sulfuretin
aurone, 6,3',4'-trihydroxy-
Identification
| Name | sulfuretin |
| IUPAC | (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one |
| CAS Number | 120-05-8 |
| EINECS | 204-366-4 |
| FDA UNII | M6410VY6MI |
| Molecular Formula | C15 H10 O5 |
| Molecular Weight | 270.24070000 |
| MDL Number | MFCD00017304 |
Regulatory
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) |
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 sulfuretin usage levels up to | not for fragrance use. |
| Recommendation for sulfuretin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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
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.