Piceatannol

Base Information

• Chemical Name: Piceatannol
• CAS No.: 10083-24-6
• Molecular Formula: C14H12O4
• Molecular Weight: 244.247
• Hs Code.: 29072990
• European Community (EC) Number: 600-132-4
• NSC Number: 622471,365798
• UNII: 6KS3LS0D4F
• DSSTox Substance ID: DTXSID6040587
• Nikkaji Number: J393.773I,J61.264B
• Wikipedia: Piceatannol
• Wikidata: Q7190608
• NCI Thesaurus Code: C1195
• Pharos Ligand ID: XVSJHYWTHGY8
• Metabolomics Workbench ID: 27947
• ChEMBL ID: CHEMBL69863
• Mol file: 10083-24-6.mol

Synonyms:3'-hydroxyresveratol;3,3',4',5-tetrahydroxystilbene;3,3',4,5'-tetrahydroxy stilbene;3,3',4,5'-tetrahydroxystilbene;3,5,3',4'-tetrahydroxy-stilbene;3,5,3',4'-tetrahydroxy-trans-stilbene;3,5,3',4'-tetrahydroxystilbene;astringinin;demethyl isorhapontigenin;piceatannol;piceatanol;RSVL-1

Chemical Property of Piceatannol

Chemical Property:

• Appearance/Colour: light tan to yellow powder
• Vapor Pressure: 6.51E-11mmHg at 25°C
• Melting Point: 223-227 °C
• Refractive Index: 1.8
• Boiling Point: 507.277 °C at 760 mmHg
• PKA: 9.17±0.10(Predicted)
• Flash Point: 252.174 °C
• PSA: 80.92000
• Density: 1.468 g/cm³
• LogP: 2.67940
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.5 mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 244.07355886
• Heavy Atom Count: 18
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

Piceatannol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O)O)O)O
• Recent NIPH Clinical Trials: 8-week study of supplement
• Description: Piceatannol is a chemical compound with similar structure to resveratrol, being widely existed in vegetables such as grapes, blueberries and passion fruit. It is capable of inhibiting the growth of immature adipocytes, so as to achieve the purpose of weight loss. In addition, it also helps prevent cancer, heart disease and neurological diseases. In early April 2012, researchers in Purdue University has published a new study in 《Biochemistry》journal, finding that piceatannol can delay the production of new fat cells, and inhibit the growth of immature fat cells into mature cells, which can help control the obesity. The researchers also claim that while this study shows that red wine helps to lose weight, further research is needed to improve the stability and solubility of the white fat to maximize its effect. Laboratory preparation: 3, 4-dimethoxybenzyl alcohol is used as the starting material; to obtain the target product; the raw material needs to undergo bromination, Arbuzov rearrangement reaction, Wittig-Horner reaction and demethylation reaction. Piceatannol (10083-24-6) is a naturally occurring analog of resveratrol (Cat.# 10-1057). Inhibits nonreceptor kinases Syk and Lyk (IC50 approximately 10 μM).1 Piceatannol stimulates Sirt1.2
• Uses: A human metabolite of Resveratrol (R150000). A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant. Piceatannol has been used: to study its effect on Ataxia-Telangiectasia Mutated (ATM) protein kinase as an inhibitor of ZAP-70 (ζ-chain-associated protein kinase 70)as an inhibitor of MRP1-mediated 2′,7′-bis-(carboxypropyl)-5(6)-carboxyfluorescein (BCPCF) transport in intact human erythrocytes and inside-out erythrocyte vesicles (IOVs)

Technology Process of Piceatannol

There total 54 articles about Piceatannol 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)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → trans-piceatannol (10083-24-6,106325-86-4)

Guidance literature:

With streptomyces avermilitis tyrosinase; benzene-1,2-diol; In aq. buffer; for 3h; pH=8; Reagent/catalyst; Enzymatic reaction;

Reference yield: 91.0%

3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene (1018449-53-0) → trans-piceatannol (10083-24-6,106325-86-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1071/CH07044

Reference yield: 90.0%

(E)-tetramethylpiceatannol (83088-26-0) → trans-piceatannol (10083-24-6,106325-86-4)

Guidance literature:

With boron tribromide; In dichloromethane; at -30 - 20 ℃; for 4h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02236

upstream raw materials:

(E)-astringin

3,4-bis(trimethylsilyloxy)benzaldehyde

3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide

piceatannol-4′-O-β-D-glucopyranoside

Downstream raw materials:

(Z)-3,5,3',4'-tetrahydroxystilbene

isorhapontigenin

(E)-5-[2-(3,4-dimethoxyphenyl)vinyl]benzene-1,3-diol

rhapontigenin

Refernces

• 1、 Murias, Marek,Handler, Norbert,Erker, Thomas,Pleban, Karin,Ecker, Gerhard,Saiko, Philipp,Szekeres, Thomas,J?ger, Walter. "Resveratrol analogues as selective cyclooxygenase-2 inhibitors: Synthesis and structure-activity relationship". . p. 5571 - 5578. Retrieved 2004.
• 2、 Fauconneau, Bernard,Waffo-Teguo, Pierre,Huguet, Francois,Barrier, Laurence,Decendit, Alain,Merillon, Jean-Michel. "Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests". . p. 2103 - 2110. Retrieved 1997.
• 3、 Camont, Laurent,Collin, Fabrice,Marchetti, Catherine,Jore, Daniel,Gardes-Albert, Monique,Bonnefont-Rousselot, Dominique. "Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of trans-resveratrol in aqueous solutions". . p. 634 - 642. Retrieved 2010.
• 4、 Boccellino, Mariarosaria,Donniacuo, Maria,Bruno, Ferdinando,Rinaldi, Barbara,Quagliuolo, Lucio,Ambruosi, Marika,Pace, Simona,De Rosa, Mario,Olga?, Abdurrahman,Banoglu, Erden,Alessio, Nicola,Massa, Antonio,Kahn, Haroon,Werz, Oliver,Fiorentino, Antonio,Filosa, Rosanna. "Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors". . p. 637 - 647. Retrieved 2019.
• 5、 Chand, Satish,Banwell, Martin G.. "Biomimetic preparation of the racemic modifications of the stilbenolignan aiphanol and three congeners". . p. 243 - 250. Retrieved 2007.
• 6、 Qiu, Xiaodong,Li, Yangyang,Zhou, Li,Chen, Peishan,Li, Fan,Zhang, Yanan,Ling, Yong. "Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage". supporting information. p. 6424 - 6428. Retrieved 2020/08/24.
• 7、 -. "Preparation method of resveratrol compound". Paragraph 0064; 0065. . Retrieved 2019/07/16.