Piceatannol

CHF 35.00
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Product Details
Synonyms CCRIS 9289; NSC365798; NSC622471; 3,3',4,5'-Tetrahydroxy-trans-stilbene; 3-Hydroxyresveratrol
Product Type Chemical
Properties
Formula

C14H12O4

MW 244.3
CAS 10083-24-6
Source/Host Chemicals Synthetic. Originally isolated from Euphorbia lagascae.
Purity Chemicals ≥98% (HPLC)
Appearance Off-white to light pink crystalline solid.
Solubility Soluble in DMSO, dimethyl formamide, ethanol, methanol, acetone or ethyl acetate. Slightly soluble in water.
InChi Key CDRPUGZCRXZLFL-OWOJBTEDBC
Smiles OC1=CC(\C=C\C2=CC=C(O)C(O)=C2)=CC(O)=C1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Wide range of tyrosine and serine/threonine protein kinase inhibitor, including Syk, p56lck, PKA, PKC, MLCK, CDPK, JNK and PI3K [1-3, 9, 14, 15].
  • Inhibits the tyrosine phosphorylation of STAT3 and STAT5 [4].
  • Potent apoptosis inducer [5].
  • Potent anticancer compound [6, 10, 16, 17].
  • Suppresses NF-kB activation through IkBα kinase inhibition [7].
  • Activator of human deacetylase SIRT1 (sirtuin 1) [8].
  • Potent antioxidant with anti-proliferative, anti-inflammatory and cardioprotective properties [10, 14, 15, 17, 19].
  • Neuoprotective [11, 14].
  • Adipogenesis inhibitor [18].
  • Promotes glucose uptake, AMPK phosphorylation and GLUT4 translocation [20].
  • Autophagy inducer [21]
Product References
  1. Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor: R.L. Geahlen, et al.; BBRC 165, 241 (1989)
  2. Inhibition of mast cell Fc epsilon R1-mediated signaling and effector function by the Syk-selective inhibitor, piceatannol: J.M. Oliver, et al.; J. Biol. Chem. 269, 29697 (1994)
  3. Inhibition of eukaryote serine/threonine-specific protein kinases by piceatannol: B.H. Wang, et al.; Planta Med. 64, 195 (1998)
  4. Distinct mechanisms of STAT phosphorylation via the interferon-alpha/beta receptor. Selective inhibition of STAT3 and STAT5 by piceatannol: L. Su & M. David; J. Biol. Chem. 275, 12661 (2000)
  5. Piceatannol, a hydroxylated analog of the chemopreventive agent resveratrol, is a potent inducer of apoptosis in the lymphoma cell line BJAB and in primary, leukemic lymphoblasts: T. Wieder, et al.; Leukemia 15, 1735 (2001)
  6. Piceatannol, a natural analog of resveratrol, inhibits progression through the S phase of the cell cycle in colorectal cancer cell lines: F. Wolter, et al.; J. Nutr. 132, 298 (2002)
  7. Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation: K.  Ashikawa, et al.; J. Immunol. 169, 6490 (2002)
  8. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan: K.T. Howitz, et al.; Nature 425, 191 (2003)
  9. Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways: B.S. Wung, et al.; Pharmacol. Res. 53, 113 (2006)
  10. Antioxidant activity of resveratrol, piceatannol and 3,3',4,4',5,5'-hexahydroxy-trans-stilbene in three leukemia cell lines: Z. Ovesna, et al.; Oncol. Rep. 16, 617 (2006)
  11. Protective effects of piceatannol against beta-amyloid-induced neuronal cell death: H.J. Kim, et al.; Ann. N Y Acad. Sci. 1095, 473 (2007)
  12. Piceatannol inhibits melanogenesis by its antioxidative actions: T. Yokozawa & Y.J. Kim; Biol. Pharm. Bull. 30, 2007 (2007)
  13. Induction of apoptosis by piceatannol in human leukemic U937 cells through down-regulation of Bcl-2 and activation of caspases: Y.H. Kim, et al.; Oncol. Rep. 19, 961 (2008)
  14. Piceatannol attenuates 4-hydroxynonenal-induced apoptosis of PC12 cells by blocking activation of c-Jun N-terminal kinase: Y.J. Jang, et al.; Ann. N Y Acad. Sci. 1171, 176 (2009)
  15. Phosphoinositide 3-kinase is a novel target of piceatannol for inhibiting PDGF-BB-induced proliferation and migration in human aortic smooth muscle cells: K.H. Choi, et al.; Cardiovasc. Res. 85, 836 (2010)
  16. Piceatannol inhibits migration and invasion of prostate cancer cells: possible mediation by decreased interleukin-6 signaling: G.T. Kwon, et al.; J. Nutr. Biochem. 23, 228 (2012)
  17. Biological activity of piceatannol: leaving the shadow of resveratrol: H. Piotrowska, et al.; Mutat. Res. 750, 60 (2012) (Review)
  18. Piceatannol, natural polyphenolic stilbene, inhibits adipogenesis via modulation of mitotic clonal expansion and insulin receptor-dependent insulin signaling in early phase of differentiation: J.Y. Kwon, et al.; J. Biol. Chem. 287, 11566 (2012)
  19. Antiproliferative and anti-invasive effect of piceatannol, a polyphenol present in grapes and wine, against hepatoma AH109A cells: Y. Kita, et al.;  J. Biomed. Biotechnol. 2012, 672416 (2012)
  20. Piceatannol, a resveratrol derivative, promotes glucose uptake through glucose transporter 4 translocation to plasma membrane in L6 myocytes and suppresses blood glucose levels in type 2 diabetic model db/db mice: M. Minakawa, et al.; BBRC 422, 469 (2012)
  21. Pro-autophagic polyphenols reduce the acetylation of cytoplasmic proteins: F. Pietrocola, et al.; Cell Cycle 11, 3851 (2012)
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