537-42-8 | 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$10.00	$7.00
5g	98%	in stock	$13.00	$9.00
10g	98%	in stock	$16.00	$11.00
25g	98%	in stock	$34.00	$24.00

Description

• Catalog Number: AI52020
• Chemical Name: 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
• CAS Number: 537-42-8
• Molecular Formula: C16H16O3
• Molecular Weight: 256.2964
• MDL Number: MFCD00238710
• SMILES: COc1cc(/C=C/c2ccc(cc2)O)cc(c1)OC
• NSC Number: 613735

Computed Properties

• Complexity: 270
• Covalently-Bonded Unit Count: 1
• Defined Bond Stereocenter Count: 1
• Heavy Atom Count: 19
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 4
• XLogP3: 3.8

Literature

• Potent Inhibition of HIV-1 Replication in Resting CD4 T Cells by Resveratrol and Pterostilbene.

  Antimicrobial agents and chemotherapy 20170901

• Hydroxystilbenes and methoxystilbenes activate human aryl hydrocarbon receptor and induce CYP1A genes in human hepatoma cells and human hepatocytes.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20170501

• ERK5/HDAC5-mediated, resveratrol-, and pterostilbene-induced expression of MnSOD in human endothelial cells.

  Molecular nutrition & food research 20160201

• Estrogen-responsive genes encoding egg yolk proteins vitellogenin and apolipoprotein II in chicken are differentially regulated by selective estrogen receptor modulators.

  Theriogenology 20160201

• Pterostilbene Ameliorates Streptozotocin-Induced Diabetes through Enhancing Antioxidant Signaling Pathways Mediated by Nrf2.

  Chemical research in toxicology 20160119

• A Novel Combinatorial Epigenetic Therapy Using Resveratrol and Pterostilbene for Restoring Estrogen Receptor-α (ERα) Expression in ERα-Negative Breast Cancer Cells.

  PloS one 20160101

• A Resveratrol Analogue Promotes ERKMAPK-Dependent Stat3 Serine and Tyrosine Phosphorylation Alterations and Antitumor Effects In Vitro against Human Tumor Cells.

  Molecular pharmacology 20150901

• Epigenetic-based combinatorial resveratrol and pterostilbene alters DNA damage response by affecting SIRT1 and DNMT enzyme expression, including SIRT1-dependent γ-H2AX and telomerase regulation in triple-negative breast cancer.

  BMC cancer 20150101

• The berry constituents quercetin, kaempferol, and pterostilbene synergistically attenuate reactive oxygen species: involvement of the Nrf2-ARE signaling pathway.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20141001

• Pterostilbene, a dimethyl ether derivative of resveratrol, reduces fat accumulation in rats fed an obesogenic diet.

  Journal of agricultural and food chemistry 20140820

• Antifungal activity of resveratrol derivatives against Candida species.

  Journal of natural products 20140725

• Proteomic identification of pterostilbene-mediated anticancer activities in HepG2 cells.

  Chemical research in toxicology 20140721

• In vitro and in vivo activities of pterostilbene against Candida albicans biofilms.

  Antimicrobial agents and chemotherapy 20140401

• Synergistic induction of human cathelicidin antimicrobial peptide gene expression by vitamin D and stilbenoids.

  Molecular nutrition & food research 20140301

• The stilbenes resveratrol, pterostilbene and piceid affect growth and stress resistance in mammalian cells via a mechanism requiring estrogen receptor beta and the induction of Mn-superoxide dismutase.

  Phytochemistry 20140201

• Differences in the glucuronidation of resveratrol and pterostilbene: altered enzyme specificity and potential gender differences.

  Drug metabolism and pharmacokinetics 20140101

• A combination of pterostilbene with autophagy inhibitors exerts efficient apoptotic characteristics in both chemosensitive and chemoresistant lung cancer cells.

  Toxicological sciences : an official journal of the Society of Toxicology 20140101

• Involvement of the Nrf2 pathway in the regulation of pterostilbene-induced apoptosis in HeLa cells via ER stress.

