Fumarprotocetraric acid - Misplaced Pages

Fumarprotocetraric acid
Names

IUPAC name 4-oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzobenzodioxepine-2-carboxylic acid
Other names Fumaroprotocetraric acid
Identifiers
CAS Number	489-50-9
3D model (JSmol)	Interactive image
ECHA InfoCard	100.006.999
PubChem CID	5317419
CompTox Dashboard (EPA)	DTXSID801313939
InChI InChI=1S/C22H16O12/c1-8-5-12(24)10(6-23)19-15(8)22(31)34-20-11(7-32-14(27)4-3-13(25)26)17(28)16(21(29)30)9(2)18(20)33-19/h3-6,24,28H,7H2,1-2H3,(H,25,26)(H,29,30)/b4-3+Key: VEGGRTFDFMUBPD-ONEGZZNKSA-N
SMILES CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=C(C(=C3COC(=O)/C=C/C(=O)O)O)C(=O)O)C)C=O)O
Properties
Chemical formula	C₂₂H₁₆O₁₂
Molar mass	472.358 g·mol
Appearance	Colorless, odorless solid with bitter taste
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Fumarprotocetraric acid is a chemical compound with the chemical formula C₂₂H₁₆O₁₂. It is a secondary metabolite produced by a variety of lichens.

Occurence

Fumarprotocetraric acid is mainly known for its occurrence in Iceland moss (Cetraria islandica), where it is present in a mass fraction of 1–2% (dried thallus).

In addition, fumarprotocetraric acid has been detected in many other lichens, including:

Callopisma teicholytum
Cetraria fahluensis
Cetraria islandica
Cladina rangiferina
Cladina silvatica
Cladonia chlorophaea
Cladonia fimbriata var. apolepta f. coniocraea
Cladonia fimbriata var. cornuto-radiata
Cladonia fimbriata var. simplex f. major
Cladonia fimbriata var. simplex f. minor
Cladonia foliacea var. alcicornis
Cladonia foliacea var. convoluta
Cladonia furcata var. pinnata
Cladonia furcata var. racemosa
Cladonia gracilis var. chordalis
Cladonia gracilis var. elongata
Cladonia pityrea var. cladomorpha
Cladonia pityrea var. Zwackhii
Cladonia pyxidata var. cereina
Cladonia pyxidata var. neglecta
Cladonia subcervicornis
Cladonia verticillata var. cervicornis f. phyllophora
Cladonia verticillata var. evoluta
Dendrographa leucophaea
Parmelia stygia

Pharmacology research

Fumarprotocetraric acid has antibacterial activity. It also induces an immunostimulating effect in vitro by triggering the formation of hydrogen peroxide. Furthermore, cytotoxicity against two cancer cell lines has been demonstrated.

References

^ Entry on Fumarprotocetrarsäure. at: Römpp Online. Georg Thieme Verlag, retrieved January 5, 2025.Error in template * unknown parameter name (Template:RömppOnline): "1"
Egon Stahl, Werner Schild (1986). Isolierung und Charakterisierung von Naturstoffen (1st ed.). Stuttgart/New York: Gustav Fischer Verlag. p. 92.
^ Wilhelm Zopf (1907). Die Flechtenstoffe in chemischer, botanischer, pharmakologischer und technischer Beziehung (1st ed.). Gustav Fischer Verlag. pp. 172–176.
^ Emil Abderhalden, ed. (1912), Biochemisches Handlexikon. Gerbstoffe, Flechtenstoffe, Saponine, Bitterstoffe, Terpene, Ätherische Öle, Harze, Kautschuk (1. Auflage ed.), Berlin/Heidelberg: Springer Verlag, pp. 74 f

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