Wikipedia

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.

Sesamol[1]
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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2 checkY
    Key: LUSZGTFNYDARNI-UHFFFAOYSA-N checkY
  • 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)
NFPA 704 four-colored diamondHealth 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).
checkY verify (what is checkY☒N ?)

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

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References

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  1. ^ Sesamol Archived 2010-01-14 at the Wayback Machine at Chemicalland21.com
  2. ^ Kim JY, Choi DS, Jung MY (May 2003). "Antiphoto-oxidative activity of sesamol in methylene blue- and chlorophyll-sensitized photo-oxidation of oil". Journal of Agricultural and Food Chemistry. 51 (11): 3460–5. doi:10.1021/jf026056p. PMID 12744684.
  3. ^ Ohsawa T (1991). "Sesamol and sesaminol as antioxidants". New Food Industry. 33 (6): 1–5.
  4. ^ Wynn JP, Kendrick A, Ratledge C (June 1997). "Sesamol as an inhibitor of growth and lipid metabolism in Mucor circinelloides via its action on malic enzyme". Lipids. 32 (6): 605–10. doi:10.1007/s11745-997-0077-1. PMID 9208389. S2CID 4015004.
  5. ^ Li JJ (2004). Contemporary drug synthesis. Hoboken, N.J.: Wiley. ISBN 978-0-471-21480-9.
  6. ^ Hassanzadeh P, Hassanzadeh A (October 2013). "Implication of NGF and endocannabinoid signaling in the mechanism of action of sesamol: a multi-target natural compound with therapeutic potential". Psychopharmacology. 229 (4): 571–578. doi:10.1007/s00213-013-3111-z. PMID 23624775. S2CID 253748878.
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