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Oxyquinoline

PubChem CID
1923
Structure
Oxyquinoline_small.png
Oxyquinoline_3D_Structure.png
Oxyquinoline__Crystal_Structure.png
Molecular Formula
Synonyms
  • 8-HYDROXYQUINOLINE
  • quinolin-8-ol
  • 148-24-3
  • 8-quinolinol
  • Oxyquinoline
Molecular Weight
145.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
8-hydroxyquinoline appears as white to off-white or faintly yellow crystalline powder. Phenolic odor. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Quinolin-8-ol is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 8. Its fungicidal properties are used for the control of grey mould on vines and tomatoes. It has a role as an antibacterial agent, an iron chelator, an antiseptic drug and an antifungal agrochemical. It derives from a hydride of a quinoline.
Oxyquinoline is a heterocyclic phenol and derivative of quinoline with antiseptic, disinfectant, and pesticide properties. It is used as a stabilizer for hydrogen peroxide, where it is sometimes added in cosmetic products.
See also: Benzoxiquine (is active moiety of); Acetic acid; oxyquinoline (component of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Oxyquinoline.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 6
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

quinolin-8-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MCJGNVYPOGVAJF-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC2=C(C(=C1)O)N=CC=C2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H7NO
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

148-24-3

2.3.3 Deprecated CAS

123574-67-4, 24804-14-6
123574-67-4

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 UN Number

2.3.7 ChEBI ID

2.3.8 ChEMBL ID

2.3.9 DrugBank ID

2.3.10 DSSTox Substance ID

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 8 Hydroxyquinoline
  • 8 Hydroxyquinoline Sulfate
  • 8 Oxyquinoline
  • 8 Quinolinol
  • 8-Hydroxyquinoline
  • 8-Hydroxyquinoline Sulfate
  • 8-Oxyquinoline
  • 8-Quinolinol
  • Bioquin
  • Chinosol
  • Khinozol
  • Leioderm
  • Oxine
  • Oxyquinol
  • Oxyquinoline
  • Oxyquinoline Potassium Sulfate (2:1)
  • Oxyquinoline Sulfate
  • Quinosol
  • Sulfate, 8-Hydroxyquinoline
  • Sulfate, Oxyquinoline
  • Superol

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
145.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
145.052763847 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
145.052763847 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
33.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
138
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

8-hydroxyquinoline appears as white to off-white or faintly yellow crystalline powder. Phenolic odor. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
White solid with a phenolic odor; [Hawley] White or tan powder; [MSDSonline]

3.2.2 Color / Form

White crystals or white crystalline powder
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600

3.2.3 Odor

Phenolic odor
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600

3.2.4 Boiling Point

513 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
267
Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
Approx 267 °C
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 832

3.2.5 Melting Point

169 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
76
Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
73-75 °C
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600

3.2.6 Solubility

less than 1 mg/mL at 61 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
Insoluble
Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
Soluble in alcohol, acetone, chloroform, benzene, and in formic, acetic, hydrochloric, and sulfuric acids and alkalies.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600
1 part in 1500 parts water
Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 495
In water, 556 mg/l @ 20 °C
Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Ver 5. Tucson, AZ: Univ AZ, College of Pharmacy (1992)

3.2.7 Density

1.034 at 408 °F (NTP, 1992) - Denser than water; will sink
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.034 @ 20 °C
Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-309

3.2.8 Vapor Pressure

0.0016 [mmHg]
1.66X10-3 mm Hg @ 25 °C
Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.

3.2.9 LogP

log Kow = 2.02
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 51

3.2.10 Stability / Shelf Life

DARKENS WHEN EXPOSED TO LIGHT.
Sax, N.I. and R.J. Lewis, Sr. (eds.). Hawley's Condensed Chemical Dictionary. 11th ed. New York: Van Nostrand Reinhold Co., 1987., p. 626

3.2.11 Decomposition

WHEN HEATED TO DECOMP EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2854

3.2.12 Dissociation Constants

pKa
5.017
Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
pKa 5.017; Ka 1.21X10-6 at 20 °C
Lide, D.R. (ed). CRC Handbook of Chemistry and Physics. 72nd ed. Boca Raton, FL: CRC Press, 1991-1992., p. 8-38
pKa1= 5.017; pKa2= 9.812 (conjugate acid)
Perrin DD; Dissociation constants of organic bases in aqueous solution. IUPAC Chem Data Ser: Suppl 1972. Buttersworth, London. (1972)

3.2.13 Collision Cross Section

122.76 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

124.77 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
123.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

3.2.14 Kovats Retention Index

Standard non-polar
1326.3 , 1348.9 , 1339 , 1312
Semi-standard non-polar
1358 , 1362 , 232.24
Standard polar
2153

3.2.15 Other Experimental Properties

Readily forms stable metal chelates
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 101 (1977)
Usually tan /Technical grade/
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600
Pale yellow, crystalline powder; slight saffron odor; burning taste; MP: 175-178 °C; freely sol in water; insol in ether; sol in about 100 parts glycerol; slightly sol in alcohol /8-Hydroxyquinoline sulfate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 832
Darkens when exposed to light
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 600

