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Stictic acid

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Stictic acid
Names
Systematic IUPAC name 1,4-Dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-1,3-dihydro-7H-2,6,12-trioxabenzocycloheptaindene-11-carbaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.161.455 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H14O9/c1-6-4-9(25-3)8(5-20)15-10(6)17(22)27-14-7(2)13(21)11-12(16(14)26-15)19(24)28-18(11)23/h4-5,19,21,24H,1-3H3Key: SKCUFZLDTAYNBZ-UHFFFAOYSA-N
SMILES
  • O=C1OC(O)C2=C3C(OC(C(C(C)=CC(OC)=C4C=O)=C4O3)=O)=C(C)C(O)=C21
Properties
Chemical formula C19H14O9
Molar mass 386.312 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Stictic acid is an aromatic organic compound, a product of secondary metabolism in some species of lichens.

Stictic acid is the subject of preliminary biomedical research. Stictic acid has cytotoxic and apoptotic effects in vitro. Computational studies suggest stictic acid may also stimulate p53 reactivation.

References

  1. Lohézic-Le Dévéhat, Françoise; Tomasi, Sophie; Elix, John A.; Bernard, Aurélie; Rouaud, Isabelle; Uriac, Philippe; Boustie, Joël (2007). "Stictic Acid Derivatives from the Lichen Usnea articulata and Their Antioxidant Activities". Journal of Natural Products. 70 (7): 1218–20. doi:10.1021/np070145k. PMID 17629329.
  2. Correché, ER; Enriz, RD; Piovano, M; Garbarino, J; Gómez-Lechón, MJ (2004). "Cytotoxic and apoptotic effects on hepatocytes of secondary metabolites obtained from lichens". Alternatives to Laboratory Animals. 32 (6): 605–15. doi:10.1177/026119290403200611. PMID 15757498. S2CID 31487885.
  3. Wassman, Christopher D.; Baronio, Roberta; Demir, Özlem; Wallentine, Brad D.; Chen, Chiung-Kuang; Hall, Linda V.; Salehi, Faezeh; Lin, Da-Wei; Chung, Benjamin P.; Wesley Hatfield, G.; Richard Chamberlin, A.; Luecke, Hartmut; Lathrop, Richard H.; Kaiser, Peter; Amaro, Rommie E. (2013). "Computational identification of a transiently open L1/S3 pocket for reactivation of mutant p53". Nature Communications. 4: 1407. Bibcode:2013NatCo...4.1407W. doi:10.1038/ncomms2361. PMC 3562459. PMID 23360998.


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