  Journal of pharmacological sciences 20140101

• Scavenging of hydroxyl radical by resveratrol and related natural stilbenes after hydrogen peroxide attack on DNA.

  Chemico-biological interactions 20131125

• 3,5,4'-Trimethoxystilbene, a natural methoxylated analog of resveratrol, inhibits breast cancer cell invasiveness by downregulation of PI3K/Akt and Wnt/β-catenin signaling cascades and reversal of epithelial-mesenchymal transition.

  Toxicology and applied pharmacology 20131101

• The molecular basis for the inhibition of phosphodiesterase-4D by three natural resveratrol analogs. Isolation, molecular docking, molecular dynamics simulations, binding free energy, and bioassay.

  Biochimica et biophysica acta 20131001

• Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2.

  Bioorganic & medicinal chemistry 20131001

• Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia.

  Journal of agricultural and food chemistry 20130626

• Ebselen reduces the toxicity of mechlorethamine in A-431 cells via inhibition of apoptosis.

  Journal of biochemical and molecular toxicology 20130601

• Pterostilbene induces mitochondrially derived apoptosis in breast cancer cells in vitro.

  The Journal of surgical research 20130401

• Nutritional Supplement-5 with a Combination of Proteasome Inhibitors (Resveratrol, Quercetin, δ-Tocotrienol) Modulate Age-Associated Biomarkers and Cardiovascular Lipid Parameters in Human Subjects.

  Journal of clinical & experimental cardiology 20130302

• Pterostilbene exerts antitumor activity against human osteosarcoma cells by inhibiting the JAK2/STAT3 signaling pathway.

  Toxicology 20130208

• Pterostilbene, a natural analogue of resveratrol, potently inhibits 7,12-dimethylbenz[a]anthracene (DMBA)/12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse skin carcinogenesis.

  Food & function 20121101

• Pterostilbene ameliorates tumor necrosis factor alpha-induced pancreatitis in vitro.

  The Journal of surgical research 20121101

• Inhibitory effects of (-)-epigallocatechin-3-gallate and pterostilbene on pancreatic cancer growth in vitro.

  The Journal of surgical research 20121001

• Low-dose pterostilbene, but not resveratrol, is a potent neuromodulator in aging and Alzheimer's disease.

  Neurobiology of aging 20120901

• Antihyperuricemic and nephroprotective effects of resveratrol and its analogues in hyperuricemic mice.

  Molecular nutrition & food research 20120901

• Co-expression of VpROMT gene from Chinese wild Vitis pseudoreticulata with VpSTS in tobacco plants and its effects on the accumulation of pterostilbene.

  Protoplasma 20120701

• Activation of AMPK by pterostilbene suppresses lipogenesis and cell-cycle progression in p53 positive and negative human prostate cancer cells.

  Journal of agricultural and food chemistry 20120627

• Genomic analysis of pterostilbene predicts its antiproliferative effects against pancreatic cancer in vitro and in vivo.

  Journal of gastrointestinal surgery : official journal of the Society for Surgery of the Alimentary Tract 20120601

• Long term induction by pterostilbene results in autophagy and cellular differentiation in MCF-7 cells via ROS dependent pathway.

  Molecular and cellular endocrinology 20120515

• In planta production of the highly potent resveratrol analogue pterostilbene via stilbene synthase and O-methyltransferase co-expression.

  Plant biotechnology journal 20120401

• Pterostilbene and cancer: current review.

  The Journal of surgical research 20120401

• [Simultaneous determination of five active components in resina draconis and its extract by HPLC].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120401

• Resveratrol increases the expression and activity of the low density lipoprotein receptor in hepatocytes by the proteolytic activation of the sterol regulatory element-binding proteins.

  Atherosclerosis 20120201

• 3,5-dibenzyloxy-4'-hydroxystilbene induces early caspase-9 activation during apoptosis in human K562 chronic myelogenous leukemia cells.

