Wikiwand AI

Aesculetin

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Aesculetin[1]
Names
Preferred IUPAC name
6,7-Dihydroxy-2H-1-benzopyran-2-one
Other names
esculetin
cichorigenin
6,7-dihydroxycoumarin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.602 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H checkY
    Key: ILEDWLMCKZNDJK-UHFFFAOYSA-N checkY
  • InChI=1/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
    Key: ILEDWLMCKZNDJK-UHFFFAOYAQ
  • C1=CC(=O)OC2=CC(=C(C=C21)O)O
  • O=C/2Oc1cc(O)c(O)cc1\C=C\2
Properties
C9H6O4
Molar mass 178.14 g mol−1
Appearance white or light yellow powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)
Close

It is present in chicory and in many toxic and medicinal plants, in form of glycosides and caffeic acid conjugates.[2]

This compound is used in some sunscreens, but there is evidence that it acts as a photosensitizer for DNA damage.[3] The sodium salt of its methyl-derivative is used in dermatology for the treatment of varicose veins.[4]

It is a blue fluorescence compound found in plants.[5] 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.[6]

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

Aesculetin can be synthesized by condensation of hydroxyhydroquinone triacetate with malic acid in concentrated sulfuric acid.[8]

See also

References

Related Articles

Timelines

Top Qs

Fact Checks