Fumarprotocetraric acid

Fumarprotocetraric acid

Names
IUPAC name 4-[[(E)-3-Carboxyprop-2-enoyl]oxymethyl]-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
Other names Fumaroprotocetraric acid
Identifiers
CAS Number	489-50-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:144157
ChEMBL	ChEMBL366861
ChemSpider	4476288
ECHA InfoCard	100.006.999
EC Number	207-698-8
PubChem CID	5317419
UNII	5VJ6J3A960
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^−1
Appearance	Colorless, odorless solid with bitter taste[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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).[2]

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

• Callopisma teicholytum [Ach.][3]
• Cetraria fahluensis [L.][3][4]
• Cetraria islandica [L.][3][4]
• Cladina rangiferina [L.][3][4]
• Cladina silvatica [L.][3][4]
• Cladonia chlorophaea [Flörke][3][4]
• Cladonia fimbriata [L.] var. apolepta [Ach.] f. coniocraea [Flörke][4]
• Cladonia fimbriata [L.] var. cornuto-radiata [Coem.][3][4]
• Cladonia fimbriata [L.] var. simplex [Weis] f. major [Hag.][3][4]
• Cladonia fimbriata [L.] var. simplex [Weis] f. minor [Hag.][3][4]
• Cladonia foliacea [Huds.] var. alcicornis [Lightf.][4]
• Cladonia foliacea [Huds.] var. convoluta [Lam.][4]
• Cladonia furcata [Huds.] var. pinnata [Flörke][4]
• Cladonia furcata [Huds.] var. racemosa [Hoffm.][4]
• Cladonia gracilis [L.] var. chordalis [Flörke][3][4]
• Cladonia gracilis [L.] var. elongata [Jacq.][4]
• Cladonia pityrea [Flörke] var. cladomorpha [Flörke][3][4]
• Cladonia pityrea [Flörke] var. Zwackhii [Wainio][4]
• Cladonia pyxidata [L.] var. cereina [Arnold][4]
• Cladonia pyxidata [L.] var. neglecta [Flörke][4]
• Cladonia subcervicornis [Wainio][3][4]
• Cladonia verticillata [Hoffm.] var. cervicornis [Ach.] f. phyllophora [(Flörke) Sandstede][4]
• Cladonia verticillata [Hoffm.] var. evoluta [Wainio][4]
• Dendrographa leucophaea [Tuck.][3][4]
• Parmelia stygia [(L.) Ach.][1]

Pharmacology research

Fumarprotocetraric acid has antibacterial activity.[1] It also induces an immunostimulating effect in vitro by triggering the formation of hydrogen peroxide.[1] Furthermore, cytotoxicity against two cancer cell lines has been demonstrated.[1]

References

1. Entry on Fumarprotocetrarsäure. at: Römpp Online. Georg Thieme Verlag, retrieved January 5, 2025.Error in template * unknown parameter name (Template:RömppOnline): "1"
2. Egon Stahl, Werner Schild (1986). Isolierung und Charakterisierung von Naturstoffen (1st ed.). Stuttgart/New York: Gustav Fischer Verlag. p. 92.
3. Wilhelm Zopf (1907). Die Flechtenstoffe in chemischer, botanischer, pharmakologischer und technischer Beziehung (1st ed.). Gustav Fischer Verlag. pp. 172–176.
4. 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