Nalidixic Acid

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  • Identifiers

    CAS number
    389-08-2

    Molecular formula
    C12H12N2O3

    SMILES
    CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 54.52%
    Roasted 30.12%
    Burnt 27.14%
    Nutty 26.17%
    Bitter 26.08%
    Animal 25.03%
    Grape 22.08%
    Phenolic 21.54%
    Musty 20.94%
    Popcorn 20.42%

     

    Flavor
    Bitter 69.13%
    Odorless 43.35%
    Mild 27.66%
    Bread crust 21.18%
    Nutty 20.85%
    Nitrile 20.77%
    Roasted peanuts 20.56%
    Orange flower 20.47%
    Taco 20.43%
    Lovage 20.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    4.97 (weak acid)

    Molecular weight
    232.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    460°C

    Melting point expt.

    • 444 to 446 °F (NTP, 1992)
    • 229.5 °C
    • 229-230 °C

    Flash point

    • 212.5 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 70 °F (NTP, 1992)
    • 100 mg/L (at 23 °C)
    • Soly at 23 °C (mg/ml): chloroform 35; toluene 1.6; methanol 1.3; ethanol 0.6; water 0.1; ether 0.1.
    • PRACTICALLY INSOL IN WATER; SOL IN SOLN OF CARBONATES
    • 2.30e+00 g/L

  • Synonyms

    • nalidixic acid
    • 389-08-2
    • Nalidixate
    • Nalidixin
    • NegGram
    • Nevigramon
    • Uronidix
    • Innoxalon
    • Nalidixan
    • Nalitucsan
    • Sicmylon
    • Unaserus
    • Nalidic acid
    • Nalidixinic acid
    • Wintomylon
    • Dixiben
    • Dixinal
    • Jicsron
    • Nalurin
    • Naxuril
    • Cybis
    • Nalix
    • Nogram
    • Urisal
    • Uroman
    • Acide nalidixique
    • 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
    • Betaxina
    • Kusnarin
    • Nalidicron
    • Nicelate
    • Specifen
    • Specifin
    • Urodixin
    • Narigix
    • Negram
    • Poleon
    • Uralgin
    • Uriben
    • Uriclar
    • Uroneg
    • Uropan
    • Naldixic acid
    • Acido nalidixico
    • Acide nalidixico
    • WIN 18,320
    • Acidum nalidixicum
    • NSC-82174
    • Eucistin
    • 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
    • Acido nalidissico
    • 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
    • Nalidixane
    • NCI-C56199
    • 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
    • MFCD00006884
    • 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
    • 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
    • 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one
    • CCRIS 2365
    • Acide nalidixique [INN-French]
    • Acido nalidixico [INN-Spanish]
    • Acidum nalidixicum [INN-Latin]
    • HSDB 3241
    • 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid
    • EINECS 206-864-7
    • UNII-3B91HWA56M
    • WIN-18320
    • 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure
    • BRN 0750515
    • 3B91HWA56M
    • DTXSID3020912
    • CHEBI:100147
    • NSC82174
    • Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico
    • Nalidixic acid (NegGram)
    • DTXCID70912
    • MLS000028504
    • Win 18320
    • 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
    • 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
    • 5-25-07-00384 (Beilstein Handbook Reference)
    • NCGC00018181-08
    • SMR000058264
    • Wintron
    • Nalidixic acid [USAN:USP:INN:BAN:JAN]
    • Acid, Nalidixic
    • Nalidixic acid 100 microg/mL in Acetonitrile
    • 1,8-Naphthyridine-3-carboxylic acid,1-ethyl-1,4-dihydro-7-methyl-4-oxo-
    • Acido nalidissico [DCIT]
    • Acide nalidixico [Italian]
    • Acide nalidixique [French]
    • NALIDIXIC ACID (MART.)
    • NALIDIXIC ACID [MART.]
    • Acide nalidixique (INN-French)
    • Acido nalidixico (INN-Spanish)
    • Acidum nalidixicum (INN-Latin)
    • 1-Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
    • Nalidixic
    • NALIDIXIC ACID (EP IMPURITY)
    • NALIDIXIC ACID [EP IMPURITY]
    • NALIDIXIC ACID (USP IMPURITY)
    • NALIDIXIC ACID [USP IMPURITY]
    • CAS-389-08-2
    • Nalidixic acid (USAN:USP:INN:BAN:JAN)
    • NegGram (TN)
    • wil 18,320
    • Innoxalomn
    • Nalidixinsaure
    • Eucisten
    • nalidixic-acid
    • SR-01000003086
    • 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-(1,8)naphthyridine-3-carboxylic acid
    • 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]
    • Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]
    • NALIDIXICACID
    • WIN 183203
    • CHEMBL5
    • Spectrum_000918
    • Maybridge1_007101
    • Opera_ID_1064
    • Prestwick0_000187
    • Prestwick1_000187
    • Prestwick2_000187
    • Prestwick3_000187
    • Spectrum2_001360
    • Spectrum3_000075
    • Spectrum4_000817

