120-05-8

Basic information

• Product Name: SULFURETIN
• Synonyms: SULFURETIN;6,3',4'-TRIHYDROXYAURONE;3',4',6-TRIHYDROXYAURONE;2-(3,4-dihydroxybenzylidene)-6-hydroxy-2H-benzofuran-3-one;(Z)-2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-2H-benzofuran-3-one;SULPHURETIN;SULFURETIN WITH HPLC;SULFURETIN hplc
• CAS NO: 120-05-8
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24
• EINECS: 204-366-4
• Product Categories: Aurones
• Mol File: 120-05-8.mol

Chemical Properties

• Melting Point: 295°C
• Boiling Point: 585 °C at 760 mmHg
• Flash Point: 228.8 °C
• Appearance: /
• Density: 1.597 g/cm³
• Vapor Pressure: 2.79E-14mmHg at 25°C
• Refractive Index: 1.793
• CAS DataBase Reference: SULFURETIN(CAS DataBase Reference)
• NIST Chemistry Reference: SULFURETIN(120-05-8)
• EPA Substance Registry System: SULFURETIN(120-05-8)

Safety Data

• Hazardous Substances Data: 120-05-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Sulfuretin is used as a therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer properties. It has shown promising results in the treatment of skin conditions such as dermatitis and eczema, as well as in aiding insulin sensitivity and reducing the risk of diabetes.
Used in Cosmetic Industry:
Sulfuretin is used as a natural pigment in cosmetics for its yellow and orange coloring properties, derived from its presence in various plants.
Used in Healthcare Research:
Sulfuretin is used as a subject of ongoing research to further explore its potential applications in medicine and healthcare, particularly in the areas of anti-cancer effects and treatment of skin conditions.

InChI:InChI=1/C15H10O5/c16-9-2-3-10-13(7-9)20-14(15(10)19)6-8-1-4-11(17)12(18)5-8/h1-7,16-18H/b14-6+

Upstream product

• 6272-26-0 6-hydroxybenzofuran-3-one 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 36685-46-8 (Z)-2-(3,4-dimethoxybenzylidene)-6-methoxybenzofuran-3(2H)-one 
• 113739-06-3 methyl 6-hydroxybenzofuran-3(2H)-one 
• 108-46-3 recorcinol 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 1360878-02-9 sulphuretin 3'-O-β-glucopyranoside 

Downstream Products

• 5965-85-5 6-acetoxy-2-((Z)-3,4-diacetoxy-benzylidene)-benzofuran-3-one 
• 1005324-89-9 2-(3,4-dihydroxybenzyl)-6-hydroxybenzofuran-3(2H)-one 

Related news

SULFURETIN (cas 120-05-8) 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-κB in RAW 264.7 murine macrophage cells09/05/2019

It has been reported that Rhus verniciflua exhibits anti-inflammatory, anti-oxidant and anti-cancer activities. However, little is known about biological activity of sulfuretin, a flavonoid isolated from R. verniciflua. In the present study, we investigated the anti-inflammatory effect and the u...detailed

Anti-inflammatory effects of SULFURETIN (cas 120-05-8) from Rhus verniciflua Stokes via the induction of heme oxygenase-1 expression in murine macrophages09/04/2019

Rhus verniciflua Stokes (Anacardiaceae) has traditionally been used as an ingredient in East Asian medicines used to treat oxidative damage and cancer. Sulfuretin is one of the major flavonoid components isolated from R. verniciflua. In the present study, we isolated sulfuretin from R. vernicifl...detailed

SULFURETIN (cas 120-05-8) inhibits 6-hydroxydopamine-induced neuronal cell death via reactive oxygen species-dependent mechanisms in human neuroblastoma SH-SY5Y cells09/02/2019

Sulfuretin, a potent anti-oxidant, has been thought to provide health benefits by decreasing the risk of oxidative stress-related diseases. In this study, we investigated the mechanisms of sulfuretin protection of neuronal cells from cell death induced by the Parkinson’s disease (PD)-related ne...detailed

SULFURETIN (cas 120-05-8) attenuates allergic airway inflammation in mice08/31/2019

Sulfuretin is one of the main flavonoids produced by Rhus verniciflua, which is reported to inhibit the inflammatory response by suppressing the NF-κB pathway. Because NF-κB activation plays a pivotal role in the pathogenesis of allergic airway inflammation, we here examined the effect of sulf...detailed

Relevant articles and documents

Design, synthesis and biological activities of dihydroaurones

To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2

In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2.

Aurones as new porcine pancreatic α-amylase inhibitors

Background: Aurones, (Z)-2-benzylidenebenzofuran-3-one derivatives, are naturally-occurring structural isomers of flavones, with promising pharmacological potential. Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α-amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds between the OH groups of the A or B ring of (Z)-benzylidenebenzofuran-3-one derivatives and the catalytic residues of the binding site are crucial for their inhibitory activities. Conclusion: It seems that the OH groups in aurones inhibit α-amylase in a manner similar to that of OH groups in flavones and flavonols.

