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Sesamin

CAS No.:
607-80-7
Catalog Number:
AG0037F9
Molecular Formula:
C20H19O6
Molecular Weight:
355.3613
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%(HPLC)
In Stock USA
United States
$61
- +
25mg
98%(HPLC)
In Stock USA
United States
$144
- +
100mg
98%(HPLC)
In Stock USA
United States
$401
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Product Description
Catalog Number:
AG0037F9
Chemical Name:
Sesamin
CAS Number:
607-80-7
Molecular Formula:
C20H19O6
Molecular Weight:
355.3613
MDL Number:
MFCD00216134
IUPAC Name:
5-[(3S,3aR,6S,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxole
InChI:
InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
InChI Key:
PEYUIKBAABKQKQ-AFHBHXEDSA-N
SMILES:
C1OC2=CC=[CH](C=C2O1)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc2c(c1)OCO2
EC Number:
612-029-1
UNII:
S7946O4P76
Properties
Complexity:
482  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
354.11g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
354.358g/mol
Monoisotopic Mass:
354.11g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
55.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7  
Literature
Title Journal
Discovery of a sesamin-metabolizing microorganism and a new enzyme. Proceedings of the National Academy of Sciences of the United States of America 20160809
Sesamin ameliorates doxorubicin-induced cardiotoxicity: involvement of Sirt1 and Mn-SOD pathway. Toxicology letters 20140113
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages. Journal of ethnopharmacology 20130307
Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway. Journal of agricultural and food chemistry 20130206
Comparison of metabolism of sesamin and episesamin by drug-metabolizing enzymes in human liver. Drug metabolism and disposition: the biological fate of chemicals 20121001
Sesamin modulates gene expression without corresponding effects on fatty acids in Atlantic salmon (Salmo salar L.). Lipids 20120901
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase. Bioorganic & medicinal chemistry letters 20120815
Chondroprotective and anti-inflammatory effects of sesamin. Phytochemistry 20120801
Modulatory effects of sesamin on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. Neuropharmacology 20120601
Tolbutamide hydroxylation by hepatic microsomes from Atlantic salmon (Salmo salar L.). Molecular biology reports 20120601
Quercetin and sesamin protect neuronal PC12 cells from high-glucose-induced oxidation, nitrosative stress, and apoptosis. Rejuvenation research 20120601
Plasma and tissue concentrations of α-tocopherol and δ-tocopherol following high dose dietary supplementation in mice. Nutrients 20120601
Sesamin exerts renoprotective effects by enhancing NO bioactivity in renovascular hypertensive rats fed with high-fat-sucrose diet. European journal of pharmacology 20120515
Anti-inflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii. Bioorganic & medicinal chemistry letters 20120401
How is sesamin metabolised in the human liver to show its biological effects? Expert opinion on drug metabolism & toxicology 20120101
Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice. Nutrition and cancer 20120101
[Anti-lipotoxic action of sesamin on renovascular hypertensive rats fed with a high-fat, high-sucrose diet]. Yao xue xue bao = Acta pharmaceutica Sinica 20120101
Sesamin stimulates osteoblast differentiation through p38 and ERK1/2 MAPK signaling pathways. BMC complementary and alternative medicine 20120101
Identification of the metabolites of episesamin in rat bile and human liver microsomes. Biological & pharmaceutical bulletin 20120101
Quercetin and sesamin protect dopaminergic cells from MPP+-induced neuroinflammation in a microglial (N9)-neuronal (PC12) coculture system. Oxidative medicine and cellular longevity 20120101
A phytochemical investigation of Zanthoxylum setulosum. Natural product communications 20111201
Sesamin induces melanogenesis by microphthalmia-associated transcription factor and tyrosinase up-regulation via cAMP signaling pathway. Acta biochimica et biophysica Sinica 20111001
Experimental antithrombotic effects of sesame seed whole grains and extracts. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20110901
Sequential metabolism of sesamin by cytochrome P450 and UDP-glucuronosyltransferase in human liver. Drug metabolism and disposition: the biological fate of chemicals 20110901
Sesamin induces autophagy in colon cancer cells by reducing tyrosine phosphorylation of EphA1 and EphB2. International journal of oncology 20110701
