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Updating {{chembox}} (changes to verified and watched fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBo... |
I am a representative of Merck (Sigma Aldrich), and as there was a recent website migration, the existing link for the text (5273-86-9 "http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=11108|FLUKA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC") on the page has expired and hence updated with the appropriate one. Thank You! Tags: Mobile edit Mobile web edit |
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| verifiedrevid = 457630359 |
| verifiedrevid = 457630359 |
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| ImageFileL1 = Alpha-Asaron.svg |
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|Name = α-Asarone |
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| ImageSizeL1 = 120px |
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|ImageFile= Alpha-asarone-2D-skeletal.png |
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| ImageCaptionL1 = α-Asarone |
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|ImageSize=200px |
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| ImageFileR1 = Beta-Asaron.svg |
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|ImageFile1 = Trans-asarone-3D-balls.png |
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| ImageSizeR1 = 120px |
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|IUPACName=1,2,4-Trimethoxy-5-[(''E'')-prop-1-enyl]benzene |
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| ImageCaptionR1 = β-Asarone |
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|OtherNames=alpha-Azaron<br>cis-Isoelemicin<br>2,4,5-Trimethoxyphenyl-2-propene |
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| IUPACName = 1,2,4-Trimethoxy-5-[(''E'')-prop-1-enyl]benzene (α)<br>1,2,4-Trimethoxy-5-[(''Z'')-prop-1-enyl]benzene (β) |
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|Section1= {{Chembox Identifiers |
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| OtherNames =''alpha''-Azaron<br>''cis''-Isoelemicin<br>2,4,5-Trimethoxyphenyl-2-propene |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 552532 |
| ChemSpiderID = 552532 |
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| ChemSpiderID_Comment= (α) |
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| InChI = 1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ |
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| ChemSpiderID1 = 4445072 |
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| InChIKey = RKFAZBXYICVSKP-AATRIKPKBQ |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| SMILES1 = O(c1cc(c(OC)cc1OC)/C=C/C)C |
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| ChemSpiderID1_Comment= (β) |
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| SMILES = O(c1cc(c(OC)cc1OC)/C=C/C)C |
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| SMILES_Comment = (α) |
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| SMILES1 = C/C=C\c1cc(c(cc1OC)OC)OC |
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| SMILES1_Comment = (β) |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ |
| StdInChI = 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RKFAZBXYICVSKP-AATRIKPKSA-N |
| StdInChIKey = RKFAZBXYICVSKP-AATRIKPKSA-N |
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| |
| InChI3_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI3 = 1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5- |
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| CASNo=2883-98-9 |
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| |
| InChIKey3_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey3 = RKFAZBXYICVSKP-WAYWQWQTSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 2883-98-9 |
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| CASNo_Comment = (α) |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 5273-86-9 |
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| CASNo1_Comment = (β) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = DQY9PNE5FK |
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| UNII_Comment = (α) |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = IGA3MH6IUW |
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| UNII1_Comment = (β) |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 333306 |
| ChEMBL = 333306 |
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| PubChem=636822 |
| PubChem =636822 |
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| PubChem_Comment = (α) |
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| SMILES=CC=CC1=CC(=C(C=C1OC)OC)OC |
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| PubChem1 =5281758 |
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| PubChem1_Comment = (β) |
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}} |
}} |
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|Section2= |
|Section2={{Chembox Properties |
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| C=12 | H=16 | O=3 |
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| Formula=C<sub>12</sub>H<sub>16</sub>O<sub>3</sub> |
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| Appearance =Colorless solid |
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| MolarMass= 208.254 g mol<sup>−1</sup> |
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| Density = α: 1.028 g/cm<sup>−3</sup> <ref name=spider>[http://www.chemspider.com/Chemical-Structure.552532.html ''Data for α-Asarone at ChemSpider'']</ref> |
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| Appearance=colorless solid substance |
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| MeltingPtC = 62 to 63 |
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| Density=1.028 g/cm<sup>−3</sup> <ref name=spider>[http://www.chemspider.com/Chemical-Structure.552532.html ''Data for α-Asarone at ChemSpider'']</ref> |
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| MeltingPt_notes = (α) |
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| MeltingPt=62-63 °C <ref name="merck">{{cite encyclopedia |
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| MeltingPt_ref = <ref name="merck">{{cite encyclopedia |
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| title = Asarone |
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| encyclopedia = The Merck Index |
| title = Asarone |
