Esculetin

Title: Esculetin
CAS Registry Number: 305-01-1
CAS Name: 6,7-Dihydroxy-2H-1-benzopyran-2-one
Additional Names: 6,7-dihydroxycoumarin; cichorigenin
Molecular Formula: C9H6O4
Molecular Weight: 178.14
Percent Composition: C 60.68%, H 3.39%, O 35.93%
Literature References: The aglucon of esculin and of cichoriin. By hydrolysis of esculin or of cichoriin: Merz, Arch. Pharm. 270, 486 (1932). By synthesis: Gattermann, Köbner, Ber. 32, 288 (1899); Bert, Compt. Rend. 214, 230 (1942). Review: Sethna, Shah, Chem. Rev. 36, 1 (1945).
Properties: Prisms from glacial acetic acid; leaflets by vacuum sublimation. mp 268-270°. Soluble in dil alkalies with blue fluorescence; moderately sol in hot alcohol and in glacial acetic acid; almost insol in ether, in boiling water.
Melting point: mp 268-270°
Use: In filters for absorption of ultraviolet light.
Esculin Eseridine Esmolol Esparto Wax Estazolam

Aesculetin[1]
Aesculetin.svg
Identifiers
CAS number 305-01-1 YesY
PubChem 5281416
ChemSpider 4444764 YesY
KEGG C09263 YesY
ChEBI CHEBI:490095 YesY
ChEMBL CHEMBL244743 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H6O4
Molar mass 178.14 g mol−1
Appearance white or light yellow powder
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.[2]

Esculetin-containing preparations used systemically can have an anticoagulant effect and might interact with anticoagulent drugs such as warfarin.

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]