(+)-sesamin

(1S-(1alpha,3a alpha,4alpha,6a alpha))-5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl) bis-5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl)

CAS: 607-80-7 C20 H18 O6 MW: 354.35866000

Identification

Name(+)-sesamin
CAS Number607-80-7
FDA UNIIS7946O4P76
Molecular FormulaC20 H18 O6
Molecular Weight354.35866000
MDL NumberMFCD00216134
Nikkaji NumberJ9.612A

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 123.00 to 124.00 °C. @ 760.00 mm Hg
Boiling Point 504.00 to 505.00 °C. @ 760.00 mm Hg (est)
Flash Point 414.00 °F. TCC ( 212.30 °C. ) (est)
logP (o/w) 4.064 (est)
Soluble in water, 6.555 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
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 (+)-sesamin usage levels up tonot for fragrance use.
Recommendation for (+)-sesamin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

baboonwood ginkgo biloba sesame oil

Synonyms

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 fagarol dextro-(+)- sesamin epi- sesamin (1S-(1alpha,3a alpha,4alpha,6a alpha))-5,5'-( tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl) bis-5,5'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl) PubMed: Sesamin suppresses macrophage-derived chemokine expression in human monocytes via epigenetic regulation. PubMed: Differentiation therapy: sesamin as an effective agent in targeting cancer stem-like side population cells of human gallbladder carcinoma. PubMed: Combined effect of sesamin and soybean phospholipid on hepatic fatty acid metabolism in rats. PubMed: Antinociceptive and anti-inflammatory activities of the sesame oil and sesamin. PubMed: Sesamin reduces acute hepatic injury induced by lead coupled with lipopolysaccharide. PubMed: Influence of oral supplementation with sesamin on longevity of Caenorhabditis elegans and the host defense. PubMed: Sesamin and sesamolin as unexpected contaminants in various cold-pressed plant oils: NP-HPLC/FLD/DAD and RP-UPLC-ESI/MS(n) study. PubMed: α-Tocopherol transfer protein is not required for the discrimination against γ-tocopherol in vivo but protects it from side-chain degradation in vitro. PubMed: Hepatoprotective properties of sesamin against CCl4 induced oxidative stress-mediated apoptosis in mice via JNK pathway. PubMed: ¹H NMR-based metabolomics studies on the effect of sesamin in Atlantic salmon (Salmo salar). PubMed: [Isolation and identification of impurities in the natural vitamin E]. PubMed: Antioxidant activity-guided separation of coumarins and lignan from Melicope glabra (Rutaceae). PubMed: Effects of Sesamin on Streptozotocin (STZ)-Induced NIT-1 Pancreatic β-Cell Damage. PubMed: Sesamin modulation of lipid class and fatty acid profile in early juvenile teleost, Lates calcarifer, fed different dietary oils. PubMed: Sesamin protects mouse liver against nickel-induced oxidative DNA damage and apoptosis by the PI3K-Akt pathway. PubMed: Sesamin extends the mean lifespan of fruit flies. PubMed: Hypoglycaemic and hypolipidaemic activities of sesamin from sesame meal and its ability to ameliorate insulin resistance in KK-Ay mice. PubMed: Long-term intake of sesamin improves left ventricular remodelling in spontaneously hypertensive rats. PubMed: Fish oil at low dietary levels enhances physiological activity of sesamin to increase hepatic fatty acid oxidation in rats. PubMed: In vitro inhibition of 7-ethoxyresorufin-O-deethylase (EROD) and p-nitrophenol hydroxylase (PNPH) activities by sesamin in hepatic microsomes from two fish species. PubMed: Tissue distribution and cytochrome P450 inhibition of sesaminol and its tetrahydrofuranoid metabolites. PubMed: Sesamin modulates gene expression without corresponding effects on fatty acids in Atlantic salmon (Salmo salar L.). PubMed: Combined effect of sesamin and α-lipoic acid on hepatic fatty acid metabolism in rats. PubMed: Interrelated effects of dihomo-γ-linolenic and arachidonic acids, and sesamin on hepatic fatty acid synthesis and oxidation in rats. PubMed: Tolbutamide hydroxylation by hepatic microsomes from Atlantic salmon (Salmo salar L.). PubMed: Fatty acids and gene expression responses to bioactive compounds in Atlantic salmon (Salmo salar L.) hepatocytes. PubMed: [Nutritional value of sesame seeds]. PubMed: Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans. PubMed: Interaction of sesamol (3,4-methylenedioxyphenol) with tyrosinase and its effect on melanin synthesis. PubMed: Estrogenic activities of sesame lignans and their metabolites on human breast cancer cells. PubMed: Sesame seed lignans: potent physiological modulators and possible ingredients in functional foods & nutraceuticals. PubMed: 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. PubMed: 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. PubMed: Effects of dietary ingredients on function and expression of P-glycoprotein in human intestinal epithelial cells. PubMed: Assessing the neuroprotective effect of antioxidant food factors by application of lipid-derived dopamine modification adducts. PubMed: Sesamin mitigates inflammation and oxidative stress in endothelial cells exposed to oxidized low-density lipoprotein. PubMed: Identification and characterization of sesaminol metabolites in the liver. PubMed: Assessing the neuroprotective effect of antioxidative food factors by