Asarone
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| Names | |
|---|---|
| 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 | |
2883-98-9  | |
| ChEMBL | ChEMBL333306  |
| ChemSpider | 552532 |
| |
| Jmol-3D images | Image Image |
| PubChem | 636822 |
| |
| Properties | |
| C12H16O3 | |
| Molar mass | 208.254 g mol−1 |
| Appearance | colorless solid substance |
| Density | 1.028 g/cm−3 [1] |
| Melting point | 62 to 63 °C (144 to 145 °F; 335 to 336 K)[2] |
| Boiling point | 296 °C (565 °F; 569 K)[2] |
| insoluble | |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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
- Elemicin
- Sweet Flag
- 2,4,5-Trimethoxypropiophenone
Notes and references
- ↑ Data for α-Asarone at ChemSpider
- ↑ 2.0 2.1 2.2 "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
- ↑ 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.
- ↑ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Act. 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.Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats. Biological & Pharmaceutical Bulletin. 33(5):836-43, 2010.