  The Journal of toxicological sciences 20120201

• Pterostilbene protects vascular endothelial cells against oxidized low-density lipoprotein-induced apoptosis in vitro and in vivo.

  Apoptosis : an international journal on programmed cell death 20120101

• Inhibitory effects of garcinol and pterostilbene on cell proliferation and adipogenesis in 3T3-L1 cells.

  Food & function 20120101

• Comparison of conventional and non conventional methods of extraction of heartwood of Pterocarpus marsupium Roxb.

  Acta poloniae pharmaceutica 20120101

• Inhibition of nitric oxide and inflammatory cytokines in LPS-stimulated murine macrophages by resveratrol, a potent proteasome inhibitor.

  Lipids in health and disease 20120101

• Pterostilbene-induced tumor cytotoxicity: a lysosomal membrane permeabilization-dependent mechanism.

  PloS one 20120101

• Resveratrol modulates MED28 (Magicin/EG-1) expression and inhibits epidermal growth factor (EGF)-induced migration in MDA-MB-231 human breast cancer cells.

  Journal of agricultural and food chemistry 20111109

• The antiproliferative effects of pterostilbene on breast cancer in vitro are via inhibition of constitutive and leptin-induced Janus kinase/signal transducer and activator of transcription activation.

  American journal of surgery 20111101

• Inhibitory effects of resveratrol and pterostilbene on human colon cancer cells: a side-by-side comparison.

  Journal of agricultural and food chemistry 20111026

• Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats.

  Cancer chemotherapy and pharmacology 20110901

• Synthesis and antimicrobial activity of (E) stilbene derivatives.

  Bioorganic & medicinal chemistry 20110901

• Pterostilbene suppresses benzo[a]pyrene-induced airway remodeling.

  Journal of agricultural and food chemistry 20110727

• Development of a reversed phase high performance liquid chromatography method based on the use of cyclodextrins as mobile phase additives to determine pterostilbene in blueberries.

  Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110501

• Identification of reference genes suitable for qRT-PCR in grapevine and application for the study of the expression of genes involved in pterostilbene synthesis.

  Molecular genetics and genomics : MGG 20110401

• Pterostilbene is more potent than resveratrol in preventing azoxymethane (AOM)-induced colon tumorigenesis via activation of the NF-E2-related factor 2 (Nrf2)-mediated antioxidant signaling pathway.

  Journal of agricultural and food chemistry 20110323

• Fluorinated N,N-dialkylaminostilbenes for Wnt pathway inhibition and colon cancer repression.

  Journal of medicinal chemistry 20110310

• Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids.

  Journal of agricultural and food chemistry 20110309

• The effectiveness of stilbenes in resistant Vitaceae: ultrastructural and biochemical events during Plasmopara viticola infection process.

  Plant physiology and biochemistry : PPB 20110301

• Suppression of Heregulin-β1/HER2-Modulated Invasive and Aggressive Phenotype of Breast Carcinoma by Pterostilbene via Inhibition of Matrix Metalloproteinase-9, p38 Kinase Cascade and Akt Activation.

  Evidence-based complementary and alternative medicine : eCAM 20110101

• Kinetic mechanism and product characterization of the enzymatic peroxidation of pterostilbene as model of the detoxification process of stilbene-type phytoalexins.

  Phytochemistry 20110101

• Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.

  Chemico-biological interactions 20101205

• Pterostilbene induces autophagy and apoptosis in sensitive and chemoresistant human bladder cancer cells.

  Molecular nutrition & food research 20101201

• Pterostilbene and tamoxifen show an additive effect against breast cancer in vitro.

  American journal of surgery 20101101

• In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer.

  European journal of medicinal chemistry 20100901

• Pterostilbene inhibits colorectal aberrant crypt foci (ACF) and colon carcinogenesis via suppression of multiple signal transduction pathways in azoxymethane-treated mice.

  Journal of agricultural and food chemistry 20100811

• Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer.