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Nitrogen Compounds -> Quinolines
Industrial compound
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

3.4.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956

3.4.2 Cosmetics

Cosmetic ingredients (Oxyquinoline) -> CIR (Cosmetic Ingredient Review)
Stabilizing
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.4.3 Pesticides

Bactericides, Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
1H NMR: 24 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Benzol Products Company, Newark, New Jersey
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Varian A-60
Source of Sample
Benzol Products Company, Newark, New Jersey
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Research Organic/Inorganic Chemical Corporation, Sun Valley, California
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
see comment
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

145 99.99

117 56.13

90 15.66

89 15.18

146 10.97

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License
CC BY-NC-SA
2 of 7
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI M-80A
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

145 99.99

117 69.41

89 22.97

90 21.53

63 20.33

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License
CC BY-NC-SA

4.2.2 LC-MS

1 of 7
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
8.051 min
Precursor m/z
146.06
Precursor Adduct
[M+H]+
Top 5 Peaks

146.0601 999

118.065 15

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).
2 of 7
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
60
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
8.051 min
Precursor m/z
146.06
Precursor Adduct
[M+H]+
Top 5 Peaks

146.0601 999

118.0652 150

128.0496 43

86.0035 24

91.0542 16

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).

4.2.3 Other MS

1 of 3
View All
Other MS
MASS: 65043 (NIST/MSDC/EPA Mass Spectral Database, 1990 version)
2 of 3
View All
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI M-80
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

145 999

117 561

90 157

89 152

146 110

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License
CC BY-NC-SA

4.3 UV Spectra

SADTLER REF NUMBER: 187 (IR, PRISM); 63 (IR, GRATING); MAX ABSORPTION (ALCOHOL): 240 NM (LOG E= 4.60); 308 NM (LOG E= 3.47)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-485
UV: 76 (Sadtler Research Laboratories Spectral Collection)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V5 4886

4.4 IR Spectra

IR Spectra
IR: 5568 (Coblentz Society Spectral Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aceto Chemical Company, Flushing, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company LLC
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/aldrich/CDS007114>CDS007114</a>
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Inc.
Catalog Number
H-6878
Lot Number
95C-0045
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fluka, Sigma-Aldrich Company Llc.
Catalog Number
36524
Lot Number
SZBB192XV
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

1 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fluka, Sigma-Aldrich Company Llc.
Catalog Number
36524
Lot Number
SZBB192XV
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fisher Scientific
Catalog Number
O-261
Lot Number
711804
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Other Spectra

Intense mass spectral peaks: 145 m/z (100%), 117 m/z (78%), 90 m/z (30%), 89 m/z (29%)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V5 4886

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Oxyquinoline is used as a biocidal component of several over the counter products. These products are marketed for the purposes of inhibiting abnormal biological growth in the vagina and restoring natural pH.

7.2 Drug Labels

Drug and label
Active ingredient and drug

7.3 Therapeutic Uses

A BACTERIOSTATIC & FUNGISTATIC COMPOUND; USED PRINCIPALLY IN TREATMENT OF MINOR BURNS & OF HEMORRHOIDS.
Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1111
OXYQUINOLINE SULFATE ... IS ... USED ... IN TREATMENT OF ATHLETE'S FOOT, VAGINITIS, & AS A GARGLE, EYEWASH, NASAL DOUCHE, & IN HEMORRHOIDAL PREPARATIONS ... /OXYQUINOLINE SULFATE/
Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1111
/OVER THE COUNTER/ HYDROXYQUINOLINE IS 1 OF 4 ANTIFUNGAL AGENTS RECOMMENDED FOR ACTIVE TREATMENT OF FUNGUS ASSOCIATED WITH DIAPER RASH & PRICKLY HEAT IN BABIES. /HYDROXYQUINOLINE/
SADIK F; J AM PHARM ASSOC NS10 (JAN): 19-24 (1970)
8-HYDROXYQUNIOLINE SULFATE INHIBITED FORMATION OF ARTIFICIAL CALCULUS IN VITRO & RAT CALCULUS IN VIVO. IN RATS, IT PREVENTED CALCULUS FORMATION WHEN APPLIED BY SWABBING OR BY INTRAORAL INSTILLATION. IN DOGS, FORMATION OF DENTAL PLAQUE WAS INHIBITED 33 TO 98% IN COMPARISON TO PLACEBO. ALSO, 25 TO 58% OF ESTABLISHED PLAQUE ACCUMULATIONS WERE REMOVED, WHEREAS PLACEBO REMOVED 2 TO 22%.
DEPALMA PD ET AL; J DENT RES 55 (2): 292-8 (1976)
For more Therapeutic Uses (Complete) data for 8-HYDROXYQUINOLINE (7 total), please visit the HSDB record page.

8 Agrochemical Information

8.1 Agrochemical Category

Bactericides, Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

9 Pharmacology and Biochemistry

9.1 Pharmacodynamics

Oxyquinoline acts as a biocide to eliminate bacteria and fungi.

