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Names | |||
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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 (JSmol)
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ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.018.858 | ||
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |||
C12H16O3 | |||
Molar mass | 208.257 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).
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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][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).[9]
See also
Notes and references
- ^ Data for α-Asarone at ChemSpider
- ^ a b c "Asarone". The Merck Index. Vol. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1.
- ^ Beta asarone has CAS# 5273-86-9
- ^ 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" (PDF). Journal of Medicinal Plants Research. 5 (20): 5132–5137.
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: CS1 maint: multiple names: authors list (link) - ^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "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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