Resveratrol

Base Information

• Chemical Name: Resveratrol
• CAS No.: 501-36-0
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• Hs Code.: 29072990
• European Community (EC) Number: 610-504-8
• NSC Number: 327430
• UNII: Q369O8926L
• DSSTox Substance ID: DTXSID4031980
• Nikkaji Number: J524.694F,J11.775G
• Wikipedia: Resveratrol
• Wikidata: Q407329
• NCI Thesaurus Code: C1215
• RXCUI: 1000492
• Pharos Ligand ID: GZ9FHWTXFT11
• Metabolomics Workbench ID: 27946
• ChEMBL ID: CHEMBL165
• Mol file: 501-36-0.mol

Synonyms:3,4',5-stilbenetriol;3,4',5-Trihydroxystilbene;3,5,4'-trihydroxystilbene;cis Resveratrol;cis-resveratrol;resveratrol;Resveratrol 3 sulfate;Resveratrol, (Z)-;resveratrol-3-sulfate;SRT 501;SRT-501;SRT501;trans Resveratrol;trans Resveratrol 3 O sulfate;trans-resveratrol;trans-resveratrol-3-O-sulfate

Chemical Property of Resveratrol

Chemical Property:

• Appearance/Colour: Off-White to Tan Powder
• Vapor Pressure: 1.11E-08mmHg at 25°C
• Melting Point: 253-255 °C
• Refractive Index: 1.762
• Boiling Point: 449.1 °C at 760 mmHg
• PKA: 9.22±0.10(Predicted)
• Flash Point: 222.3 °C
• PSA: 60.69000
• Density: 1.359 g/cm³
• LogP: 2.97380
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
• Water Solubility.: Soluble in water (3 mg/100mL), ethanol (50 mg/mL), DMSO (16 mg/mL), DMF (~65 mg/mL), PBS (pH 7.2) (~100µg/mL), methanol
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 228.078644241
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

99% ^*data from raw suppliers

Resveratrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/38-36-43-22
• Safety Statements: 26-39-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Herbal and Dietary Supplements
• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O)O)O
• Recent ClinicalTrials: Effect of Resveratrol on Serum IGF2 Among African American Women
• Recent EU Clinical Trials: Phase I/IIa multicentre phase I/IIa study of infusion of autologous peripheral blood T lymphocytes expanded and genetically modified using Sleeping Beauty family transposons to express a chimeric antigenic receptor with anti-CD19 specificity conjugated to the 4-1BB co-stimulatory and signal-transduction region CD3z and huEGFRt (TranspoCART19) in patients with relapsed or refractory B-cell lymphoma.
• Recent NIPH Clinical Trials: Foods high in melinjo resveratrol in the treatment of mild periodontitis patients
• Definition and Occurrence: Resveratrol (RE; (3,4鈥?,5 trihydroxystilbene)) is a stilbenoid natural polyphenol found in over 70 plant species, with high concentrations in the skin of red grapes. Other sources include tea, berries, pomegranates, nuts, blueberries, and dark chocolate.
• Isomeric Forms and Production: Resveratrol exists as two isomeric forms, cis and trans, with the transform being predominant and possessing the most potent therapeutic benefits. The transform can be obtained from yeast extracts and is utilized as a food supplement or cosmetic ingredient. Isomerization to the cis form can occur upon exposure to heat, light, or ultraviolet radiation.
• Therapeutic Benefits: Resveratrol exhibits a wide range of therapeutic benefits, including anti-inflammatory, antioxidant, anti-platelet, anti-hyperlipidemic, immuno-modulatory, anti-carcinogenic, cardioprotective, vasorelaxant, and neuroprotective effects. It maintains or enhances human cerebrovascular functions, modulates angiogenesis, stimulates immune cell functions, promotes cell viability and proliferation, ameliorates mitochondrial respiratory dysfunction, and enhances cellular reprogramming mediated by the activation of Sirtuins.
• Cardioprotective Activities: Resveratrol demonstrates proven cardioprotective activities by improving endothelial function, scavenging reactive oxygen species (ROS), reducing inflammation, inhibiting platelet aggregation, and ameliorating lipid profiles, all of which contribute to preventing atherosclerosis. Redox-associated mechanisms, including preservation of mitochondrial function, upregulation of antioxidant enzymes like peroxidase and superoxide dismutase (SOD), and modulation of nitric oxide (NO) production, are implicated in its cardioprotective effects.
• Potent Antioxidant: Resveratrol exhibits potent antioxidant activity, reducing lipid synthesis in the liver, inhibiting platelet aggregation, and acting as a potent antioxidant more powerful than vitamin E. It also inhibits reactive oxygen species (ROS) production and may contribute to increased nitric oxide (NO) production.
• Wide-ranging Effects: Resveratrol's benefits extend to various areas, including antiangiogenic, immunomodulatory, antimicrobial, anticancer, antidiabetic, and prevention of cardiovascular diseases. It reduces inflammation and oxidative stress, improves blood glucose and insulin resistance in diabetes, prevents obesity, and affects mitochondrial dysfunction, angiogenesis, oxidative stress, inflammation, and apoptosis. It also affects pathways like NF-kB, IGF-1R/Akt/Wnt, and PI3K/Akt, regulating cellular development, tumorigenesis, proliferation, and differentiation.

