Aesculetin

Not to be confused with aesculin or aescin.

Aesculetin

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Names
IUPAC name 6,7-dihydroxy-2-chromenone
Other names esculetin cichorigenin 6,7-dihydroxycoumarin
Identifiers
CAS Number	305-01-1 Y
ChEBI	CHEBI:490095 Y
ChEMBL	ChEMBL244743 Y
ChemSpider	4444764 Y
IUPHAR/BPS	5180
Jmol 3D model	Interactive image Interactive image
KEGG	C09263 Y
PubChem	5281416
InChI InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H Y Key: ILEDWLMCKZNDJK-UHFFFAOYSA-N Y 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
SMILES C1=CC(=O)OC2=CC(=C(C=C21)O)O O=C/2Oc1cc(O)c(O)cc1\C=C\2
Properties
Chemical formula	C9H6O4
Molar mass	178.14 g mol−1
Appearance	white or light yellow powder
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

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. 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.

See also

• Umbelliferone