9.2 ATC Code

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AC - Quinoline derivatives

G01AC30 - Oxyquinoline

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB07 - Oxyquinoline

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AH - Quinoline derivatives

D08AH03 - Oxyquinoline

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA14 - Oxyquinoline

9.3 Absorption, Distribution and Excretion

Route of Elimination
Oxyquinoline is excreted in both the primarily in the urine with some in the bile.
IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES. MORE 8-HYDROXYQUINOLINE GLUCURONIDE WAS EXCRETED IN URINE THAN 8-HYDROXYQUINOLINE SULFATE CONJUGATE. ONLY THE GLUCURONIDE CONJUGATE WAS EXCRETED IN BILE.
KIWADA H ET AL; CHEM PHARM BULL 25 (7): 1566-73 (1977)
8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. THE GLUCURONIDES WERE EXCRETED IN BILE & URINE, BUT THE SULFATES WERE EXCRETED EXCLUSIVELY IN THE URINE. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.
SAWADA Y ET AL; CHEM PHARM BULL 26 (5): 1357-63 (1978)

9.4 Metabolism / Metabolites

In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates. In the bile, 9% of the total dose is found as glucuronide conjugates.
IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES.
KIWADA H ET AL; CHEM PHARM BULL 25 (7): 1566-73 (1977)
8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.
SAWADA Y ET AL; CHEM PHARM BULL 26 (5): 1357-63 (1978)

9.5 Mechanism of Action

The mechanism by which oxyquinoline exerts its biocidal effect is unknown.

9.6 Biochemical Reactions

9.7 Transformations

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Oxyquinoline
EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as an antiseptic, hydrogen peroxide stabilizer, chemical reagent, corrosion inhibitor, stabilizer in nylon, chelating agent, fungicide, and brightener of steel sheets in electroplating baths; Also used to make dyes; [HSDB]
Industrial Processes with risk of exposure

Steel Producing [Category: Industry]

Electroplating [Category: Plate]

Using Disinfectants or Biocides [Category: Clean]

For 8-Hydroxyquinoline (USEPA/OPP Pesticide Code: 059803) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on 8-Hydroxyquinoline (148-24-3). Available from, as of September 26, 2001: https://npirspublic.ceris.purdue.edu/ppis/
CHEMICAL INTERMEDIATE FOR THE ANTI-INFECTIVE AGENT, OXYQUINOLINE BENZOATE; FOR THE FUNGICIDE, COPPER 8-QUINOLINATE; FOR DIIODOHYDROXYQUIN; FOR FUNGICIDAL SALTS IN TEXTILE PRODUCTS; ANTISEPTIC IN NUMEROUS APPLICATIONS; STABILIZER FOR HYDROGEN PEROXIDE.
SRI
ANALYTICAL COLORIMETRIC REAGENT & FOR PRECIPITATION & SEPARATION OF METALS; PREPN OF NUMBER OF DERIVATIVES USED IN MEDICINE & INDUSTRIAL APPLICATIONS; USED TO MAKE ITS COPPER CHELATE, COPPER 8-HYDROXYQUINOLATE FOR FUNGICIDE IN AGRICULTURAL & INDUST APPLICATIONS; USED IN MFR OF DYES.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 103 (1977)
Corrosion inhibitor.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V19 546 (1982)
For more Uses (Complete) data for 8-HYDROXYQUINOLINE (12 total), please visit the HSDB record page.

Use (kg; approx.) in Germany (2009): >750

Consumption (g per capita; approx.) in Germany (2009): 0.00916

Excretion rate: 1

Calculated removal (%): 75.6

10.1.1 Use Classification

Cosmetics -> Stabilizing
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
Bactericides, Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

10.1.2 Household Products

California Safe Cosmetics Program (CSCP)

Cosmetics product ingredient: quinolin-8-ol (8-hydroxyquinoline; Oxyquinoline)

Reason for Listing: Classified by the European Union as a reproductive toxicant Category 1B in Annex VI to Regulation (EC) 1272/2008

Potential Health Impacts: Reproductive Toxicity

Product count: 5

10.2 Methods of Manufacturing

SRI
By sulfonation fusion of quinoline, by hydrolysis of 8-chloroquinoline (93% (yield) or by a modified Skraup method with o-aminophenol (80% yield).
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. VV20 (1996) 784
Acid hydrolysis of the appropriate aminoquinoline at temps 180-235 °C.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V20 (1996) 784

10.3 Formulations / Preparations

USEPA/OPP Pesticide Code 059803; Trade Names: Fennosan H 30, NCI-C55298, Tumex, USAF EK-794, Quinophenol.
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on 8-Hydroxyquinoline (148-24-3). Available from, as of September 26, 2001: https://npirspublic.ceris.purdue.edu/ppis/
... AVAILABLE IN USA IN TECHNICAL & REAGENT GRADES. IT IS ALSO AVAILABLE AS 0.5% SOLN (OR AEROSOL) SUITABLE FOR TOPICAL USE.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 102 (1977)

