3-Hydroxyanthranilic Acid

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  • Identifiers

    CAS number
    548-93-6

    Molecular formula
    C7H7NO3

    SMILES
    C1=CC(=C(C(=C1)O)N)C(=O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 70.83%
    Phenolic 42.05%
    Bitter 27.02%
    Burnt 25.52%
    Balsamic 22.85%
    Milky 20.83%
    Vanilla 20.8%
    Savory 20.6%
    Animal 19.36%
    Smoky 18.46%

     

    Flavor
    Odorless 55.08%
    Phenolic 51.8%
    Mild 51.43%
    Nutty 39.82%
    Bitter 34.16%
    Faint 29.03%
    Sour 28.38%
    Very mild 26.47%
    Urine 23.84%
    Cadaverous 22.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    6.73 (neutral)

    Molecular weight
    153.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    375°C

    Melting point expt.

    • 240 °C
    • 164 °C

    Flash point

    • 188.42 ˚C est.

    Solubility expt.

    • SLIGHTLY SOL IN WATER, SOL IN HOT WATER, ALCOHOL, ETHER; SOL IN CHLOROFORM

  • Synonyms

    • 2-Amino-3-hydroxybenzoic acid
    • 3-Hydroxyanthranilic acid
    • 548-93-6
    • 3-Ohaa
    • 2-AMINO-3-HYDROXY-BENZOIC ACID
    • 3-hydroxyanthranilate
    • Anthranilic acid, 3-hydroxy-
    • Benzoic acid, 2-amino-3-hydroxy-
    • 1UQB1BT4OT
    • DTXSID40203290
    • NSC-522891
    • CHEBI:15793
    • CHEBI:36559
    • 3 Hydroxyanthranilic Acid
    • Acid, 3-Hydroxyanthranilic
    • RefChem:94252
    • DTXCID40125781
    • 208-962-5
    • 2-amino-3-hydroxybenzoate
    • 3-Hydroxy anthranilic acid
    • 3-Hydroxy-anthranilsaeure
    • MFCD00007700
    • 3-Hydroxy-anthranilsaeure [German]
    • Benzoic acid, 2-amino-3-hydroxy-, hydrochloride
    • 3-oh-anthranilic acid
    • CCRIS 4427
    • 3-hydroxy-anthranilate
    • HSDB 4040
    • EINECS 208-962-5
    • UNII-1UQB1BT4OT
    • NSC 522891
    • BRN 0973356
    • 3-Hydroxy-2-aminobenzoic acid
    • AI3-52837
    • 3-Oxyanthranilate
    • 3-hydroxanthranilate
    • 1u1w
    • Mesalazine Impurity 41
    • 3-hydroxyantranilic acid
    • WLN: ZR BQ FVQ
    • 3-Hydroxy-2-aminobenzoate
    • 3-hydroxy-Anthranilic acid
    • bmse000321
    • 2-amino-3-hydroxy-Benzoate
    • Oprea1_735317
    • SCHEMBL88229
    • 4-14-00-02071 (Beilstein Handbook Reference)
    • MLS001066415
    • 3-HAA, 3-HANA
    • CHEMBL445304
    • orb1302634
    • SCHEMBL27556194
    • SCHEMBL29430959
    • 3-Hydroxyanthranilic acid, 97%
    • ACon1_002137
    • 2-Aminobenzoic acid, 3-hydroxy-
    • HMS2231F22
    • HMS3373P15
    • ALBB-024973
    • HY-W001171R
    • 3-HAA,NSC 522891
    • 2-AMINO-3-HYDROXYBENZOICACID
    • 3-Hydroxyanthranilic acid (Standard)
    • EBC-48179
    • MSK407013
    • NSC522891
    • s3355
    • SBB072170
    • STK894860
    • AKOS015856349
    • Anthranilic acid, 3-hydroxy- (8CI)
    • CS-W001171
    • DB03644
    • FH66789
    • GS-4375
    • HY-W001171
    • SB76097
    • NCGC00179794-01
    • AC-23861
    • PD006740
    • SMR000471838
    • SY030553
    • DB-023057
    • A0316
    • NS00014716
    • ST45027624
    • EN300-98786
    • 2-AMINO-3-HYDROXY-BENZOIC ACID [HSDB]
    • C00632
    • 548A936
    • F077960
    • Q2823213
    • 6B30EFED-FCCC-46EA-A7A4-40DDB1804913
    • BRD-K27265817-001-01-4
    • Z1255485352
    • InChI=1/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11
    • 548-93-6

