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533-31-3 | Sesamol
CAS No: 533-31-3 Catalog No: AG003DH2 MDL No:MFCD00005827
Product Description
Catalog Number:
AG003DH2
Chemical Name:
Sesamol
CAS Number:
533-31-3
Molecular Formula:
C7H6O3
Molecular Weight:
138.1207
MDL Number:
MFCD00005827
IUPAC Name:
1,3-benzodioxol-5-ol
InChI:
InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChI Key:
LUSZGTFNYDARNI-UHFFFAOYSA-N
SMILES:
Oc1ccc2c(c1)OCO2
EC Number:
208-561-5
UNII:
94IEA0NV89
NSC Number:
59256
Properties
Complexity:
126
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
138.032g/mol
Formal Charge:
0
Heavy Atom Count:
10
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
138.122g/mol
Monoisotopic Mass:
138.032g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
38.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.2
Literature
| Title | Journal |
|---|---|
| Sesamol induced apoptotic effect in lung adenocarcinoma cells through both intrinsic and extrinsic pathways. | Chemico-biological interactions 20160725 |
| Hepatoprotective effects of sesamol loaded solid lipid nanoparticles in carbon tetrachloride induced sub-chronic hepatotoxicity in rats. | Environmental toxicology 20160501 |
| Sesamol alleviates diet-induced cardiometabolic syndrome in rats via up-regulating PPARγ, PPARα and e-NOS. | The Journal of nutritional biochemistry 20121101 |
| Efficacy of sesamol on plasma and tissue lipids in isoproterenol-induced cardiotoxicity in Wistar rats. | Archives of pharmacal research 20120801 |
| Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite. | The Journal of organic chemistry 20120706 |
| Patterns of carbohydrate and fatty acid changes under nitrogen starvation in the microalgae Haematococcus pluvialis and Nannochloropsis sp. | Applied microbiology and biotechnology 20120601 |
| Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles. | Molecules (Basel, Switzerland) 20120503 |
| Sesamol attenuates oxidative stress-mediated experimental acute pancreatitis in rats. | Human & experimental toxicology 20120401 |
| Multiple roles of dihomo-γ-linolenic acid against proliferation diseases. | Lipids in health and disease 20120101 |
| PPARα as a Transcriptional Regulator for Detoxification of Plant Diet-Derived Unfavorable Compounds. | PPAR research 20120101 |
| Metabolic engineering of yeast and plants for the production of the biologically active hydroxystilbene, resveratrol. | Journal of biomedicine & biotechnology 20120101 |
| Delivery of sesamol-loaded solid lipid nanoparticles to the brain for menopause-related emotional and cognitive central nervous system derangements. | Rejuvenation research 20111201 |
| Physicochemical insights on the free radical scavenging activity of sesamol: importance of the acid/base equilibrium. | The journal of physical chemistry. B 20111110 |
| Therapeutic sesamol attenuates monocrotaline-induced sinusoidal obstruction syndrome in rats by inhibiting matrix metalloproteinase-9. | Cell biochemistry and biophysics 20111101 |
| Sesamol as a potential radioprotective agent: in vitro studies. | Radiation research 20111101 |
| Selective recognition of sesamol using molecularly imprinted polymers containing magnetic wollastonite. | Journal of separation science 20111101 |
| Anti-hepatotoxic effects of 3,4-methylenedioxyphenol and N-acetylcysteine in acutely acetaminophen-overdosed mice. | Human & experimental toxicology 20111001 |
| Effects of sesamol on apoptosis and steroidogenesis in MA-10 mouse Leydig tumor cells. | Journal of agricultural and food chemistry 20110928 |
| Experimental antithrombotic effects of sesame seed whole grains and extracts. | Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20110901 |
| Modulation of nitrergic pathway by sesamol prevents cognitive deficits and associated biochemical alterations in intracerebroventricular streptozotocin administered rats. | European journal of pharmacology 20110601 |
| Chondroprotective role of sesamol by inhibiting MMPs expression via retaining NF-κB signaling in activated SW1353 cells. | Journal of agricultural and food chemistry 20110511 |
| Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans. | Journal of agricultural and food chemistry 20110413 |
| Neuropsychopharmacological effect of sesamol in unpredictable chronic mild stress model of depression: behavioral and biochemical evidences. | Psychopharmacology 20110401 |
