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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.<ref>{{cite journal |vauthors=Björnstad K, Helander A, Hultén P, Beck O | title = Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications| journal = J Anal Toxicol| volume = 33| issue = 9| pages = 604–9| year = 2009| pmid = 20040135| doi = 10.1093/jat/33.9.604| url = | doi-access = free}}</ref> |
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.<ref>{{cite journal |vauthors=Björnstad K, Helander A, Hultén P, Beck O | title = Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications| journal = J Anal Toxicol| volume = 33| issue = 9| pages = 604–9| year = 2009| pmid = 20040135| doi = 10.1093/jat/33.9.604| url = | doi-access = free}}</ref> |
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The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly [[carcinogen]]ic<ref>{{Cite journal| |
The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly [[carcinogen]]ic<ref>{{Cite journal|last1=Cartus|first1=Alexander T.|last2=Stegmüller|first2=Simone|last3=Simson|first3=Nadine|last4=Wahl|first4=Andrea|last5=Neef|first5=Sylvia|last6=Kelm|first6=Harald|last7=Schrenk|first7=Dieter|date=2015-08-26|title=Hepatic Metabolism of Carcinogenic β-Asarone|journal=Chemical Research in Toxicology|volume=28|issue=9|pages=1760–1773|doi=10.1021/acs.chemrestox.5b00223|pmid=26273788|issn=0893-228X}}</ref> and has proposed limits for its concentration in flavorings such as [[bitters]] made from ''[[Acorus calamus]]'' (sweet flag).<ref>{{cite journal | date = 8 January 2002 | title = Opinion of the Scientific Committee on Food on the presence of β-asarone in flavourings and other food ingredients with flavouring properties | publisher = European Commission Scientific Committee on Food | url = http://ec.europa.eu/food/fs/sc/scf/out111_en.pdf}}</ref> |
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β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in ''Aspergillus niger''.<ref>{{Cite journal| |
β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in ''Aspergillus niger''.<ref>{{Cite journal|last1=Venkatesan|first1=Ramya|last2=Karuppiah|first2=Prakash Shyam|last3=Arumugam|first3=Gnanamani|last4=Balamuthu|first4=Kadalmani|date=2017-11-10|title=β-Asarone Exhibits Antifungal Activity by Inhibiting Ergosterol Biosynthesis in ''Aspergillus niger'' ATCC 16888|journal=Proceedings of the National Academy of Sciences, India Section B: Biological Sciences|volume=89|language=en|pages=173–184|doi=10.1007/s40011-017-0930-4|s2cid=46005148|issn=0369-8211}}</ref> However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.<ref>{{cite journal | doi = 10.1002/ptr.2650090604 | title = Anthelmintic and pesticidal activity of ''Acorus gramineus'' (Araceae) is associated with phenylpropanoid asarones | year = 1995 | last1 = Perrett | first1 = Sheena | last2 = Whitfield | first2 = Philip J. | journal = Phytotherapy Research | volume = 9 | issue = 6 | pages = 405}}</ref> |
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== See also == |
== See also == |
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Revision as of 00:49, 4 September 2020
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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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| 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
- ^ 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 [dead link]
- ^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49.
- ^ 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.
- ^ Cartus, Alexander T.; Stegmüller, Simone; Simson, Nadine; Wahl, Andrea; Neef, Sylvia; Kelm, Harald; Schrenk, Dieter (2015-08-26). "Hepatic Metabolism of Carcinogenic β-Asarone". Chemical Research in Toxicology. 28 (9): 1760–1773. doi:10.1021/acs.chemrestox.5b00223. ISSN 0893-228X. 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.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Venkatesan, Ramya; Karuppiah, Prakash Shyam; Arumugam, Gnanamani; Balamuthu, Kadalmani (2017-11-10). "β-Asarone Exhibits Antifungal Activity by Inhibiting Ergosterol Biosynthesis in Aspergillus niger ATCC 16888". Proceedings of the National Academy of Sciences, India Section B: Biological Sciences. 89: 173–184. doi:10.1007/s40011-017-0930-4. ISSN 0369-8211. S2CID 46005148.
- ^ Perrett, Sheena; Whitfield, Philip J. (1995). "Anthelmintic and pesticidal activity of Acorus gramineus (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research. 9 (6): 405. doi:10.1002/ptr.2650090604.