(Z)-resveratrol

Base Information

• Chemical Name: (Z)-resveratrol
• CAS No.: 61434-67-1
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• European Community (EC) Number: 694-803-9
• UNII: AUA0K06FSB
• DSSTox Substance ID: DTXSID7032002
• Nikkaji Number: J638.332G
• Wikidata: Q27116664
• Pharos Ligand ID: GZ9VNY7FCGDX
• Metabolomics Workbench ID: 46367
• ChEMBL ID: CHEMBL87333
• Mol file: 61434-67-1.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 (Z)-resveratrol

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 1.11E-08mmHg at 25°C
• Melting Point: 167-170°C
• Refractive Index: 1.762
• Boiling Point: 449.1 °C at 760 mmHg
• PKA: 9.22±0.10(Predicted)
• Flash Point: 222.4 °C
• PSA: 60.69000
• Density: 1.359 g/cm³
• LogP: 2.97380
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• 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:

98% ^*data from raw suppliers

cis-Resveratrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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

Technology Process of (Z)-resveratrol

There total 56 articles about (Z)-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: 97.5%

C23H24O3 → resveratrol (501-36-0,61434-67-1,133294-37-8)

Guidance literature:

With acetylene; In dichloromethane; at 20 ℃; for 5h; Reagent/catalyst; Time; Inert atmosphere;

Reference yield: 97.0%

3,5,4'-tri-O-acetylresveratrol → resveratrol (501-36-0,61434-67-1,133294-37-8)

Guidance literature:

With methanol; water; for 3h; Product distribution / selectivity; Heating / reflux;

Reference yield: 92.0%

triacetyl-trans-resveratrol (42206-94-0) → resveratrol (501-36-0,61434-67-1,133294-37-8)

Guidance literature:

With methanol; potassium hydroxide; at 65 ℃; for 0.5h; Product distribution / selectivity;

upstream raw materials:

3,5,4'-trimethoxystilbene

3,5-dimethoxy-4'-hydroxystilbene

3,5-dihydroxybenzaldehyde

4-hydroxy-benzaldehyde

Downstream raw materials:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

Refernces

• 1、 Basly, Jean-Philippe,Marre-Fournier, Francoise,Bail, Jean-Christophe Le,Habrioux, Gerard,Chulia, Albert Jose. "Estrogenic/antiestrogenic and scavenging properties of (E)- and (Z)- resveratrol". . p. 769 - 777. Retrieved 2000.
• 2、 Francioso, Antonio,Boffi, Alberto,Villani, Claudio,Manzi, Lucio,D'Erme, Maria,Macone, Alberto,Mosca, Luciana. "Isolation and identification of 2,4,6-trihydroxyphenanthrene as a byproduct of trans-resveratrol photochemical isomerization and electrocyclization". . p. 9381 - 9384. Retrieved 2014.
• 3、 Mattivi, Fulvio,Reniero, Fabiano,Korhammer, Siegfried. "Isolation, Characterization, and Evolution in Red Wine Vinification of Resveratrol Monomers". . p. 1820 - 1823. Retrieved 1995.
• 4、 Figueiras, Teresa Sofia,Neves-Petersen, Maria Teresa,Petersen, Steffen B.. "Activation energy of light induced isomerization of resveratrol". . p. 1897 - 1906. Retrieved 2011.
• 5、 Hernandez,Estrella,Perez-Gordo,Alegria,Tenorio,Ruiz-Larrrea,Moreno-Arribas. "Contribution of malolactic fermentation by Oenococcus oeni and Lactobacillus plantarum to the changes in the nonanthocyanin polyphenolic composition of red wine". . p. 5260 - 5266. Retrieved 2007.
• 6、 Paulo, Luisa,Domingues, Fernanda,Queiroz, Joao Antonio,Gallardo, Eugenia. "Development and validation of an analytical method for the determination of trans - And cis -resveratrol in wine: Analysis of its contents in 186 Portuguese red wines". . p. 2157 - 2168. Retrieved 2011.
• 7、 Trela, Brent C.,Waterhouse, Andrew L.. "Resveratrol: Isomeric molar absorptivities and stability". . p. 1253 - 1257. Retrieved 1996.
• 8、 Němcová, Lenka,Zima, Ji?í,Barek, Ji?í,Janovská, Dagmar. "Determination of resveratrol in grains, hulls and leaves of common and tartary buckwheat by HPLC with electrochemical detection at carbon paste electrode". . p. 374 - 378. Retrieved 2011.
• 9、 -. "Novel resveratrol as well as derivative synthesis method and application thereof". Paragraph 0065; 0072-0073. . Retrieved 2019/08/02.
• 10、 -. "Preparation method of resveratrol". Paragraph 0057-0059. . Retrieved 2018/11/03.