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Pinosylvin

CAS No.:
22139-77-1
Catalog Number:
AG00363D
Molecular Formula:
C14H12O2
Molecular Weight:
212.2439
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Product Description
Catalog Number:
AG00363D
Chemical Name:
Pinosylvin
CAS Number:
22139-77-1
Molecular Formula:
C14H12O2
Molecular Weight:
212.2439
MDL Number:
MFCD00210544
IUPAC Name:
5-[(E)-2-phenylethenyl]benzene-1,3-diol
InChI:
InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
InChI Key:
YCVPRTHEGLPYPB-VOTSOKGWSA-N
SMILES:
Oc1cc(/C=C/c2ccccc2)cc(c1)O
UNII:
881R434AIB
NSC Number:
362430
Properties
Complexity:
221  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
212.084g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
212.248g/mol
Monoisotopic Mass:
212.084g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
40.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5  
Literature
Title Journal
Suppression of Src/ERK and GSK-3/β-catenin signaling by pinosylvin inhibits the growth of human colorectal cancer cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20130501
The natural stilbenoid pinosylvin and activated neutrophils: effects on oxidative burst, protein kinase C, apoptosis and efficiency in adjuvant arthritis. Acta pharmacologica Sinica 20121001
Antimetastatic activity of pinosylvin, a natural stilbenoid, is associated with the suppression of matrix metalloproteinases. The Journal of nutritional biochemistry 20120801
Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor. Bioorganic & medicinal chemistry 20120115
Bioactivity guided isolation of anticancer constituents from leaves of Alnus sieboldiana (Betulaceae). Phytomedicine : international journal of phytotherapy and phytopharmacology 20110415
Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids. Journal of agricultural and food chemistry 20110309
Methoxylation of resveratrol: effects on induction of NAD(P)H quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties. Bioorganic & medicinal chemistry letters 20110201
Pinosylvin suppresses LPS-stimulated inducible nitric oxide synthase expression via the MyD88-independent, but TRIF-dependent downregulation of IRF-3 signaling pathway in mouse macrophage cells. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101
Nuclear factor E2-related factor 2-mediated induction of NAD(P)H:quinone oxidoreductase 1 by 3,5-dimethoxy-trans-stilbene. Journal of pharmacological sciences 20110101
[Synthesis and HIV-1 inhibitory activity of natural products isolated from Gnetum parvifolium and their analogues]. Yao xue xue bao = Acta pharmaceutica Sinica 20101201
In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis. Neuro endocrinology letters 20100101
Formation of reactive oxygen and nitrogen species in the presence of pinosylvin - an analogue of resveratrol. Neuro endocrinology letters 20100101
Complexation of pinosylvin, an analogue of resveratrol with high antifungal and antimicrobial activity, by different types of cyclodextrins. Journal of agricultural and food chemistry 20091111
Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol. Journal of medicinal chemistry 20090409
Wounding response in xylem of Scots pine seedlings shows wide genetic variation and connection with the constitutive defence of heartwood. Tree physiology 20090101
Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene. Neuro endocrinology letters 20081001
Isolation and identification of cytotoxic compounds from the wood of Pinus resinosa. Phytotherapy research : PTR 20080701
[Studies on chemical constituents of rhizome of Matteuccia struthiopteris]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080701
Interaction of stilbene compounds with human and rainbow trout estrogen receptors. Environmental toxicology and chemistry 20080201
Vibrational spectroscopy of resveratrol. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20071101
Quinone reductase induction activity of methoxylated analogues of resveratrol. European journal of medicinal chemistry 20070601
High-performance liquid chromatographic analysis of pterostilbene in biological fluids using fluorescence detection. Journal of pharmaceutical and biomedical analysis 20070104
Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. The Journal of pharmacy and pharmacology 20061101
Involvement of nuclear factor-kappaB in the inhibition of pro-inflammatory mediators by pinosylvin. Planta medica 20060701
Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers. Molecules (Basel, Switzerland) 20060131
Pharmacometrics of stilbenes: seguing towards the clinic. Current clinical pharmacology 20060101
Determination and assay validation of pinosylvin in rat serum: application to drug metabolism and pharmacokinetics. Journal of pharmaceutical and biomedical analysis 20050601
Antibacterial and antifungal activity of pinosylvin, a constituent of pine. Fitoterapia 20050301
Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species. Journal of natural products 20050101
Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells. Bioorganic & medicinal chemistry letters 20041206
A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds in Scots pine (Pinus sylvestris) wood. Part II. Hydrophilic compounds. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20041101
New stilbene derivatives from Calligonum leucocladum. Journal of natural products 20040601
Antifungal activity of stilbenes in in vitro bioassays and in transgenic Populus expressing a gene encoding pinosylvin synthase. Plant cell reports 20040301
Taxonomic significance of flavonoid variation in temperate species of Nothofagus. Phytochemistry 20030401
Antifungal stilbenoids from Stemona collinsae. Journal of natural products 20020601
Induction of discolored wood in Scots pine (Pinus sylvestris). Tree physiology 20020401
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