10.4 U.S. Imports

(1972) 2.51X10+7 G (PRINCPL CUSTMS DISTS)
SRI
(1975) 2.98X10+7 G (PRINCPL CUSTMS DISTS)
SRI

10.5 General Manufacturing Information

EPA TSCA Commercial Activity Status
8-Quinolinol: ACTIVE
... /Has been/ discontinued by Ashland Chemical Co.
Farm Chemicals Handbook 1992. Willoughby, OH: Meister Publishing Co., 1992., p. C-285
BACTERIOSTATIC & ANTIMYCOTIC ACTIVITY OF 8-HYDROXYQUINOLINE SULFATE IN DERMATOSES IS BLOCKED BY INCORPORATION OF 8-HYDROXYQUINOLINE SULFATE IN EXSICCANT PASTE SR71, ZINC OXIDE-OIL, & ZINC OXIDE LOTION. IT IS NOT RELEASED OR IS RELEASED IN ONLY SMALL AMOUNTS FROM LIPOPHILIC BASES (EXCEPT OLEOGELS), PREPARATIONS WITH EXTERNAL LIPID PHASE & ZINC OXIDE-CONTAINING VEHICLES. /8-HYDROXYQUINOLINE SULFATE/
HORSCH W, METTE B; PHARMAZIE 29 (8): 546-7 (1974)

11 Identification

11.1 Analytic Laboratory Methods

A spectrophotometric procedure is described for the detection of 8-hydoxyquinoline and three of its halogenated derivatives: clioquinol, iodoquinol, and chiniofon. The proposed method involves the use of 2,6-dichloroquinone chlorimide as the chromogenic reagent. 8-Hydroxyquinoline produces a blue color peaking at 595 nm and the other compounds yield a green-blue color with max absorption at 650 nm. The colors produced obey Beer's law. The procedure was applied to the detection of the compounds in dosage forms.
Belal F; Analyst (London) 109 (5): 615-8 (1984)
Of 6 colorimetric methods for the determination of 8-hydroxyquinoline in pharmaceutical products and tissues, one using Gibbs reagent (2,6-dibromo-benzoquinone chlorimine) was reported to be the most sensitive, with a detection limit of 0.5 ug/l. A colorimetric method for its determination in galenical preparations containing other phenols is based on its complex with a vanadium ion. Non-aqueous titration methods have been described to determine 8-hydroxyquinoline and its oxidation products and to determine 8-hydroxyquinoline and some of its metal chelates. An aqueous titration method for the determination of 8-hydroxyquinoline sulfate has been outlined and it can be determined fluorimetrically as its chelate compound with tin(2+). A fluorimetric determination of 8-hydroxyquinoline is based on its luminescence in sulfuric acid at 77 deg K and has a sensitivity of 0.12 uM. A spectrophotometric method for the determination of 8-hydroxyquinoline as the copper chelate can be used in the presence of some other metals. Paper, thin-layer and gas-liquid chromatography can also be used to determine 8-hydroxyquinoline.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 104 (1977)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 6
View All
Note
Pictograms displayed are for 99.4% (323 of 325) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.6% (2 of 325) of reports.
Pictogram(s)
Corrosive
Acute Toxic
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H301 (46.2%): Toxic if swallowed [Danger Acute toxicity, oral]

H302 (53.2%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (46.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (46.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H360 (37.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]

H400 (46.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (46.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P317, P302+P352, P305+P354+P338, P317, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 325 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 325 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 19 notifications provided by 323 of 325 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Acute Tox. 3 (46.2%)

Acute Tox. 4 (53.2%)

Skin Sens. 1 (46.5%)

Eye Dam. 1 (46.5%)

Repr. 1B (37.2%)

Aquatic Acute 1 (46.5%)

Aquatic Chronic 1 (46.5%)

Acute toxicity (ingestion) - category 4

Eye damage - category 1

Reproductive toxicity - category 2

Skin sensitisation - category 1

Hazardous to the aquatic environment (acute) - category 1

12.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and respiratory tract. It also causes irritation of the gastrointestinal tract.

ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may be harmful by inhalation or skin absorption. It is an irritant of the skin, eyes, IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.1.4 Fire Hazards

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.1.5 Hazards Summary

Oral LD50 (rat) = 1.2 g/kg; Causes convulsions when given intraperitoneally(ip) with an LD50 (rat) = 50 mg/kg; [HSDB] An irritant; Harmful if swallowed; Causes mutagenic effects and tumors in animals after high-dose feeding studies; [MSDSonline]

12.1.6 Fire Potential

Combustible when exposed to heat or flame.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2854

12.2 First Aid Measures

12.2.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.4 Accidental Release Measures

12.4.1 Isolation and Evacuation

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

12.4.2 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

12.5 Handling and Storage

12.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.6 Exposure Control and Personal Protection

12.6.1 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.7 Stability and Reactivity

12.7.1 Air and Water Reactions

Insoluble in water.

