Asarone
Chemical compound found in certain plants
| IUPAC Name: | 1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene |
| Other Names: | 2,4,5-Trimethoxy-1-propenylbenzene |
| Identifiers | |
| CAS Number | |
| PubChem | 5281351 |
| ChemSpider | 4447590 |
| SMILES | C/C=C/C1=CC(=C(C=C1OC)OC)OC |
| InChI | 1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5-8H,1-4H3/b6-5+ |
| InChIKey | QWVGKYWNOKOFNN-AATRIKPKSA-N |
| StdInChI | |
| StdInChIKey | |
| Properties | |
| Chemical formula | C12H16NO3 |
| Appearance | Colorless to pale yellow liquid |
| Density | 1.08 g/cm³ |
| Melting Point | 61-62 °C |
| Boiling Point | 296-298 °C |
| Solubility | |
| Hazards | |
| Main Hazards | |
| Flash Point | |
| Autoignition Temperature | |
Asarone is a chemical compound found in certain plants, notably in the sweet flag (Acorus calamus) and the European wild ginger (Asarum europaeum). It is an aromatic ether and is structurally related to phenylpropanoids. Asarone exists in two isomeric forms: α-asarone and β-asarone.
Chemical Structure and Properties[edit | edit source]
Asarone is classified as a phenylpropene, a type of phenylpropanoid. The IUPAC name for asarone is 1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene. It has a molecular formula of C12H16O3 and a molar mass of 208.25 g/mol. Asarone is a colorless to pale yellow liquid with a density of 1.08 g/cm³, a melting point of 61-62 °C, and a boiling point of 296-298 °C.
Occurrence[edit | edit source]
Asarone is primarily found in the essential oils of certain plants. The sweet flag (Acorus calamus) is one of the most well-known sources of asarone. The compound is also present in the European wild ginger (Asarum europaeum) and other related species.
Uses[edit | edit source]
Asarone has been used in traditional medicine for its purported therapeutic properties. It has been studied for its potential effects on the central nervous system, including its possible use as a sedative and anticonvulsant. However, the safety and efficacy of asarone for these uses have not been conclusively established.
Toxicity[edit | edit source]
Asarone has been shown to have toxic effects in high doses. It is considered to be a potential carcinogen, and its use in food and medicine is regulated in many countries. The compound can cause liver damage and other adverse effects if ingested in large quantities.
Related Compounds[edit | edit source]
Asarone is related to other phenylpropanoids, such as eugenol and safrole. These compounds share similar structural features and are also found in various plant species.
See Also[edit | edit source]
References[edit | edit source]
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