0.590 (est) |
| Soluble in | water, 1.891e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for fraxetin usage levels up to | not for fragrance use. |
| Recommendation for fraxetin flavor usage levels up to | not for flavor use. |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Potential Uses
Natural Occurrence
Synonyms
coumarin, 7,8-dihydroxy-6-methoxy
7,8-
dihydroxy-6-methoxy-2-benzopyrone
7,8-
dihydroxy-6-methoxy-2H-1-benzopyran-2-one
7,8-
dihydroxy-6-methoxy-2H-chromen-2-one
7,8-
dihydroxy-6-methoxychromen-2-one
7,8-
dihydroxy-6-methoxycoumarin
fraxetine
6-
methoxy-7,8-dihydroxycoumarin
PubMed:
Antibacterial mechanism of fraxetin against Staphylococcus aureus.
PubMed:
Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives.
PubMed:
Two new coumarins from the seeds of Solanum indicum.
PubMed:
Purification of Coumarin Compounds From Cortex fraxinus by Adsorption Chromatography.
PubMed:
Identification and characterization of human UDP-glucuronosyltransferases responsible for the glucuronidation of fraxetin.
PubMed:
The hepatoprotective effect of fraxetin on carbon tetrachloride induced hepatic fibrosis by antioxidative activities in rats.
PubMed:
Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry.
PubMed:
Looking beyond sugars: phytochemical profiling and standardization of manna exudates from Sicilian Fraxinus excelsior L.
PubMed:
Antihyperglycemic effect of fraxetin on hepatic key enzymes of carbohydrate metabolism in streptozotocin-induced diabetic rats.
PubMed:
[Relationship between the inhibitory effect of fraxetin on breast cancer and estrogen signaling pathway].
PubMed:
Coumarins in horse chestnut flowers: isolation and quantification by UPLC method.
PubMed:
[Antioxidant activity of hydroxy derivatives of coumarin].
PubMed:
[Chemical constituents of Datura stramonium seeds].
PubMed:
[Quantitative method for simultaneous assay of four coumarins with one marker in Fraxini Cortex].
PubMed:
Protective effects of cortex fraxini coumarines against oxonate-induced hyperuricemia and renal dysfunction in mice.
PubMed:
Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds.
PubMed:
Inhibitory effects of coumarins from the stem barks of Fraxinus rhynchophylla on adipocyte differentiation in 3T3-L1 cells.
PubMed:
Natural coumarins as a novel class of neuroprotective agents.
PubMed:
Dual anti-oxidative effects of fraxetin isolated from Fraxinus rhinchophylla.
PubMed:
Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships.
PubMed:
Coumarin glycosides from Euphorbia soongarica (Boiss).
PubMed:
[Studies on chemical constituents from stem barks of Fraxinus paxiana].
PubMed:
[Coumarins from branch of Fraxinus sieboldiana and their antioxidative activity].
PubMed:
[Studies on chemical constituents of Sarcandra glabra].
PubMed:
Simultaneous analysis of coumarins and secoiridoids in Cortex Fraxini by high-performance liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry.
PubMed:
Water-soluble constituents of the root barks of Fraxinus rhynchophylla (Chinese drug Qinpi).
PubMed:
A new C9 nor-isoprenoid glucoside from Rantherium suaveolens.
PubMed:
Metabolic fate of fraxin administered orally to rats.
PubMed:
Fraxetin inhibits the induction of anti-Fas IgM, tumor necrosis factor-alpha and interleukin-1beta-mediated apoptosis by Fas pathway inhibition in human osteoblastic cell line MG-63.
PubMed:
Bone morphogenetic protein-2 and -4 (BMP-2 and -4) mediates fraxetin-induced maturation and differentiation in human osteoblast-like cell lines.
PubMed:
Fraxetin prevents rotenone-induced apoptosis by induction of endogenous glutathione in human neuroblastoma cells.
PubMed:
Effect of fraxetin on antioxidant defense and stress proteins in human neuroblastoma cell model of rotenone neurotoxicity. Comparative study with myricetin and N-acetylcysteine.
PubMed:
Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography.
PubMed:
Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities.
PubMed:
Neuroprotective effect of fraxetin and myricetin against rotenone-induced apoptosis in neuroblastoma cells.
PubMed:
Effect of fraxetin and myricetin on rotenone-induced cytotoxicity in SH-SY5Y cells: comparison with N-acetylcysteine.
PubMed:
Suppression of lipid hydroperoxide-induced oxidative damage to cellular DNA by esculetin.
PubMed:
Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity.
PubMed:
HIV gp41 binding phenolic components from Fraxinus sieboldiana var. angustata.
PubMed:
Antioxidant activity of Fraxetin: in vivo and ex vivo parameters in normal situation versus induced stress.
PubMed:
Effects of fraxetin on glutathione redox status.
PubMed:
Modifications on antioxidant capacity and lipid peroxidation in mice under fraxetin treatment.
PubMed:
Antioxidative effectiveness of some natural antioxidants in sunflower oil.
PubMed:
Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential.
PubMed:
Minor constituents from Bupleurum fruticosum roots.
PubMed:
Pharmacologically active components of a Peruvian medicinal plant, huanarpo (Jatropha cilliata).
PubMed:
Superoxide anion scavenging effect of coumarins.
PubMed:
Effect of some hydroxycoumarins on complement-mediated hemolysis in human serum.
PubMed:
Superoxide scavenging activity in leukocytes and absence of cellular toxicity of a series of coumarins.
PubMed:
Methyltransferase activity in Allanthm altissima cell suspension cultures.
PubMed:
Effects of coumarin derivatives on superoxide anion generation.
PubMed:
The sensitizing capacity of coumarins (II).
PubMed:
Inhibition of the formation of 5-hydroxy-6,8,11,14-eicosatetraenoic acid from arachidonic acid in polymorphonuclear leukocytes by various coumarins.
PubMed:
Chemical constituents of Echites hirsuta (Apocynaceae).