Asarone

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α-Asarone
IUPAC name

1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene

Other names

alpha-Azaron
cis-Isoelemicin
2,4,5-Trimethoxyphenyl-2-propene

Identifiers
CAS number 2883-98-9 N
PubChem 636822
ChemSpider 552532 YesY
ChEMBL CHEMBL333306 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C12H16O3
Molar mass 208.254 g mol−1
Appearance colorless solid substance
Density 1.028 g/cm−3 [1]
Melting point 62-63 °C [2]
Boiling point 296 °C [2]
Solubility in water insoluble
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Asarone, which includes alpha (trans) and beta[3] (cis) types, is an ether found in certain plants such as acorus and asarum.[2] As a volatile fragrance oil, it is used in killing plant fungal[4] pests and bacteria.[5] The toxicity and carcinogenicity of asarone means that it may be difficult to develop practical anthelmintics and insecticides based on it.[6]

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.[7] Beta-asarone may be a potential candidate for development as a therapeutic agent to manage cognitive impairment associated with conditions such as Alzheimer's disease.[8]

See also

Notes and references

  1. ↑ Data for α-Asarone at ChemSpider
  2. ↑ 2.0 2.1 2.2 "Asarone". The Merck Index. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1. 
  3. ↑ Beta asarone has CAS# 5273-86-9
  4. ↑ Suvarna Shenvi, Vinod, Rajendra Hegde, Anil Kush and G. Chandrasekara Reddy (2011). "A unique water soluble formulation of β-asarone from sweet flag (Acorus calamus L.) and its in vitro activity against some fungal plant pathogens". Journal of Medicinal Plants Research 5 (20): 5132–5137. 
  5. ↑ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Act. Biol. Szeg. 53 (1): 45–49. 
  6. ↑ Perrett, Sheena; Whitfield, Philip J. (1995). "Anthelmintic and pesticidal activity ofAcorus gramineus (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research 9 (6): 405. doi:10.1002/ptr.2650090604. 
  7. ↑ 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. PMID 20040135. 
  8. ↑ Geng Y. Li C. Liu J. Xing G. Zhou L. Dong M. Li X. Niu Y.Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats. Biological & Pharmaceutical Bulletin. 33(5):836-43, 2010.
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