12.7.2 Reactive Group

Amines, Phosphines, and Pyridines

Phenols and Cresols

12.7.3 Reactivity Profile

8-HYDROXYQUINOLINE darkens on exposure to light. This chemical readily forms stable metal chelates. It is incompatible with strong oxidizers. It is also incompatible with many metal ions. (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.8 Transport Information

12.8.1 DOT Label

Poison

12.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 8-Quinolinol
California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Reproductive Toxicity

Authoritative List - EC Annex VI CMRs - Cat. 1B

Report - if used as a fragrance or flavor ingredient

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
8-Hydroquinoline: Does not have an individual approval but may be used under an appropriate group standard

12.9.1 FIFRA Requirements

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Quinolinol is found on List D. Case No: 4047; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): quinolinol; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.315 (Spring, 1998) EPA 738-R-98-002

12.10 Other Safety Information

Chemical Assessment
IMAP assessments - Quinolinols: Human health tier II assessment

12.10.1 Special Reports

Toxicology Review; Internist 15 (1): 7 (1974)
Toxicology Review; Archives of Environmental Health 23: 6 (1971)
DHHS/NTP; Toxicology & Carcinogenesis Studies of 8-Hydroxyquinoline in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 276 (1985) NIH Publication No. 85-2532

13 Toxicity

13.1 Toxicological Information

13.1.1 Evidence for Carcinogenicity

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. S7 64 (1987)

13.1.2 Carcinogen Classification

1 of 2
IARC Carcinogenic Agent
8-Hydroxyquinoline
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs

Volume 13: (1977) Some Miscellaneous Pharmaceutical Substances

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2 of 2
NTP Technical Report
TR-276: Toxicology and Carcinogenesis Studies of 8-Hydroxyquinoline (CASRN 148-24-3) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1985 )
Peer Review Date
Conclusion for Male Rat
No Evidence No Evidence
Conclusion for Female Rat
No Evidence No Evidence
Conclusion for Male Mice
No Evidence No Evidence
Conclusion for Female Mice
No Evidence No Evidence
Summary
Under the conditions of these studies, there was no evidence of carcinogenicity for male and female F344/N rats or for male and female B6C3F1 mice given 8-hydroxyquinoline in feed at concentrations of 1,500 or 3,000 ppm for 103 weeks.

13.1.3 Adverse Effects

Neurotoxin - Other CNS neurotoxin

13.1.4 Acute Effects

13.1.5 Toxicity Data

LC50 (rat) > 1,210 mg/m3/6h

13.1.6 Interactions

AFTER LETHAL IM DOSES IN MICE (30 MG/KG) INJECTED D-PENICILLAMINE (1 G/KG) PREVENTED /TOXIC/ SYMPTOMS & DEATH BUT NOT TRANSIENT HYPERGLYCEMIA.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-383
THE INFLUENCE OF RADIOPROTECTORS, CYSTEAMINE & AMINOETHYLISOTHIOURONIUM AS WELL AS OF THE AMINO ACIDS L-ALANINE, L-CYSTEINE, L-ARGININE, L-ASPARAGINE, L-GLUTAMIC ACID, L-HISTIDINE, & L-METHIONINE, ON THE CYTOGENETIC ACTION OF 8-HYDROXYQUINOLINE SULFATE WAS TESTED IN HUMAN LYMPHOCYTE CULTURES IN VITRO. EXCESS L-CYSTEINE, CYSTEAMINE, & L-ASPARAGINE ADDED SIMULTANEOUSLY WITH 8-HYDROXYQUINOLINE SULFATE DISTINCTLY REDUCED THE CHROMOSOME. DAMAGING EFFECT OF 8-HYDROXYQUINOLINE. L-GLUTAMIC ACID & AMINOETHYLISOTHIOURONIUM EXERTED LESSER PROTECTIVE ACTIVITY. L-METHIONINE DISPLAYED SOME EFFECT ONLY IN REDUCING THE RELATIVELY RARE ISOCHROMATID ABERRATIONS INDUCED BY 8-HYDROXYQUINOLINE SULFATE. THE OTHER AMINO ACIDS HAD NO EFFECT.
GEBHART E; MUTAT RES 18 (3): 353-61 (1973)
The formation of DNA-strand breaks was studied in cultured human lung cells (A 549) subjected to iron, either in the form of iron(III) citrate or in combination with the metal chelators ethylene diamine tetra-acetic acid (EDTA), nitrilo triacetic acid (NTA), or 8-hydroxyquinoline (8HQ). After 15 min exposure to 5 uM iron(III) citrate or iron chelate, the cellular levels of iron were found to be three times higher in cells subjected to iron-8HQ than in cells subjected to iron(III) citrate, iron-EDTA or iron-NTA. Exposure to iron-8HQ caused extensive DNA-strand breakage, whereas no such breakage was found in cells exposed to iron-EDTA or iron-NTA. The DNA damage caused by iron-8HQ increased with time and dose, and DNA-strand breakage was clearly demonstrable in cells after 15 min exposure to as little as 0.1 uM iron-8HQ. Moreover, iron-8HQ was strongly toxic to the cells and inhibited their growth after exposure. Along with the formation of DNA-strand breaks, the concentration of cellular malondialdehyde increased four-fold after exposure to iron-8HQ and two-fold after exposure to iron-EDTA or iron-NTA, suggesting that reactive oxygen metabolites might be involved in the toxic action. Moreover, both iron-EDTA and iron-NTA caused a considerable hydroxylation of deoxyguanosine (dG) residues in DNA in vitro, whereas iron(III) citrate and iron-8HQ only caused a minor hydroxylation of dG. This points to the possibility that iron-8HQ-mediated DNA-strand breakage in cells might be due to the action of a metal-bound oxyl radical formed from the iron-8HQ complex rather than to the formation of hydroxyl radicals. Altogether, these findings indicate that iron bound to the lipophilic chelator, 8HQ, has strong toxic properties and that it may cause substantial DNA-strand breakage and lipid peroxidation in living cells.
Leanderson P, Tagesson C; Carcinogenesis 17 (3): 545-50 (1996)