| Inhibitory activity of natural occurring antioxidants on Thiyl radical-induced trans-arachidonic acid formation. | Journal of agricultural and food chemistry 20110309 |
| Electrostatic spraying of antioxidants on the oxidative quality of ground beef. | Journal of animal science 20110301 |
| Interaction of sesamol (3,4-methylenedioxyphenol) with tyrosinase and its effect on melanin synthesis. | Biochimie 20110301 |
| A modified sesamol derivative inhibits progression of atherosclerosis. | Arteriosclerosis, thrombosis, and vascular biology 20110301 |
| Intracavernous delivery of a designed angiopoietin-1 variant rescues erectile function by enhancing endothelial regeneration in the streptozotocin-induced diabetic mouse. | Diabetes 20110301 |
| Normal and delayed wound healing is improved by sesamol, an active constituent of Sesamum indicum (L.) in albino rats. | Journal of ethnopharmacology 20110127 |
| Estrogenic activities of sesame lignans and their metabolites on human breast cancer cells. | Journal of agricultural and food chemistry 20110112 |
| Sesamol attenuates isoproterenol-induced acute myocardial infarction via inhibition of matrix metalloproteinase-2 and -9 expression in rats. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101 |
| What is new for an old molecule? Systematic review and recommendations on the use of resveratrol. | PloS one 20110101 |
| Antihypertensive and antioxidant effects of dietary black sesame meal in pre-hypertensive humans. | Nutrition journal 20110101 |
| Changes of blood biochemistry in the rabbit animal model in atherosclerosis research; a time- or stress-effect. | Lipids in health and disease 20110101 |
| Ameliorative effects of herbal combinations in hyperlipidemia. | Oxidative medicine and cellular longevity 20110101 |
| p66Shc aging protein in control of fibroblasts cell fate. | International journal of molecular sciences 20110101 |
| A novel role of sesamol in inhibiting NF-κB-mediated signaling in platelet activation. | Journal of biomedical science 20110101 |
| Analysis of expression sequence tags from a full-length-enriched cDNA library of developing sesame seeds (Sesamum indicum). | BMC plant biology 20110101 |
| Potent antiplatelet activity of sesamol in an in vitro and in vivo model: pivotal roles of cyclic AMP and p38 mitogen-activated protein kinase. | The Journal of nutritional biochemistry 20101201 |
| Sesamol inhibits UVB-induced ROS generation and subsequent oxidative damage in cultured human skin dermal fibroblasts. | Archives of dermatological research 20101201 |
| Protection of cellular DNA and membrane from γ-radiation-induced damages and enhancement in DNA repair by sesamol. | Cancer biotherapy & radiopharmaceuticals 20101201 |
| Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo [4,5- b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones. | Molecular diversity 20101101 |
| Towards a unifying, systems biology understanding of large-scale cellular death and destruction caused by poorly liganded iron: Parkinson's, Huntington's, Alzheimer's, prions, bactericides, chemical toxicology and others as examples. | Archives of toxicology 20101101 |
| Sesamol down-regulates the lipopolysaccharide-induced inflammatory response by inhibiting nuclear factor-kappa B activation. | Innate immunity 20101001 |
| Sesamol suppresses neuro-inflammatory cascade in experimental model of diabetic neuropathy. | The journal of pain : official journal of the American Pain Society 20101001 |
| Sesamin attenuates intercellular cell adhesion molecule-1 expression in vitro in TNF-alpha-treated human aortic endothelial cells and in vivo in apolipoprotein-E-deficient mice. | Molecular nutrition & food research 20100901 |
| Apoptosis-inducing action of two products from oxidation of sesamol, an antioxidative constituent of sesame oil: a possible cytotoxicity of oxidized antioxidant. | Toxicology in vitro : an international journal published in association with BIBRA 20100901 |
| Influence of chemical structures of benzodioxole-based coinitiators on the properties of the unfilled dental resin. | Acta biomaterialia 20100801 |
| Protective effect of sesamol against 3-nitropropionic acid-induced cognitive dysfunction and altered glutathione redox balance in rats. | Basic & clinical pharmacology & toxicology 20100701 |
| Protective effect of sesamol on the pulmonary inflammatory response and lung injury in endotoxemic rats. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100701 |
