MedKoo Cat#: 463430 | Name: Fumarprotocetraric acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fumarprotocetraric acid is a natural antimicrobial agent, showing neuroprotective, expectorant, and antioxidant activities.

Chemical Structure

Fumarprotocetraric acid
Fumarprotocetraric acid
CAS#489-50-9

Theoretical Analysis

MedKoo Cat#: 463430

Name: Fumarprotocetraric acid

CAS#: 489-50-9

Chemical Formula: C22H16O12

Exact Mass: 472.0642

Molecular Weight: 472.36

Elemental Analysis: C, 55.94; H, 3.41; O, 40.64

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Fumarprotocetraric acid; NSC-685588; NSC685588; NSC 685588;
IUPAC/Chemical Name
(E)-9-(((3-carboxyacryloyl)oxy)methyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid
InChi Key
VEGGRTFDFMUBPD-ONEGZZNKSA-N
InChi Code
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+
SMILES Code
OC(C1=C(C)C2=C(OC(C(C(C)=CC(O)=C3C=O)=C3O2)=O)C(COC(/C=C/C(O)=O)=O)=C1O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 472.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Komaty S, Sauvager A, Bazureau JP, Tomasi S, Paquin L. Efficiency and selectivity of ionic liquids in microwave-assisted extraction of major lichen phenolic compounds: a scalable process with recycling of ionic liquids. Phytochem Anal. 2020 Nov 4. doi: 10.1002/pca.3008. Epub ahead of print. PMID: 33150689. 2: Elshobary ME, Becker MG, Kalichuk JL, Chan AC, Belmonte MF, Piercey-Normore MD. Tissue-specific localization of polyketide synthase and other associated genes in the lichen, Cladonia rangiferina, using laser microdissection. Phytochemistry. 2018 Dec;156:142-150. doi: 10.1016/j.phytochem.2018.09.011. Epub 2018 Oct 5. PMID: 30296707. 3: Shukla I, Azmi L, Gupta SS, Upreti DK, Rao CV. Amelioration of anti- hepatotoxic effect by Lichen rangiferinus against alcohol induced liver damage in rats. J Ayurveda Integr Med. 2019 Jul-Sep;10(3):171-177. doi: 10.1016/j.jaim.2017.08.007. Epub 2018 Feb 1. PMID: 29395895; PMCID: PMC6822147. 4: Fernández-Moriano C, Divakar PK, Crespo A, Gómez-Serranillos MP. In vitro neuroprotective potential of lichen metabolite fumarprotocetraric acid via intracellular redox modulation. Toxicol Appl Pharmacol. 2017 Feb 1;316:83-94. doi: 10.1016/j.taap.2016.12.020. Epub 2016 Dec 29. PMID: 28041784. 5: Elshobary ME, Osman ME, Abo-Shady AM, Komatsu E, Perreault H, Sorensen J, Piercey-Normore MD. Algal carbohydrates affect polyketide synthesis of the lichen-forming fungus Cladonia rangiferina. Mycologia. 2016 Jul- Aug;108(4):646-56. doi: 10.3852/15-263. Epub 2016 Apr 18. PMID: 27091386. 6: Fernández-Moriano C, Divakar PK, Crespo A, Gómez-Serranillos MP. Neuroprotective activity and cytotoxic potential of two Parmeliaceae lichens: Identification of active compounds. Phytomedicine. 2015 Aug 15;22(9):847-55. doi: 10.1016/j.phymed.2015.06.005. Epub 2015 Jun 27. PMID: 26220632. 7: Igoli JO, Gray AI, Clements CJ, Kantheti P, Singla RK. Antitrypanosomal activity & docking studies of isolated constituents from the lichen Cetraria islandica: possibly multifunctional scaffolds. Curr Top Med Chem. 2014;14(8):1014-21. doi: 10.2174/1568026614666140324122323. PMID: 24660683. 