SESAMOL

PRODUCT IDENTIFICATION
CAS NO. 533-31-3

SESAMOL

EINECS NO. 208-561-5
FORMULA C7H6O3
MOL WT. 138.12

H.S. CODE

  

TOXICITY

  
SYNONYMS 1,3-Benzodioxol-5-ol; 3,4-Methylenedioxyphenol;
3,4-(Methylenedioxy)Phenol; oxyhydroquinone, Methylene ether; 5-Hydroxy-1,3-benzodioxole; Methylene ether of oxyhydroquinone;
SMILES

 

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE white to off-white crystalline powder
MELTING POINT 62 - 65 C
BOILING POINT

 

SPECIFIC GRAVITY

 

SOLUBILITY IN WATER slightly soluble

SOLVENT SOLUBILITY

  
pH  
VAPOR DENSITY

 

REFRACTIVE INDEX

  
AUTOIGNITION

 

NFPA RATINGS Health: 1; Flammability: 1; Reactivity: 0
FLASH POINT

 

STABILITY

Stable under ordinary conditions

GENERAL DESCRIPTION  APPLICATIONS
Effects of lignan compounds (sesamol, sesamin, and sesamolin) extracted from roasted sesame oil on the autoxidation at 60กษ for 7 days and thermal oxidation at 180กษ for 10 hr of sunflower oil were studied by determining conjugated dienoic acid (CDA) contents, p-anisidine values (PAV), and fatty acid composition. Contents of lignan compounds during the oxidations were also monitored. a-Tocopherol was used as a reference antioxidant. Addition of lignan compounds decreased CDA contents and PAY of the oils during oxidation at 60กษ or heating at 180กษ, which indicated that sesame oil lignans lowered the autoxidation and thermal oxidation of sunflower oil. Sesamol was the most effective in decreasing CDA formation and hydroperoxide decomposition in the auto a- and thermo-oxidation of oil, and its antioxidant activity was significantly higher than that of a-tocopherol. Sesamol, sesamin, and sesamolin added to sunflower oil were degraded during the oxidations of oils, with the fastest degradation of sesamol. Degradation of sesamin and sesamolin during the oxidations of the oil were lower than that of -tocopherol. The results strongly indicate that the oxidative stability of sunflower oil can be improved by the addition of sesamol, sesamin, or sesamolin extracted from roasted sesame oil.( http://www.earticle.net/)

Sesamol, which is derived from sesame seed lignans, is reportedly an antioxidant. Nitric oxide (NO), the most important vascular relaxing factor, is regulated in the endothelium. In addition, NO is involved in protecting endothelium and has antiatherosclerotic and antithrombotic activities. The endothelium produces NO through the regulation of both endothelial NO synthase (eNOS) expression and activity in endothelial cells. This study sought to investigate the effect of sesamol on NO released from human umbilical vein endothelial cells (HUVEC) and to examine the expression and activity of eNOS. Sesamol induced NO release from endothelial cells in a dose-dependent manner (from 1 to 10 microM), as measured 24 h after treatment; the expression of the eNOS gene at both transcription and translation levels; and NOS activity in endothelial cells. The content of cGMP was also increased by sesamol through NO signaling. The transcription of eNOS induced by sesamol was confirmed through the activation of PI-3 kinase-Akt (protein kinase B) signaling. The results demonstrate that sesamol induces NOS signaling pathways in HUVEC and suggest a role for sesamol in cardiovascular reactivity in vivo.(http://www.ncbi.nlm.nih.gov/)

Sesamin and sesamolin, with two methylenedioxy bridges have potentially 4 functional OH groups, and scavenged ROS in cell-free condition better than sesamol with 2 OH groups. This suggests that the higher inhibition of LPS-induced NO production by sesamin and sesamolin may be due to the difference in numbers of functional OH group. A watersoluble form of sesamol, 1,2,4-benzenetriol, has a similar potency in inhibiting LPS-induced NO production (our unpublished observation). The methylenedioxy bridge of sesamin and sesamolin, is formed by a redox reaction of cytochrome P450 in the presence of O2 and NADPH. Sesamin is metabolized in the liver and converted to an antioxidative form that inhibits superoxide production in aortic endothelium. The metabolized forms of sesamin show stronger scavenging activity than sesamin against ROS in O2- ,.OH, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) and TBARS assay. However, the free radical scavenging power of sesame crude extract by the DPPH. assay shows the order: sesamin> sesamolin> sesaminol triglucoside>sesaminol diglucoside. Using DPPH. kinetic model to study the free radical scavenging capacity, the second-order rate constant k2 values of the sesame antioxidants are calculated for the quenching reaction with DPPH. radical. The k2 values are in the order sesamol>sesamol dimmer>sesamin> sesamolin> sesaminol triglucoside>sesaminol diglucoside (http://www.bentham.org/)

Sesamol, can be naturally obtained from sesame seed (Sesamum indicum L.) has been reported to have antioxidant property which protect the body from damage from free radicals. It is a white crystalline solid sparingly soluble in water, but miscible with most oils. It also may inhibit the growth of fungi and yeasts in oils. Sesamol derivatives prepared with nicotinic acid and clofibric acid are expected to have synergistic hypolipidemic agents. Sesamol is used in the synthesis of anticancer drugs and antidepressants (Paroxetine).
SALES SPECIFICATION

APPEARANCE

 white to off-white crystalline powder

ASSAY

98.0% min
MELTING POINT 62 - 65 C

LOSS ON DRYING

0.5% max

HEAVY METAL

20ppm max
TRANSPORTATION
PACKING

5kgs in can

HAZARD CLASS Not regulated
UN NO.  
OTHER INFORMATION
Hazard Symbols: n/a, Risk Phrases: n/a, Safety Phrases: 24/25-28A-37-45