Quininic acid

Base Information

• Chemical Name: Quininic acid
• CAS No.: 86-68-0
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 2933499090
• European Community (EC) Number: 617-906-2
• NSC Number: 403610
• UNII: FS902DD40C
• DSSTox Substance ID: DTXSID70323339
• Nikkaji Number: J4.263C
• Wikidata: Q27278170
• Metabolomics Workbench ID: 123428
• ChEMBL ID: CHEMBL1396390
• Mol file: 86-68-0.mol

Synonyms:Quininic acid;86-68-0;6-methoxyquinoline-4-carboxylic acid;6-Methoxy-4-quinolinecarboxylic acid;6-METHOXY-QUINOLINE-4-CARBOXYLIC ACID;6-Methoxycinchoninic acid;Quininic acid [MI];Cinchoninic acid, 6-methoxy-;NSC-403610;4-Quinolinecarboxylic acid, 6-methoxy-;UNII-FS902DD40C;FS902DD40C;MFCD00024013;Chininsaure;RHODINYLACETATE;Prestwick0_001103;Prestwick1_001103;Prestwick2_001103;Oprea1_238538;SCHEMBL39557;SPBio_003083;CHEMBL1396390;DTXSID70323339;HMS1571M08;HY-N7354;4-Quinolinecarboxylicacid,6-methoxy-;NSC403610;AKOS022505953;SB39106;CAS-86-68-0;NCGC00016341-01;AS-41373;SY055224;CS-0113794;FT-0631408;M2751;A19249;EN300-629989;AE-562/43287134;Q27278170;Z1508915640

Chemical Property of Quininic acid

Chemical Property:

• Vapor Pressure: 1.25E-06mmHg at 25°C
• Melting Point: 280°C (decompose)
• Refractive Index: 1.648
• Boiling Point: 385.4 °C at 760 mmHg
• PKA: 5.53(at 25℃)
• Flash Point: 186.9 °C
• PSA: 59.42000
• Density: 1.325 g/cm³
• LogP: 1.94160
• Storage Temp.: 2-8°C
• Solubility.: Solubility Slightly soluble in water, cold ethanol, ether
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 244

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

6-Methoxyquinoline-4-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1)C(=O)O
• Description: 6-Methoxy-4-quinolinecarboxylic Acid is a derivative of 4-quinolinecarboxylic acids, which is a potential antitumor (such as leukemia) and antiviral agent. It also has the potential to be used as immunosuppressive reagent as well as for the treatment of skin and epithelial diseases.
• Uses: 6-methoxyquinoline-4-carboxylic Acid is used in the preparation of tetrahydroisoquinoline amides as multidrug resistance reversers.

Technology Process of Quininic acid

There total 28 articles about Quininic acid 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: 90.0%

isopropyl alcohol (67-63-0,8013-70-5) + 6'-methoxycinchonidone (84-31-1) → 6-methoxyquinoline-4-carboxylic acid (86-68-0) + isopropyl 2-((3R,4S)-3-vinylpiperidin-4-yl)acetate (345223-64-5)

Guidance literature:

isopropyl alcohol; With potassium tert-butylate; oxygen; In tetrahydrofuran; at 0 ℃; for 1h;

6'-methoxycinchonidone; With oxygen; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja9100276

Reference yield: 89.4%

quinine sulfate (50-54-4,549-56-4,747-45-5,804-63-7,3106-14-7,7778-93-0,20317-85-5,62389-49-5,62409-09-0,85135-87-1) → 6-methoxyquinoline-4-carboxylic acid (86-68-0)

Guidance literature:

quinine sulfate; With chromium(VI) oxide; manganese(IV) oxide; sulfuric acid; In water; for 3h; Reflux;

With ammonia; In water; at 100 ℃; for 18h;

DOI:10.1080/14756366.2020.1747449

Reference yield:

potassium tert-butylate (865-47-4) + tert-butyl alcohol (75-65-0) + 6'-methoxycinchoninone (14528-53-1) → tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate (52346-11-9) + 6-methoxyquinoline-4-carboxylic acid (86-68-0)

Guidance literature:

DOI:10.1021/ja01208a017

upstream raw materials:

6-methoxyquinoline-4-carbonitrile

6-methoxyquinoline-4-carboxylic acid ethyl ester

2-iodo-6-methoxy-quinoline-4-carboxylic acid

6-methoxy-4-styryl-quinoline

Downstream raw materials:

6-hydroxyquinoline-4-carboxylic acid

methyl 6-methoxyquinoline-4-carboxylate

6-methoxyquinoline-4-carboxylic acid ethyl ester

methylene chloride

Refernces

• 1、 Bartolucci, Gianluca,Braconi, Laura,Colabufo, Nicola Antonio,Contino, Marialessandra,Dei, Silvia,Giampietro, Roberta,Manetti, Dina,Perrone, Maria Grazia,Riganti, Chiara,Romanelli, Maria Novella,Teodori, Elisabetta,Chiaramonte, Niccolò. "6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers". . p. 974 - 992. Retrieved 2020/04/24.
• 2、 Jansen, Koen,Heirbaut, Leen,Cheng, Jonathan D.,Joossens, Jurgen,Ryabtsova, Oxana,Cos, Paul,Maes, Louis,Lambeir, Anne-Marie,De Meester, Ingrid,Augustyns, Koen,Van Der Veken, Pieter. "Selective inhibitors of fibroblast activation protein (FAP) with a (4-quinolinoyl)-glycyl-2-cyanopyrrolidine scaffold". supporting information. p. 491 - 496. Retrieved 2013/07/19.