(E)-pinosylvin

1,3-benzenediol, 5-(2-phenylethenyl)-, (E)- (9CI)

CAS: 22139-77-1 C14 H12 O2 MW: 212.24804000

Identification

Name(E)-pinosylvin
IUPAC5-[(E)-2-phenylethenyl]benzene-1,3-diol
CAS Number22139-77-1
FDA UNII881R434AIB
Molecular FormulaC14 H12 O2
Molecular Weight212.24804000
MDL NumberMFCD00210544
Nikkaji NumberJ10.798K
Beilstein1870942

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 397.60 °C. @ 760.00 mm Hg (est)
Flash Point 383.00 °F. TCC ( 194.90 °C. ) (est)
logP (o/w) 3.680 (est)
Soluble in water, 130.1 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 20 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for (E)-pinosylvin usage levels up tonot for fragrance use.
Recommendation for (E)-pinosylvin flavor usage levels up tonot for flavor use.

BOC Sciences

Best of Chemicals Supplier

Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...

View All Website 1-631-485-4226 account@bocsci.com

Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

1,3- benzenediol, 5-(2-phenylethenyl)-, (E)- (9CI) 1,3- benzenediol, 5-[(E)-2-phenylethenyl]- 3,5- dihydroxystilbene trans-3,5- dihydroxystilbene (E)-5-(2- phenyl ethenyl)-1,3-benzene diol (E)-5-(2- phenylethenyl)-1,3-benzenediol 5-[(1E)-2- phenylethenyl]benzene-1,3-diol 5-[(E)-2- phenylethenyl]benzene-1,3-diol 5-((1E)-2- phenylvinyl)benzene-1,3-diol 5-[(E)-2- phenylvinyl]-1,3-benzenediol 5-[(E)-2- phenylvinyl]-1,3-benzoldiol 5-[(E)-2- phenylvinyl]benzene-1,3-diol pinosylvin trans- pinosylvin pinosylvine (E)- pinosylvine stilbene, 3,5-dihydroxy-, trans- (E)-3,5- stilbenediol E-3,5- stilbenediol 3,5- stilbenediol, (E)- PubMed: Metabolic engineering of Escherichia coli for the biosynthesis of various phenylpropanoid derivatives. PubMed: Inhibitory effect of the branches of Hovenia dulcis Thunb. and its constituent pinosylvin on the activities of IgE-mediated mast cells and passive cutaneous anaphylaxis in mice. PubMed: Pinosylvin and Monomethylpinosylvin, Constituents of an Extract from the Knot of Pinus sylvestris, Reduce Inflammatory Gene Expression and Inflammatory Responses in Vivo. PubMed: Metabolic engineering of Escherichia coli for the synthesis of the plant polyphenol pinosylvin. PubMed: Pinosylvin at a high concentration induces AMPK-mediated autophagy for preventing necrosis in bovine aortic endothelial cells. PubMed: Markers of inflammation and oxidative stress studied in adjuvant-induced arthritis in the rat on systemic and local level affected by pinosylvin and methotrexate and their combination. PubMed: Pinosylvin-mediated protection against oxidative stress in human retinal pigment epithelial cells. PubMed: Novel Lignan and stilbenoid mixture shows anticarcinogenic efficacy in preclinical PC-3M-luc2 prostate cancer model. PubMed: Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents. PubMed: Strategies to improve the solubility and stability of stilbene antioxidants: a comparative study between cyclodextrins and bile acids. PubMed: Austrian pine phenolics are likely contributors to systemic induced resistance against Diplodia pinea. PubMed: Quantification of pinosylvin in rat plasma by liquid chromatography-tandem mass spectrometry: application to a pre-clinical pharmacokinetic study. PubMed: [Chemical constitunents of seeds of Oroxylum indicum]. PubMed: The antimicrobial effects of wood-associated polyphenols on food pathogens and spoilage organisms. PubMed: Modulation of TRP channels by resveratrol and other stilbenoids. PubMed: Suppression of Src/ERK and GSK-3/β-catenin signaling by pinosylvin inhibits the growth of human colorectal cancer cells. PubMed: Pharmacological influence on processes of adjuvant arthritis: Effect of the combination of an antioxidant active substance with methotrexate. PubMed: Involvement of caspase-3 in stilbene derivatives induced apoptosis of human neutrophils in vitro. PubMed: Polyphenol derivatives - potential regulators of neutrophil activity. PubMed: Decreased activity and accelerated apoptosis of neutrophils in the presence of natural polyphenols. PubMed: The natural stilbenoid pinosylvin and activated neutrophils: effects on oxidative burst, protein kinase C, apoptosis and efficiency in adjuvant arthritis. PubMed: Pinosylvin induces cell survival, migration and anti-adhesiveness of endothelial cells via nitric oxide production. PubMed: Nutritional and pathogenic fungi associated with the pine engraver beetle trigger comparable defenses in Scots pine. PubMed: Analysis of 3-methoxypterostilbene in biological fluids by high-performance liquid chromatography: application to pre-clinical pharmacokinetics. PubMed: Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor. PubMed: Antimetastatic activity of pinosylvin, a natural stilbenoid, is associated with the suppression of matrix metalloproteinases. PubMed: Utilization of adjuvant arthritis model for evaluation of new approaches in rheumatoid arthritis therapy focused on regulation of immune processes and oxidative stress. PubMed: Nuclear factor E2-related factor 2-mediated induction of NAD(P)H:quinone oxidoreductase 1 by 3,5-dimethoxy-trans-stilbene. PubMed: 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. PubMed: [Synthesis and HIV-1 inhibitory activity of natural products isolated from Gnetum parvifolium and their analogues]. PubMed: Total synthesis of chiricanine A, arahypin-1, trans-arachidin-2, trans-arachidin-3, and arahypin-5 from peanut seeds. PubMed: Formation of reactive oxygen and nitrogen species in the presence of pinosylvin - an analogue of resveratrol. PubMed: In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis. PubMed: Bioactivity guided isolation of anticancer constituents from leaves of Alnus sieboldiana (Betulaceae). PubMed: In vivo and in vitro mixed-function oxygenase activity and vitellogenin induction in fish and in fish and rat liver cells by stilbenes isolated from scotch pine (Pinus sylvestris). PubMed: Use of reversed phase high pressure liquid chromatography for the physicochemical and thermodynamic characterization of oxyresveratrol/beta-cyclodextrin complexes. PubMed: Complexation of pinosylvin, an analogue of resveratrol with high antifungal and antimicrobial activity, by different types of cyclodextrins. PubMed: Engineering of plant-specific phenylpropanoids biosynthesis in Streptomyces venezuelae. PubMed: Identification of genes upregulated by pinewood nematode inoculation in Japanese red pine. PubMed: Wounding response in xylem of Scots pine seedlings shows wide genetic variation and connection with the constitutive defence of heartwood. PubMed: Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene. PubMed: [Studies on chemical constituents of rhizome of Matteuccia struthiopteris]. PubMed: Pharmacometrics of stilbenes: seguing towards the clinic. PubMed: Isolation and identification of cytotoxic compounds from the wood of Pinus resinosa. PubMed: Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers. PubMed: Precursor-directed biosynthesis of stilbene methyl ethers in Escherichia coli. PubMed: Vibrational spectroscopy of resveratrol. PubMed: Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. PubMed: High-performance liquid chromatographic analysis of pterostilbene in biological fluids using fluorescence detection. PubMed: Involvement of nuclear factor-kappaB in the inhibition of pro-inflammatory mediators by pinosylvin. PubMed: Qualitative and quantitative determination of extractives in heartwood of Scots pine (Pinus sylvestris L.) by gas chromatography. PubMed: Expression of transgenic stilbene synthases in wheat causes the accumulation of unknown stilbene derivatives with antifungal activity. PubMed: Determination and assay validation of pinosylvin in rat serum: application to drug metabolism and pharmacokinetics. PubMed: Antibacterial and antifungal activity of pinosylvin, a constituent of pine. PubMed: Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species. PubMed: Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells. PubMed: A UV resonance Raman (UVRR) spectroscopic study on the extractable compounds in Scots pine (Pinus sylvestris) wood. Part II. Hydrophilic compounds. PubMed: In vitro androgenicity in pulp and paper mill effluents. PubMed: Antibacterial effects of knotwood extractives on paper mill bacteria. PubMed: Antifungal activity of stilbenes in in vitro bioassays and in transgenic Populus expressing a gene encoding pinosylvin synthase. PubMed: Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. PubMed: Feeding response of Ips paraconfusus to phloem and phloem metabolites of Heterobasidion annosum-inoculated ponderosa pine, Pinus ponderosa. PubMed: Taxonomic significance of flavonoid variation in temperate species of Nothofagus. PubMed: Antifungal stilbenoids from Stemona collinsae. PubMed: Induction of discolored wood in Scots pine (Pinus sylvestris). PubMed: A stilbene synthase from Japanese red pine (Pinus densiflora): implications for phytoalexin accumulation and down-regulation of flavonoid biosynthesis. PubMed: Diverse chalcone synthase superfamily enzymes from the most primitive vascular plant, Psilotum nudum. PubMed: In vitro inhibition of Sphaeropsis sapinea by natural stilbenes. PubMed: Molecular cloning and functional expression of a stress-induced multifunctional O-methyltransferase with pinosylvin methyltransferase activity from Scots pine (Pinus sylvestris L.). PubMed: Gene induction of stilbene biosynthesis in Scots pine in response to ozone treatment, wounding, and fungal infection. PubMed: Characterization of a pine multigene family containing elicitor-responsive stilbene synthase genes. PubMed: Differential Inhibition of Sphaeropsis sapinea Morphotypes by a Phenolic Compound and Several Monoterpenes of Red Pine. PubMed: A comparison of the effectiveness of predator odor and plant antifeedant in deterring small mammal feeding damage on lodgepole pine seedlings. PubMed: Wood-derived estrogens: studies in vitro with breast cancer cell lines and in vivo in trout. PubMed: Molecular and enzymatic characterization of two stilbene synthases from Eastern white pine (Pinus strobus). A single Arg/His difference determines the activity and the pH dependence of the enzymes. PubMed: Stilbene synthase from Scots pine (Pinus sylvestris). PubMed: Influence of the plant antifeedant, pinosylvin, on suppression of feeding by snowshoe hares. PubMed: Pine stilbene synthase cDNA, a tool for probing environmental stress. PubMed: Molecular analysis of chalcone and dihydropinosylvin synthase from Scots pine (Pinus sylvestris), and differential regulation of these and related enzyme activities in stressed plants. PubMed: Biochemical Plant Responses to Ozone : II. Induction of Stilbene Biosynthesis in Scots Pine (Pinus sylvestris L.) Seedlings. PubMed: Pinosylvin and pinosylvin methyl ether as feeding deterrents in green alder. PubMed: The effect of the phytoalexins, lubimin, (-)-maackiain, pinosylvin, and the related compounds dehydroloroglossol and hordatine M on human lymphoblastoid cell lines. PubMed: Pinosylvin methyl ether deters snowshoe hare feeding on green alder.