13.1.7 Antidote and Emergency Treatment

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 181-2
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 182

13.1.8 Human Toxicity Excerpts

VARIOUS HALOGENATED DERIVATIVES USED IN TREATING AMEBIASIS IN MAN ARE ... COMPARATIVELY BENIGN EXCEPT FOR FREQUENT ALLERGIC REACTIONS ... /8-HYDROXYQUINOLINE SULFATE/
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-383

13.1.9 Non-Human Toxicity Excerpts

Hydroxyquinoline is moderately toxic in rats (oral LD50 1.2 g/kg). When injected, it is distinctly toxic (rat ip LD50 50 mg/kg) & causes marked stimulation of CNS. Mice given large doses exhibited confusion, resp difficulty, hind leg paralysis & violent convulsions, with death within 2 hr. After smaller fatal doses, death was delayed several days. Toxic symptoms then included anorexia, malaise, & general indifference to sound or light.
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-383
TESTS BY INJECTION OF 0.01 MOLAR SOLN INTO RABBIT CORNEA CAUSED VERY SLIGHT REACTION, GRADED 5 ON A SCALE OF 0-100. IV INJECTIONS OF /0.04-0.075 G/KG/ IN RABBITS CAUSED PROMPT & TRANSIENT PROPTOSIS ASSOC WITH VENOUS ENGORGEMENT, HYPERPNEA, RAPID PULSE, & SALIVATION.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 503
A GROUP OF 49 CC57W MICE WERE GIVEN 1.5 MG/ANIMAL ... /ORALLY/ IN SUNFLOWER OIL 6 TIMES/WK FOR 660 DAYS (TOTAL DOSE, 852 MG/ANIMAL). OF 21 SURVIVING AT ... APPEARANCE OF 1ST TUMOR (460 DAYS) 4 DEVELOPED 2 LYMPHOMAS, 2 LUNG ADENOMAS & 1 HEMANGIOMA OF LIVER. TUMOR INCIDENCE IN UNTREATED CC57W MICE ... WAS ... 17%. (ABSENCE OF CONCURRENT CONTROLS WAS NOTED)
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 104 (1977)
A GROUP OF 15 6-WK OLD MALE FISCHER F344 RATS RECEIVED 0.8% ... IN DIET FOR 78 WK, AT WHICH TIME 13 SURVIVED. ... 4 LEYDIG-CELL TUMORS OF THE TESTIS /WERE OBSERVED/. HYPERPLASIA OF INTERSTITIAL CELLS OF TESTIS WAS OBSERVED IN 2/8 SURVIVING CONTROLS. (THE SMALL NUMBER OF ANIMALS & SHORT DURATION OF EXPT WERE NOTED)
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 105 (1977)
For more Non-Human Toxicity Excerpts (Complete) data for 8-HYDROXYQUINOLINE (31 total), please visit the HSDB record page.

13.1.10 Non-Human Toxicity Values

LD50 Rat oral 1200 mg/kg
DHHS/NTP; Toxicology and Carcinogenesis Studies of 8-Hydroxyquinoline in F344/N Rats and B6C3F1 Mice (Feed Studies) p.15 (1985) Technical Rpt Series No. 276 NIH Pub No. 85-2532
LD50 Mice ip 48 mg/kg
DHHS/NTP; Toxicology and Carcinogenesis Studies of 8-Hydroxyquinoline in F344/N Rats and B6C3F1 Mice (Feed Studies) p.15 (1985) Technical Rpt Series No. 276 NIH Pub No. 85-2532
LD50 Rat ip 50 mg/kg
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-383
LD50 Mouse sc 83,600 ug/kg
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2855
For more Non-Human Toxicity Values (Complete) data for 8-HYDROXYQUINOLINE (6 total), please visit the HSDB record page.

13.1.11 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=148-24-3]

13.1.12 National Toxicology Program Studies

8-Hydroxyquinoline, given at 1500-3000 ppm in the feed of male and female F344/N rats and B6C3F1 mice for 103 wk, showed no evidence of carcinogenicity. Survival was similar to that of controls, with slight decreases in appetite and body weight with the high dose level.
DHHS/NTP; Toxicology and Carcinogenesis Studies of 8-Hydroxyquinoline in F344/N Rats and B6C3F1 Mice (Feed Studies) p.9 (1985) Technical Rpt Series No. 276 NIH Pub No. 85-2532