| Evaluation of the effects of selected phytochemicals on quality indices and sensorial properties of raw and cooked pork stored in different packaging systems. | Meat science 20100601 |
| Effect of lutein, sesamol, ellagic acid and olive leaf extract on the quality and shelf-life stability of packaged raw minced beef patties. | Meat science 20100401 |
| Comparing antioxidant effectiveness of natural and synthetic free radical scavengers in thermally-oxidized lard using DPPH method. | Journal of food science 20100401 |
| Low-cost fluorimetric determination of radicals based on fluorogenic dimerization of the natural phenol sesamol. | Analytical chemistry 20100215 |
| Development of a novel fluorometric assay for nitric oxide utilizing sesamol and its application to analysis of nitric oxide-releasing drugs. | Luminescence : the journal of biological and chemical luminescence 20100101 |
| Studies on natural p-terphenyls: total syntheses of vialinin A and terrestrin B. | Bioscience, biotechnology, and biochemistry 20100101 |
| Protective effect of sesamol against myocardial infarction caused by isoproterenol in Wistar rats. | Redox report : communications in free radical research 20100101 |
| The Ayurvedic drug, Ksheerabala, ameliorates quinolinic acid-induced oxidative stress in rat brain. | International journal of Ayurveda research 20100101 |
| Efficacy of vitamin C and ethanolic extract of Sesamum indicum in promoting fertility in male Wistar rats. | Journal of human reproductive sciences 20100101 |
| Biodetoxification of toxins generated from lignocellulose pretreatment using a newly isolated fungus, Amorphotheca resinae ZN1, and the consequent ethanol fermentation. | Biotechnology for biofuels 20100101 |
| Comments on Vennila and Pugalendi. Vennila L, Pugalendi KV. Protective effect of sesamol against myocardial infarction caused by isoproterenol in Wistar rats. Redox Rep 2010; 15: 36-42. | Redox report : communications in free radical research 20100101 |
| Glucose sensing neurons in the ventromedial hypothalamus. | Sensors (Basel, Switzerland) 20100101 |
| The non-peptide chemical 3,4-methylenedioxyphenol blocked lipopolysaccharide (LPS) from binding to LPS-binding protein and inhibited pro-inflammatory cytokines. | Innate immunity 20091201 |
| Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-alpha production. | Organic letters 20091105 |
| A new cross-coupling-based synthesis of carpanone. | Organic letters 20091001 |
| The effect of lutein, sesamol, ellagic acid and olive leaf extract on lipid oxidation and oxymyoglobin oxidation in bovine and porcine muscle model systems. | Meat science 20091001 |
| Effects of a diet rich in sesame ( Sesamum indicum) pericarp on the expression of oestrogen receptor alpha and oestrogen receptor beta in rat prostate and uterus. | The British journal of nutrition 20090901 |
| Antioxidant potential of sesamol and its role on radiation-induced DNA damage in whole-body irradiated Swiss albino mice. | Environmental toxicology and pharmacology 20090901 |
| Improving the stability and antioxidant properties of sesame oil: water-soluble spray-dried emulsions from new transesterified phenolic derivatives. | Journal of agricultural and food chemistry 20090826 |
| Fat content influences the color, lipid oxidation, and volatiles of irradiated ground beef. | Journal of food science 20090801 |
| Attenuation of renoinflammatory cascade in experimental model of diabetic nephropathy by sesamol. | Journal of agricultural and food chemistry 20090722 |
| The protective effect of sesamol against mitochondrial oxidative stress and hepatic injury in acetaminophen-overdosed rats. | Shock (Augusta, Ga.) 20090701 |
| Administration of sesamol improved blood-brain barrier function in streptozotocin-induced diabetic rats. | Experimental brain research 20090701 |
| Sesamol: an efficient antioxidant with potential therapeutic benefits. | Medicinal chemistry (Shariqah (United Arab Emirates)) 20090701 |
| A previously uncultured, paper mill Propionibacterium is able to degrade O-aryl alkyl ethers and various aromatic hydrocarbons. | Chemosphere 20090601 |
| Cytometric analysis of cytotoxicity of polyphenols and related phenolics to rat thymocytes: potent cytotoxicity of resveratrol to normal cells. | Basic & clinical pharmacology & toxicology 20090601 |
| Elimination and metabolism of sesamol, a bioactive compound in sesame oil, in rats. | Molecular nutrition & food research 20090501 |
