Asarone
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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
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100.018.858 | ||
PubChem CID
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UNII |
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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 | |||
-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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Asarone is chemical compound of the phenylpropanoid class found in certain plants such as Acorus and Asarum.[2] There are two isomers, α (or trans) and β (or cis).[3] As a volatile fragrance oil, it is used in killing pests and bacteria.[4]
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.[5]
The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic[6] and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).[7]
β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger.[8] However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.[9]
See also
Notes and references
- ^ Data for α-Asarone at ChemSpider
- ^ 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.
- PMID 20040135.
- PMID 26273788.
- ^ "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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- S2CID 84823162.