Elemicin: Difference between revisions

{{Short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 410138806

| IUPAC_name = 1,2,3-Trimethoxy-5-(prop-2-en-1-yl)benzene

| image = ElemicinSVG.svg

| alt = Skeletal formula of elemicin

| image2 = Elemicin-3D-balls.png

| alt2 = Ball-and-stick model of the elemicin molecule

<!--Clinical data-->| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| dependency_liability = None

| addiction_liability = Low / None

<!--Pharmacokinetic data-->| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion = <!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 487-11-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HSZ191AKAN

| ATC_prefix =

| ATC_suffix =

| PubChem = 10248

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9830

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10451

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 458690

<!--Chemical data-->| C = 12

| H = 16

| O = 3

| smiles = C=CCC1=CC(OC)=C(OC)C(OC)=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BPLQKQKXWHCZSS-UHFFFAOYSA-N

'''Elemicin''' is a [[phenylpropene]], a natural [[organic compound]], and is a constituent of several plant species' [[essential oils]].<ref name='Baser' /><ref name=ChemOfSpices />

==Natural occurrence==

Elemicin is a constituent of the [[oleoresin]] and the essential oil of ''[[Canarium luzonicum]]'' (also referred to as elemi). Elemicin is named after this tree. One study found it to compose 2.4% of the fresh essential oil.<ref name='Baser'>

{{cite journal | vauthors = Villanueva MA, Torres RC, Baser KH, Özek T, Kürkçüoglu M | title = The Composition of Manila Elemi Oil | journal = Flavour and Fragrance Journal | year = 1993 | volume = 8 | pages = 35–37 | doi = 10.1002/ffj.2730080107 }}</ref> Elemicin is also present in the oils of the spices [[nutmeg]] and [[mace (spice)|mace]], with it composing 2.4% and 10.5% of those oils respectively.<ref name=ChemOfSpices>{{cite book| vauthors = Leela N |title=Chemistry of Spices|year=2008|publisher=Biddles Ltd. |location=Calicut, Kerala, India |isbn=9781845934057|pages=165–188 [170] |url=https://books.google.com/books?id=5WY08iuJyawC&q=Chemistry+of+Spices}}</ref> Structurally, elemicin is similar to [[myristicin]], differing only by myristicin's methyl group that joins the two oxygen atoms that make up its dioxymethy moiety, with both constituents being found in nutmeg and mace.

==Isolation==

Elemicin was first isolated from elemi oil using [[vacuum distillation]]. Specifically, the substance was collected between 162-165&nbsp;°C at a reduced pressure of 10 [[torr]].<ref>{{cite journal |title=Constituents of Essential Oils. Elemicin, a High-boiling Constituent of Elemi Oil, and the Displacement of Alkyloxygroups in the Benzene Nucleus by Hydrogen|journal=Journal of the Chemical Society, Abstracts|year=1908|volume=94|issue=A493|pages=557–558|url=https://books.google.com/books?id=JGJFAQAAIAAJ&q=Constituents+of+Essential+Oils.+Elemicin%2C+a+High-boiling+Constituent+of+Elemi+Oil%2C+and+the+Displacement+of+Alkyloxygroups+in+the+Benzene+Nucleus+by+Hydrogen&pg=PA557|doi=10.1039/CA9089400493}}</ref><ref>{{cite journal| vauthors = Semmler F |title=Zur Kenntnis der Bestandteile der ätherischen Öle. (Über das Elemicin, einen hochsiedenden Bestandteil des Elemiöls, und über Ersetzung von Alkyloxy-gruppen am Benzolkern durch Wasserstoff.)|journal=Berichte der Deutschen Chemischen Gesellschaft|date=1908|volume=41|issue=2|pages=1768–1775 |doi=10.1002/cber.19080410240 |url=https://zenodo.org/record/1426299}}</ref>