application of lipid-derived dopamine modification adducts. PubMed: Lipid metabolism and nutrigenomics - impact of sesame lignans on gene expression profiles and fatty acid oxidation in rat liver. PubMed: Genomics for food functionality and palatability. PubMed: Comparative study of sesame lignans (sesamin, episesamin and sesamolin) affecting gene expression profile and fatty acid oxidation in rat liver. PubMed: Comparison of atmospheric pressure chemical ionization and electrospray ionization mass spectrometry for the detection of lignans from sesame seeds. PubMed: Sesamin increases alpha-linolenic acid conversion to docosahexaenoic acid in atlantic salmon (Salmo salar L.) hepatocytes: role of altered gene expression. PubMed: 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. PubMed: Sex differences in the inhibition of gamma-tocopherol metabolism by a single dose of dietary sesame oil in healthy subjects. PubMed: Dietary tocotrienol reduces UVB-induced skin damage and sesamin enhances tocotrienol effects in hairless mice. PubMed: Effect of the form of the sesame-based diet on the absorption of lignans. PubMed: Hydroxymatairesinol and sesaminol act differently on tocopherol concentrations in rats. PubMed: Suppression of ochratoxin biosynthesis by naturally occurring alkaloids. PubMed: Quantitative NMR analysis of a sesamin catechol metabolite in human urine. PubMed: Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. PubMed: Assessing exposure to lignans and their metabolites in humans. PubMed: Nondestructive determination of lignans and lignan glycosides in sesame seeds by near infrared reflectance spectroscopy. PubMed: Dietary sesamin and docosahexaenoic and eicosapentaenoic acids synergistically increase the gene expression of enzymes involved in hepatic peroxisomal fatty acid oxidation in rats. PubMed: Antioxidant activity and bioactive compounds of tea seed (Camellia oleifera Abel.) oil. PubMed: Beyond vitamin E supplementation: an alternative strategy to improve vitamin E status. PubMed: Dietary sesamin is converted to enterolactone in humans. PubMed: Consumption of sesame oil muffins decreases the urinary excretion of gamma-tocopherol metabolites in humans. PubMed: Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. PubMed: A benzenoid from the stem of Acanthopanax senticosus. PubMed: Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats. PubMed: Interaction of dietary fat types and sesamin on hepatic fatty acid oxidation in rats. PubMed: Species differences in the physiological activity of dietary lignan (sesamin and episesamin) in affecting hepatic fatty acid metabolism. PubMed: Effects of sesamin and capsaicin on the mRNA expressions of delta6 and delta5 desaturases in rat primary cultured hepatocytes. PubMed: Free radical scavenging behavior of antioxidant compounds of sesame (sesamum indicum L.) in DPPH(*) system. PubMed: Comparative effects of flaxseed and sesame seed on vitamin E and cholesterol levels in rats. PubMed: Dietary sesame lignans decrease lipid peroxidation in rats fed docosahexaenoic acid. PubMed: Dietary (+)-catechin and BHT markedly increase alpha-tocopherol concentrations in rats by a tocopherol-omega-hydroxylase-independent mechanism. PubMed: Novel antioxidative metabolites in rat liver with ingested sesamin. PubMed: Comparative effect of sesamin and episesamin on the activity and gene expression of enzymes in fatty acid oxidation and synthesis in rat liver. PubMed: Dietary sesame seed and its lignans inhibit 2,7,8-trimethyl- 2(2'-carboxyethyl)-6-hydroxychroman excretion into urine of rats fed gamma-tocopherol. PubMed: Dietary manipulations of body fat-reducing potential of conjugated linoleic acid in rats. PubMed: Sesamin, a sesame lignan, decreases fatty acid synthesis in rat liver accompanying the down-regulation of sterol regulatory element binding protein-1. PubMed: Effects of dietary sesame seeds on plasma tocopherol levels. PubMed: Hepatothermic therapy of obesity: rationale and an inventory of resources. PubMed: Effect of sesame seeds rich in sesamin and sesamolin on fatty acid oxidation in rat liver. PubMed: Effects of dietary phenolic compounds on tocopherol, cholesterol, and fatty acids in rats. PubMed: Sesamin and alpha-tocopherol synergistically suppress lipid-peroxide in rats fed a high docosahexaenoic acid diet. PubMed: Sesamin, a sesame lignan, is a potent inducer of hepatic fatty acid oxidation in the rat. PubMed: Dietary defatted sesame flour decreases susceptibility to oxidative stress in hypercholesterolemic rabbits. PubMed: Effect of dietary fats and sesamin on the lipid metabolism and immune function of Sprague-Dawley rats. PubMed: Effects of dietary sesaminol and sesamin on eicosanoid production and immunoglobulin level in rats given ethanol. PubMed: Effects of sesamin and alpha-tocopherol, individually or in combination, on the polyunsaturated fatty acid metabolism, chemical mediator production, and immunoglobulin levels in Sprague-Dawley rats. PubMed: Sesame seed and its lignans produce marked enhancement of vitamin E activity in rats fed a low alpha-tocopherol diet. PubMed: Sesamin (a compound from sesame oil) increases tocopherol levels in rats fed ad libitum. PubMed: Sesame seed lignans and gamma-tocopherol act synergistically to produce vitamin E activity in rats.