Sesamol

Names

[ CAS No. ]:
533-31-3

[ Name ]:
Sesamol

[Synonym ]:
5-Benzodioxolol
MFCD00005827
5-Hydroxy-1,3-benzodioxole
EINECS 208-561-5
Phenol, 3,4- (methylenedioxy)-
Sesamol
4,5-methylenedioxyphenol
3,4-Methylenedioxyphenol
1-hydroxy-3,4-methylenedioxybenzene
4-hydroxy-1,2-methylenedioxy-benzene
5-hydroxy-1,3-benzodioxolane
3,4-(Methylenedioxy)phenol
Methylene ether of oxyhydroquinone
1,3-benzodioxol-5-ol

Biological Activity

[Description]:

Sesamol is a constituent of sesame oil. Sesamol shows a free radical scavenging activity. Sesamol shows an IC50=5.95±0.56 μg/mL in the DPPH assay. Anti-oxidant activities[1]. Anticancer activities[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Phenols

[In Vitro]

Sesamol has also been shown to be a classical inhibitor of lipid peroxidation[1]. Sesamol (0-1 mM) efficiently induces the apoptosis of human liver hepatocellular carcinoma (HepG2) cells. Sesamol suppresses cell proliferation and induces intrinsic and extrinsic apoptosis in HepG2 cells. Sesamol treatment elicites mitochondrial dysfunction by inducing a loss of mitochondrial membrane potential. Sesamol inhibits mitophagy and autophagy through impeding the PI3K Class III/Belin-1 pathway. Sesamol decreases the expression of anti-apoptotic protein Bcl-2, but shows no effect on the expression of apoptotic signal Bax. Sesamol improves the protein expression of Fas/FasL, and activates tBid and caspase-8 which are all involved in the extrinsic apoptosis pathway[2].

[In Vivo]

Sesamol treatment for 35 days does not significantly impact body weight, although the tumor volume is dramatically inhibited (40.56% size inhibitory rate with Sesamol at 200 mg/kg compared to the control group). However, a lower dose (100 mg/kg Sesamol) only has significant anti-tumor growth effect up to 27 days after the first treatment. The Bcl-2/Bax ratio in tumor tissues is also decreased. Moreover, in the Sesamol treatment group, levels of the cell proliferation marker Ki76 are down-regulated, and levels of the cell apoptosis marker cleaved-caspase 3 are increased when compared to control. The expression of LC3 protein is remarkably decreased by Sesamol in a dose-dependent manner[2]

[References]

[1]. Kapadia GJ, et al. Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barrvirus early antigen activation assay and the mouse skin two-stage carcinogenesis. Pharmacol Res. 2002 Jun;45(6):499-505.

[2]. Liu Z, et al. Sesamol Induces Human Hepatocellular Carcinoma Cells Apoptosis by Impairing MitochondrialFunction and Suppressing Autophagy. Sci Rep. 2017 Apr 4;7:45728.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
274.0±29.0 °C at 760 mmHg

[ Melting Point ]:
62-65 °C(lit.)

[ Molecular Formula ]:
C₇H₆O₃

[ Molecular Weight ]:
138.121

[ Flash Point ]:
119.5±24.3 °C

[ Exact Mass ]:
138.031693

[ PSA ]:
38.69000

[ LogP ]:
1.52

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.609

[ Storage condition ]:
−20°C

[ Water Solubility ]:
slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SM0890000

CHEMICAL NAME :: Phenol, 3,4-(methylenedioxy)-

CAS REGISTRY NUMBER :: 533-31-3

BEILSTEIN REFERENCE NO. :: 0127405

LAST UPDATED :: 199709

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C7-H6-O3

MOLECULAR WEIGHT :: 138.13

WISWESSER LINE NOTATION :: T56 BO DO CHJ GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 874 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1092 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1612 gm/kg/96W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1092 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors

REFERENCE :: JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
SM0890000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator.

Photochem. Photobiol. Sci. 12(2) , 323-9, (2013)

A benzodioxole derivative, 4-(2-(benzodioxol-5-yloxy)ethoxy)benzophenone (BPC2BDO), based on 4-hydroxybenzophenone and sesamol was synthesized, and used as a one-component Type II photoinitiator. The ...

Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles.

Molecules 17(5) , 5126-38, (2012)

Antioxidant activity of a number of small (low molecular weight) natural compounds found in spices, condiments or drugs (gallic acid, sesamol, eugenol, thymol, carvacrol, vanillin, salicylaldehyde, li...

The interaction of sesamol with DNA and cytotoxicity, apoptosis, and localization in HepG2 cells.

Food Chem. 141(1) , 289-96, (2013)

Sesamol, a nutritional antioxidant phenolic compound present in sesame seed, has a potential therapeutic molecule effect against cancers. In this study, the interaction between sesamol and DNA was inv...

Related Compounds

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