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| encyclopedia = The Merck Index |
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| volume = 14th edition |
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| pages = 135 |
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| publisher = Merck Research Laboratories |
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| year = 2006 |
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| isbn = 978-0-911910-00-1}}</ref> |
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| accessdate = |
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| BoilingPtC = 296 |
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| isbn = 978-0-911910-00-1 }}</ref> |
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| BoilingPt_notes = (α) |
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| BoilingPt=296 °C <ref name="merck">">{{cite encyclopedia |
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| BoilingPt_ref = <ref name="merck">{{cite encyclopedia |
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| title = Asarone |
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| encyclopedia = The Merck Index |
| title = Asarone |
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| encyclopedia = The Merck Index |
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| volume = 14th edition |
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| pages = 135 |
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| publisher = Merck Research Laboratories |
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| year = 2006 |
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| isbn = 978-0-911910-00-1}}</ref> |
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| accessdate = |
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| Solubility =Insoluble |
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| isbn = 978-0-911910-00-1 }}</ref> |
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| MagSus = -131.4·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Solubility=insoluble |
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}} |
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|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| Autoignition= |
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}} |
}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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'''Asarone''' |
'''Asarone''' is [[chemical compound]] of the [[phenylpropanoid]] class found in certain plants such as ''[[Acorus]]'' and ''[[Asarum]]''.<ref name="merck"/> There are two [[isomer]]s, α (or ''trans'') and β (or ''cis'').<ref>Beta asarone has CAS# [https://www.sigmaaldrich.com/US/en/product/aldrich/221074 5273-86-9]</ref> As a volatile [[fragrance oil]], it is used in killing [[Pest (organism)|pest]]s and bacteria.<ref>{{cite journal |vauthors=Asha DS, Ganjewala D | year = 2009 | title = Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract | journal = Acta Biol. Szeg. | volume = 53 | issue = 1 | pages = 45–49}}</ref> |
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== Pharmacology == |
== Pharmacology == |
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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 |
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| doi-access = free}}</ref> |
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| author = Björnstad K, Helander A, Hultén P, Beck O |
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| title = Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications |
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| journal = J Anal Toxicol |
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| volume = 33 |
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| issue = 9 |
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| pages = 604–9 |
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| year = 2009 |
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| pmid = 20040135 |
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| doi = |
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| url = |
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}}</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|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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==See also== |
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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| s2cid = 84823162 }}</ref> |
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== See also == |
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* [[Elemicin]] |
* [[Elemicin]] |
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* [[2,4,5-Trimethoxypropiophenone]] |
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* [[Sweet Flag]] |
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==Notes and references== |
== Notes and references == |
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{{reflist}} |
{{reflist}} |
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[[Category: |
[[Category:Phenylpropenes]] |
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[[Category: |
[[Category:O-methylated phenylpropanoids]] |
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[[Category:Plant toxins]] |
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{{organic-compound-stub}} |
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[[ca:Asarona]] |
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[[de:Asaron]] |
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[[es:Asarona]] |
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[[hu:Azaron]] |
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[[ru:Азарон]] |
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[[sv:Asaron]] |
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Latest revision as of 09:36, 23 February 2022
| |||
| 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)
|
| ||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.018.858 | ||
PubChem CID
|
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| UNII |
| ||
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).
| |||
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[edit]
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[edit]
Notes and references[edit]
- ^ 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
- ^ 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. S2CID 84823162.