Sesamin inhibits macrophage-induced vascular endothelial growth factor and matrix metalloproteinase-9 expression and proangiogenic activity in breast cancer cells. Inflammation 20110601
Involvement of heme oxygenase-1 induction via Nrf2/ARE activation in protection against H2O2-induced PC12 cell death by a metabolite of sesamin contained in sesame seeds. Bioorganic & medicinal chemistry 20110315
Genotoxicity evaluation of sesamin and episesamin. Mutation research 20110203
Influence of dietary sesamin, a bioactive compound on fatty acids and expression of some lipid regulating genes in Baltic Atlantic salmon (Salmo salar L.) juveniles. Physiological research 20110101
The mechanism underlying the synergetic hypocholesterolemic effect of sesamin and α-tocopherol in rats fed a high-cholesterol diet. Journal of pharmacological sciences 20110101
Sesamin ameliorates oxidative stress and mortality in kainic acid-induced status epilepticus by inhibition of MAPK and COX-2 activation. Journal of neuroinflammation 20110101
Fatty acids and gene expression responses to bioactive compounds in Atlantic salmon (Salmo salar L.) hepatocytes. Neuro endocrinology letters 20110101
Absolute configuration of antifibrotic (+)-episesamin isolated from Lindera obtusiloba BLUME. Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101
Metabolism of sesamin by cytochrome P450 in human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals 20101201
Obtusilactone A and (-)-sesamin induce apoptosis in human lung cancer cells by inhibiting mitochondrial Lon protease and activating DNA damage checkpoints. Cancer science 20101201
A new 3,4-seco-lupane-type triterpenoid from the pulp of Acanthopanax senticosus (Rupr. et Maxim) Harms. Natural product research 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
Antioxidants from the leaves of Cinnamomum kotoense. Natural product communications 20100601
Sesamin manifests chemopreventive effects through the suppression of NF-kappa B-regulated cell survival, proliferation, invasion, and angiogenic gene products. Molecular cancer research : MCR 20100501
Sesquiterpenes from Oplopanax horridus. Journal of natural products 20100423
Specific dietary polyphenols attenuate atherosclerosis in apolipoprotein E-knockout mice by alleviating inflammation and endothelial dysfunction. Arteriosclerosis, thrombosis, and vascular biology 20100401
Sesamin attenuates behavioral, biochemical and histological alterations induced by reversible middle cerebral artery occlusion in the rats. Chemico-biological interactions 20100105
Angiogenic activity of sesamin through the activation of multiple signal pathways. Biochemical and biophysical research communications 20100101
Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts. Methods in molecular biology (Clifton, N.J.) 20100101
Effects of dietary ingredients on function and expression of P-glycoprotein in human intestinal epithelial cells. Biological & pharmaceutical bulletin 20100101
Sesamin mitigates inflammation and oxidative stress in endothelial cells exposed to oxidized low-density lipoprotein. Journal of agricultural and food chemistry 20091209
Use of high resolution LC-MSn analysis in conjunction with mechanism-based stress studies: identification of asarinin, an impurity from sesame oil in an animal health product. Journal of pharmaceutical and biomedical analysis 20091205
Metabolic engineering of lignan biosynthesis in Forsythia cell culture. Plant & cell physiology 20091201
Antirejection effect of Herba Asari extract in rats after cardiac allograft implantation. Transplantation proceedings 20091201
Inhibition of 20-hydroxyeicosatetraenoic acid synthesis using specific plant lignans: in vitro and human studies. Hypertension (Dallas, Tex. : 1979) 20091101
Sesamin improves endothelial dysfunction in renovascular hypertensive rats fed with a high-fat, high-sucrose diet. European journal of pharmacology 20091012
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
Sesamin as a co-initiator for unfilled dental restorations. Acta biomaterialia 20090901
[Studies on the chemical constituents from Euphorbia chrysocoma]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090901
Metabolites of sesamin, a major lignan in sesame seeds, induce neuronal differentiation in PC12 cells through activation of ERK1/2 signaling pathway. Journal of neural transmission (Vienna, Austria : 1996) 20090701
Effect of schisandrin B and sesamin mixture on CCl(4)-induced hepatic oxidative stress in rats. Phytotherapy research : PTR 20090201
Antihypertensive effects of sesamin in humans. Journal of nutritional science and vitaminology 20090201
Amides and benzenoids from Zanthoxylum ailanthoides with inhibitory activity on superoxide generation and elastase release by neutrophils. Journal of natural products 20090101
