Aesculetin

Not to be confused with aesculin or aescin.

Aesculetin[1]
IUPAC name 6,7-Dihydroxy-2-chromenone
Other names Esculetin Cichorigenin 6,7-Dihydroxycoumarin
Identifiers
CAS number	305-01-1 Y
PubChem	5281416
ChemSpider	4444764 Y
KEGG	C09263 Y
ChEBI	CHEBI:490095 Y
ChEMBL	CHEMBL244743 Y
Jmol-3D images	Image 1 Image 2
SMILES C1=CC(=O)OC2=CC(=C(C=C21)O)O O=C/2Oc1cc(O)c(O)cc1\C=C\2
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
Properties
Molecular formula	C9H6O4
Molar mass	178.14 g/mol
Exact mass	178.026609
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 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]

See also

• Aesculin, the glucoside of aesculetin
• Umbelliferone

References

1. ^ Aesculetin at Sigma-Aldrich
2. ^ Plant biochemistry (1997) P. M. Dey & Jeffrey B. Harborne (eds.)
3. ^ Hausen BM, Schmieder M (September 1986). "The sensitizing capacity of coumarins (I)". Contact Dermatitis 15 (3): 157–63. doi:10.1111/j.1600-0536.1986.tb01317.x. PMID 3780217. 
4. ^ "Permethol" Data Sheet