U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H6O3
Molecular Weight 138.1207
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3,4-METHYLENEDIOXYPHENOL

SMILES

OC1=CC=C2OCOC2=C1

InChI

InChIKey=LUSZGTFNYDARNI-UHFFFAOYSA-N
InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2

HIDE SMILES / InChI

Molecular Formula C7H6O3
Molecular Weight 138.1207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Protection of cellular DNA and membrane from γ-radiation-induced damages and enhancement in DNA repair by sesamol.
2010-12
Sesamol inhibits UVB-induced ROS generation and subsequent oxidative damage in cultured human skin dermal fibroblasts.
2010-12
Potent antiplatelet activity of sesamol in an in vitro and in vivo model: pivotal roles of cyclic AMP and p38 mitogen-activated protein kinase.
2010-12
Biodetoxification of toxins generated from lignocellulose pretreatment using a newly isolated fungus, Amorphotheca resinae ZN1, and the consequent ethanol fermentation.
2010-11-22
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.
2010-11
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.
2010-11
Sesamol suppresses neuro-inflammatory cascade in experimental model of diabetic neuropathy.
2010-10
Sesamol down-regulates the lipopolysaccharide-induced inflammatory response by inhibiting nuclear factor-kappa B activation.
2010-10
Apoptosis-inducing action of two products from oxidation of sesamol, an antioxidative constituent of sesame oil: a possible cytotoxicity of oxidized antioxidant.
2010-09
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.
2010-09
Influence of chemical structures of benzodioxole-based coinitiators on the properties of the unfilled dental resin.
2010-08
Protective effect of sesamol on the pulmonary inflammatory response and lung injury in endotoxemic rats.
2010-07
Protective effect of sesamol against 3-nitropropionic acid-induced cognitive dysfunction and altered glutathione redox balance in rats.
2010-07
Evaluation of the effects of selected phytochemicals on quality indices and sensorial properties of raw and cooked pork stored in different packaging systems.
2010-06
Comparing antioxidant effectiveness of natural and synthetic free radical scavengers in thermally-oxidized lard using DPPH method.
2010-04
Effect of lutein, sesamol, ellagic acid and olive leaf extract on the quality and shelf-life stability of packaged raw minced beef patties.
2010-04
Low-cost fluorimetric determination of radicals based on fluorogenic dimerization of the natural phenol sesamol.
2010-02-15
Efficacy of vitamin C and ethanolic extract of Sesamum indicum in promoting fertility in male Wistar rats.
2010-01
The Ayurvedic drug, Ksheerabala, ameliorates quinolinic acid-induced oxidative stress in rat brain.
2010-01
Glucose sensing neurons in the ventromedial hypothalamus.
2010
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.
2010
Protective effect of sesamol against myocardial infarction caused by isoproterenol in Wistar rats.
2010
Studies on natural p-terphenyls: total syntheses of vialinin A and terrestrin B.
2010
The non-peptide chemical 3,4-methylenedioxyphenol blocked lipopolysaccharide (LPS) from binding to LPS-binding protein and inhibited pro-inflammatory cytokines.
2009-12
Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-alpha production.
2009-11-05
A comparative evaluation of medicated oils prepared using ayurvedic and modified processes.
2009-11
A new cross-coupling-based synthesis of carpanone.
2009-10-01
The effect of lutein, sesamol, ellagic acid and olive leaf extract on lipid oxidation and oxymyoglobin oxidation in bovine and porcine muscle model systems.
2009-10
Antioxidant potential of sesamol and its role on radiation-induced DNA damage in whole-body irradiated Swiss albino mice.
2009-09
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.
2009-09
Improving the stability and antioxidant properties of sesame oil: water-soluble spray-dried emulsions from new transesterified phenolic derivatives.
2009-08-26
Fat content influences the color, lipid oxidation, and volatiles of irradiated ground beef.
2009-08
Attenuation of renoinflammatory cascade in experimental model of diabetic nephropathy by sesamol.
2009-07-22
Assessment of the medicinal potentials of the methanol extracts of the leaves and stems of Buddleja saligna.
2009-07-06
Sesamol: an efficient antioxidant with potential therapeutic benefits.
2009-07
Administration of sesamol improved blood-brain barrier function in streptozotocin-induced diabetic rats.
2009-07
Effect of infrared heating on the formation of sesamol and quality of defatted flours from Sesamum indicum L.
2009-06-04
Cytometric analysis of cytotoxicity of polyphenols and related phenolics to rat thymocytes: potent cytotoxicity of resveratrol to normal cells.
2009-06
A previously uncultured, paper mill Propionibacterium is able to degrade O-aryl alkyl ethers and various aromatic hydrocarbons.
2009-06
Development of a novel fluorometric assay for nitric oxide utilizing sesamol and its application to analysis of nitric oxide-releasing drugs.
2009-05-28
Storage stability of sunflower oil with added natural antioxidant concentrate from sesame seed oil.
2009
Antiproliferative effects of honey and of its polyphenols: a review.
2009
Sesamol attenuate 3-nitropropionic acid-induced Huntington-like behavioral, biochemical, and cellular alterations in rats.
2009
Effects of aging time and natural antioxidants on the color, lipid oxidation and volatiles of irradiated ground beef.
2008-11
Ethnopharmacology.
2008-10
Sesamin modulates tyrosine hydroxylase, superoxide dismutase, catalase, inducible NO synthase and interleukin-6 expression in dopaminergic cells under MPP+-induced oxidative stress.
2008-08-21
3,4-Dihydroxy-phenyl 3,4,5-trimethoxy-benzoate.
2007-12-06
Synergistic antimicrobial activities of phytoestrogens in crude extracts of two sesame species against some common pathogenic microorganisms.
2007-06-10
Photoprotective effect of sesamol on UVB-radiation induced oxidative stress in human blood lymphocytes in vitro.
2005-07
Use of antioxidants to reduce lipid oxidation and off-odor volatiles of irradiated pork homogenates and patties.
2003-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:18:25 GMT 2025
Edited
by admin
on Mon Mar 31 19:18:25 GMT 2025
Record UNII
94IEA0NV89
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,3-BENZODIOXOL-5-OL
Preferred Name English
3,4-METHYLENEDIOXYPHENOL
INCI  
INCI  
Official Name English
PHENOL, 3,4-(METHYLENEDIOXY)-
Systematic Name English
3,4-(METHYLENEDIOXY)PHENOL
Systematic Name English
4-HYDROXY-1,2-METHYLENEDIOXYBENZENE
Systematic Name English
ORISTAR MDP
Common Name English
NSC-59256
Code English
BENZODIOXOL-5-OL
Systematic Name English
5-HYDROXY-1,3-BENZODIOXOLE
Systematic Name English
SESAMOL
Common Name English
Code System Code Type Description
WIKIPEDIA
SESAMOL
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-561-5
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
MESH
C025583
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
PUBCHEM
68289
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID9021267
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
CAS
533-31-3
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
FDA UNII
94IEA0NV89
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
NSC
59256
Created by admin on Mon Mar 31 19:18:25 GMT 2025 , Edited by admin on Mon Mar 31 19:18:25 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Natural antioxidant found in cultivated sesame oil.
Related Record Type Details
PARENT -> IMPURITY