13.1.13 TSCA Test Submissions

The mutagenicity of 8-hydroxyquinoline was evaluated in Salmonella tester strains TA1535, TA1537, TA92, TA98 and TA100 (Ames Test), both in the presence and absence of added metabolic activation by either Aroclor or phenobarbital-induced rat liver S9 fraction. 8-Hydroxyquinoline, diluted in DMSO, was tested at concentrations up to 60ug/plate. 8-Hydroxyquinoline produced a positive response in Salmonella tester strain TA100 in the presence of added metabolic activation. The treatments failed to produce a positive response in any of the remaining tester strains with or without metabolic activation.
H.R. Skeggs & M.M. Cook; Microbial Mutagen Tests, (1978), EPA Document No. FYI-OTS-0584-0315, Fiche No. OTS0000315-0
The mutagenicity of 8-hydroxyquinoline was evaluated in Salmonella tester strains TA1537, TA92, TA98 and TA100 (Ames Test), both in the presence and absence of metabolic activation by Aroclor or phenobarbital-induced rat liver preparation. 8-Hydroxyquinoline, diluted in DMSO, was tested at concentrations up to 100mcg/plate. 8-Hydroxyquinoline produced a positive response only in Salmonella tester strains TA92 with metabolic activation and TA100 with and without metabolic activation.
H.R. Skeggs; Microbial Mutagen Tests, (1977), EPA Document No. FYI-OTS-0584-0315, Fiche No. OTS0000315-0

13.2 Ecological Information

13.2.1 Environmental Fate / Exposure Summary

8-Hydroxyquinoline's production and use as a chemical intermediate and in steel electroplating may result in its release to the environment through various waste streams. It's former use as a fungicide may have resulted in its direct release to the environment. If released to air, a vapor pressure of 1.66X10-3 mm Hg at 25 °C indicates 8-hydroxyquinoline will exist solely as a vapor. Vapor-phase 8-hydroxyquinoline will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2.0 hrs. 8-Hydroxyquinoline is expected to undergo photolysis in the atmosphere based upon aquatic photolytic experiments. The half-life for the photolytic degradation of 8-hydroxyquinoline in aqueous solution illuminated with filtered light, simulating daylight, ranged from 40-64 hours. If released to soil, 8-hydroxyquinoline is expected to have slight mobility based upon an estimated Koc of 3,000. Volatilization from water and moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole. Biodegradation in soil or water is not likely to be an important environmental fate process based on a 0% theoretical BOD using sewage sludge. If released into water, 8-hydroxyquinoline is expected to adsorb to suspended solids and sediment based upon the estimated Koc. An estimated BCF of 7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. Occupational exposure to 8-hydroxyquinoline may have occured through inhalation of dust and dermal contact with this compound at workplaces where 8-hydroxyquinoline was produced or used. (SRC)

13.2.2 Natural Pollution Sources

... IS NOT KNOWN TO OCCUR IN NATURE.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 104 (1977)

13.2.3 Artificial Pollution Sources

8-Hydroxyquinoline's production and use as a chemical intermediate(1-3) and in steel electroplating(4) may result in its release to the environment through various waste streams(SRC). It's former use as a fungicide(5) may have resulted in its direct release to the environment(SRC).
(1) Ross E et al; Ullmann's Encycl Indus Chem. 5th ed. Gerhartz W, ed. Deerfield Beach, FL: VCH Publ A14: 142 (1989)
(2) Hunger K et al; Ullmann's Encycl Indus Chem. 5th ed. Gerhartz W, ed. Deerfield Beach, FL: VCH Publ A3: 254 (1985)
(3) Howard WL, Wilson DA; Kirk-Othmer Encycl Chem Tech. 4th ed. NY, NY: John Wiley and Sons 5: 768 (1993)
(4) Finley KT; Kirk-Othmer Encycl Chem Tech. 4th ed. NY, NY: John Wiley and Sons 20: 779 (1996)
(5) IARC; Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva, Switzerland: World Health Organization, Inter Agency Res Cancer 19: 103 (1977)

13.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a structure estimation method(2), indicates that 8-hydroxyquinoline is expected to have slight mobility in soil(SRC). Volatilization of 8-hydroxyquinoline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 1.66X10-3 mm Hg(3), and water solubility, 556 mg/l(4). 8-Hydroxyquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation in soil is not an important environmental fate process based on a 0% theoretical BOD using sewage sludge(5).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Daubert, TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1989)
(4) Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth Ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)
(5) Heukelekian H, Rand MC; J Water Pollut Control Assoc 27: 1040-53 (1955)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,000(SRC), determined from a structure estimation method(2), indicates that 8-hydroxyquinoline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.66X10-3 mm Hg(4) and water solubility, 556 mg/l(5). According to a classification scheme(6), an estimated BCF of 7(SRC), from its log Kow of 2.02(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). To test for photolytic degradation in aqueous solution, 8-hydroxyquinoline was illuminated with filtered light, simulating daylight(9). The half-life for the photolytic degradation of 8-hydroxyquinoline ranged from 40-64 hours. Biodegradation in water is not an important environmental fate process based on a 0% theoretical BOD using sewage sledge(10).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Daubert, TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1989)
(5) Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth Ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)
(6) Franke C et al; Chemosphere 29: 1501-14 (1994)
(7) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 51 (1995)
(8) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(9) Svenson A, Bjorndal; Chemosphere 17: 2397-2405 (1988)
(10) Heukelekian H, Rand MC; J Water Pollut Control Assoc 27: 1040-53 (1955)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 8-hydroxyquinoline, which has a vapor pressure of 1.66X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 8-hydroxyquinoline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.0 hrs(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). 8-Hydroxyquinoline is expected to undergo photolysis in the atmosphere based upon aquatic photolytic experiments. The half-life for the photolytic degradation of 8-hydroxyquinoline in aqueous solution illuminated with filtered light, simulating daylight, ranged from 40-64 hours(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Daubert, TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1989)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Svenson A, Bjorndal; Chemosphere 17: 2397-2405 (1988)

