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Sesamol

Chemical compound From Wikipedia, the free encyclopedia

Sesamol
This article is about the component of sesame oil. For the drug sold as Sesamol, see Flucloxacillin.

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.

Quick Facts Names, Identifiers ...
Sesamol[1]
Thumb
Chemical structure of 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)
ThumbHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sesamol has been found to be an antioxidant that may prevent the spoilage of oils.[2][3] It also may prevent the spoilage of oils by acting as an antifungal.[4] It can be used in the synthesis of paroxetine.[5]: 138–141 

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.[6]

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

See also

References

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