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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 397.60 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 383.00 °F. TCC ( 194.90 °C. ) (est)
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| logP (o/w): | 3.680 (est) |
| Soluble in: |
| | water, 130.1 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| Pinosylvin > 95%
Odor: characteristic Use: Pinosylvin isolated from the herbs of Pinus yunnanensis. Pinosylvin in low concentrations, can promote cell proliferation to endothelial cells and inhibit lipopolysaccharide-induced THP-1 cell adhesion to endothelial cells.
antibacterial; antimicrobial; antifungal; |
| Coompo |
| For experimental / research use only. |
| Pinosylvin from Plants ≥96%
Odor: characteristic Use: Antibacterial agent. Shows fungistatic props.
When bovine aortic endothelial cells (BAECs) were treated with pinosylvin, etoposide- or starvation-induced apoptosis was shown to be significantly reduced. The anti-apoptotic effect of pinosylvin was mediated by inhibition of caspase-3. Moreover, pinosylvin was shown to activate endothelial nitric oxide synthetase (eNOS). At 1 pM, pinosylvin appeared to have a cell-proliferative effect in the endothelial cell. The pinosylvin-induced cell proliferation was declined by treatment with L-NAME, an eNOS inhibitor. Then, we found that pinosylvin had a stimulatory effect on cell migration and tube formation. These stimulatory effects suggest that pinosylvin is likely to act as a pro-angiogenic factor. Yet another effect of pinosylvin was inhibition of lipopolysaccharide-induced THP-1 cell adhesion to endothelial cells. Altogether, we propose that pinosylvin may be utilized as a phytotherapic agent for the prevention of cardiovascular inflammatory diseases.
The antibacterial and antifungal activities of pinosylvin, a constituent of pine, were studied and compared with those of resveratrol. Pinosylvin exhibited more potent growth inhibitory activity against Candida albicans and Saccharomyces cerevisiae.
Pinosylvin significantly inhibited LPS-induced NF-?B activation in a concentration- dependent manner. Additionally, pinosylvin was found to inhibit the LPS-induced phosphorylation and degradation of I?B a in THP-1 cells. Therefore, we have attempted to determine whether pinosylvin can inhibit the expression of cytokines possessing NF-?B binding sites in their promoter regions. In a consistent result, pinosylvin inhibited LPS-induced production of TNF a and interleukin-8 (IL-8). |
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Pinosylvin ≥97.0% (HPLC)
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Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
intraperitoneal-mouse LD50 20 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 300, 1982.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for (E)-pinosylvin usage levels up to: | | | not for fragrance use.
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| Recommendation for (E)-pinosylvin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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)- |
Articles:
| 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. |
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