Technology Process of Resveratrol

There total 211 articles about Resveratrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(E)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)-ethene (89946-06-5) → (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0)

Guidance literature:

(E)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)-ethene; With aluminum (III) chloride; triethylamine; In chlorobenzene; at 0 - 80 ℃; for 10h;

With water; In chlorobenzene; at 0 ℃; for 2h; Product distribution / selectivity;

Reference yield: 100.0%

3,5,4'-trimethoxy-trans-stilbene (22255-22-7) → (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 30 ℃;

DOI:10.1021/acs.joc.7b02720

Reference yield: 97.0%

3,5-dihydroxybenzaldehyde (26153-38-8) + dimethyl (4-hydroxybenzyl)phosphonate (68997-88-6) → (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0)

Guidance literature:

With RS₀₀₄ catalyst; In ethanol; at 20 ℃; for 6h;

upstream raw materials:

3,5,4'-trimethoxystilbene

3,5-dimethoxy-4'-hydroxystilbene

3,5-dihydroxybenzaldehyde

4-hydroxy-benzaldehyde

Downstream raw materials:

3,5,4'-trimethoxy-trans-stilbene

trans-δ-viniferin

3,5-dimethoxy-4'-hydroxy-trans-stilbene

(E)-5-((±)-6-hydroxy-2-(4-hydroxyphenyl)-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran-3-yl)benzene-1,3-diol

Refernces

• 1、 Xue, Yemin,Zhang, Zonghui,Hou, Jingjing,Cao, Zhigang,Zhang, Lingxian,Lou, Fen,Xu, Puxu. "Resveratrol and arctigenin production from polydatin and arctiin respectively by a thermostable β-glucosidase from Thermotoga maritima". . p. 414 - 430. Retrieved 2018.
• 2、 Waterhouse,Lamuela-Raventos. "The occurrence of piceid, a stilbene glucoside, in grape berries". . p. 571 - 573. Retrieved 1994.
• 3、 Azzolini, Michele,Mattarei, Andrea,La Spina, Martina,Marotta, Ester,Zoratti, Mario,Paradisi, Cristina,Biasutto, Lucia. "Synthesis and Evaluation as Prodrugs of Hydrophilic Carbamate Ester Analogues of Resveratrol". . p. 3441 - 3454. Retrieved 2015.
• 4、 Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua. "Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products". supporting information. p. 5317 - 5322. Retrieved 2021/06/28.
• 5、 Jia, Xiaofan,Frye, Lucas I.,Zhu, Weihao,Gu, Shunyan,Gunnoe, T. Brent. "Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation". supporting information. p. 10534 - 10543. Retrieved 2020/06/08.