{{distinguish|aesculin|aescin}} {{chembox | Watchedfields = changed | verifiedrevid = 477243187 | Reference=<ref>{{cite web|url = http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/246573|title = Aesculetin|publisher = Sigma-Aldrich}}</ref> | ImageFile=Aesculetin.svg | ImageClass = skin-invert-image | PIN=6,7-Dihydroxy-2''H''-1-benzopyran-2-one | OtherNames=esculetin<br>cichorigenin<br>6,7-dihydroxycoumarin |Section1={{Chembox Identifiers | IUPHAR_ligand = 5180 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444764 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C09263 | InChI = 1/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H | SMILES1 = O=C/2Oc1cc(O)c(O)cc1\C=C\2 | InChIKey = ILEDWLMCKZNDJK-UHFFFAOYAQ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 244743 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ILEDWLMCKZNDJK-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=305-01-1 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SM2XD6V944 | PubChem=5281416 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 490095 | SMILES=C1=CC(=O)OC2=CC(=C(C=C21)O)O }} |Section2={{Chembox Properties | C=9 | H=6 | O=4 | MolarMass = 178.14&nbsp;g&nbsp;mol<sup>&minus;1</sup> | Appearance = white or light yellow powder | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Aesculetin''' (also known as '''esculetin''', '''6,7-dihydroxycoumarin''' and '''cichorigenin''') is a derivative of coumarin. It is a natural lactone that derives from the intramolecular cyclization of a cinnamic acid derivative.

It is present in chicory and in many toxic and medicinal plants, in form of glycosides and caffeic acid 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 = Academic Press|isbn = 9780122146749}}</ref>

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 dermatology for the treatment of varicose veins.<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>

It is a blue fluorescence 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> Aesculin, the glucoside of aesculetin, will fluoresce under long wave ultraviolet light (360&nbsp;nm). The hydrolysis of aesculin results in loss of this fluorescence. Aesculetin has the ability to quench the inner fluorescence of bovine serum albumin.<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>

Aesculetin can be transformed into scopoletin (7-hydroxy-6-methoxycoumarin) and isoscopoletin (6-hydroxy-7-methoxycoumarin) through incubation with rat liver catechol-O-methyltransferase.<ref>{{cite journal|title = 6.7-Dihydroxycoumarin (Aesculetin) as a substrate for catechol-''o''-methyltransferase|journal = Z. Naturforsch. C|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>

Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malic 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>

== See also == * Umbelliferone

== References == {{Reflist}}

{{Coumarin}}

Category:Coumarins Category:Catechols