Aesculetin

Last updated
Aesculetin [1]
Aesculetin.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H Yes check.svgY
    Key: ILEDWLMCKZNDJK-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancewhite or light yellow powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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 malic 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).[ permanent dead link ]
  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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