| Renoprotective effects of sesamol in ferric nitrilotriacetate-induced oxidative renal injury in rats. | Basic & clinical pharmacology & toxicology 20090401 |
| Effects of germination on chemical composition and functional properties of sesame (Sesamum indicum L.) seeds. | Bioresource technology 20090201 |
| Glycosylation of sesamol by cultured plant cells. | Phytochemistry 20090101 |
| Effect of antioxidant application methods on the color, lipid oxidation, and volatiles of irradiated ground beef. | Journal of food science 20090101 |
| Effect of infrared heating on the formation of sesamol and quality of defatted flours from Sesamum indicum L. | Journal of food science 20090101 |
| Sesamol attenuate 3-nitropropionic acid-induced Huntington-like behavioral, biochemical, and cellular alterations in rats. | Journal of Asian natural products research 20090101 |
| Assessment of the medicinal potentials of the methanol extracts of the leaves and stems of Buddleja saligna. | BMC complementary and alternative medicine 20090101 |
| Antiproliferative effects of honey and of its polyphenols: a review. | Journal of biomedicine & biotechnology 20090101 |
| Storage stability of sunflower oil with added natural antioxidant concentrate from sesame seed oil. | Journal of oleo science 20090101 |
| A comparative evaluation of medicated oils prepared using ayurvedic and modified processes. | Indian journal of pharmaceutical sciences 20090101 |
| Effects of aging time and natural antioxidants on the color, lipid oxidation and volatiles of irradiated ground beef. | Meat science 20081101 |
| Metabolic transformation of sesamol and ex vivo effect on 2,2'-azo-bis(2-amidinopropane)dihydrochloride-induced hemolysis. | Journal of agricultural and food chemistry 20081022 |
| Sesamol attenuates diclofenac-induced acute gastric mucosal injury via its cyclooxygenase-independent antioxidative effect in rats. | Shock (Augusta, Ga.) 20081001 |
| Ethnopharmacology. | Indian journal of pharmacology 20081001 |
| Bioavailability and tissue distribution of sesamol in rat. | Journal of agricultural and food chemistry 20080827 |
| The prophylactic protective effect of sesamol against ferric-nitrilotriacetate-induced acute renal injury in mice. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080801 |
| Effect of sesamol on diabetes-associated cognitive decline in rats. | Experimental brain research 20080301 |
| Relationship between metabolic and genomic diversity in sesame (Sesamum indicum L.). | BMC genomics 20080101 |
| Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress. | Oxidative medicine and cellular longevity 20080101 |
| 3,4-Dihydroxy-phenyl 3,4,5-trimethoxy-benzoate. | Acta crystallographica. Section E, Structure reports online 20080101 |
| The effect of sesamol on systemic oxidative stress and hepatic dysfunction in acutely iron-intoxicated mice. | Shock (Augusta, Ga.) 20071101 |
| First total synthesis of vialinin A, a novel and extremely potent inhibitor of TNF-alpha production. | Organic letters 20071011 |
| Scavenging effects of phenolic compounds on reactive oxygen species. | Biopolymers 20070615 |
| Effects of methyl parathion on Chasmagnathus granulatus hepatopancreas: protective role of sesamol. | Ecotoxicology and environmental safety 20070501 |
| Practical and convenient synthesis of coumarins from phenols and propiolic acid esters. | Nature protocols 20070101 |
| Evaluation of coumarin derivatives as anti-fungal agents against soil-borne fungal pathogens. | Communications in agricultural and applied biological sciences 20070101 |
| Synergistic antimicrobial activities of phytoestrogens in crude extracts of two sesame species against some common pathogenic microorganisms. | African journal of traditional, complementary, and alternative medicines : AJTCAM 20070101 |
| Effect of sesamol on radiation-induced cytotoxicity in Swiss albino mice. | Mutation research 20061210 |
| Diet supplementation for 5 weeks with polyphenol-rich cereals improves several functions and the redox state of mouse leucocytes. | European journal of nutrition 20061201 |
| Characteristics of structured lipid prepared by lipase-catalyzed acidolysis of roasted sesame oil and caprylic acid in a bench-scale continuous packed bed reactor. | Journal of agricultural and food chemistry 20060712 |
| Sesamol delays mortality and attenuates hepatic injury after cecal ligation and puncture in rats: role of oxidative stress. | Shock (Augusta, Ga.) 20060501 |
