Lecanoric acid

From Wikipedia, the free encyclopedia
Lecanoric acid
Lecanoric acid.svg
Names
Preferred IUPAC name
4-[(2,4-Dihydroxy-6-methylbenzoyl)oxy]-2-hydroxy-6-methylbenzoic acid
Other names
Orsellinate depside
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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
  • CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)O)O)O)O
Properties
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).

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] The acid is named after the lichen Lecanora. 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[edit]

  1. ^ "Lecanoric acid". PubChem. National Center for Biotechnology Information. Retrieved 27 June 2019.
  2. ^ 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. doi:10.1007/s00300-009-0602-9. S2CID 9256291.
  3. ^ 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.
  4. ^ 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.
  5. ^ Elix, John A.; Wardlaw, Judith H. (2002). "5-Chlorolecanoric acid, a new depside from Punctelia species" (PDF). Australasian Lichenology. 50: 6–9.