Purpurogallin

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

MedKoo CAT#: 406451

CAS#: 569-77-7

Description: Purpurogallin is a red, crystalline compound, and the aglycon of several glycosides from nutgalls and oak barks. It can inhibit hydroxyestradiol methylation by catechol-O-methyltransferase. It potently and specifically inhibits PLK, TLR1/TLR2 activation pathway. Purpurogallin showed antiplatelet and antithrombotic activities; anti‑inflammatory effects; antitumor activity, anti-oxidation activities; hepatoprotecting effects; antibacterial activity toward gram-positive bacteria.


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Purpurogallin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 406451
Name: Purpurogallin
CAS#: 569-77-7
Chemical Formula: C11H8O5
Exact Mass: 220.03717
Molecular Weight: 220.17822
Elemental Analysis: C, 60.00; H, 3.66; O, 36.33


Synonym: Purpurogallin

IUPAC/Chemical Name: 2,3,4,5-tetrahydroxy-6H-benzo[7]annulen-6-one.

InChi Key: WDGFFVCWBZVLCE-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)

SMILES Code: O=C1C=CC=C(C=C(O)C(O)=C2O)C2=C1O


Technical Data

Appearance:
red 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, not in water

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Ku SK, Bae JS. Antiplatelet and antithrombotic activities of purpurogallin in vitro and in vivo. BMB Rep. 2013 Dec 1. pii: 2493. [Epub ahead of print] PubMed PMID: 24286332.

2: Park HY, Kim TH, Kim CG, Kim GY, Kim CM, Kim ND, Kim BW, Hwang HJ, Choi YH. Purpurogallin exerts anti inflammatory effects in lipopolysaccharide stimulated BV2 microglial cells through the inactivation of the NF κB and MAPK signaling pathways. Int J Mol Med. 2013 Nov;32(5):1171-8. doi: 10.3892/ijmm.2013.1478. Epub 2013 Aug 30. PubMed PMID: 24002379.

3: Ghadiri M, Kariminia HR, Roosta Azad R. Spectrophotometric determination of sulfide based on peroxidase inhibition by detection of purpurogallin formation. Ecotoxicol Environ Saf. 2013 May;91:117-21. doi: 10.1016/j.ecoenv.2013.01.015. Epub 2013 Feb 20. PubMed PMID: 23433554.

4: Kim TH, Ku SK, Lee IC, Bae JS. Anti-inflammatory functions of purpurogallin in LPS-activated human endothelial cells. BMB Rep. 2012 Mar;45(3):200-5. doi: 10.5483/BMBRep.2012.45.3.200. PubMed PMID: 22449709.

5: Remias D, Schwaiger S, Aigner S, Leya T, Stuppner H, Lütz C. Characterization of an UV- and VIS-absorbing, purpurogallin-derived secondary pigment new to algae and highly abundant in Mesotaenium berggrenii (Zygnematophyceae, Chlorophyta), an extremophyte living on glaciers. FEMS Microbiol Ecol. 2012 Mar;79(3):638-48. doi: 10.1111/j.1574-6941.2011.01245.x. Epub 2011 Nov 30. PubMed PMID: 22092588.

6: Huang YL, Tsujita T, Tanaka T, Matsuo Y, Kouno I, Li DP, Nonaka G. Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa. Phytochemistry. 2011 Nov;72(16):2006-14. doi: 10.1016/j.phytochem.2011.07.007. Epub 2011 Aug 8. PubMed PMID: 21831402.

7: Mahmoud ME, Hafez OF, Osman MM, Yakout AA, Alrefaay A. Hybrid inorganic/organic alumina adsorbents-functionalized-purpurogallin for removal and preconcentration of Cr(III), Fe(III), Cu(II), Cd(II) and Pb(II) from underground water. J Hazard Mater. 2010 Apr 15;176(1-3):906-12. doi: 10.1016/j.jhazmat.2009.11.122. Epub 2009 Nov 27. PubMed PMID: 20031308.

8: Nakano S, Sakamoto K, Takenobu A, Kawashima T. Flow-injection chemiluminescent determination of vanadium(IV) and total vanadium by means of catalysis on the periodate oxidation of purpurogallin. Talanta. 2002 Dec 6;58(6):1263-70. PubMed PMID: 18968864.

9: Miyazaki K, Arai S, Iwamoto T, Takasaki M, Tomoda A. Metabolism of pyrogallol to purpurogallin by human erythrocytic hemoglobin. Tohoku J Exp Med. 2004 Aug;203(4):319-30. PubMed PMID: 15297737.

10: O'Coinceanainn M, Astill C, Baderschneider B. Coordination of aluminium with purpurogallin and theaflavin digallate. J Inorg Biochem. 2003 Sep 1;96(4):463-8. PubMed PMID: 13678812.

11: Abou-Karam M, Shier WT. Inhibition of oncogene product enzyme activity as an approach to cancer chemoprevention. Tyrosine-specific protein kinase inhibition by purpurogallin from Quercus sp. nutgall. Phytother Res. 1999 Jun;13(4):337-40. PubMed PMID: 10404543.

12: Sheu SY, Lai CH, Chiang HC. Inhibition of xanthine oxidase by purpurogallin and silymarin group. Anticancer Res. 1998 Jan-Feb;18(1A):263-7. PubMed PMID: 9568088.

13: Zeng LH, Rootman DS, Burnstein A, Wu J, Wu TW. Morin hydrate: a better protector than purpurogallin of corneal endothelial cell damage induced by xanthine oxidase and SIN-1. Curr Eye Res. 1998 Feb;17(2):149-52. PubMed PMID: 9523092.

14: Inamori Y, Muro C, Sajima E, Katagiri M, Okamoto Y, Tanaka H, Sakagami Y, Tsujibo H. Biological activity of purpurogallin. Biosci Biotechnol Biochem. 1997 May;61(5):890-2. PubMed PMID: 9178568.

15: Wu TW, Zeng LH, Wu J, Fung KP, Weisel RD, Hempel A, Camerman N. Molecular structure and antioxidant specificity of purpurogallin in three types of human cardiovascular cells. Biochem Pharmacol. 1996 Oct 11;52(7):1073-80. PubMed PMID: 8831727.

16: Fung KP, Wu TW, Lui CP. Purpurogallin inhibits DNA synthesis of murine fibrosarcoma L-929 and human U-87 MG glioblastoma cells in vitro. Chemotherapy. 1996 May-Jun;42(3):199-205. PubMed PMID: 8983887.

17: Nozaki O, Ji X, Kricka LJ. New enhancers for the chemiluminescent peroxidase catalysed chemiluminescent oxidation of pyrogallol and purpurogallin. J Biolumin Chemilumin. 1995 May-Jun;10(3):151-6. PubMed PMID: 7676857.

18: Prasad K, Kapoor R, Lee P. Purpurogallin, a scavenger of polymorphonuclear leukocyte-derived oxyradicals. Mol Cell Biochem. 1994 Oct 12;139(1):27-32. PubMed PMID: 7854340.

19: Rootman DS, Bindish R, Zeng LH, Hasany SM, Wu TW. Purpurogallin as a cytoprotector of cultured rabbit corneal endothelium. Can J Ophthalmol. 1994 Oct;29(5):220-3. PubMed PMID: 7859173.

20: Prasad K, Laxdal VA. Evaluation of hydroxyl radical-scavenging property of purpurogallin using high pressure liquid chromatography. Mol Cell Biochem. 1994 Jun 29;135(2):153-8. PubMed PMID: 7838143.