| Revision as of 20:13, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443372760 of page Aesculetin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 21:58, 28 January 2023 edit OAbot (talk | contribs)Bots441,761 editsm Open access bot: doi added to citation with #oabot. |
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{{distinguish|aesculin|aescin}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443371332 |
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| verifiedrevid = 477243187 |
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|Reference=<ref>at ]</ref> |
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| Reference=<ref>{{cite web|url = http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/246573|title = Aesculetin|publisher = ]}}</ref> |
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|ImageFile=Aesculetin.svg |
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| ImageFile=Aesculetin.svg |
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|ImageSize=200px |
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|IUPACName=6,7-Dihydroxy-2-chromenone |
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| PIN=6,7-Dihydroxy-2''H''-1-benzopyran-2-one |
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|OtherNames=Esculetin<br/>Cichorigenin<br/>6,7-Dihydroxycoumarin |
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| OtherNames=esculetin<br>cichorigenin<br>6,7-dihydroxycoumarin |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 5180 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444764 |
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| ChemSpiderID = 4444764 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=305-01-1 |
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| CASNo=305-01-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=5281416 |
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| UNII = SM2XD6V944 |
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| PubChem=5281416 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 490095 |
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| ChEBI = 490095 |
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| SMILES=C1=CC(=O)OC2=CC(=C(C=C21)O)O |
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| SMILES=C1=CC(=O)OC2=CC(=C(C=C21)O)O |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=9 | H=6 | O=4 |
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| Formula = C<sub>9</sub>H<sub>6</sub>O<sub>4</sub> |
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| MolarMass = 178.14 g/mol |
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| MolarMass = 178.14 g mol<sup>−1</sup> |
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| Appearance = white or light yellow powder |
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| ExactMass = 178.026609 |
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'''Aesculetin''' (also known as '''esculetin''', '''6,7-dihydroxycoumarin''' and '''cichorigenin''') is a derivative of ]. It is a natural ] that derives from the intramolecular ] of a ] derivative. |
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It is present in ] and in many ] and ]s, in form of ]s and ] conjugates.<ref>{{cite book|url = https://books.google.com/books?id=NmKF0hxhpdMC&q=esculetin&pg=PA388|title = Plant Biochemistry|year = 1997|editor1-last = Dey|editor1-first = P. M.|editor2-last = Harborne|editor2-first = J. B.|editor2-link = Jeffrey Barry Harborne|publisher = ]|isbn = 9780122146749}}</ref> |
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This compound is used in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage.<ref>{{cite journal|author1 = Hausen, B. M.|author2 = Schmieder, M.|title = The sensitizing capacity of coumarins (I)|journal = Contact Dermatitis|volume = 15|issue = 3|pages = 157–163|date=September 1986|pmid = 3780217|doi = 10.1111/j.1600-0536.1986.tb01317.x|s2cid = 221575607}}</ref> The sodium salt of its methyl-derivative is used in ] for the treatment of ].<ref>{{cite web|url=http://www.in-cosmetics.com/ExhibitorLibrary/606/Permethol-VA-020209-FT_3.pdf |title="Permethol" Data Sheet }}{{dead link|date=June 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> |
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It is a blue ] compound found in plants.<ref>{{cite journal|author1=Lang, M.|author2=Stober, F.|last3=Lichtenthaler|first3=H.K.|author-link3=Hartmut K. Lichtenthaler|year=1991|title=Fluorescence emission spectra of plant leaves and plant constituents|journal=Radiation and Environmental Biophysics|volume=30|issue=4|pages=333–347|doi=10.1007/BF01210517|pmid=1961919|s2cid=25892031}}</ref> ], the ] of aesculetin, will ] under long wave ] light (360 ]). The hydrolysis of aesculin results in loss of this fluorescence. Aesculetin has the ability to quench the inner fluorescence of ].<ref>{{cite journal|title = Interaction between natural pharmaceutical homologues of coumarin and bovine serum albumin|last1 = Liu|first1 = X.-F.|last2 = Xia|first2 = Y.-M.|last3 = Fang|first3 = Y.|last4 = Zou|first4 = L.|last5 = Liu|first5 = L.-L.|journal = Huaxue Xuebao|year = 2004|volume = 62|issue = 16|pages = 1484–1490}} {{INIST|16312595}}</ref> |
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Aesculetin can be transformed into ] (7-hydroxy-6-methoxycoumarin) and ] (6-hydroxy-7-methoxycoumarin) through incubation with rat liver ].<ref>{{cite journal|title = 6.7-Dihydroxycoumarin (Aesculetin) as a substrate for catechol-''o''-methyltransferase|journal = ]|year = 1976|issue = 5–6|volume = 31|pages = 280–284|author1 = Müller-Enoch, D.|author2 = Seidl, E.|author3 = Thomas, H.|doi = 10.1515/znc-1976-5-611|pmid = 134569|s2cid = 82796973|language = de|doi-access = free}}</ref> |
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Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malonic acid in concentrated sulfuric acid.<ref>{{Cite book| publisher = I. K. International Pvt Ltd| isbn = 978-81-88237-33-3| last1 = Ahluwalia| first1 = V. K.| last2 = Bhagat| first2 = Pooja| last3 = Aggarwal| first3 = Renu| last4 = Chandra| first4 = Ramesh| title = Intermediates for Organic Synthesis| page = 213 | date = 2013-12-30}}</ref> |
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== See also == |
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* ] |
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== References == |
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{{Reflist}} |
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{{Coumarin}} |
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] |
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] |