Aesculetin

Quality 0.50 · 1 view · Updated 2 months ago

title: "Aesculetin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["coumarins", "catechols"] topic_path: "general/coumarins" source: "https://en.wikipedia.org/wiki/Aesculetin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477243187 | Reference= | 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 = | ChemSpiderID = 4444764 | KEGG_Ref = | 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 = | ChEMBL = 244743 | StdInChI_Ref = | StdInChI = 1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H | StdInChIKey_Ref = | StdInChIKey = ILEDWLMCKZNDJK-UHFFFAOYSA-N | CASNo_Ref = | CASNo=305-01-1 | UNII_Ref = | UNII = SM2XD6V944 | PubChem=5281416 | ChEBI_Ref = | 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.

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

It is a blue fluorescence compound found in plants. 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.

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

Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malic acid in concentrated sulfuric acid.

References

References

  1. "Aesculetin". [[Sigma-Aldrich]].
  2. (1997). "Plant Biochemistry". [[Academic Press]].
  3. (September 1986). "The sensitizing capacity of coumarins (I)". Contact Dermatitis.
  4. (June 2017). ""Permethol" Data Sheet }}{{dead link".
  5. (1991). "Fluorescence emission spectra of plant leaves and plant constituents". Radiation and Environmental Biophysics.
  6. (2004). "Interaction between natural pharmaceutical homologues of coumarin and bovine serum albumin". Huaxue Xuebao.
  7. (1976). "6.7-Dihydroxycoumarin (Aesculetin) as a substrate for catechol-''o''-methyltransferase". [[Z. Naturforsch. C]].
  8. (2013-12-30). "Intermediates for Organic Synthesis". I. K. International Pvt Ltd.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

coumarinscatechols