View source for Sesamol

{{About|the component of sesame oil|the drug sold as Sesamol|Flucloxacillin}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 464389525
| Name = Sesamol
| Reference =<ref>[http://www.chemicalland21.com/lifescience/phar/3,4-METHYLENEDIOXYPHENOL.htm Sesamol] {{webarchive|url=https://web.archive.org/web/20100114222133/http://www.chemicalland21.com/lifescience/phar/3,4-METHYLENEDIOXYPHENOL.htm |date=2010-01-14 }} at Chemicalland21.com</ref>
| ImageFile = Sesamol.png
| ImageName = Chemical structure of sesamol
| PIN = 2''H''-1,3-Benzodioxol-5-ol
| OtherNames = 1,3-Benzodioxol-5-ol<br />Benzo[''d''][1,3]dioxol-5-ol<br />Sesamol<br />3,4-Methylenedioxyphenol
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61586
| PubChem = 68289
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10832
| InChI = 1/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
| InChIKey = LUSZGTFNYDARNI-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LUSZGTFNYDARNI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 533-31-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 94IEA0NV89
| SMILES = O1c2ccc(O)cc2OC1
}}
|Section2={{Chembox Properties
| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>3</sub>
| MolarMass = 138.12 g/mol
| MeltingPtC = 62 to 65
| MeltingPt_notes =
| BoilingPtC = 121 to 127
| BoilingPt_notes = at 5 mmHg
}}
|Section7={{Chembox Hazards
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
}}
}}
'''Sesamol''' is a natural [[organic compound]] which is a component of [[sesame seeds]] and [[sesame oil]], with anti-[[Inflammation|inflammatory]], [[antioxidant]], [[antidepressant]] and [[Neuroprotection|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.<ref name="pmid12744684">{{cite journal | vauthors = Kim JY, Choi DS, Jung MY | title = Antiphoto-oxidative activity of sesamol in methylene blue- and chlorophyll-sensitized photo-oxidation of oil | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 11 | pages = 3460–5 | date = May 2003 | pmid = 12744684 | doi = 10.1021/jf026056p }}</ref><ref>{{cite journal | vauthors = Ohsawa T | title = Sesamol and sesaminol as antioxidants. | journal = New Food Industry | date = 1991 | volume = 33 | issue = 6 | pages = 1–5 }}</ref>  It also may prevent the spoilage of oils by acting as an [[antifungal]].<ref name="pmid9208389">{{cite journal | vauthors = Wynn JP, Kendrick A, Ratledge C | title = Sesamol as an inhibitor of growth and lipid metabolism in Mucor circinelloides via its action on malic enzyme | journal = Lipids | volume = 32 | issue = 6 | pages = 605–10 | date = June 1997 | pmid = 9208389 | doi = 10.1007/s11745-997-0077-1 | s2cid = 4015004 }}</ref> It can be used in the synthesis of [[paroxetine]].<ref>{{cite book| vauthors = Li JJ |title=Contemporary drug synthesis|date=2004|publisher=Wiley|location=Hoboken, N.J.|isbn=978-0-471-21480-9}}</ref>{{rp|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 system|endocannabinoid signalling]] under the regulatory drive of the [[Cannabinoid receptor type 1|CB1]] receptors.<ref>{{cite journal | vauthors = Hassanzadeh P, Hassanzadeh A | title = Implication of NGF and endocannabinoid signaling in the mechanism of action of sesamol: a multi-target natural compound with therapeutic potential | journal = Psychopharmacology | volume = 229 | issue = 4 | pages = 571–578 | date = October 2013 | pmid = 23624775 | doi = 10.1007/s00213-013-3111-z | s2cid = 253748878 }}</ref>
[[Alexander Shulgin]] used sesamol in his book [[PiHKAL]] to make [[MMDA-2]].
== See also ==
* [[Sesamin]] and [[sesamolin]], two lignans found in sesame oil
== References ==
{{reflist}}
[[Category:Natural phenols]]
[[Category:Phenol antioxidants]]
[[Category:Benzodioxoles]]
[[Category:Sesame]]