4-Hydroxyquinoline | CAS#611-36-9 | quinolone compound

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

MedKoo CAT#: 558610

CAS#: 611-36-9

Description: 4-Hydroxyquinoline is a quinolone compound which forms the core moiety of antibacterials.

Chemical Structure

4-Hydroxyquinoline

CAS# 611-36-9

Instruction

Theoretical Analysis

MedKoo Cat#: 558610
Name: 4-Hydroxyquinoline
CAS#: 611-36-9
Chemical Formula: C9H12N2O
Exact Mass: 164.09
Molecular Weight: 164.210
Elemental Analysis: C, 65.83; H, 7.37; N, 17.06; O, 9.74

Price and Availability

Size	Price	Availability
5g	USD 250	2 Weeks
25g	USD 900	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 4-Hydroxyquinoline; 4 Hydroxyquinoline; 4Hydroxyquinoline; Kynurine;

IUPAC/Chemical Name: 4-Hydroxyquinoline

InChi Key: PMZDQRJGMBOQBF-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)

SMILES Code: OC1=CC=NC2=CC=CC=C12

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: 2934.99.03.00

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 164.21 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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Horta P, Kuş N, Henriques MS, Paixão JA, Coelho L, Nogueira F, O'Neill PM, Fausto R, Cristiano ML. Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity. J Org Chem. 2015 Dec 18;80(24):12244-57. doi: 10.1021/acs.joc.5b02169. Epub 2015 Nov 23. PubMed PMID: 26551438.

2: Ortori CA, Dubern JF, Chhabra SR, Cámara M, Hardie K, Williams P, Barrett DA. Simultaneous quantitative profiling of N-acyl-L-homoserine lactone and 2-alkyl-4(1H)-quinolone families of quorum-sensing signaling molecules using LC-MS/MS. Anal Bioanal Chem. 2011 Jan;399(2):839-50. doi: 10.1007/s00216-010-4341-0. Epub 2010 Oct 28. PubMed PMID: 21046079.

3: Sabatini S, Gosetto F, Manfroni G, Tabarrini O, Kaatz GW, Patel D, Cecchetti V. Evolution from a natural flavones nucleus to obtain 2-(4-Propoxyphenyl)quinoline derivatives as potent inhibitors of the S. aureus NorA efflux pump. J Med Chem. 2011 Aug 25;54(16):5722-36. doi: 10.1021/jm200370y. Epub 2011 Aug 3. PubMed PMID: 21751791.

4: Liu ZQ, Han K, Lin YJ, Luo XY. Antioxidative or prooxidative effect of 4-hydroxyquinoline derivatives on free-radical-initiated hemolysis of erythrocytes is due to its distributive status. Biochim Biophys Acta. 2002 Mar 15;1570(2):97-103. PubMed PMID: 11985893.

5: Gai YL, Xiong KC, Chen L, Bu Y, Li XJ, Jiang FL, Hong MC. Visible and NIR photoluminescence properties of a series of novel lanthanide-organic coordination polymers based on hydroxyquinoline-carboxylate ligands. Inorg Chem. 2012 Dec 17;51(24):13128-37. doi: 10.1021/ic301261g. Epub 2012 Dec 3. PubMed PMID: 23205639.

6: Sherin PS, Gritsan NP, Tsentalovich YP. Experimental and quantum chemical study of photochemical properties of 4-hydroxyquinoline. Photochem Photobiol Sci. 2009 Nov;8(11):1550-7. doi: 10.1039/b9pp00017h. Epub 2009 Sep 3. PubMed PMID: 19862413.

7: Ragos GC, Demertzis MA, Issopoulos PB. A high-sensitive spectrofluorimetric method for the determination of micromolar concentrations of iron(III) in bovine liver with 4-hydroxyquinoline. Farmaco. 1998 Aug-Sep;53(8-9):611-6. PubMed PMID: 10081826.

