aesculetin

{{distinguish|aesculin|aescin}}

{{chembox

| Watchedfields = changed

| verifiedrevid = 477243187

| Reference={{cite web|url = http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/246573|title = Aesculetin|publisher = Sigma-Aldrich}}

| ImageFile=Aesculetin.svg

| ImageClass = skin-invert-image

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

| OtherNames=esculetin
cichorigenin
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 g mol⁻¹

| 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.{{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}}

This compound is used in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage.{{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}} The sodium salt of its methyl-derivative is used in dermatology for the treatment of varicose veins.{{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 }}

It is a blue fluorescence compound found in plants.{{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}} Aesculin, the glucoside of aesculetin, will fluoresce under long wave ultraviolet light (360 nm). The hydrolysis of aesculin results in loss of this fluorescence. Aesculetin has the ability to quench the inner fluorescence of bovine serum albumin.{{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}}

Aesculetin can be transformed into scopoletin (7-hydroxy-6-methoxycoumarin) and isoscopoletin (6-hydroxy-7-methoxycoumarin) through incubation with rat liver catechol-O-methyltransferase.{{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}}

Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malonic acid in concentrated sulfuric acid.{{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}}