Assessing the neuroprotective effect of antioxidative food factors by application of lipid-derived dopamine modification adducts. Methods in molecular biology (Clifton, N.J.) 20090101
Effect of the form of the sesame-based diet on the absorption of lignans. The British journal of nutrition 20081201
Sesamin supplementation increases white muscle docosahexaenoic acid (DHA) levels in rainbow trout (Oncorhynchus mykiss) fed high alpha-linolenic acid (ALA) containing vegetable oil: metabolic actions. Lipids 20081101
Sesamin increases alpha-linolenic acid conversion to docosahexaenoic acid in atlantic salmon (Salmo salar L.) hepatocytes: role of altered gene expression. Lipids 20081101
First chemical synthesis of antioxidative metabolites of sesamin. Chemical & pharmaceutical bulletin 20081101
HPTLC fingerprinting and quantification of lignans as markers in sesame oil and its polyherbal formulations. Journal of pharmaceutical and biomedical analysis 20080805
Dietary tocotrienol reduces UVB-induced skin damage and sesamin enhances tocotrienol effects in hairless mice. Journal of nutritional science and vitaminology 20080401
Dietary sesamin suppresses aortic NADPH oxidase in DOCA salt hypertensive rats. Clinical and experimental pharmacology & physiology 20080301
Constituents of Asarum sieboldii with inhibitory activity on lipopolysaccharide (LPS)-induced NO production in BV-2 microglial cells. Chemistry & biodiversity 20080201
A survey of sesamin and composition of tocopherol variability from seeds of eleven diverse sesame (Sesamum indicum L.) genotypes using HPLC-PAD-ECD. Phytochemical analysis : PCA 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
Trypanocidal and antileishmanial dihydrochelerythrine derivatives from Garcinia lucida. Journal of natural products 20071001
Sesamin, a lignan of sesame, down-regulates cyclin D1 protein expression in human tumor cells. Cancer science 20070901
Anti-inflammatory benzenoids from Antrodia camphorata. Journal of natural products 20070601
Suppression of ochratoxin biosynthesis by naturally occurring alkaloids. Food additives and contaminants 20070401
Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. The British journal of nutrition 20070101
An efficient and stereoselective dearylation of asarinin and sesamin tetrahydrofurofuran lignans to acuminatolide by methyltrioxorhenium/H(2)O(2) and UHP systems. Journal of natural products 20070101
Electrospray ionization ion-trap time-of-flight tandem mass spectrometry of two furofurans: sesamin and gmelinol. Rapid communications in mass spectrometry : RCM 20070101
Effect of sesamin on serum cholesterol and triglycerides levels in LDL receptor-deficient mice. European journal of nutrition 20061201
Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin. The Journal of pharmacology and experimental therapeutics 20060701
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
Decomposition reaction of sesamin in supercritical water. Bioscience, biotechnology, and biochemistry 20060501
Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats. Metabolism: clinical and experimental 20060301
Antioxidant activity and bioactive compounds of tea seed (Camellia oleifera Abel.) oil. Journal of agricultural and food chemistry 20060208
The epimerization of sesamin and asarinin. Journal of natural products 20051101
Sesamin ingestion regulates the transcription levels of hepatic metabolizing enzymes for alcohol and lipids in rats. Alcoholism, clinical and experimental research 20051101
NMR spectroscopic, mass spectroscopic, X-ray crystallographic, and theoretical studies of molecular mechanics of natural products: farformolide B and sesamin. Biophysical chemistry 20050401
Sesamin inhibits lipopolysaccharide-induced cytokine production by suppression of p38 mitogen-activated protein kinase and nuclear factor-kappaB. Immunology letters 20050215
Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. Journal of agricultural and food chemistry 20050112
Effect of sesamin in Acanthopanax senticosus HARMS on behavioral dysfunction in rotenone-induced parkinsonian rats. Biological & pharmaceutical bulletin 20050101
Modulating effect of sesamin, a functional lignan in sesame seeds, on the transcription levels of lipid- and alcohol-metabolizing enzymes in rat liver: a DNA microarray study. Bioscience, biotechnology, and biochemistry 20050101
Sesamin induces nitric oxide and decreases endothelin-1 production in HUVECs: possible implications for its antihypertensive effect. Journal of hypertension 20041201
Effects of vitamin E and sesamin on hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats. Clinical and experimental pharmacology & physiology 20041201
