asarone
{{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)
1,2,4-Trimethoxy-5-[(Z)-prop-1-enyl]benzene (β)
| OtherNames =alpha-Azaron
cis-Isoelemicin
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−3 [http://www.chemspider.com/Chemical-Structure.552532.html Data for α-Asarone at ChemSpider]
| MeltingPtC = 62 to 63
| MeltingPt_notes = (α)
| MeltingPt_ref = {{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}}
| BoilingPtC = 296
| BoilingPt_notes = (α)
| BoilingPt_ref = {{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}}
| Solubility =Insoluble
| MagSus = −131.4·10−6 cm3/mol
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Asarone is chemical compound of the phenylpropanoid class found in certain plants such as Acorus and Asarum. There are two isomers, α (or trans) and β (or cis).Beta asarone has CAS# [https://www.sigmaaldrich.com/US/en/product/aldrich/221074 5273-86-9] As a volatile fragrance oil, it is used in killing pests and bacteria.{{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}}
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.{{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}}
The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic{{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}} and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).{{cite journal | 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}}
β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger.{{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}} However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.{{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 }}