10083-24-6

Basic information

• Product Name: PICEATANNOL
• Synonyms: TRANS-3,3',4,5'-TETRAHYDROXYSTILBENE;PICEATANNOL;PICEATANNOL (3,3',4,5'-TETRAHYDROXY-TRAN;(e)-4-[2-(3,5dihydroxyphenyl)ethenyl]1,2-benzenediol;4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol;(E)-3,3',4,5'-Tetrahydroxystilbene;(E)-Piceatannol;Astringenin
• CAS NO: 10083-24-6
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• EINECS: 1592732-453-0
• Product Categories: Stilbenes (substituted);Protein Kinase;Aromatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Syk;Inhibitors
• Mol File: 10083-24-6.mol
• Article Data: 39

Chemical Properties

• Melting Point: 223-227 °C
• Boiling Point: 108°C/0.04mmHg(lit.)
• Flash Point: 252.174 °C
• Appearance: light tan to yellow/powder
• Density: 1.1245 (rough estimate)
• Vapor Pressure: 6.51E-11mmHg at 25°C
• Refractive Index: 1.5190 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.5 mg/mL
• PKA: 9.17±0.10(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
• CAS DataBase Reference: PICEATANNOL(CAS DataBase Reference)
• NIST Chemistry Reference: PICEATANNOL(10083-24-6)
• EPA Substance Registry System: PICEATANNOL(10083-24-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 10083-24-6(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 10083-24-6 differently. You can refer to the following data:
1. 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.
2. 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

Application

Antioxidants, having anti-inflammatory, anti-thrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia, anti-bacterial activities.

Chemical Properties

yellow to golden or green crystalline powder

Uses

Different sources of media describe the Uses of 10083-24-6 differently. You can refer to the following data:
1. A human metabolite of Resveratrol (R150000).
2. A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant.
3. 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)

Definition

ChEBI: A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.

General Description

A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 μM), PKC (IC50 = 8 μM), MLCK (IC50 = 12 μM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca2+-dependent protein kinase (CDPK) (IC50 = 19 μM), and p72syk (IC50 = 10 μM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.

Biological Activity

Anti-inflammatory, immunomodulatory and antiproliferative agent. Inhibits p56 lck and syk protein tyrosine kinases and inhibits TNF-induced NF- κ B activation and gene expression. Synthesis results from conversion of resveratrol (5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3,benzenediol ) by cytochrome P450 1B1.

Biochem/physiol Actions

Cell permeable: yes

References

1) Seow et al. (2002), Piceatannol, a Syk-selective tyrosine kinase inhibitor, attenuated antigen challenge of guinea pig airways in vitro; Eur. J. Pharmacol., 443 189 2) Howitz et al. (2003), Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan; Nature, 425 191

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

Upstream product

• 29884-49-9 (E)-astringin 
• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 475231-21-1 (trans)-4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-benzenediol 
• 42206-94-0 triacetyl-trans-resveratrol 
• 122616-63-1 (E)-5-(3,4-dihydroxystyryl)-1,3-phenylene diacetate 
• 7786-61-0 3-methoxy-4-hydroxystyrene 
• 113231-14-4 1,3-dihydroxy-5-vinylbenzene 
• 1018449-53-0 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene 
• 83088-26-0 (E)-tetramethylpiceatannol 
• 10586-13-7 3,4-bis(trimethylsilyloxy)benzaldehyde 
• 29680-77-1 (3,5-dihydroxybenzyl)triphenylphosphonium bromide 
• 150258-78-9 (E)-1-<3,4-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 
• 94356-26-0 piceatannol 3'-O-β-D-glucopyranoside 
• 116181-54-5 piceatannol-4′-O-β-D-glucopyranoside 

Downstream Products

• 32507-66-7 isorhapontigenin 
• 629643-27-2 (E)-5-[2-(3,4-dimethoxyphenyl)vinyl]benzene-1,3-diol 
• 500-65-2 rhapontigenin 
• 113681-38-2 2',4'-dibromo-3,3',4,5'-tetramethoxystilbene 
• 90275-02-8 3,4-O-isopropylidene-3,3',4,5'-tetrahydroxystilbene 
• 22318-80-5 Dihydropiceatannol 
• 113681-39-3 (E)-2'-bromo-3,3'4,5'-tetramethoxystilbene 
• 113681-37-1 (E)-2',4'-dibromo-3,3',4,5'-tetramethoxystilbene 

Relevant articles and documents

Enzymatic synthesis of catechol-functionalized polyphenols with excellent selectivity and productivity

Polyphenol products have become more and more attractive due to their strong anti-oxidant properties and a great variety of promising pharmacological activities and beneficial effects on human health. In this study, mushroom tyrosinase immobilized as cross-linked enzyme aggregates (CLEAs) was used as the catalyst for ortho-hydroxylation reactions to produce 3,4-dihydroxyphenylacetic acid, piceatannol and 3′-hydroxypterostilbene from 4-hydroxyphenylacetic acid, resveratrol and pterostilbene, respectively, with excellent selectivity and productivity. This is the first report of synthesizing these three polyphenolic compounds with tyrosinase CLEAs as catalyst, and the first study of biocatalytic production of 3′-hydroxypterostilbene. Introducing a deep eutectic solvent (DES) into the tyrosinase CLEA preparation exhibited a positive effect in terms of enhancing the catalytic activity of the immobilized enzyme and also promoting the synthesis of the polyphenol products.

Regioselective synthesis of piceatannol from resveratrol: Catalysis by two-component flavin-dependent monooxygenase HpaBC in whole cells

Piceatannol, a valuable biologically active stilbene derivative, was efficiently synthesized from resveratrol. Whole-cell catalysis with HpaBC monooxygenase enabled the regioselective hydroxylation of resveratrol to produce 23 mM (5.2 g L-1) of piceatannol.

Radical-induced oxidation of trans-resveratrol

trans-Resveratrol (RVT) (3,5,4′-trihydroxystilbene), a polyphenolic constituent of red wine, is thought to be beneficial in reducing the incidence of cardiovascular diseases, partly via its antioxidant properties. However, the mechanism of action by which trans-resveratrol displays its antioxidant effect has not been totally unravelled. This study aimed at establishing a comprehensive scheme of the reaction mechanisms of the direct scavenging of HO and O2- radicals generated by water gamma radiolysis. Aerated aqueous solutions of trans-RVT (from 10 to 100 μmol L-1) were irradiated with increasing radiation doses (from 25 to 400 Gy) and further analyzed by UV-visible absorption spectrophotometry for detection of trans-RVT oxidation products. Separation and quantification of RVT and its four oxidation products previously identified by mass spectrometry, i.e., piceatannol (PCT), 3,5-dihydroxybenzoic acid (3,5-DHBA), 3,5-dihydroxybenzaldehyde (3,5-DHB) and para-hydroxybenzaldehyde (PHB), were performed by HPLC/UV-visible spectrophotometry. Determination of the radiolytic yields of trans-RVT consumption and oxidation product formation has allowed us to establish balance between trans-RVT disappearance and the sum of oxidation products formation. Under our conditions, O2- radicals seemed to poorly initiate oxidation of trans-RVT, whereas the latter, whatever its initial concentration, quantitatively reacted with HO radicals, via a dismutation mechanism. Two reaction pathways involving HO-induced trans-RVT primary radicals have been proposed to explain the formation of the oxidation end-products of trans-RVT.

Production of anti-cancer agent using microbial biotransformation

Microbial biotransformation is a great model system to produce drugs and biologically active compounds. In this study, we elucidated the fermentation and production of an anti-cancer agent from a microbial process for regiospecific hydroxylation of resveratrol. Among the strains examined, a potent strain showed high regiospecific hydroxylation activity to produce piceatannol. In a 5 L (w/v 3 L) jar fermentation, this wild type Streptomyces sp. in the batch system produced 205 mg of piceatannol (i.e., 60% yields) from 342 mg of resveratrol in 20 h. Using the product, an in vitro anti-cancer study was performed against a human cancer cell line (HeLa). It showed that the biotransformed piceatannol possessed a significant anticancer activity. This result demonstrates that a biotransformation screening method might be of therapeutic interest with respect to the identification of anti-cancer drugs.

A focused multiple reaction monitoring (MRM) quantitative method for bioactive grapevine stilbenes by ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ)

Grapevine stilbenes are a family of polyphenols which derive from trans-resveratrol having antifungal and antimicrobial properties, thus being considered as phytoalexins. In addition to their diverse bioactive properties in animal models, they highlight a strong potential in human health maintenance and promotion. Due to this relevance, highly-specific qualitative and quantitative methods of analysis are necessary to accurately analyze stilbenes in different matrices derived from grapevine. Here, we developed a rapid, sensitive, and specific analysis method using ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ) in MRM mode to detect and quantify five grapevine stilbenes, trans-resveratrol, trans-piceid, trans-piceatannol, trans-pterostilbene, and trans-?-viniferin, whose interest in relation to human health is continuously growing. The method was optimized to minimize in-source fragmentation of piceid and to avoid co-elution of cis-piceid and trans-resveratrol, as both are detected with resveratrol transitions. The applicability of the developed method of stilbene analysis was tested successfully in different complex matrices including cellular extracts of Vitis vinifera cell cultures, reaction media of biotransformation assays, and red wine.

Regioselective hydroxylation of trans -resveratrol via inhibition of tyrosinase from streptomyces avermitilis MA4680

Secreted tyrosinase from melanin-forming Streptomyces avermitilis MA4680 was involved in both ortho-hydroxylation and further oxidation of trans-resveratrol, leading to the formation of melanin. This finding was confirmed by constructing deletion mutants of melC2 and melD 2 encoding extracellular and intracellular tyrosinase, respectively; the melC2 deletion mutant did not produce piceatannol as well as melanin, whereas the melD2 deletion mutant oxidized resveratrol and synthesized melanin with the same yields, suggesting that MelC2 is responsible for ortho-hydroxylation of resveratrol. Extracellular tyrosinase (MelC2) efficiently converted trans-resveratrol into piceatannol in the presence of either tyrosinase inhibitors or reducing agents such as catechol, NADH, and ascorbic acid. Reducing agents slow down the dioxygenase reaction of tyrosinase. In the presence of catechol, the regio-specific hydroxylation of trans-resveratrol was successfully performed by whole cell biotransformation, and further oxidation of trans-resveratrol was efficiently blocked. The yield of this ortho-hydroxylation of trans-resveratrol was dependent upon inhibitor concentration. Using 1.8 mg of wild-type Streptomyces avermitilis cells, the conversion yield of 100 μM trans-resveratrol to piceatannol was 78% in 3 h in the presence of 1 mM catechol, indicating 14 μM piceatannol h-1 DCW mg-1 specific productivity, which was a 14-fold increase in conversion yield compared to that without catechol, which is a remarkably higher reaction rate than that of P450 bioconversion. This method could be generally applied to biocatalysis of various dioxygenases.

Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological activity and molecular modelling evidence for cooperativity between viniferin enantiomers

To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.

Synthesis method of piceatannol

The invention provides piceatannol. A target product piceatannol is prepared through the steps of taking 3-hydroxyl-4-methoxybenzaldehyde as a starting raw material, carrying out wittig reaction to generate 3-hydroxyl-4-methoxystyrene, carrying out Heck r