| Development and evaluation of sesamol as an antiaging agent. | International journal of dermatology 20060301 |
| Attenuation of endotoxin-induced oxidative stress and multiple organ injury by 3,4-Methylenedioxyphenol in rats. | Shock (Augusta, Ga.) 20060301 |
| Effect of sesame oil on diuretics or Beta-blockers in the modulation of blood pressure, anthropometry, lipid profile, and redox status. | The Yale journal of biology and medicine 20060301 |
| Protective effect of 1,2,4-benzenetriol on LPS-induced NO production by BV2 microglial cells. | Journal of biomedical science 20060101 |
| Genetic relationship and diversity in a sesame (Sesamum indicum L.) germplasm collection using amplified fragment length polymorphism (AFLP). | BMC genetics 20060101 |
| Diastereoselective synthesis of some novel benzopyranopyridine derivatives. | Beilstein journal of organic chemistry 20060101 |
| Synthesis and HIV-1 integrase inhibitory activities of caffeic acid dimers derived from Salvia officinalis. | Bioorganic & medicinal chemistry letters 20051115 |
| Sesamol induces nitric oxide release from human umbilical vein endothelial cells. | Lipids 20050901 |
| Photoprotective effect of sesamol on UVB-radiation induced oxidative stress in human blood lymphocytes in vitro. | Environmental toxicology and pharmacology 20050701 |
| Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals. | Journal of agricultural and food chemistry 20050615 |
| Radioprotective effect of sesamol on gamma-radiation induced DNA damage, lipid peroxidation and antioxidants levels in cultured human lymphocytes. | Toxicology 20050505 |
| Free radical reactions and antioxidant activities of sesamol: pulse radiolytic and biochemical studies. | Journal of agricultural and food chemistry 20050406 |
| Sesamol regulates plasminogen activator gene expression in cultured endothelial cells: a potential effect on the fibrinolytic system. | The Journal of nutritional biochemistry 20050101 |
| Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. | Journal of agricultural and food chemistry 20041006 |
| Sesame lignans enhance antioxidant activity of vitamin E in lipid peroxidation systems. | Molecular and cellular biochemistry 20040701 |
| Thermodynamic study of sesamol, piperonyl alcohol, piperonylic acid and homopiperonylic acid: a combined experimental and theoretical investigation. | Organic & biomolecular chemistry 20040321 |
| Free radical scavenging behavior of antioxidant compounds of sesame (sesamum indicum L.) in DPPH(*) system. | Journal of agricultural and food chemistry 20040225 |
| Far-infrared radiation increases the antioxidant properties of rice hull extract in cooked turkey meat. | Journal of agricultural and food chemistry 20040128 |
| Comprehensive study on vitamin C equivalent antioxidant capacity (VCEAC) of various polyphenolics in scavenging a free radical and its structural relationship. | Critical reviews in food science and nutrition 20040101 |
| The sesame seed oil constituent, sesamol, induces growth arrest and apoptosis of cancer and cardiovascular cells. | Annals of the New York Academy of Sciences 20031201 |
| Antiphoto-oxidative activity of sesamol in methylene blue- and chlorophyll-sensitized photo-oxidation of oil. | Journal of agricultural and food chemistry 20030521 |
| Use of double packaging and antioxidant combinations to improve color, lipid oxidation, and volatiles of irradiated raw and cooked turkey breast patties. | Poultry science 20030501 |
| Action of pyrethrum-based formulations against grain weevils. | International journal of pharmaceutics 20030430 |
| Use of antioxidants to reduce lipid oxidation and off-odor volatiles of irradiated pork homogenates and patties. | Meat science 20030101 |
| Effect of antioxidants on the quality of irradiated sausages prepared with turkey thigh meat. | Poultry science 20020801 |
| Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barr virus early antigen activation assay and the mouse skin two-stage carcinogenesis. | Pharmacological research 20020601 |
| Palladium-catalyzed intramolecular C-O bond formation. | Journal of the American Chemical Society 20011212 |
| Cytotoxicity effects of di- and tri-hydroxybenzaldehydes as a chemopreventive potential agent on tumor cells. | Toxicology 20010328 |
| Increased survival after cecal ligation and puncture in mice consuming diets enriched with sesame seed oil. | Critical care medicine 20010101 |
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