8: de Barros Alves GM, de Sousa Maia MB, de Souza Franco E, Galvão AM, da Silva TG, Gomes RM, Martins MB, da Silva Falcão EP, de Castro CM, da Silva NH. Expectorant and antioxidant activities of purified fumarprotocetraric acid from Cladonia verticillaris lichen in mice. Pulm Pharmacol Ther. 2014 Apr;27(2):139-43. doi: 10.1016/j.pupt.2013.07.002. Epub 2013 Jul 19. PMID: 23872116. 9: Lohézic-Le Dévéhat F, Legouin B, Couteau C, Boustie J, Coiffard L. Lichenic extracts and metabolites as UV filters. J Photochem Photobiol B. 2013 Mar 5;120:17-28. doi: 10.1016/j.jphotobiol.2013.01.009. Epub 2013 Jan 26. PMID: 23416709. 10: Pompilio A, Pomponio S, Di Vincenzo V, Crocetta V, Nicoletti M, Piovano M, Garbarino JA, Di Bonaventura G. Antimicrobial and antibiofilm activity of secondary metabolites of lichens against methicillin-resistant Staphylococcus aureus strains from cystic fibrosis patients. Future Microbiol. 2013 Feb;8(2):281-92. doi: 10.2217/fmb.12.142. PMID: 23374132. 11: Celenza G, Segatore B, Setacci D, Perilli M, Brisdelli F, Bellio P, Piovano M, Garbarino JA, Amicosante G, Nicoletti M. Antibacterial activity of selected metabolites from Chilean lichen species against methicillin-resistant staphylococci. Nat Prod Res. 2013;27(17):1528-31. doi: 10.1080/14786419.2012.730043. Epub 2012 Oct 2. PMID: 23030591. 12: Kosanić M, Ranković B. Antioxidant and antimicrobial properties of some lichens and their constituents. J Med Food. 2011 Dec;14(12):1624-30. doi: 10.1089/jmf.2010.0316. Epub 2011 Aug 23. PMID: 21861720. 13: Hauck M, Jürgens SR, Huneck S, Leuschner C. High acidity tolerance in lichens with fumarprotocetraric, perlatolic or thamnolic acids is correlated with low pKa1 values of these lichen substances. Environ Pollut. 2009 Oct;157(10):2776-80. doi: 10.1016/j.envpol.2009.04.022. Epub 2009 May 22. PMID: 19464777. 14: Wang XY, Hur H, Lee YM, Bae F, Koh YJ, Hur JS. Cladonia peziziformis (Lichenized Ascomycota, Cladoniaceae) New to Korea. Mycobiology. 2008 Sep;36(3):193-4. doi: 10.4489/MYCO.2008.36.3.193. Epub 2008 Sep 30. PMID: 23997624; PMCID: PMC3755193. 15: Hauck M. Susceptibility to acidic precipitation contributes to the decline of the terricolous lichens Cetraria aculeata and Cetraria islandica in central Europe. Environ Pollut. 2008 Apr;152(3):731-5. doi: 10.1016/j.envpol.2007.06.046. Epub 2007 Nov 28. PMID: 18053625. 16: Kristmundsdóttir T, Jónsdóttir E, Ogmundsdóttir HM, Ingólfsdóttir K. Solubilization of poorly soluble lichen metabolites for biological testing on cell lines. Eur J Pharm Sci. 2005 Apr;24(5):539-43. doi: 10.1016/j.ejps.2005.01.011. PMID: 15784343. 17: Bézivin C, Tomasi S, Rouaud I, Delcros JG, Boustie J. Cytotoxic activity of compounds from the lichen: Cladonia convoluta. Planta Med. 2004 Sep;70(9):874-7. doi: 10.1055/s-2004-827240. PMID: 15386197. 18: Yilmaz M, Türk AO, Tay T, Kivanç M. The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents. Z Naturforsch C J Biosci. 2004 Mar- Apr;59(3-4):249-54. doi: 10.1515/znc-2004-3-423. PMID: 15241936. 19: Hausen BM, Emde L, Marks V. An investigation of the allergenic constituents of Cladonia stellaris (Opiz) Pous & Vezda ('silver moss', 'reindeer moss' or 'reindeer lichen'). Contact Dermatitis. 1993 Feb;28(2):70-6. doi: 10.1111/j.1600-0536.1993.tb03344.x. PMID: 8458221. 20: Dahlquist I, Fregert S. Contact allergy to atranorin in lichens and perfumes. Contact Dermatitis. 1980 Jan;6(2):111-9. doi: 10.1111/j.1600-0536.1980.tb03917.x. PMID: 7398261.