Asarone
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| 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 (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.018.858 | ||
| PubChem CID |
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| 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
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]
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
Notes and references
- ↑ Data for α-Asarone at ChemSpider
- 1 2 3 "Asarone". The Merck Index. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1.
- ↑ Beta asarone has CAS# 5273-86-9
- ↑ 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. PMID 20040135. doi:10.1093/jat/33.9.604.
- ↑ 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.
- ↑ "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.