==Preparation==

Elemicin has been [[Organic synthesis|synthesized]] from [[syringol]] and [[allyl bromide]] using [[Williamson ether synthesis]] and [[Claisen rearrangement]].<ref>{{cite journal| vauthors = Mauthner F |title=Die Synthese des Elemicins und Isoelemicins|journal=Justus Liebigs Annalen der Chemie|year=1918|volume=414|issue=2|pages=250–255|doi=10.1002/jlac.19184140213|url=https://zenodo.org/record/1427645}}</ref><ref>{{cite journal |title=Synthesis of Elemicin and of isoElemicin|journal=Journal of the Chemical Society, Abstracts|year=1918|volume=114|pages=i428|doi=10.1039/CA9181400421}}</ref> The [[electrophilic aromatic substitution]] entering the [[Arene substitution pattern|''para'']]-position was made possible by secondary [[Cope rearrangement]].<ref>{{cite book| vauthors = Thomas L |title=Named Organic Reactions, 2nd Edition|year=2005|publisher=John Wiley & Sons, Ltd.|location=Wolfsburg, Germany|isbn=978-0470010402|pages=58–60 [59]|url=https://books.google.com/books?id=-BEdbO-08WMC&q=Named+Organic+Reactions,+2nd+Edition+2005}}</ref> This is due to syringol's allyl [[aromatic]] [[ether]] being blocked by ethers in both ''ortho''-positions. When blocked the allyl group migrates to the ''para''-position, in this case with yields above 85%.<ref>{{cite book| vauthors = Adams R |title=Organic Reactions| volume = II |year=1944|publisher=John Wiley & Sons, Inc.|location=New York|pages=2–44 [44]|doi=10.1002/0471264180.or002.01 |chapter=The Claisen Rearrangement |isbn=978-0471264187 }}</ref>

==Uses==

Elemicin has been used to synthesize the proto-[[alkaloid]] [[mescaline]].<ref>{{cite journal| vauthors = Hahn G, Wassmuth H |title=Über β-[Oxyphenyl]-äthylamine und ihre Umwandlungen, I. Mitteil.: Synthese des Mezcalins |journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series) |year=1934 |volume=67 |issue=4 |pages=696–708 |doi= 10.1002/cber.19340670430}}</ref>

==Pharmacology==

Raw nutmeg causes [[anticholinergic]]-like effects, which are attributed to elemicin and [[myristicin]].<ref name="pmid15249817">

{{cite journal | vauthors = McKenna A, Nordt SP, Ryan J | title = Acute nutmeg poisoning | journal = European Journal of Emergency Medicine | volume = 11 | issue = 4 | pages = 240–241 | date = August 2004 | pmid = 15249817 | doi = 10.1097/01.mej.0000127649.69328.a5 | s2cid = 21133983 }}</ref><ref>{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines | journal = Psychopharmacology Bulletin | volume = 4 | issue = 3 | pages = 13 | date = December 1967 | pmid = 5615546 | url = http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK | access-date = 2015-09-02 | url-status = dead | format = pdf | archive-url = https://web.archive.org/web/20140420142511/http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK | archive-date = 2014-04-20 }}</ref> Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity.<ref>{{Cite web |title=Elemicin |url=https://www.chemsrc.com/en/cas/487-11-6_954455.html |access-date=2022-10-28 |website=www.chemsrc.com |language=en}}</ref><ref>{{Cite web |title=Elemicin {{!}} Stearoyl-CoA Desaturase (SCD) Inhibitor {{!}} Targetmol |url=https://www.targetmol.com/compound/elemicin |website=targetmol.com}}</ref> Excess consumption of raw nutmeg results in delirium and disorientation.<ref>{{Citation |title=elemicin |url=https://medical-dictionary.thefreedictionary.com/elemicin |work=The Free Dictionary |access-date=2022-10-28}}</ref>

Elemicin's psychoactivity is still a point of research, however some research suggests it may act like an agonist of the [[5-HT2A receptor|5-HT2A receptors]], similar to many psychedelics.<ref>[http://herbpedia.wdfiles.com/local--files/attachments/Elemicin_2014_Journal.pdf Evaluation of 5-HT2A Receptor Agonistic Property of Elemicin]</ref> However, this is controversial as the psychoactive effects of elemicin and plants it is found in, such as nutmeg, seem to cause more [[deliriant]]-like effects than psychedelic ones.<ref>{{cite journal | vauthors = Kelly BD, Gavin BE, Clarke M, Lane A, Larkin C | title = Nutmeg and psychosis | journal = Schizophrenia Research | volume = 60 | issue = 1 | pages = 95–96 | date = March 2003 | pmid = 12505144 | doi = 10.1016/s0920-9964(02)00204-9 | s2cid = 7540364 }}</ref>

== See also ==

* [[Nutmeg oil]]

* [[Myristicin]]

* [[Phenylpropanoid]]

{{Reflist}}

[[Category:O-methylated phenylpropanoids]]

[[Category:Allyl compounds]]

[[Category:O-methylated natural phenols]]