Asarone

Asarone
α-Asarone
β-Asarone
Names
IUPAC names
1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene (α)
1,2,4-Trimethoxy-5-[(Z)-prop-1-enyl]benzene (β)
Other names
alpha-Azaron
cis-Isoelemicin
2,4,5-Trimethoxyphenyl-2-propene
Identifiers
2883-98-9 (α) N
5273-86-9 (β) N
3D model (Jmol) (α): Interactive image
(β): Interactive image
ChEMBL ChEMBL333306 YesY
ChemSpider 552532 (α) YesY
4445072 (β) N
ECHA InfoCard 100.018.858
PubChem 636822 (α)
5281758 (β)
Properties
C12H16O3
Molar mass 208.26 g·mol−1
Appearance Colorless solid
Density α: 1.028 g/cm−3 [1]
Melting point 62 to 63 °C (144 to 145 °F; 335 to 336 K)[2] (α)
Boiling point 296 °C (565 °F; 569 K)[2] (α)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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]

β-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]

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).[9]

See also

Notes and references

  1. ↑ Data for α-Asarone at ChemSpider
  2. 1 2 3 "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 Archived January 7, 2012, at the Wayback Machine.
  4. ↑ Suvarna Shenvi, Vinod; Rajendra Hegde; Anil Kush & 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" (PDF). 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". Acta 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. doi:10.1093/jat/33.9.604. PMID 20040135.
  8. ↑ Geng Y.; Li C.; Liu J.; Xing G.; Zhou L.; Dong M.; Li X.; Niu Y. (2010). "Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats". Biological & Pharmaceutical Bulletin. 33 (5): 836–43. doi:10.1248/bpb.33.836.
  9. ↑ "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.
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