  Bioorganic & medicinal chemistry 20100715

• Dietary intake of pterostilbene, a constituent of blueberries, inhibits the beta-catenin/p65 downstream signaling pathway and colon carcinogenesis in rats.

  Carcinogenesis 20100701

• Pterostilbene. Monograph.

  Alternative medicine review : a journal of clinical therapeutic 20100701

• Structural identification of mouse urinary metabolites of pterostilbene using liquid chromatography/tandem mass spectrometry.

  Rapid communications in mass spectrometry : RCM 20100630

• Pterostilbene inhibits breast cancer in vitro through mitochondrial depolarization and induction of caspase-dependent apoptosis.

  The Journal of surgical research 20100615

• Pterostilbene inhibits lung cancer through induction of apoptosis.

  The Journal of surgical research 20100601

• In vitro evaluation of the cytotoxic, anti-proliferative and anti-oxidant properties of pterostilbene isolated from Pterocarpus marsupium.

  Toxicology in vitro : an international journal published in association with BIBRA 20100601

• New stilbene dimers against amyloid fibril formation.

  Bioorganic & medicinal chemistry letters 20100601

• Pterostilbene inhibits pancreatic cancer in vitro.

  Journal of gastrointestinal surgery : official journal of the Society for Surgery of the Alimentary Tract 20100501

• The assay of pterostilbene in spiked matrices by liquid chromatography tandem mass spectrometry and isotope dilution method.

  Journal of mass spectrometry : JMS 20100401

• Differential effects of resveratrol and its naturally occurring methylether analogs on cell cycle and apoptosis in human androgen-responsive LNCaP cancer cells.

  Molecular nutrition & food research 20100301

• Antioxidant effect of trans-resveratrol, pterostilbene, quercetin and their combinations in human erythrocytes in vitro.

  Plant foods for human nutrition (Dordrecht, Netherlands) 20100301

• Determination and imaging of metabolites from Vitis vinifera leaves by laser desorption/ionisation time-of-flight mass spectrometry.

  Rapid communications in mass spectrometry : RCM 20100201

• Pterostilbene, a natural dimethylated analog of resveratrol, inhibits rat aortic vascular smooth muscle cell proliferation by blocking Akt-dependent pathway.

  Vascular pharmacology 20100101

• Molecular targets of the natural antioxidant pterostilbene: effect on protein kinase C, caspase-3 and apoptosis in human neutrophils in vitro.

  Neuro endocrinology letters 20100101

• In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis.

  Neuro endocrinology letters 20100101

• Determination of pterostilbene in rat plasma by a simple HPLC-UV method and its application in pre-clinical pharmacokinetic study.

  Biomedical chromatography : BMC 20091201

• Effects of pterostilbene on melanoma alone and in synergy with inositol hexaphosphate.

  American journal of surgery 20091101

• Induction of defence mechanisms in grapevine leaves by emodin- and anthraquinone-rich plant extracts and their conferred resistance to downy mildew.

  Plant physiology and biochemistry : PPB 20090901

• Cytotoxic constituents of Soymida febrifuga from Myanmar.

  Journal of natural products 20090901

• Pterostilbene inhibited tumor invasion via suppressing multiple signal transduction pathways in human hepatocellular carcinoma cells.

  Carcinogenesis 20090701

• Anti-inflammatory action of pterostilbene is mediated through the p38 mitogen-activated protein kinase pathway in colon cancer cells.

  Cancer prevention research (Philadelphia, Pa.) 20090701

• Physicochemical study of the complexation of pterostilbene by natural and modified cyclodextrins.

  Journal of agricultural and food chemistry 20090624

• Dietary administration of high doses of pterostilbene and quercetin to mice is not toxic.

  Journal of agricultural and food chemistry 20090422

• Synthesis and biological evaluation of a library of resveratrol analogues as inhibitors of COX-1, COX-2 and NF-kappaB.

  Bioorganic & medicinal chemistry 20090201

• Pterostilbene from Vitis coignetiae protect H2O2-induced inhibition of gap junctional intercellular communication in rat liver cell line.

