Lecanoric acid

Lecanoric acid
Names
	Preferred IUPAC name 4-[(2,4-Dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoic acid
	Other names Orsellinate depside
Identifiers
CAS Number	480-56-8;
3D model (JSmol)	Interactive image;
3DMet	B00509;
ChEBI	CHEBI:15871;
ChEMBL	ChEMBL1451874;
ChemSpider	89997;
KEGG	C02868;
PubChem CID	99613;
UNII	D0M65TKS0F;
CompTox Dashboard (EPA)	DTXSID60197384 ;
	InChI InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21) Key: HEMSJKZDHNSSEW-UHFFFAOYSA-N;
	SMILES CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)O)O)O)O;
Properties
Chemical formula	C16H14O7
Molar mass	318.281 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lecanoric acid is a chemical produced by several species of lichen.^[1] Lecanoric acid is classified as a polyphenol and a didepside, and it functions as an antioxidant.^[2] It is an ester of orsellinic acid with itself.

The acid is named after the lichen Lecanora, in which it was discovered. The acid has also been isolated from Usnea subvacata, Parmotrema stuppuem, Parmotrema tinctorum, Parmotrema grayana, Xanthoparmelia arida and Xanthoparmelia lecanorica.^[3]^[4] A related compound, 5-chlorolecanoric acid, is found in some species of Punctelia.^[5]

References

^ "Lecanoric acid". PubChem. National Center for Biotechnology Information. Retrieved 27 June 2019.
^ Luo, Heng; Yamamoto, Yoshikazu; A Kim, Jung; Jung, Jae Sung; Koh, Young Jin; Hur, Jae-Seoun (13 March 2009). "Lecanoric acid, a secondary lichen substance with antioxidant properties from Umbilicaria antarctica in maritime Antarctica (King George Island)". Polar Biology. 32 (7): 1033–1040. Bibcode:2009PoBio..32.1033L. doi:10.1007/s00300-009-0602-9. S2CID 9256291.
^ Hale, Mason E. (1990). A synopsis of the lichen genus Xanthoparmelia (Vainio) Hale (Ascomycotina, Parmeliaceae) /. Washington, D.C.: Smithsonian Institution Press. doi:10.5962/bhl.title.123253.
^ White, Pollyanna; Oliveira, Rita; Oliveira, Aldeidia; Serafini, Mairim; Araújo, Adriano; Gelain, Daniel; Moreira, Jose; Almeida, Jackson; Quintans, Jullyana; Quintans-Junior, Lucindo; Santos, Marcio (12 September 2014). "Antioxidant Activity and Mechanisms of Action of Natural Compounds Isolated from Lichens: A Systematic Review". Molecules. 19 (9): 14496–14527. doi:10.3390/molecules190914496. PMC 6271897. PMID 25221871.
^ Elix, John A.; Wardlaw, Judith H. (2002). "5-Chlorolecanoric acid, a new depside from Punctelia species" (PDF). Australasian Lichenology. 50: 6–9.