Succinprotocetraric acid

Succinprotocetraric acid
Names
	IUPAC name Succinprotocetraric acid
	Systematic IUPAC name 4-(3-carboxypropanoyloxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:144306;
PubChem CID	102239721;
	InChI InChI=1S/C22H18O12/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/h5-6,24,28H,3-4,7H2,1-2H3,(H,25,26)(H,29,30) Key: ROISWLBRDLJEFL-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=C(C(=C3COC(=O)CCC(=O)O)O)C(=O)O)C)C=O)O;
Properties
Chemical formula	C22H18O12
Molar mass	474.374 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Succinprotocetraric acid is an organic chemical compound with the formula C₂₂H₁₈O₁₂. It is the ester of succinic acid and protocetraric acid and it is classified as a depsidone.

Succinprotocetraric acid is produced by certain lichens.[1]

Known sources

Buellia capensis
Chondropsis semiviridis
Menegazzia petraea
Parmelia reptans
Cladonia metacorallifera[2]
Cladonia rangiferina[3]
Cladonia arbuscula[3]
Cetraria islandica, though only of a specific chemotype[4]

References

Baker, C.; Elix, J. A.; Murphy, D. P. H.; Kurokawa, S.; Sargent, M. V. (1973). "Parmelia reptans, a new lichen species producing the depsidone, succinprotocetraric acid". Australian Journal of Botany. 21 (1): 137–140. doi:10.1071/bt9730137. ISSN 1444-9862.
Sepúlveda, Beatriz; Cornejo, Alberto; Bárcenas-Pérez, Daniela; Cheel, José; Areche, Carlos (1 February 2022). "Two New Fumarprotocetraric Acid Lactones Identified and Characterized by UHPLC-PDA/ESI/ORBITRAP/MS/MS from the Antarctic Lichen Cladonia metacorallifera". Separations. 9 (2): 41. doi:10.3390/separations9020041.
Shishido, Tânia Keiko; Wahlsten, Matti; Laine, Pia; Rikkinen, Jouko; Lundell, Taina; Auvinen, Petri (22 June 2021). "Microbial Communities of Cladonia Lichens and Their Biosynthetic Gene Clusters Potentially Encoding Natural Products". Microorganisms. 9 (7): 1347. doi:10.3390/microorganisms9071347. hdl:10138/331759. PMC 8304397. PMID 34206222.
Xu, Maonian; Heidmarsson, Starri; Thorsteinsdottir, Margret; Kreuzer, Marco; Hawkins, Julie; Omarsdottir, Sesselja; Olafsdottir, Elin Soffia (April 2018). "Authentication of Iceland Moss (Cetraria islandica) by UPLC-QToF-MS chemical profiling and DNA barcoding" (PDF). Food Chemistry. 245: 989–996. doi:10.1016/j.foodchem.2017.11.073. PMID 29287470.

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[1] Baker, C.; Elix, J. A.; Murphy, D. P. H.; Kurokawa, S.; Sargent, M. V. (1973). "Parmelia reptans, a new lichen species producing the depsidone, succinprotocetraric acid". Australian Journal of Botany. 21 (1): 137–140. doi:10.1071/bt9730137. ISSN 1444-9862.

[2] Sepúlveda, Beatriz; Cornejo, Alberto; Bárcenas-Pérez, Daniela; Cheel, José; Areche, Carlos (1 February 2022). "Two New Fumarprotocetraric Acid Lactones Identified and Characterized by UHPLC-PDA/ESI/ORBITRAP/MS/MS from the Antarctic Lichen Cladonia metacorallifera". Separations. 9 (2): 41. doi:10.3390/separations9020041.

[rudolph-3] Shishido, Tânia Keiko; Wahlsten, Matti; Laine, Pia; Rikkinen, Jouko; Lundell, Taina; Auvinen, Petri (22 June 2021). "Microbial Communities of Cladonia Lichens and Their Biosynthetic Gene Clusters Potentially Encoding Natural Products". Microorganisms. 9 (7): 1347. doi:10.3390/microorganisms9071347. hdl:10138/331759. PMC 8304397. PMID 34206222.

[4] Xu, Maonian; Heidmarsson, Starri; Thorsteinsdottir, Margret; Kreuzer, Marco; Hawkins, Julie; Omarsdottir, Sesselja; Olafsdottir, Elin Soffia (April 2018). "Authentication of Iceland Moss (Cetraria islandica) by UPLC-QToF-MS chemical profiling and DNA barcoding" (PDF). Food Chemistry. 245: 989–996. doi:10.1016/j.foodchem.2017.11.073. PMID 29287470.