Sesamol

Sesamol is a natural organic compound which is a component of sesame seeds and sesame oil. 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.

This article is about the component of sesame oil. For the drug sold as Sesamol, see Flucloxacillin.
Sesamol[1]
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 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]

Sesame oil is used in Ayurvedic Medicine.[5]

It can be used in the synthesis of paroxetine.[6]: 138–141 

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

See also

References
  1. Sesamol Archived 2010-01-14 at the Wayback Machine at Chemicalland21.com
  2. Joo Yeon Kim, Dong Seong Choi and Mun Yhung Jung "Antiphoto-oxidative Activity of Sesamol in Methylene Blue- and Chlorophyll-Sensitized Photo-oxidation of Oil" J. Agric. Food Chem., 51 (11), 3460 -3465, 2003.
  3. Ohsawa, Toshiko. "Sesamol and sesaminol as antioxidants." New Food Industry (1991), 33(6), 1-5.
  4. Wynn, James P.; Kendrick, Andrew; Ratledge, Colin. "Sesamol as an inhibitor of growth and lipid metabolism in Mucor circinelloides via its action on malic enzyme." Lipids (1997), 32(6), 605-610.
  5. "A Closer Look at Ayurvedic Medicine". Focus on Complementary and Alternative Medicine. Bethesda, Maryland: National Center for Complementary and Alternative Medicine (NCCAM), US National Institutes of Health (NIH). 12 (4). Fall 2005 – Winter 2006. Archived from the original on 2006-12-09.
  6. Li, Jie Jack (2004). Contemporary drug synthesis. Hoboken, N.J.: Wiley. ISBN 978-0-471-21480-9.
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