29700-22-9 Usage
Description
4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol, also known as Oxyresveratrol, is a natural hydroxystilbene derived from various plant sources. It is a white powder with similar bioactivity to resveratrol and possesses a range of biological properties, including tyrosinase inhibition, anti-tussive, anti-asthmatic, antioxidant, anti-inflammatory, and analgesic effects. Its chemical structure allows it to interact with various biological targets, making it a promising candidate for pharmaceutical and industrial applications.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 29700-22-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,7,0 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 29700-22:
(7*2)+(6*9)+(5*7)+(4*0)+(3*0)+(2*2)+(1*2)=109
109 % 10 = 9
So 29700-22-9 is a valid CAS Registry Number.
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+
29700-22-9Relevant articles and documents
Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives
Ran, Lu,Li, Hongpeng,Chao, Ge,Kang, Xiaodong,Lei, Tian,Li, Wenling
, p. 1809 - 1812 (2020/09/18)
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.
Φ-order spectrophotokinetic characterisation and quantification of trans-cis oxyresveratrol reactivity, photodegradation and actinometry
Maafi, Mounir,Al-Qarni, Mohammed Ahmed
, p. 64 - 71 (2017/07/11)
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.
Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones
Huang, Xihua,Liu, Jie,Sheng, Jianfei,Song, Xianheng,Du, Zhibo,Li, Mingkang,Zhang, Xuejing,Zou, Yong
, p. 804 - 808 (2018/03/06)
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.
