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.

Not to be confused with aesculin or aescin.
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
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 checkY☒N ?)
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]

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

See also

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.
  8. Ahluwalia, V. K.; Bhagat, Pooja; Aggarwal, Renu; Chandra, Ramesh (2013-12-30). Intermediates for Organic Synthesis. I. K. International Pvt Ltd. p. 213. ISBN 978-81-88237-33-3.
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