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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-trioxabenzo[5,6]cyclohepta[1,2-e]indene-11-carbaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.161.455 Edit this at Wikidata
  • 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,1-3H3
    Key: SKCUFZLDTAYNBZ-UHFFFAOYSA-N
  • O=C1OC(O)C2=C3C(OC(C(C(C)=CC(OC)=C4C=O)=C4O3)=O)=C(C)C(O)=C21
Properties
C19H14O9
Molar mass 386.312 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stictic acid is an aromatic organic compound, a product of secondary metabolism in some species of lichens.[1]

Stictic acid is the subject of preliminary biomedical research. Stictic acid has cytotoxic and apoptotic effects in vitro.[2] Computational studies suggest stictic acid may also stimulate p53 reactivation.[3]

References

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  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.