  • Applications

    Nalidixic Acid (CAS 389-08-2) is used in the pharmaceutical sector as an antibacterial agent and as a chemical building block for the synthesis of quinolones, also serving as an intermediate for producing later quinolone antibiotics. In industrial manufacturing, it is commonly employed as an intermediate to prepare other quinolone compounds. In research and analytical settings, it is used as a reference standard and reagent in antimicrobial testing workflows (e.g., susceptibility assays and related analytical methods). Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.14
    methanol 1.57
    isopropanol 0.81
    water 0.04
    ethyl acetate 0.9
    n-propanol 1.03
    acetone 1.49
    n-butanol 1.15
    acetonitrile 0.84
    DMF 24.4
    toluene 0.43
    isobutanol 1.23
    1,4-dioxane 1.64
    methyl acetate 1.2
    THF 13.44
    2-butanone 1.9
    n-pentanol 1.51
    sec-butanol 0.84
    n-hexane 0.02
    ethylene glycol 1.81
    NMP 45.28
    cyclohexane 0.02
    DMSO 32.37
    n-butyl acetate 2.54
    n-octanol 0.57
    chloroform 0.99
    n-propyl acetate 1.6
    acetic acid 3.17
    dichloromethane 2.32
    cyclohexanone 8.18
    propylene glycol 2.09
    isopropyl acetate 0.91
    DMAc 25.55
    2-ethoxyethanol 5.33
    isopentanol 1.97
    n-heptane 0.03
    ethyl formate 2.34
    1,2-dichloroethane 1.98
    n-hexanol 1.98
    2-methoxyethanol 14.14
    isobutyl acetate 1.58
    tetrachloromethane 0.24
    n-pentyl acetate 1.95
    transcutol 5.2
    n-heptanol 1.23
    ethylbenzene 0.51
    MIBK 1.84
    2-propoxyethanol 10.71
    tert-butanol 1.75
    MTBE 0.36
    2-butoxyethanol 5.5
    propionic acid 2.44
    o-xylene 0.65
    formic acid 4.53
    diethyl ether 0.14
    m-xylene 0.8
    p-xylene 0.89
    chlorobenzene 1.21
    dimethyl carbonate 1.82
    n-octane 0.02
    formamide 6.37
    cyclopentanone 16.45
    2-pentanone 1.56
    anisole 1.21
    cyclopentyl methyl ether 2.54
    gamma-butyrolactone 21.52
    1-methoxy-2-propanol 8.5
    pyridine 3.84
    3-pentanone 0.92
    furfural 21.06
    n-dodecane 0.02
    diethylene glycol 13.39
    diisopropyl ether 0.12
    tert-amyl alcohol 1.64
    acetylacetone 3.48
    n-hexadecane 0.03
    acetophenone 3.94
    methyl propionate 1.85
    isopentyl acetate 3.33
    trichloroethylene 4.68
    n-nonanol 0.68
    cyclohexanol 1.75
    benzyl alcohol 4.16
    2-ethylhexanol 1.66
    isooctanol 1.37
    dipropyl ether 0.5
    1,2-dichlorobenzene 1.96
    ethyl lactate 3.33
    propylene carbonate 9.73
    n-methylformamide 7.77
    2-pentanol 0.58
    n-pentane 0.01
    1-propoxy-2-propanol 5.88
    1-methoxy-2-propyl acetate 4.83
    2-(2-methoxypropoxy) propanol 5.97
    mesitylene 0.54
    ε-caprolactone 8.2
