Piceatannol

Names

[ Name ]:
Piceatannol

[Synonym ]:
3,3',4'5-Tetrahydroxystilbene
E-Piceatannol
1,2-Benzenediol, 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-
3,3′,4,5′-Tetrahydroxy-trans-stilbene
3,3',4,5'-Tetrahydroxy-trans-stilbene
3,4,3',5'-Tetrahydroxy-trans-stilbene
4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol
3,5,3',4'-tetrahydroxystilbene
4-[(E)-2-(3,5-Dihydroxyphenyl)vinyl]-1,2-benzenediol
Piceatannol
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
MFCD00221715
4-(2-(3,5-Dihydroxyphenyl)vinyl)-1,2-benzenediol
(E)-4-[2-(3,5Dihydroxyphenyl)ethenyl]1,2-benzenediol
(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol
5-[(E)-2-(3,4-Dihydroxyphenyl)vinyl]benzene-1,3-diol
trans-3,3',4,5'-tetrahydroxystilbene
3,3',4,5'-tetrahydroxystilbene
Piceatannol, (E)-

Biological Activity

[Description]:

Piceatannol is a selective inhibitor of protein tyrosine kinase Syk. It could inhibit ICa,L, Ito, IKr, Ca2+ transients and Na+-Ca2+ exchange except IK1. Shows multiple biological activities such as anti-inflammatory, antiproliferative and immunomodulatory effects.In vitro: The treatment of human myeloid cells with piceatannol suppressed TNF-induced DNA binding activity of NF-κB. The effect of piceatannol was not restricted to myeloid cells, as TNF-induced NF-κB activation was also suppressed in lymphocyte and epithelial cells. Piceatannol also inhibited NF-κB activated by H2O2, PMA, LPS, okadaic acid, and ceramide. [1]

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Syk

Research Areas >> Cancer

Natural Products >> Phenols

[References]

[1]. Kazuhiro Ashikawa et al. Piceatannol Inhibits TNF-Induced NF-κB Activation and NF-κB-Mediated Gene Expression Through Suppression of IκBα Kinase and p65 Phosphorylation. J Immunol, 2002 Dec 1, 169(11):6490-7.

[2]. Wen-Pin Chen et al. Piceatannol, a derivative of resveratrol, moderately slows INa inactivation and exerts antiarrhythmic action in ischaemia-reperfused rat hearts. Br J Pharmacol.2009 Jun, 157(3), 381-391.

[Related Small Molecules]

Entospletinib | cerdulatinib | BAY-61-3606 | R788 (disodium hexahydrate) | R406 | PRT062607 (P505-15, BIIB057) HCl | TAK-659 hydrochloride | PRT-060318 | RO9021 | ASN-002 | MDBN | R 112

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
507.3±38.0 °C at 760 mmHg

[ Melting Point ]:
223-227ºC

[ Molecular Formula ]:
C₁₄H₁₂O₄

[ Molecular Weight ]:
244.243

[ Flash Point ]:
252.2±21.4 °C

[ Exact Mass ]:
244.073563

[ PSA ]:
80.92000

[ LogP ]:
2.69

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.801

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 0.5 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2907299090

Customs

[ HS Code ]: 2907299090

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%

Articles

A unique mechanism of curcumin inhibition on F1 ATPase

Biochem. Biophys. Res. Commun. 452(4) , 940-4, (2014)

• Polyphenols lowered the rotation rate of F1 ATPase by increasing catalytic dwell. • Curcumin showed different inhibitory mechanism from other polyphenols. • γ subunit carboxyl terminus is not requir...

Antibody-opsonized bacteria evoke an inflammatory dendritic cell phenotype and polyfunctional Th cells by cross-talk between TLRs and FcRs.

J. Immunol. 194(4) , 1856-66, (2015)

During secondary immune responses, Ab-opsonized bacteria are efficiently taken up via FcRs by dendritic cells. We now demonstrate that this process induces cross-talk between FcRs and TLRs, which resu...

TH2 cells and their cytokines regulate formation and function of lymphatic vessels.

Nat. Commun. 6 , 6196, (2015)

Lymphatic vessels (LVs) are critical for immune surveillance and involved in the pathogenesis of diverse diseases. LV density is increased during inflammation; however, little is known about how the r...