Sesamol

Sesamol
Names
Preferred IUPAC name
2H-1,3-Benzodioxol-5-ol
Other names
1,3-Benzodioxol-5-ol
Benzo[d][1,3]dioxol-5-ol
Sesamol
3,4-Methylenedioxyphenol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.784
KEGG
UNII
  • InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2 Y
    Key: LUSZGTFNYDARNI-UHFFFAOYSA-N Y
  • InChI=1/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
    Key: LUSZGTFNYDARNI-UHFFFAOYAT
  • O1c2ccc(O)cc2OC1
Properties
C7H6O3
Molar mass 138.12 g/mol
Melting point 62 to 65 °C (144 to 149 °F; 335 to 338 K)
Boiling point 121 to 127 °C (250 to 261 °F; 394 to 400 K) at 5 mmHg
Hazards
NFPA 704 (fire diamond)
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Sesamol is a natural organic compound which is a component of sesame seeds and sesame oil, with anti-inflammatory, antioxidant, antidepressant and neuroprotective properties. It is a white crystalline solid that is a derivative of phenol. It is sparingly soluble in water, but miscible with most oils. It can be produced by organic synthesis from heliotropine.

Sesamol has been found to be an antioxidant that may prevent the spoilage of oils. It also may prevent the spoilage of oils by acting as an antifungal. It can be used in the synthesis of paroxetine.

Sesamol's molecular targets and mechanism of action, at least for its antidepressant-like effects, is found to be through the brain nerve growth factor (NGF) and endocannabinoid signalling under the regulatory drive of the CB1 receptors.

Alexander Shulgin used sesamol in his book PiHKAL to make MMDA-2.