EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

sulfuretin
aurone, 6,3',4'-trihydroxy-

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Name:(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
CAS Number: 120-05-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:204-366-4
FDA UNII: M6410VY6MI
MDL:MFCD00017304
XlogP3-AA:2.50 (est)
Molecular Weight:270.24070000
Formula:C15 H10 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:yellow powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 303.00 °C. @ 760.00 mm Hg
Boiling Point: 585.00 °C. @ 760.00 mm Hg (est)
Flash Point: 444.00 °F. TCC ( 228.80 °C. ) (est)
logP (o/w): 1.980 (est)
Soluble in:
 water, 1188 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Sulfuretin >98%
Odor: characteristic
Use: Sulfuretin is a natural flavonoid found in the herbs of Rhus verniciflua. Sulfuretin shows anti-inflammatory activity, which is associated with the suppression of NF-kappaB transcriptional activity via the inhibitory regulation of IKKbeta phosphorylation anti-oxidant, anti-inflammatory
Carbosynth
For experimental / research use only.
Sulfuretin
Coompo
For experimental / research use only.
Sulfuretin from Plants 96%
ExtraSynthese
For experimental / research use only.
Sulfuretin (HPLC) ≥99%
 
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 sulfuretin usage levels up to:
 not for fragrance use.
 
Recommendation for sulfuretin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5321560
National Institute of Allergy and Infectious Diseases:Data
(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
Chemidplus:0000120058
 
References:
 (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5321560
Pubchem (sid):135025792
 
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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 aurone, 6,3',4'-trihydroxy-
(Z)-2-((3,4-dihydroxyphenyl)methylene)-6-hydroxy-2H-benzofuran-3-one
(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
6,3',4'-trihydroxyaurone
 

Articles:

PubMed:Practical, Modular, and General Synthesis of 3-Coumaranones through Gold-Catalyzed Intermolecular Alkyne Oxidation Strategy.
PubMed:The cytoprotective effect of sulfuretin against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2/ARE and JNK/ERK MAPK-mediated heme oxygenase-1 expression.
PubMed:Sulfuretin inhibits 6-hydroxydopamine-induced neuronal cell death via reactive oxygen species-dependent mechanisms in human neuroblastoma SH-SY5Y cells.
PubMed:Simultaneous determination of bioactive phenolic compounds in the stem extract of Rhus verniciflua stokes by high performance liquid chromatography.
PubMed:Potential neuroprotective flavonoid-based inhibitors of CDK5/p25 from Rhus parviflora.
PubMed:Protective effect of detoxified Rhus verniciflua stokes on human keratinocytes and dermal fibroblasts against oxidative stress and identification of the bioactive phenolics.
PubMed:Sulfuretin-induced miR-30C selectively downregulates cyclin D1 and D2 and triggers cell death in human cancer cell lines.
PubMed:Suppression of TPA-induced tumor cell invasion by sulfuretin via inhibition of NF-κB-dependent MMP-9 expression.
PubMed:Antiviral activities of flavonoids isolated from the bark of Rhus verniciflua stokes against fish pathogenic viruses In Vitro.
PubMed:Sulfuretin, a major flavonoid isolated from Rhus verniciflua, ameliorates experimental arthritis in mice.
PubMed:Sulfuretin from heartwood of Rhus verniciflua triggers apoptosis through activation of Fas, Caspase-8, and the mitochondrial death pathway in HL-60 human leukemia cells.
PubMed:Preparative isolation and purification of neuroprotective compounds from Rhus verniciflua by high speed counter-current chromatography.
PubMed:Neuroprotective and anti-inflammatory effects of flavonoids isolated from Rhus verniciflua in neuronal HT22 and microglial BV2 cell lines.
PubMed:A scaffold hopping approach to identify novel monoamine oxidase B inhibitors.
PubMed:Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum.
PubMed:Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells.
PubMed:HPLC-DAD-MS analysis of dyes identified in textiles from Mount Athos.
PubMed:Chemical constituents of the bark of Dipteryx alata vogel, an active species against Bothrops jararacussu venom.
PubMed:Sulfuretin attenuates allergic airway inflammation in mice.
PubMed:Sulfuretin protects against cytokine-induced beta-cell damage and prevents streptozotocin-induced diabetes.
PubMed:Sulfuretin isolated from heartwood of Rhus verniciflua inhibits LPS-induced inducible nitric oxide synthase, cyclooxygenase-2, and pro-inflammatory cytokines expression via the down-regulation of NF-kappaB in RAW 264.7 murine macrophage cells.
PubMed:Anti-inflammatory effects of sulfuretin from Rhus verniciflua Stokes via the induction of heme oxygenase-1 expression in murine macrophages.
PubMed:Cotinus coggygria wood: novel flavanone dimer and development of an HPLC/UV/MS method for the simultaneous determination of fourteen phenolic constituents.
PubMed:Comparison of extraction methods for the analysis of natural dyes in historical textiles by high-performance liquid chromatography.
PubMed:Selective cytotoxic effects on human cancer cell lines of phenolic-rich ethyl-acetate fraction from Rhus verniciflua Stokes.
PubMed:Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles.
PubMed:Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts.
PubMed:Sulfur-substituted naphthalimides as photoactivatable anticancer agents: DNA interaction, fluorescence imaging, and phototoxic effects in cultured tumor cells.
PubMed:Phenolic-rich fraction from Rhus verniciflua Stokes (RVS) suppress inflammatory response via NF-kappaB and JNK pathway in lipopolysaccharide-induced RAW 264.7 macrophages.
PubMed:[Chemical constituents from branch of Broussonetia papyrifera].
PubMed:Rhus verniciflua stokes extract: radical scavenging activities and protective effects on H2O2-induced cytotoxicity in macrophage RAW 264.7 cell lines.
PubMed:Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus.
PubMed:Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes.
PubMed:Flavonoids purified from Rhus verniciflua Stokes actively inhibit cell growth and induce apoptosis in human osteosarcoma cells.
PubMed:Extract from Rhus verniciflua Stokes is capable of inhibiting the growth of human lymphoma cells.
PubMed:Antimutagenic activity of flavonoids from the heartwood of Rhus verniciflua.
PubMed:Antirheumatoid arthritis effect of Rhus verniciflua and of the active component, sulfuretin.
PubMed:Antioxidant activity from the stem bark of Albizzia julibrissin.
PubMed:Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean).
PubMed:Identification of Rhus verniciflua Stokes compounds that exhibit free radical scavenging and anti-apoptotic properties.
PubMed:Activity-guided isolation of antioxidative constituents of Cotinus coggygria.
PubMed:Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera.
PubMed:Natural polyhydroxylated compounds as inhibitors of xanthine oxidase.
PubMed:The sensitizing capacity of sulfuretin.
PubMed:Contact dermatitis to sesquiterpene lactones in Inula viscosa Aiton.
 
Notes:
the chalcone c ring closes into a 5 instead of the more typical 6 membered ring leaving a phenyl methane at the 2 position instead of the typical phenyl.
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