Sesamol
[CAS# 533-31-3]

Identification

• Classification: Natural product >> Natural phenols
• Name: Sesamol
• Synonyms: 3,4-(Methylenedioxy)phenol; 1,3-Benzodioxol-5-ol; 5-Benzodioxolol
• Molecular Formula: C₇H₆O₃
• Molecular Weight: 138.12
• CAS Registry Number: 533-31-3
• EC Number: 208-561-5
• SMILES: C1OC2=C(O1)C=C(C=C2)O

Properties

• Melting point: 63-65 °C
• Water solubility: slightly soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Serious eye damage	Eye Dam.	1	H318
Carcinogenicity	Carc.	2	H351

Discovery and Applications

Sesamol is a natural organic compound classified as a phenolic antioxidant, chemically known as 3,4-methylenedioxyphenol. It is a white crystalline substance derived primarily from sesame seeds and sesame oil, where it occurs as a minor constituent. The molecular structure of sesamol consists of a benzene ring substituted with a hydroxyl group (–OH) at the 1-position and a methylenedioxy group (–O–CH₂–O–) bridging the 3 and 4 positions of the aromatic ring.

Sesamol was first isolated and identified in the early 20th century during studies aimed at understanding the antioxidative properties of sesame oil. The compound is a product of the thermal degradation and oxidation of lignans naturally present in sesame seeds, such as sesamin and sesamolin, during oil extraction or heating processes. Its discovery contributed to the elucidation of sesame oil’s stability and resistance to rancidity compared to other vegetable oils.

The primary application of sesamol lies in its antioxidant capacity. It effectively scavenges free radicals and inhibits lipid peroxidation, making it valuable both as a natural preservative and as a bioactive compound with potential health benefits. In the food industry, sesamol is used to enhance the shelf life of oils and fat-containing products by preventing oxidative spoilage. Its antioxidant properties are attributed to the phenolic hydroxyl group and the methylenedioxy substituent, which stabilize the compound’s radical form after donating hydrogen atoms.

Beyond food preservation, sesamol has been investigated for pharmacological activities, including anti-inflammatory, anticancer, neuroprotective, and cardioprotective effects. These biological activities have been demonstrated in various in vitro and in vivo studies, where sesamol modulates signaling pathways associated with oxidative stress, inflammation, and apoptosis. For example, its ability to reduce reactive oxygen species (ROS) levels and inhibit pro-inflammatory cytokines contributes to its potential therapeutic roles.

Sesamol is also utilized in cosmetic formulations due to its photoprotective and skin-soothing properties. It can protect skin cells from ultraviolet (UV)-induced damage by neutralizing free radicals generated by UV exposure. This feature has led to its inclusion in sunscreens, anti-aging products, and formulations aimed at reducing skin inflammation.

In analytical chemistry, sesamol is identified and quantified using techniques such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and ultraviolet-visible (UV-Vis) spectroscopy. Its characteristic absorption maxima in the UV region allow for sensitive detection. Nuclear magnetic resonance (NMR) spectroscopy confirms the presence of the methylenedioxy and hydroxyl functional groups, supporting structural elucidation.

Sesamol is a solid at room temperature with moderate solubility in water and good solubility in organic solvents such as ethanol, methanol, and acetone. It is relatively stable under normal storage conditions but can degrade upon prolonged exposure to strong acids, bases, or high temperatures.

In summary, sesamol is a naturally occurring phenolic antioxidant found in sesame oil, known for its potent free radical scavenging activity. It has important applications in food preservation, cosmetics, and emerging pharmacological fields due to its antioxidative, anti-inflammatory, and photoprotective properties. Its discovery helped explain the notable oxidative stability of sesame oil and continues to inspire research into natural antioxidants.

References

2019. Synthesis and insecticidal activity of sulfonate derivatives of sesamol against Mythimna separata in vivo. Journal of Asian Natural Products Research, 21(5).
DOI: 10.1080/10286020.2019.1616289

2017. Sesamol ameliorates diet-induced obesity in C57BL/6J mice and suppresses adipogenesis in 3T3-L1 cells via regulating mitochondria-lipid metabolism. Molecular Nutrition & Food Research, 61(2).
DOI: 10.1002/mnfr.201600717

2003. The Sesame Seed Oil Constituent, Sesamol, Induces Growth Arrest and Apoptosis of Cancer and Cardiovascular Cells. Annals of the New York Academy of Sciences, 1010.
DOI: 10.1196/annals.1299.068