Consumption of sesame oil muffins decreases the urinary excretion of gamma-tocopherol metabolites in humans. Annals of the New York Academy of Sciences 20041201
Dietary sesame oils inhibits iron-induced oxidative stress in rats [corrected]. The British journal of nutrition 20041001
Lignoids in insects: chemical probes for the study of ecdysis, excretion and Trypanosoma cruzi-triatomine interactions. Toxicon : official journal of the International Society on Toxinology 20040915
Protective effects of sesamin and sesamolin on murine BV-2 microglia cell line under hypoxia. Neuroscience letters 20040826
Antifungal constituents of Melicope borbonica. Phytotherapy research : PTR 20040701
Interaction of dietary fat types and sesamin on hepatic fatty acid oxidation in rats. Biochimica et biophysica acta 20040601
Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae. Pest management science 20040401
Species differences in the physiological activity of dietary lignan (sesamin and episesamin) in affecting hepatic fatty acid metabolism. The British journal of nutrition 20040301
Free radical scavenging behavior of antioxidant compounds of sesame (sesamum indicum L.) in DPPH(*) system. Journal of agricultural and food chemistry 20040225
Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study. BioFactors (Oxford, England) 20040101
Effects of sesamin on aortic oxidative stress and endothelial dysfunction in deoxycorticosterone acetate-salt hypertensive rats. Biological & pharmaceutical bulletin 20031201
Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes. Journal of nutritional science and vitaminology 20031201
Protective effect of sesamin administration on exercise-induced lipid peroxidation. International journal of sports medicine 20031001
Protective effects of sesamin and sesamolin on hypoxic neuronal and PC12 cells. Journal of neuroscience research 20031001
Effect of dietary fat level and sesamin on the polyunsaturated fatty acid metabolism in rats. Journal of nutritional science and vitaminology 20031001
Dietary sesame lignans decrease lipid peroxidation in rats fed docosahexaenoic acid. Journal of nutritional science and vitaminology 20030801
Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides. Planta medica 20030401
Novel antioxidative metabolites in rat liver with ingested sesamin. Journal of agricultural and food chemistry 20030312
Antioxidant and anti-inflammatory effects of a diet supplemented with sesamin on hepatic ischemia-reperfusion injury in rats. Hepato-gastroenterology 20030101
Combined effects of dietary conjugated linoleic acid and sesamin triacylglycerol and ketone body production in rat liver. Journal of nutritional science and vitaminology 20021001
Antihypertensive effect of sesamin. IV. Inhibition of vascular superoxide production by sesamin. Biological & pharmaceutical bulletin 20020901
Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography. Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20020701
Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source. The Journal of organic chemistry 20020517
Sesamin, a sesame lignan, decreases fatty acid synthesis in rat liver accompanying the down-regulation of sterol regulatory element binding protein-1. Biochimica et biophysica acta 20011130
Effects of vitamin E and sesamin on hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats. Hypertension research : official journal of the Japanese Society of Hypertension 20011101
Dietary manipulations of body fat-reducing potential of conjugated linoleic acid in rats. Bioscience, biotechnology, and biochemistry 20011101
C-H insertion approach to the synthesis of endo,exo-furofuranones: synthesis of (+/-)-asarinin, (+/-)-epimagnolin A, and (+/-)-fargesin. The Journal of organic chemistry 20011005
Effect of sesame seeds rich in sesamin and sesamolin on fatty acid oxidation in rat liver. Journal of agricultural and food chemistry 20010501
Effect of sesamin on mitochondrial and peroxisomal beta-oxidation of arachidonic and eicosapentaenoic acids in rat liver. Lipids 20010501
[Studies on the chemical constituents of the herba of Cuscuta chinensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20010501
Sesamin a potent antifeedant principle from Piper mullesua. Phytotherapy research : PTR 20010201
Effects of dietary sesame seeds on plasma tocopherol levels. Nutrition and cancer 20010101
Separation and NMR studies on lignans of Raulinoa echinata. Phytochemical analysis : PCA 20010101
Differential in vitro anti-HIV activity of natural lignans. Zeitschrift fur Naturforschung. C, Journal of biosciences 19900101
Properties