  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20090201

• Cellular and behavioral effects of stilbene resveratrol analogues: implications for reducing the deleterious effects of aging.

  Journal of agricultural and food chemistry 20081126

• A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine.

  Plant physiology 20081101

• Natural polyphenols facilitate elimination of HT-29 colorectal cancer xenografts by chemoradiotherapy: a Bcl-2- and superoxide dismutase 2-dependent mechanism.

  Molecular cancer therapeutics 20081001

• Structure-efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene.

  Neuro endocrinology letters 20081001

• Pterostilbene suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages.

  Journal of agricultural and food chemistry 20080827

• Pterostilbene is equally potent as resveratrol in inhibiting 12-O-tetradecanoylphorbol-13-acetate activated NFkappaB, AP-1, COX-2, and iNOS in mouse epidermis.

  Molecular nutrition & food research 20080601

• Design, synthesis, biological evaluation and docking studies of pterostilbene analogs inside PPARalpha.

  Bioorganic & medicinal chemistry 20080401

• Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, antiinflammatory, antioxidant and analgesic activity.

  Phytotherapy research : PTR 20080201

• New polyphenols active on beta-amyloid aggregation.

  Bioorganic & medicinal chemistry letters 20080115

• Pterostilbene induces apoptosis and cell cycle arrest in human gastric carcinoma cells.

  Journal of agricultural and food chemistry 20070919

• Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans-resveratrol methyl ethers.

  Molecular nutrition & food research 20070501

• Nitric oxide mediates natural polyphenol-induced Bcl-2 down-regulation and activation of cell death in metastatic B16 melanoma.

  The Journal of biological chemistry 20070202

• High-performance liquid chromatographic analysis of pterostilbene in biological fluids using fluorescence detection.

  Journal of pharmaceutical and biomedical analysis 20070104

• Pterostilbene, an active constituent of blueberries, suppresses aberrant crypt foci formation in the azoxymethane-induced colon carcinogenesis model in rats.

  Clinical cancer research : an official journal of the American Association for Cancer Research 20070101

• The antioxidant role of pterostilbene in streptozotocin-nicotinamide-induced type 2 diabetes mellitus in Wistar rats.

  The Journal of pharmacy and pharmacology 20061101

• Effect of pterostilbene on hepatic key enzymes of glucose metabolism in streptozotocin- and nicotinamide-induced diabetic rats.

  Life sciences 20060710

• Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells.

  Journal of medicinal chemistry 20060518

• Microsphere-based protease assays and screening application for lethal factor and factor Xa.

  Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

• Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities.

  Xenobiotica; the fate of foreign compounds in biological systems 20060401

• Pharmacometrics of stilbenes: seguing towards the clinic.

  Current clinical pharmacology 20060101

• Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells.

  Journal of medicinal chemistry 20051103

• Pterostilbene and 3'-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells.

  The international journal of biochemistry & cell biology 20050801

• Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor alpha-isoform, lowers plasma lipoproteins and cholesterol in hypercholesterolemic hamsters.

  Journal of agricultural and food chemistry 20050504

• Selective COX-2 inhibition by a Pterocarpus marsupium extract characterized by pterostilbene, and its activity in healthy human volunteers.

  Planta medica 20050501

• Association between pterostilbene and quercetin inhibits metastatic activity of B16 melanoma.

  Neoplasia (New York, N.Y.) 20050101

• Resveratrol, pterostilbene, and piceatannol in vaccinium berries.

  Journal of agricultural and food chemistry 20040728

• Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents.

  Journal of medicinal chemistry 20030731

• Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.

  Phytochemistry 20020801

• Antineoplastic agents. 465. Structural modification of resveratrol: sodium resverastatin phosphate.

  Journal of medicinal chemistry 20020606

• Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol.

  Journal of agricultural and food chemistry 20020605

• Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol.

  The Journal of biological chemistry 20010622