{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457630359 | ImageFileL1 = Alpha-Asaron.svg | ImageSizeL1 = 120px | ImageCaptionL1 = α-Asarone | ImageFileR1 = Beta-Asaron.svg | ImageSizeR1 = 120px | ImageCaptionR1 = β-Asarone | IUPACName = 1,2,4-Trimethoxy-5-[(''E'')-prop-1-enyl]benzene (α)<br>1,2,4-Trimethoxy-5-[(''Z'')-prop-1-enyl]benzene (β) | OtherNames =''alpha''-Azaron<br>''cis''-Isoelemicin<br>2,4,5-Trimethoxyphenyl-2-propene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 552532 | ChemSpiderID_Comment= (α) | ChemSpiderID1 = 4445072 | ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1_Comment= (β) | SMILES = O(c1cc(c(OC)cc1OC)/C=C/C)C | SMILES_Comment = (α) | SMILES1 = C/C=C\c1cc(c(cc1OC)OC)OC | SMILES1_Comment = (β) | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RKFAZBXYICVSKP-AATRIKPKSA-N | InChI3_Ref = {{stdinchicite|correct|chemspider}} | InChI3 = 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5- | InChIKey3_Ref = {{stdinchicite|correct|chemspider}} | InChIKey3 = RKFAZBXYICVSKP-WAYWQWQTSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 2883-98-9 | CASNo_Comment = (α) | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1 = 5273-86-9 | CASNo1_Comment = (β) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = DQY9PNE5FK | UNII_Comment = (α) | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = IGA3MH6IUW | UNII1_Comment = (β) | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 333306 | PubChem =636822 | PubChem_Comment = (α) | PubChem1 =5281758 | PubChem1_Comment = (β) }} |Section2={{Chembox Properties | C=12 | H=16 | O=3 | Appearance =Colorless solid | Density = α: 1.028 g/cm<sup>−3</sup> <ref name=spider>[http://www.chemspider.com/Chemical-Structure.552532.html ''Data for α-Asarone at ChemSpider'']</ref> | MeltingPtC = 62 to 63 | MeltingPt_notes = (α) | MeltingPt_ref = <ref name="merck">{{cite encyclopedia | title = Asarone | encyclopedia = The Merck Index | volume = 14th edition | pages = 135 | publisher = Merck Research Laboratories | year = 2006 | isbn = 978-0-911910-00-1}}</ref> | BoilingPtC = 296 | BoilingPt_notes = (α) | BoilingPt_ref = <ref name="merck">{{cite encyclopedia | title = Asarone | encyclopedia = The Merck Index | volume = 14th edition | pages = 135 | publisher = Merck Research Laboratories | year = 2006 | isbn = 978-0-911910-00-1}}</ref> | Solubility =Insoluble | MagSus = −131.4·10<sup>−6</sup> cm<sup>3</sup>/mol }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Asarone''' is chemical compound of the phenylpropanoid class found in certain plants such as ''Acorus'' and ''Asarum''.<ref name="merck"/> There are two isomers, α (or ''trans'') and β (or ''cis'').<ref>Beta asarone has CAS# [https://www.sigmaaldrich.com/US/en/product/aldrich/221074 5273-86-9]</ref> As a volatile fragrance oil, it is used in killing pests and bacteria.<ref>{{cite journal |vauthors=Asha DS, Ganjewala D | year = 2009 | title = Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract | journal = Acta Biol. Szeg. | volume = 53 | issue = 1 | pages = 45–49}}</ref>
== Pharmacology == The main clinical symptom of asarone is prolonged vomiting that sometimes lasted more than 15 hours. Asarone is not metabolized to trimethoxyamphetamine as has been claimed by online vendors.<ref>{{cite journal |vauthors=Björnstad K, Helander A, Hultén P, Beck O | title = Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications| journal = J Anal Toxicol| volume = 33| issue = 9| pages = 604–9| year = 2009| pmid = 20040135| doi = 10.1093/jat/33.9.604| doi-access = free}}</ref>
The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic<ref>{{Cite journal|last1=Cartus|first1=Alexander T.|last2=Stegmüller|first2=Simone|last3=Simson|first3=Nadine|last4=Wahl|first4=Andrea|last5=Neef|first5=Sylvia|last6=Kelm|first6=Harald|last7=Schrenk|first7=Dieter|date=2015-08-26|title=Hepatic Metabolism of Carcinogenic β-Asarone|journal=Chemical Research in Toxicology|volume=28|issue=9|pages=1760–1773|doi=10.1021/acs.chemrestox.5b00223|pmid=26273788|issn=0893-228X}}</ref> and has proposed limits for its concentration in flavorings such as bitters made from ''Acorus calamus'' (sweet flag).<ref>{{cite web | date = 8 January 2002 | title = Opinion of the Scientific Committee on Food on the presence of β-asarone in flavourings and other food ingredients with flavouring properties | publisher = European Commission Scientific Committee on Food | url = http://ec.europa.eu/food/fs/sc/scf/out111_en.pdf}}</ref>
β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in ''Aspergillus niger''.<ref>{{Cite journal|last1=Venkatesan|first1=Ramya|last2=Karuppiah|first2=Prakash Shyam|last3=Arumugam|first3=Gnanamani|last4=Balamuthu|first4=Kadalmani|date=2017-11-10|title=β-Asarone Exhibits Antifungal Activity by Inhibiting Ergosterol Biosynthesis in ''Aspergillus niger'' ATCC 16888|journal=Proceedings of the National Academy of Sciences, India Section B: Biological Sciences|volume=89|language=en|pages=173–184|doi=10.1007/s40011-017-0930-4|s2cid=46005148|issn=0369-8211}}</ref> However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.<ref>{{cite journal | doi = 10.1002/ptr.2650090604 | title = Anthelmintic and pesticidal activity of ''Acorus gramineus'' (Araceae) is associated with phenylpropanoid asarones | year = 1995 | last1 = Perrett | first1 = Sheena | last2 = Whitfield | first2 = Philip J. | journal = Phytotherapy Research | volume = 9 | issue = 6 | pages = 405| s2cid = 84823162 }}</ref>
== See also == * Elemicin * 2,4,5-Trimethoxypropiophenone
== Notes and references == {{reflist}}
Category:Phenylpropenes Category:O-methylated phenylpropanoids Category:Plant toxins