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Consalazinic acid

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Consalazinic acid
Names
IUPAC name 5,13,17-trihydroxy-4,12-bis(hydroxymethyl)-7-methyl-2,10,16-trioxatetracyclooctadeca-1(11),3(8),4,6,12,14(18)-hexaene-9,15-dione
Other names 1,4,10-Trihydroxy-5,11-bis(hydroxymethyl)-8-methyl-7H-isobenzofurobenzodioxepin-3,7(1H)-dione
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
InChI
  • InChI=1S/C18H14O10/c1-5-2-8(21)6(3-19)13-9(5)16(23)27-14-7(4-20)12(22)10-11(15(14)26-13)18(25)28-17(10)24/h2,18-22,25H,3-4H2,1H3Key: VHKZGPSNCSPDGX-UHFFFAOYSA-N
SMILES
  • CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3CO)O)C(=O)OC4O)CO)O
Properties
Chemical formula C18H14O10
Molar mass 390.300 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Consalazinic acid is a chemical compound with the molecular formula C18H14O10. It is classified as a depsidone and is a secondary metabolite produced by a variety of lichens.

Consalazinic acid was first isolated from Parmotrema subisidiosum and described in 1980. It has since been identified in many other lichens.

References

  1. O'Donovan, Donal G.; Roberts, George; Keogh, Myles F. (1980). "Structure of the β-orcinol depsidones, connorstictic and consalazinic acids". Phytochemistry. 19 (11): 2497–2499. Bibcode:1980PChem..19.2497O. doi:10.1016/S0031-9422(00)91070-7.
  2. Culberson, Chicita F.; Culberson, William Louis; Johnson, Anita (1981). "A Standardized TLC Analysis of β-Orcinol Depsidones". The Bryologist. 84 (1): 16–29. doi:10.2307/3242974. JSTOR 3242974.
  3. Skult, Henrik (1984). "The Parmelia omphalodes (Ascomycetes) complex in Eastern Fennoscandia. Chemical and morphological variation". Annales Botanici Fennici. 21 (2): 117–142.
  4. Huneck, S.; Kalb, K. (1990). "Chemistry of South African lichens". Pharmazie. 45 (4): 297.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Feige, G.B.; Lumbsch, H.T.; Huneck, S.; Elix, J.A. (1993). "Identification of lichen substances by a standardized high-performance liquid chromatographic method". Journal of Chromatography A. 646 (2): 417–427. doi:10.1016/0021-9673(93)83356-W.
  6. Narui, Takao; Culberson, Chicita F.; Culberson, William Louis; Johnson, Anita; Shibata, Shoji (1996). "A Contribution to the Chemistry of the Lichen Family Umbilicariaceae (Ascomycotina)". The Bryologist. 99 (2): 199–211. doi:10.2307/3244550. JSTOR 3244550.
  7. Stocker-Wörgötter, Elfie; Elix, John A.; Grube, Martin (2004). "Secondary Chemistry of Lichen-forming Fungi: Chemosyndromic Variation and DNA-analyses of Cultures and Chemotypes in the Ramalina farinacea Complex". The Bryologist. 107 (2): 152. doi:10.1639/0007-2745(2004)107[0152:SCOLFC]2.0.CO;2. ISSN 0007-2745.
  8. Torres-Benítez, Alfredo; Rivera-Montalvo, María; Sepúlveda, Beatriz; Castro, Olivio; Nagles, Edgar; Simirgiotis, Mario; García-Beltrán, Olimpo; Areche, Carlos (2017). "Metabolomic Analysis of Two Parmotrema Lichens: P. Robustum (Degel.) Hale and P. Andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS". Molecules. 22 (11): 1861. doi:10.3390/molecules22111861. PMC 6150355. PMID 29084151.
  9. Kumar, K.; Siva, Bandi; Sarma, V.U.M.; Mohabe, Satish; Reddy, A. Madhusudana; Boustie, Joel; Tiwari, Ashok K.; Rao, N. Rama; Babu, K. Suresh (2018). "UPLC–MS/MS quantitative analysis and structural fragmentation study of five Parmotrema lichens from the Eastern Ghats" (PDF). Journal of Pharmaceutical and Biomedical Analysis. 156: 45–57. doi:10.1016/j.jpba.2018.04.017. PMID 29689468.
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