Asarone

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Asarone
Alpha-Asaron.svg
α-Asarone
Beta-Asaron.svg
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
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.018.858
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
-131.4·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 pests and bacteria.[4] The toxicity and carcinogenicity of asarone means that it may be difficult to develop practical anthelmintics and insecticides based on it.[5]

Pharmacology[edit]

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.[6]

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.[7][non-primary source needed]

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).[8]

See also[edit]

Notes and references[edit]

  1. ^ Data for α-Asarone at ChemSpider
  2. ^ a b c "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[dead link]
  4. ^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ "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.