PURPUROGALLIN

Base Information

• Chemical Name: PURPUROGALLIN
• CAS No.: 569-77-7
• Molecular Formula: C11H8 O5
• Molecular Weight: 220.182
• Hs Code.: 2914400090
• Mol file: 569-77-7.mol

Synonyms:Purpurogallin(6CI); 2,3,4,6-Tetrahydroxy-5H-benzo[a]cyclohepten-5-one; NSC 35676; NSC 646653

Chemical Property of PURPUROGALLIN

Chemical Property:

• Vapor Pressure: 1.46E-06mmHg at 25°C
• Melting Point: 275 °C (dec.)(lit.)
• Refractive Index: 1.5140 (estimate)
• Boiling Point: 357.9°Cat760mmHg
• PKA: 6.75±0.20(Predicted)
• Flash Point: 184.5°C
• PSA: 97.99000
• Density: 1.74g/cm³
• LogP: 1.02240
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetrahydroxy-5H-benzo[7]annulen-5-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Purpurogallin is a phenol that has been found in D. divisa and a derivative of pyrogallol that has diverse biological activities, including antimicrobial, antioxidant, and enzyme inhibitory properties. It is active against the Gram-positive bacteria S. aureus, methicillin-resistant S. aureus (MRSA), S. epidermidis, and B. subtilis (MICs = 11-110 μg/ml), the Gram-negative bacteria S. marcescens, P. vulgaris, K. pneumoniae, E. coli, S. typhi, and E. cloacae (MIC = 110 μg/ml for all), as well as P. falciparum strain FCB1 clone NC-1 (IC50 = 55 μM). Purpurogallin (2, 5, and 10 μM) scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay and reduces hydrogen peroxide- and radiation-induced production of reactive oxygen species (ROS) in HaCaT keratinocytes. It inhibits the activity of EGFR, glutathione-S-transferase (GST), prolyl endopeptidase, and glyoxalase I (IC50s = 27.5, 8, 16, and 50 μM, respectively), as well as catechol O-methyltransferase (COMT; Ki = 0.074 μM), in cell-free assays.
• Uses: xanthine oxidase inhibitor, antioxidant

Technology Process of PURPUROGALLIN

There total 30 articles about PURPUROGALLIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-hydroxyresorcinol (87-66-1) → purpurogallin (569-77-7)

Guidance literature:

With dihydrogen peroxide; oxygen; In ethanol; at 27 ℃; for 2h; under 760.051 Torr;

DOI:10.1002/cctc.201901659

Reference yield: 11.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + 2-hydroxyresorcinol (87-66-1) → LDN-0096728 (947-60-4) + purpurogallin (569-77-7)

Guidance literature:

With dihydrogen peroxide; horseradish peroxidase; In acetone; pH=5.0;

Reference yield:

(-)-epigallocathechin gallate (2596-50-1,4233-96-9,5127-64-0,19065-20-4,107965-88-8,137766-94-0,989-51-5) + 2-hydroxyresorcinol (87-66-1) → purpurogallin (569-77-7) + epitheaflagallin 3-O-gallate (102067-92-5)

Guidance literature:

With sodium hydrogencarbonate; potassium hexacyanoferrate(III); In water; for 1h;

DOI:10.1248/cpb.34.61

upstream raw materials:

purpurogallin-4-carboxylic acid

p-benzoquinone

2-hydroxyresorcinol

(-)-epigallocathechin gallate

Downstream raw materials:

2,3,4,6-tetramethoxy-5H-benzo[7]annulen-5-one

4-hydroxy-2,3,6-trimethoxy-5H-benzo[7]annulen-5-one

3-Chlor-4',5',6'-trihydroxy-3'-benzolsulfonyl-6,7-benzo-tropolon

3'-Chlor-4',5',6'-trihydroxy-3-benzolsulfonyl-6,7-benzo-tropolon

Refernces

• 1、 Chen, Yao,Wojtas, Lukasz,Ma, Shengqian,Zaworotko, Michael J.,Zhang, Zhenjie. "Post-synthetic transformation of a Zn(II) polyhedral coordination network into a new supramolecular isomer of HKUST-1". . p. 8866 - 8869. Retrieved 2017.
• 2、 Maurya, Mannar R.,Chaudhary, Nikita,Avecilla, Fernando,Correia, Isabel. "Mimicking peroxidase activity by a polymer-supported oxidovanadium(IV) Schiff base complex derived from salicylaldehyde and 1,3-diamino-2-hydroxypropane". . p. 181 - 192. Retrieved 2015.
• 3、 Yamaguchi, Hiroyasu,Tsubouchi, Kaori,Kawaguchi, Kazuhide,Horita, Eri,Harada, Akira. "Peroxidase activity of cationic metalloporphyrin-antibody complexes". . p. 6179 - 6186. Retrieved 2004.
• 4、 Huang, Cancan,Bai, Hua,Li, Chun,Shi, Gaoquan. "A graphene oxide/hemoglobin composite hydrogel for enzymatic catalysis in organic solvents". . p. 4962 - 4964. Retrieved 2011.
• 5、 Maurya, Mannar R.,Uprety, Bhawna,Avecilla, Fernando. "Dioxidomolybdenum(VI) Complexes of Tripodal Tetradentate Ligands for Catalytic Oxygen Atom Transfer between Benzoin and Dimethyl Sulfoxide and for Oxidation of Pyrogallol". . p. 4802 - 4813. Retrieved 2016.
• 6、 Maurya, Mannar R.,Sarkar, Bithika,Avecilla, Fernando,Correia, Isabel. "Vanadium Complexes Derived from Acetyl Pyrazolone and Hydrazides: Structure, Reactivity, Peroxidase Mimicry and Efficient Catalytic Activity for the Oxidation of 1-Phenylethanol". . p. 4028 - 4044. Retrieved 2016.
• 7、 Wang, Qigang,Yang, Zhimou,Ma, Manlung,Chang, Chi K.,Xu, Bing. "High catalytic activities of artificial peroxidases based on supramolecular hydrogels that contain heme models". . p. 5073 - 5078. Retrieved 2008.
• 8、 Kar, Tanmoy,Mandal, Subhra Kanti,Das, Prasanta Kumar. "Influence of pristine SWNTs in supramolecular hydrogelation: Scaffold for superior peroxidase activity of cytochrome c". . p. 8389 - 8391. Retrieved 2012.
• 9、 Ferlin, Francesco,Marini, Alberto,Ascani, Nicola,Ackermann, Lutz,Lanari, Daniela,Vaccaro, Luigi. "Heterogeneous Manganese-Catalyzed Oxidase C?H/C?O Cyclization to Access Pharmaceutically Active Compounds". . p. 449 - 454. Retrieved 2019/12/12.
• 10、 Huang, Xuri,Li, Zhengqiang,Liu, Min,Ma, Li,Sun, Xiaoli,Wang, Zhi,Yan, Jiaqing,Yuan, Long,Zhao, Zijian. "Activity adaptability of a DhHP-6 peroxidase-mimic in wide pH and temperature ranges and solvent media". . p. 1848 - 1857. Retrieved 2020/04/09.