13.2.5 Environmental Biodegradation

AEROBIC: 8-Hydroxyquinoline, concentration not specified, reached 0% of its theoretical BOD in 5 days using a sewage sludge inoculum and standard dilution method(1).
(1) Heukelekian H, Rand MC; J Water Pollut Control Assoc 27: 1040-53 (1955)

13.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of 8-hydroxyquinoline with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.0 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 8-Hydroxyquinoline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). To test for photolytic degradation in aqueous solution, 8-hydroxyquinoline was illuminated with filtered light, simulating daylight(3). The half-life for the photolytic degradation of 8-hydroxyquinoline ranged from 40-64 hours.
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5 (1990)
(3) Svenson A, Bjorndal; Chemosphere 17: 2397-2405 (1988)

13.2.7 Environmental Bioconcentration

An estimated BCF of 7 was calculated for 8-hydroxyquinoline(SRC), using a log Kow of 2.02(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p. 51 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

13.2.8 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 8-hydroxyquinoline can be estimated to be 3,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 8-hydroxyquinoline is expected to have slight mobility in soil.
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

13.2.9 Volatilization from Water / Soil

The Henry's Law constant for 8-hydroxyquinoline is estimated as 5.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.66X10-3 mm Hg(1), and water solubility, 556 mg/l(2). This Henry's Law constant indicates that 8-hydroxyquinoline is not expected to volatilize from water surfaces(3). 8-Hydroxyquinoline estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 8-Hydroxyquinoline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) Daubert, TE, Danner RP; Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis (1989)
(2) Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth Ed, Tucson, AZ: Univ Az, College of Pharmacy (1992)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

13.2.10 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 13,728 workers (9,645 of these are female) were potentially exposed to 8-hydroxyquinoline in the US(1). Occupational exposure to 8-hydroxyquinoline may have occured through inhalation of dust and dermal contact with this compound at workplaces where 8-hydroxyquinoline was produced or used(SRC).
(1) NIOSH; National Occupational Exposure Survey (NOES) (1983)

14 Associated Disorders and Diseases

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Chemical Co-Occurrences in Literature

15.7 Chemical-Gene Co-Occurrences in Literature

15.8 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Drug-Drug Interactions

17.4 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 KEGG: ATC

20.5 KEGG: Risk Category of Japanese OTC Drugs

20.6 WHO ATC Classification System

20.7 ChemIDplus

20.8 CAMEO Chemicals

20.9 ChEMBL Target Tree

20.10 UN GHS Classification

20.11 EPA CPDat Classification

20.12 NORMAN Suspect List Exchange Classification

20.13 CCSBase Classification

20.14 EPA DSSTox Classification

20.15 International Agency for Research on Cancer (IARC) Classification

20.16 EPA TSCA and CDR Classification

20.17 LOTUS Tree

20.18 EPA Substance Registry Services Tree

20.19 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
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    CAMEO Chemical Reactivity Classification
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    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  13. California Safe Cosmetics Program (CSCP) Product Database
    quinolin-8-ol (8-hydroxyquinoline; Oxyquinoline)
    https://cscpsearch.cdph.ca.gov/search/detailresult/3040
  14. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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  15. ChEBI
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  17. Open Targets
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  18. CCSbase
    CCSbase Classification
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    8-QUINOLINOL
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
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    https://creativecommons.org/publicdomain/zero/1.0/
  27. The Cambridge Structural Database
  28. DailyMed
  29. IUPAC Digitized pKa Dataset
  30. Hazardous Chemical Information System (HCIS), Safe Work Australia
  31. NITE-CMC
    8-Quinolinol - FY2009 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/09-mhlw-0031e.html
    8-Quinolinol - FY2021 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/21-mhlw-2080e.html
    8-Quinolinol - FY2018 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/18-mhlw-2062e.html
  32. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
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    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    quinolin-8-ol; 8-hydroxyquinoline
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  33. NMRShiftDB
  34. MassBank Europe
  35. International Agency for Research on Cancer (IARC)
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    https://publications.iarc.fr/Terms-Of-Use
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    https://www.iarc.fr/
  36. NTP Technical Reports
  37. Japan Chemical Substance Dictionary (Nikkaji)
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
  39. Natural Product Activity and Species Source (NPASS)
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  42. SpectraBase
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  49. Springer Nature
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  57. PubChem
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  60. MolGenie
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  61. PATENTSCOPE (WIPO)
CONTENTS