"On water" synthesis of aurones: First synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia

A simple and green method for the synthesis of aurones by condensation of benzofuranone with aromatic aldehyde in neat water has been developed. The main advantages of this protocol include good yields, absence of catalyst, reagent, organic solvent, work-up and chromatographic purification. 4,5,3',4',5'-Pentamethoxy-6-hydroxyaurone, isolated from Smilax riparia was synthesized for the first time from 3-benzyloxy-4,5-dimethoxybenzaldehyde in five steps. {figure presented}.

Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

The comparison of neuroprotective effects of isoliquiritigenin and its Phase I metabolites against glutamate-induced HT22 cell death

It is becoming increasingly important to investigate drug metabolites to evaluate their toxic or preventive effects after administration of the parent compound. In our previous study, isoliquiritigenin isolated from Glycyrrhizae Radix effectively protected mouse-derived hippocampal neuronal cells (HT22) against 5 mM glutamate-induced oxidative stress. However, there is little information on the protective effects of the metabolites of isoliquiritigenin on HT22 cells. In this study, isoliquiritigenin and its Phase I metabolites were prepared and their neuroprotective activities on glutamate-treated HT22 cells were compared. The prepared metabolites were liquiritigenin (1), 2′,4,4′,5′-tetrahydroxychalcone (2), sulfuretin (3), butein (4), davidigenin (5), and cis-6,4′-dihydroxyaurone (6). Among the six metabolites, 4 showed better neuroprotective effects than the parent compound, isoliquiritigenin. Our study suggests that the neuroprotective effect of isoliquiritigenin could be elevated by its active metabolite 4, which is a chalcone containing a catechol group in the B ring.

Fabrication, characterisation and in vitro biological activities of a sulfuretin-supplemented nanofibrous composite scaffold for tissue engineering

Electrospun micro/nanofibrous scaffolds are widely used in various tissue regeneration applications because they have a similar structure to the extracellular matrix and can induce high attachment, proliferation and even differentiation of cultured cells. Here, we designed a new composite scaffold consisting of poly(ε-caprolactone) (PCL), bone morphogenetic protein (BMP-2) and sulfuretin fabricated using a combined process, i.e. electrospinning/plasma-treatment/coating. In the composite, we introduced a new bioactive component, sulfuretin, which was used as a cell stimulant to regenerate bone tissue. Sulfuretin release from the composite was controlled by coating of a fixed concentration of alginate. The in vitro biocompatibilities of the fibrous composites were examined using preosteoblasts (MC3T3-E1s), and the composite showed high cell adhesion and differentiation for a limited range of sulfuretin compared to the control, which lacked sulfuretin. These results suggest sulfuretin to be an effective supplemental bioactive agent for enhancing bone tissue growth on fibrous composite scaffolds.

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

Investigation of binding-site homology between mushroom and bacterial tyrosinases by using aurones as effectors

Tyrosinase is a copper-containing enzyme found in plants and bacteria, as well as in humans, where it is involved in the biosynthesis of melanin-type pigments. Tyrosinase inhibitors have attracted remarkable research interest as whitening agents in cosmetology, antibrowning agents in food chemistry, and as therapeutics. In this context, commercially available tyrosinase from mushroom (TyM) is frequently used for the identification of inhibitors. This and bacterial tyrosinase (TyB) have been the subjects of intense biochemical and structural studies, including X-ray diffraction analysis, and this has led to the identification of structural homology and divergence among enzymes from different sources. To better understand the behavior of potential inhibitors of TyM and TyB, we selected the aurone family - previously identified as potential inhibitors of melanin biosynthesis in human melanocytes. In this study, a series of 24 aurones with different hydroxylation patterns at the A- and B-rings were evaluated on TyM and TyB. The results show that, depending on the hydroxylation pattern of A- and B-rings, aurones can behave as inhibitors, substrates, and activators of both enzymes. Computational analysis was performed to identify residues surrounding the aurones in the active sites of both enzymes and to rationalize the interactions. Our results highlight similarities and divergence in the behavior of TyM and TyB toward the same set of molecules. A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

Biflavonoids from flowers of Butea monosperma (Lam.) Taub.

A new aurone glucoside (1) and three new biflavonoids (12 - 14), together with fourteen known compounds, were isolated from the flowers of Butea monosperma (Lam.) Taub. The structures of the new compounds were established by 1D, 2D NMR, MS and CD analyses. The isolated compounds were evaluated for their influenza A neuraminidase inhibitory activity and DPPH free-radical scavenging activity.