8: Kimmel R, Kafka S, Kosmrlj J. Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones. Carbohydr Res. 2010 Apr 19;345(6):768-79. doi: 10.1016/j.carres.2010.01.023. Epub 2010 Feb 4. PubMed PMID: 20206337.

9: Fetzner S, Drees SL. Old molecules, new biochemistry. Chem Biol. 2013 Dec 19;20(12):1438-40. doi: 10.1016/j.chembiol.2013.12.001. PubMed PMID: 24359847.

10: BACHMAN GB, WELTON DE, et al. Quinoline derivatives from 3-nitro-4-hydroxyquinoline. J Am Chem Soc. 1947 Feb;69(2):365-71. PubMed PMID: 20292440.

11: AVRON M. The inhibition of photoreactions of chloroplasts by 2-alkyl-4-hydroxyquinoline N-oxides. Biochem J. 1961 Apr;78:735-9. PubMed PMID: 13685299; PubMed Central PMCID: PMC1205463.

12: Kwak YG, Jacoby GA, Hooper DC. Induction of plasmid-carried qnrS1 in Escherichia coli by naturally occurring quinolones and quorum-sensing signal molecules. Antimicrob Agents Chemother. 2013 Aug;57(8):4031-4. doi: 10.1128/AAC.00337-13. Epub 2013 May 20. PubMed PMID: 23689721; PubMed Central PMCID: PMC3719764.

13: Samanta A, Guchhait N, Bhattacharya SC. Photophysical aspects of biological photosensitizer Kynurenic acid from the perspective of experimental and quantum chemical study. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Aug 14;129:457-65. doi: 10.1016/j.saa.2014.03.079. Epub 2014 Apr 2. PubMed PMID: 24751782.

14: LIGHTBOWN JW, JACKSON FL. Inhibition of cytochrome systems of heart muscle and certain bacteria by the antagonists of dihydrostreptomycin: 2-alkyl-4-hydroxyquinoline N-oxides. Biochem J. 1956 May;63(1):130-7. PubMed PMID: 13315258; PubMed Central PMCID: PMC1216010.

15: Elinson MN, Merkulova VM, Ilovaisky AI, Demchuk DV, Belyakov PA, Nikishin GI. Electrochemically induced multicomponent assembling of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile: a convenient and efficient way to functionalized spirocyclic [indole-3,4'-pyrano[3,2-c]quinoline] scaffold. Mol Divers. 2010 Nov;14(4):833-9. doi: 10.1007/s11030-009-9207-z. Epub 2009 Nov 17. PubMed PMID: 19921455.

16: de Melo EB. Multivariate SAR/QSAR of 3-aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase (FAS) inhibitors. Eur J Med Chem. 2010 Dec;45(12):5817-26. doi: 10.1016/j.ejmech.2010.09.044. Epub 2010 Sep 29. PubMed PMID: 20965618.

17: Rahn T, Appel B, Baumann W, Jiao H, Börner A, Fischer C, Langer P. Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions. Org Biomol Chem. 2009 May 7;7(9):1931-8. doi: 10.1039/b901092k. Epub 2009 Mar 20. PubMed PMID: 19590790.

18: REITSEMA RH. The chemistry of 4-hydroxyquinolines. Chem Rev. 1948 Aug;43(1):43-68. PubMed PMID: 18876968.

19: BUU-HOI NP, ROYER R. The application of Pfitzinger reactions to the synthesis of quinoline derivatives; a novel route to 4-hydroxyquinolines. J Chem Soc. 1948 Feb;2:106-10. PubMed PMID: 18906363.

20: El-Shennawy AM, Mohamed AH, Abass M. Studies on parasitologic and haematologic activities of an enaminone derivative of 4-hydroxyquinolin-2(1H)-one against murine schistosomiasis mansoni. MedGenMed. 2007 Jan 23;9(1):15. PubMed PMID: 17435624; PubMed Central PMCID: PMC1925031.

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4-Hydroxyquinoline featured