Asarone is chemical compound of the phenylpropanoid class found in certain plants such as Acorus and Asarum.[2] There are two isomers, α (or trans) and β (or cis).[3] As a volatile fragrance oil, it is used in killing pests and bacteria.[4]

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.[5]

The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic[6] and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).[7]

β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger.[8] However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.[9]

See also

Notes and references

  1. ^ Data for α-Asarone at ChemSpider
  2. ^ a b c "Asarone". The Merck Index. Vol. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1.
  3. ^ Beta asarone has CAS# 5273-86-9
  4. ^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49.
  5. ^ Björnstad K, Helander A, Hultén P, Beck O (2009). "Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications". J Anal Toxicol. 33 (9): 604–9. doi:10.1093/jat/33.9.604. PMID 20040135.
  6. ^ Cartus, Alexander T.; Stegmüller, Simone; Simson, Nadine; Wahl, Andrea; Neef, Sylvia; Kelm, Harald; Schrenk, Dieter (2015-08-26). "Hepatic Metabolism of Carcinogenic β-Asarone". Chemical Research in Toxicology. 28 (9): 1760–1773. doi:10.1021/acs.chemrestox.5b00223. ISSN 0893-228X. PMID 26273788.
  7. ^ "Opinion of the Scientific Committee on Food on the presence of β-asarone in flavourings and other food ingredients with flavouring properties" (PDF). European Commission Scientific Committee on Food. 8 January 2002. {{cite journal}}: Cite journal requires |journal= (help)
  8. ^ Venkatesan, Ramya; Karuppiah, Prakash Shyam; Arumugam, Gnanamani; Balamuthu, Kadalmani (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. 89: 173–184. doi:10.1007/s40011-017-0930-4. ISSN 0369-8211. S2CID 46005148.
  9. ^ Perrett, Sheena; Whitfield, Philip J. (1995). "Anthelmintic and pesticidal activity of Acorus gramineus (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research. 9 (6): 405. doi:10.1002/ptr.2650090604. S2CID 84823162.