Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Aesculetin: Difference between pages

{{distinguish|aesculin|aescin}}

| 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

| PIN=6,7-Dihydroxy-2''H''-1-benzopyran-2-one

| OtherNames=esculetin<br>cichorigenin<br>6,7-dihydroxycoumarin

| IUPHAR_ligand = 5180

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SM2XD6V944

| PubChem=5281416

| ChEBI_Ref = {{ebicite|correct|EBI}}

| C=9 | H=6 | O=4

| MolarMass = 178.14&nbsp;g&nbsp;mol^&minus;1

| Appearance = white or light yellow powder

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

| 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 plant|toxic]] and [[medicinal plant]]s, in form of [[glycoside]]s 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 [[fluorescence|fluoresce]] under long wave [[ultraviolet]] light (360&nbsp;[[nanometre|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 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>

== See also ==

* [[Umbelliferone]]

== References ==

{{Reflist}}

{{Coumarin}}

[[Category:Coumarins]]

[[Category:Catechols]]