Aesculetin

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.

Aesculetin[1]

Names
IUPAC name 6,7-dihydroxy-chromen-2-one
Other names esculetin cichorigenin 6,7-dihydroxycoumarin
Identifiers
CAS Number	305-01-1
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:490095
ChEMBL	ChEMBL244743
ChemSpider	4444764
ECHA InfoCard	100.005.602
IUPHAR/BPS	5180
KEGG	C09263
PubChem CID	5281416
UNII	SM2XD6V944
CompTox Dashboard (EPA)	DTXSID3075383
InChI InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H Key: ILEDWLMCKZNDJK-UHFFFAOYSA-N 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
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

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]

See also

• Umbelliferone

References

1. "Aesculetin". Sigma-Aldrich.
2. Dey, P. M.; Harborne, J. B., eds. (1997). Plant Biochemistry. Academic Press. ISBN 9780122146749.
3. Hausen, B. M.; Schmieder, M. (September 1986). "The sensitizing capacity of coumarins (I)". Contact Dermatitis. 15 (3): 157–163. doi:10.1111/j.1600-0536.1986.tb01317.x. PMID 3780217. S2CID 221575607.
4. ""Permethol" Data Sheet" (PDF).
5. Lang, M.; Stober, F.; Lichtenthaler, H.K. (1991). "Fluorescence emission spectra of plant leaves and plant constituents". Radiation and Environmental Biophysics. 30 (4): 333–347. doi:10.1007/BF01210517. PMID 1961919. S2CID 25892031.
6. Liu, X.-F.; Xia, Y.-M.; Fang, Y.; Zou, L.; Liu, L.-L. (2004). "Interaction between natural pharmaceutical homologues of coumarin and bovine serum albumin". Huaxue Xuebao. 62 (16): 1484–1490. INIST:16312595
7. Müller-Enoch, D.; Seidl, E.; Thomas, H. (1976). "6.7-Dihydroxycoumarin (Aesculetin) as a substrate for catechol-o-methyltransferase". Z. Naturforsch. C (in German). 31 (5–6): 280–284. doi:10.1515/znc-1976-5-611. PMID 134569. S2CID 82796973.