29700-22-9

Basic information

• Product Name: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• Synonyms: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol;4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol;Oxyresveratrol ,4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol;Oxyresveratrol;4-[2-(3,5-dihydroxyp;2,3',4,5'-Tetrahydroxy-trans-stilbene;25g;(E)-4-(3,5-dihydroxystyryl)benzene-1,3-diol
• CAS NO: 29700-22-9
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• EINECS: 300-008-4
• Product Categories: APIs;reagent;standard substance;API
• Mol File: 29700-22-9.mol

Chemical Properties

• Melting Point: 201-202.5 °C
• Boiling Point: 523.8 °C at 760 mmHg
• Flash Point: 260.9 °C
• Appearance: /
• Density: 1.468 g/cm³
• Vapor Pressure: 1.37E-11mmHg at 25°C
• Refractive Index: 1.8
• Storage Temp.: 2-8°C
• Solubility: Ethyl Acetate (Slightly), Methanol
• PKA: 9.14±0.10(Predicted)
• CAS DataBase Reference: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol(29700-22-9)
• EPA Substance Registry System: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol(29700-22-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25
• WGK Germany: 3
• Hazardous Substances Data: 29700-22-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is used as a COX-1 inhibitor for its anti-inflammatory and analgesic properties, similar to resveratrol. It is also employed as an anti-cancer agent, targeting various types of cancer by modulating oncological signaling pathways and demonstrating synergistic effects when combined with conventional chemotherapeutic drugs.
Used in Cosmetics Industry:
In the cosmetics industry, 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is used as an effective tyrosinase inhibitor, which helps in reducing the production of melanin and thus, can be utilized in skin-whitening and anti-aging products.
Used in Nutraceutical Applications:
4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol is used as a nutraceutical ingredient due to its antioxidant properties, which can help in reducing oxidative stress and promoting overall health.
Used in Drug Delivery Systems:
Similar to gallotannin, novel drug delivery systems can be developed for 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol to enhance its applications and efficacy against various diseases, including cancer. Organic and metallic nanoparticles can be employed as carriers for improved delivery, bioavailability, and therapeutic outcomes.

Biological Activity

Oxyresveratrol is neuroprotective and inhibits the apoptotic cell death in transient cerebral ischemia. It effectively scavenges H2O2, NO (IC50 = 45.3 μM), and the artificial free radical 2,2-diphenyl-l-picrylhydrazyl (IC50 = 28.9 μM)In vitro:1)oxyresveratrol exhibited more than 50% inhibition at 100 μM on L-tyrosine oxidation by murine tyrosinase activity.2) oxyresveratrol showed an IC50 value of 52.7 μM on the enzyme activity. 3) oxyresveratrol works through reversible inhibition of tyrosinase activity rather than suppression of the expression and synthesis of the enzyme.In vivo:1) Oxyresveratrol (10 or 20 mg/kg) significantly reduced the brain infarct volume by approximately 54% and 63%, respectively, when compared to vehicle-treated MCAO rats.2) oxyresveratrol treatment diminished cytochrome c release and decreasedcaspase-3 activation in MCAO rats.

Solubility in organics

Oxyresveratrol is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of oxyresveratrol in these solvents is approximately 50 mg/ml.

InChI:InChI=1/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+

Upstream product

• 33617-38-8 2,4-bis(trimethylsiloxy) benzaldehyde 
• 29680-77-1 (3,5-dihydroxybenzyl)triphenylphosphonium bromide 
• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 20578-92-1 2,3′,4,5′-tetramethoxystilbene 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 29680-76-0 3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 20578-92-1 (Z)-2,3',4,5'-tetramethoxystilbene 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 102841-42-9 oxyresveratrol-4-O-β-D-glucopyranosyl-3'-O-β-2, 4, 3', 5'-tetrahydroxystilbene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 

Downstream Products

• 24082-42-6 dihydrooxyresveratrol 
• 629643-26-1 5-[(E)-2-(4-hydroxy-2-methoxyphenyl)ethenyl]benzene-1,3-diol 
• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 80715-06-6 Ethandiyl-1-(3-benzyl-8-hydroxy-5-oxo-1,2,3,4-tetrahydro-5H-benzopyrano-<3,4-c>-9-pyridin)-2-(3-benzyl-10-hydroxy-5-oxo-1,2,3,4-tetrahydro-5H-benzopyrano-<3,4-c>-8-pyridin) 
• 80715-08-8 Ethandiyl-1-(3-benzyl-8-methoxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-benzopyrano-<3,4-c>-9-pyridin)-2-(3-benzyl-10-methoxy-5,5-dimethyl-1,2,3,4-tetrahydro-5H-benzopyrano-<3,4-c>-8-pyridin) 
• 119229-91-3 2,3',4,5'-tetraacetoxystilbene 
• 1093198-94-7 cis-oxyresveratrol 

Relevant articles and documents

Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives

Oxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish peroxidase-H 2O 2or FeCl 3·6H 2O in an acetone system predominantly produced the 8-5-coupled and 8-10-coupled dihydrobenzofuran-type dimers, respectively. This regioselective biomimetic strategy might be useful in synthesizing other dimeric oxyresveratrol derivatives.

Preparation method of resveratrol compound

The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.

Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-: Trans -stilbene and stilbenoids modification by fungal peroxygenases

This work gives first evidence that the unspecific peroxygenases (UPOs) from the basidiomycetes Agrocybe aegerita (AaeUPO), Coprinopsis cinerea (rCciUPO) and Marasmius rotula (MroUPO) are able to catalyze the regioselective hydroxylation of trans-stilbene to 4,4′-dihydroxy-trans-stilbene (DHS), a resveratrol (RSV) analogue whose preventive effects on cancer invasion and metastasis have very recently been shown. Nearly complete transformation of substrate (yielding DHS) was achieved with the three enzymes tested, using H2O2 as the only co-substrate, with AaeUPO showing exceptionally higher total turnover number (200000) than MroUPO (26000) and rCciUPO (1400). Kinetic studies demonstrated that AaeUPO was the most efficient enzyme catalyzing stilbene dihydroxylation with catalytic efficiencies (kcat/Km) one and two orders of magnitude higher than those of MroUPO and rCciUPO, so that 4-hydroxystilbene appears to be the best UPO substrate reported to date. In contrast, the peroxygenase from the ascomycete Chaetomium globosum (CglUPO) failed to hydroxylate trans-stilbene at the aromatic ring and instead produced the trans-epoxide in the alkenyl moiety. In addition, stilbenoids such as pinosylvin (Pin) and RSV were tested as substrates for the enzymatic synthesis of RSV from Pin and oxyresveratrol (oxyRSV) from both RSV and Pin. Overall, lower conversion rates and regioselectivities compared with trans-stilbene were accomplished by three of the UPOs, and no conversion was observed with CglUPO. The highest amount of RSV (63% of products) and oxyRSV (78%) were again attained with AaeUPO. True peroxygenase activity was demonstrated by incorporation of 18O from H218O2 into the stilbene hydroxylation products. Differences in the number of phenylalanine residues at the heme access channels seems related to differences in aromatic hydroxylation activity, since they would facilitate substrate positioning by aromatic-aromatic interactions. The only ascomycete UPO tested (that of C. globosum) turned out to have the most differing active site (distal side of heme cavity) and reactivity with stilbenes resulting in ethenyl epoxidation instead of aromatic hydroxylation. The above oxyfunctionalizations by fungal UPOs represent a novel and simple alternative to chemical synthesis for the production of DHS, RSV and oxyRSV.

Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones

A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

Φ-order spectrophotokinetic characterisation and quantification of trans-cis oxyresveratrol reactivity, photodegradation and actinometry

A new Φ-order kinetic method was proposed in this study for the investigation of trans-cis photoisomerization reaction of Oxyresveratrol (ORVT) subjected to non-isosbestic irradiation. In ethanolic media, it has been proven that forward (ΦA?→?Bλirr) and reverse (ΦB?→?Aλirr) reaction quantum yields were dependent on the monochromatic irradiation wavelength according to sigmoid patterns over the spectral ranges of their electronic absorption (260–360?nm). An 11.4- and 6.6-fold increases were recorded for ΦB?→?Aλirr and ΦA?→?Bλirr, respectively. The efficiencies of the former (ΦB?→?Aλirr, ranging between 2.3?×?10??2 and 26.3?×?10??2) were 33 to 60% smaller than those of the respective ΦA?→?Bλirr measured at the irradiation wavelengths selected. Overall, between 57 and 97% degradation of the initial trans-ORVT was observed under relatively weak light intensities, with the highest values recorded at the longest wavelengths. These findings strongly recommend protection from light in all situations of this biologically important phytomolecule that possesses therapeutic value of interest to pharmaceutical applications. The Φ-order kinetics also offered a simple way to develop a reliable actinometric method that proved ORVT to be an efficient actinometer for the dynamic range 295–360?nm. The usefulness of Φ-order kinetics for the investigation and quantification of phytoproducts’ photodegradation was discussed.

Method for synthesizing artificially all-trans-resveratrol and derivative thereof

The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.

A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)

The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)

Synthetic method for natural product 2,3',4,5'-tetrahydroxy bibenzyl

The invention discloses a synthetic method for a natural product 2,3',4,5'-tetrahydroxy bibenzyl. The synthetic method comprises the following steps that 3,5-dyhydroxy phenylacetic acid and 2,4-dyhydroxy benzaldehyde serve as materials and conduct a condensation reaction in the presence of alkali to obtain 3-(3,5-dyhydroxy phenyl)-7-hydroxy coumarin; then a ring opening decarboxylation reaction is conducted under an alkaline condition, and E-2,3',4,5'-tetrahydroxy toluylene is obtained; and finally a hydrogenation reaction is conducted to obtain the natural product 2,3',4,5'-tetrahydroxy bibenzyl. According to the synthetic method, the materials are easy to obtain, the reaction route is simple, atom economy is high, post-treatment is succinct, and productivity is high.

Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene

The invention discloses a synthesis method of a natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene. According to the method, 1,3-acetone dicarboxylic acid dimethyl ester is used as a starting raw material; condensation and aromatization reactions are performed to obtain 3,5-dihydroxy-2,4-dicarboxylate methyl phenyl acetate; then, hydrolysis and decarboxylation are performed to obtain 3,5-dyhydroxy phenylacetic acid; the 3,5-dyhydroxy phenylacetic acid and 2,4-dihydroxy benzaldehyde take condensation reaction under the existence of alkali to obtain 3-(3,5-dihydroxy phenyl)-7-hydroxy coumarin; next, open loop decarboxylation reaction is performed under the alkaline condition; the natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene is obtained. The method has the advantages that the raw materials are easily obtained; the reaction route is simple and fast; the operation is convenient; the yield is higher.

Method for preparing trans-o-hydroxyl stilbene compound

The invention discloses a method for preparing a trans-o-hydroxyl stilbene compound. The method comprises the steps of subjecting a 3-aryl coumarin compound to a ring-opening decarboxylation reaction in the presence of a solvent and a base, and carrying out aftertreatment, thereby obtaining the trans-o-hydroxyl stilbene compound. According to the method, the applicable range of a substrate is wide, the trans-form selectivity is high, the solvent is environmentally friendly, a decarboxylation process has no need of using a metal catalyst, and the process flow is environmentally friendly.