Chemistry:Fumarprotocetraric acid
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| 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
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| Other names
Fumaroprotocetraric acid
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| 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). | |
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Tracking categories (test):
Fumarprotocetraric acid is a chemical compound with the chemical formula C
22H
16O
12. It is a secondary metabolite produced by a variety of lichens.
Occurrence
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
- ↑ 1.0 1.1 1.2 1.3 1.4 Entry on Fumarprotocetrarsäure. at: Römpp Online. Georg Thieme Verlag, retrieved January 5, 2025.
- ↑ Egon Stahl, Werner Schild (1986). Isolierung und Charakterisierung von Naturstoffen (1st ed.). Stuttgart/New York: Gustav Fischer Verlag. pp. 92.
- ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 Wilhelm Zopf (1907). Die Flechtenstoffe in chemischer, botanischer, pharmakologischer und technischer Beziehung (1st ed.). Gustav Fischer Verlag. pp. 172–176.
- ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 4.10 4.11 4.12 4.13 4.14 4.15 4.16 4.17 4.18 4.19 4.20 4.21 4.22 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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