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]

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
CAS Number	533-31-3 Y
3D model (JSmol)	Interactive image
ChemSpider	61586 Y
ECHA InfoCard	100.007.784
KEGG	C10832 Y
PubChem CID	68289
UNII	94IEA0NV89 Y
CompTox Dashboard (EPA)	DTXSID9021267
InChI 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
SMILES O1c2ccc(O)cc2OC1
Properties
Chemical formula	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] 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

• Sesamin and sesamolin, two lignans found in sesame oil

References

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.