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fraxetin
6-methoxy-7,8-dihydroxycoumarin

Supplier Sponsors

Name:7,8-dihydroxy-6-methoxychromen-2-one
CAS Number: 574-84-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-376-2
FDA UNII:CD3GD44O3K
Nikkaji Web:J11.539H
MDL:MFCD00006873
XlogP3-AA:1.20 (est)
Molecular Weight:208.16976000
Formula:C10 H8 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Fraxetin 98%
BOC Sciences
For experimental / research use only.
Fraxetin 0.985
Odor: characteristic
Use: Fraxetin isolated from the bark of Fraxinus brngeana DC. It has protective against rotenone-induced cytotoxicity and apoptotic death. antioxidant activities
Coompo
For experimental / research use only.
Fraxetin from Plants ≥98%
Odor: characteristic
Use: Incubation of cells with the fraxetin led to a significant elevation dose-dependent of cellular GSH and this was accompanied by a marked protection against rotenone-mediated toxicity, which was also significantly reversed in the cells with buthionine sulfoximine (BSO) co-treatment. Taken together, suggested that intracellular GSH appeared to be an important factor in fraxetin-mediated cytoprotection against rotenone-toxicity in SH-SY5Y cells. Fraxetin at 10-100 muM inhibited the formation of ROS, cytochrome c release, activation of caspase-3 and 9, and suppressed the up-regulation of Bax, whereas no significant change occurred in Bcl-2 levels. Our results indicated that the anti-oxidative and anti-apoptotic properties render this natural compound potentially protective against rotenone-induced cytotoxicity. The protective action of fraxetin and suggest that it can reduce apoptosis, possibly by decreasing free radical generation in SH-SY5Y cells. Myricetin at 100 microM was without any preventive effect. Fraxetin belongs to an extensive group of natural phenolic anti-oxidants. Using a human neuroblastoma SH-SY5Y cells, we have investigated the protective effects of this compound on modifications in endogenous reduced glutalhione (GSH), intracellular oxygen species (ROS) and apoptotic death on rotenone-mediated cytoxicity.
ExtraSynthese
For experimental / research use only.
Fraxetin (HPLC) ≥95%
Sigma-Aldrich
For experimental / research use only.
Fraxetin
analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5273569
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7,8-dihydroxy-6-methoxychromen-2-one
Chemidplus:0000574845
 
References:
 7,8-dihydroxy-6-methoxychromen-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5273569
Pubchem (sid):135026055
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09265
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2932.29.3000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 ruta graveolens flower oil colombia @ 0.08%
Data GC Search Trop Picture
 
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
 

Articles:

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).
 
Notes:
None found
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