Sesamol

{{About|the component of sesame oil|the drug sold as Sesamol|Flucloxacillin}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 464389525

| Name = Sesamol

| Reference =[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

| ImageFile = Sesamol.png

| ImageName = Chemical structure of sesamol

| PIN = 2H-1,3-Benzodioxol-5-ol

| OtherNames = 1,3-Benzodioxol-5-ol
Benzo[d][1,3]dioxol-5-ol
Sesamol
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 = C₇H₆O₃

| 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-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 has been found to be an antioxidant that may prevent the spoilage of oils.{{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 }}{{cite journal | vauthors = Ohsawa T | title = Sesamol and sesaminol as antioxidants. | journal = New Food Industry | date = 1991 | volume = 33 | issue = 6 | pages = 1–5 }} It also may prevent the spoilage of oils by acting as an antifungal.{{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 }} It can be used in the synthesis of paroxetine.{{cite book| vauthors = Li JJ |title=Contemporary drug synthesis|date=2004|publisher=Wiley|location=Hoboken, N.J.|isbn=978-0-471-21480-9}}{{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 signalling under the regulatory drive of the CB1 receptors.{{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 }}

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