    p-cymene 0.99
    epichlorohydrin 19.52
    1,1,1-trichloroethane 1.04
    2-aminoethanol 3.02
    morpholine-4-carbaldehyde 23.6
    sulfolane 46.09
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 4.41
    n-hexyl acetate 1.68
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 6.17
    sec-butyl acetate 1.19
    tert-butyl acetate 1.66
    decalin 0.07
    glycerin 7.85
    diglyme 9.01
    acrylic acid 3.57
    isopropyl myristate 0.76
    n-butyric acid 3.63
    acetyl acetate 0.9
    di(2-ethylhexyl) phthalate 2.88
    ethyl propionate 1.38
    nitromethane 5.33
    1,2-diethoxyethane 0.99
    benzonitrile 4.25
    trioctyl phosphate 1.86
    1-bromopropane 0.47
    gamma-valerolactone 25.18
    n-decanol 0.56
    triethyl phosphate 2.63
    4-methyl-2-pentanol 0.84
    propionitrile 1.22
    vinylene carbonate 7.97
    1,1,2-trichlorotrifluoroethane 16.05
    DMS 2.55
    cumene 0.69
    2-octanol 0.63
    2-hexanone 2.15
    octyl acetate 1.14
    limonene 0.96
    1,2-dimethoxyethane 6.73
    ethyl orthosilicate 2.26
    tributyl phosphate 2.02
    diacetone alcohol 6.71
    N,N-dimethylaniline 1.97
    acrylonitrile 3.05
    aniline 1.65
    1,3-propanediol 5.4
    bromobenzene 0.98
    dibromomethane 1.04
    1,1,2,2-tetrachloroethane 3.71
    2-methyl-cyclohexyl acetate 3.75
    tetrabutyl urea 3.46
    diisobutyl methanol 1.0
    2-phenylethanol 4.86
    styrene 0.39
    dioctyl adipate 1.83
    dimethyl sulfate 8.02
    ethyl butyrate 2.01
    methyl lactate 4.81
    butyl lactate 3.5
    diethyl carbonate 1.78
    propanediol butyl ether 3.92
    triethyl orthoformate 2.01
    p-tert-butyltoluene 0.79
    methyl 4-tert-butylbenzoate 5.55
    morpholine 4.01
    tert-butylamine 0.48
    n-dodecanol 0.43
    dimethoxymethane 5.21
    ethylene carbonate 5.35
    cyrene 15.66
    2-ethoxyethyl acetate 2.99
    2-ethylhexyl acetate 2.48
    1,2,4-trichlorobenzene 3.08
    4-methylpyridine 4.28
    dibutyl ether 0.33
    2,6-dimethyl-4-heptanol 1.0
    DEF 4.24
    dimethyl isosorbide 15.87
    tetrachloroethylene 2.18
    eugenol 7.19
    triacetin 2.7
    span 80 4.6
    1,4-butanediol 2.69
    1,1-dichloroethane 0.74
    2-methyl-1-pentanol 2.4
    methyl formate 5.14
    2-methyl-1-butanol 1.65
    n-decane 0.03
    butyronitrile 1.53
    3,7-dimethyl-1-octanol 0.95
    1-chlorooctane 0.19
    1-chlorotetradecane 0.13
    n-nonane 0.02
    undecane 0.03
    tert-butylcyclohexane 0.07
    cyclooctane 0.01
    cyclopentanol 4.16
    tetrahydropyran 1.09
    tert-amyl methyl ether 0.52
    2,5,8-trioxanonane 9.13
    1-hexene 0.12
    2-isopropoxyethanol 3.72
    2,2,2-trifluoroethanol 2.59
    methyl butyrate 2.87

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction