Aesculetin

Aesculetin^[1]
Names
	Preferred IUPAC name 6,7-Dihydroxy-2H-1-benzopyran-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). verify (what is ?) 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.^[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]

References

^ "Aesculetin". Sigma-Aldrich.
^ Dey, P. M.; Harborne, J. B., eds. (1997). Plant Biochemistry. Academic Press. ISBN 9780122146749.
^ 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.
^ ""Permethol" Data Sheet" (PDF).^{[permanent dead link‍]}
^ 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.
^ 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
^ 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.
^ 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.

[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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See also

References