Asarone

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title: "Asarone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["phenylpropenes", "o-methylated-phenylpropanoids", "plant-toxins"] topic_path: "general/phenylpropenes" source: "https://en.wikipedia.org/wiki/Asarone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | ChemSpiderID = 552532 | ChemSpiderID_Comment= (α) | ChemSpiderID1 = 4445072 | ChemSpiderID1_Ref = | 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 = | 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 = | StdInChIKey = RKFAZBXYICVSKP-AATRIKPKSA-N | InChI3_Ref = | 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 = | InChIKey3 = RKFAZBXYICVSKP-WAYWQWQTSA-N | CASNo_Ref = | CASNo = 2883-98-9 | CASNo_Comment = (α) | CASNo1_Ref = | CASNo1 = 5273-86-9 | CASNo1_Comment = (β) | UNII_Ref = | UNII = DQY9PNE5FK | UNII_Comment = (α) | UNII1_Ref = | UNII1 = IGA3MH6IUW | UNII1_Comment = (β) | ChEMBL_Ref = | 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 | 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). As a volatile fragrance oil, it is used in killing pests and bacteria.

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.

The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).

β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger. However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.

References

  1. [http://www.chemspider.com/Chemical-Structure.552532.html ''Data for α-Asarone at ChemSpider'']
  2. Beta asarone has CAS# [https://www.sigmaaldrich.com/US/en/product/aldrich/221074 5273-86-9]
  3. (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg..
  4. (2009). "Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications". J Anal Toxicol.
  5. (2015-08-26). "Hepatic Metabolism of Carcinogenic β-Asarone". Chemical Research in Toxicology.
  6. (8 January 2002). "Opinion of the Scientific Committee on Food on the presence of β-asarone in flavourings and other food ingredients with flavouring properties". European Commission Scientific Committee on Food.
  7. (2017-11-10). "β-Asarone Exhibits Antifungal Activity by Inhibiting Ergosterol Biosynthesis in ''Aspergillus niger'' ATCC 16888". Proceedings of the National Academy of Sciences, India Section B: Biological Sciences.
  8. (1995). "Anthelmintic and pesticidal activity of ''Acorus gramineus'' (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research.

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phenylpropeneso-methylated-phenylpropanoidsplant-toxins