  • Applications

    3-Hydroxyanthranilic Acid (CAS 548-93-6) is primarily used as an intermediate in the synthesis of biologically relevant heterocycles and other fine chemicals. It serves as a building block for the preparation of heterocyclic compounds such as quinoxaline derivatives and related dye and pigment chemistries. In polymer and materials science, it is employed as a functional building block or coupling partner for specialty polymers and crosslinked networks. The compound also functions as a ligand and metal-chelating agent in analytical and coordination chemistry, enabling metal-ion complexation studies. In pharmaceutical research, it is used as a reference or starting material for the synthesis of kynurenine-pathway–related compounds and other small molecules of interest. It may be used in R&D settings and is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.07
    methanol 4.54
    isopropanol 1.51
    water 1.66
    ethyl acetate 2.69
    n-propanol 0.94
    acetone 6.83
    n-butanol 1.7
    acetonitrile 0.81
    DMF 41.38
    toluene 0.3
    isobutanol 1.12
    1,4-dioxane 7.18
    methyl acetate 2.7
    THF 180.66
    2-butanone 5.3
    n-pentanol 2.61
    sec-butanol 1.68
    n-hexane 0.19
    ethylene glycol 9.58
    NMP 43.19
    cyclohexane 0.04
    DMSO 146.96
    n-butyl acetate 4.38
    n-octanol 4.5
    chloroform 0.48
    n-propyl acetate 2.04
    acetic acid 4.33
    dichloromethane 0.48
    cyclohexanone 6.91
    propylene glycol 2.84
    isopropyl acetate 3.44
    DMAc 64.43
    2-ethoxyethanol 22.22
    isopentanol 4.2
    n-heptane 0.48
    ethyl formate 2.86
    1,2-dichloroethane 0.94
    n-hexanol 8.91
    2-methoxyethanol 33.11
    isobutyl acetate 0.73
    tetrachloromethane 1.31
    n-pentyl acetate 4.05
    transcutol 9.13
    n-heptanol 9.23
    ethylbenzene 0.6
    MIBK 8.0
    2-propoxyethanol 32.72
    tert-butanol 11.47
    MTBE 3.98
    2-butoxyethanol 20.33
    propionic acid 2.14
    o-xylene 0.85
    formic acid 17.35
    diethyl ether 1.26
    m-xylene 0.96
    p-xylene 0.7
    chlorobenzene 0.31
    dimethyl carbonate 5.22
    n-octane 0.27
    formamide 22.51
    cyclopentanone 30.51
    2-pentanone 7.33
    anisole 3.22
    cyclopentyl methyl ether 9.55
    gamma-butyrolactone 33.61
    1-methoxy-2-propanol 22.61
    pyridine 1.89
    3-pentanone 3.26
    furfural 16.85
    n-dodecane 0.21
    diethylene glycol 40.23
    diisopropyl ether 1.37
    tert-amyl alcohol 9.36
    acetylacetone 13.39
    n-hexadecane 0.23
    acetophenone 4.49
    methyl propionate 4.26
    isopentyl acetate 4.52
    trichloroethylene 1.8
    n-nonanol 4.81
    cyclohexanol 1.68
    benzyl alcohol 2.8
    2-ethylhexanol 4.99
    isooctanol 6.98
    dipropyl ether 4.22
    1,2-dichlorobenzene 0.81
    ethyl lactate 4.7
    propylene carbonate 6.67
    n-methylformamide 11.81
    2-pentanol 2.19
    n-pentane 0.07
    1-propoxy-2-propanol 17.21
    1-methoxy-2-propyl acetate 9.62
    2-(2-methoxypropoxy) propanol 12.65
    mesitylene 1.09
    ε-caprolactone 5.98
    p-cymene 1.49
    epichlorohydrin 24.29
    1,1,1-trichloroethane 1.3
    2-aminoethanol 7.57
    morpholine-4-carbaldehyde 30.0
    sulfolane 65.86
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 16.15
    n-hexyl acetate 4.58
    isooctane 0.23
    2-(2-butoxyethoxy)ethanol 15.17
    sec-butyl acetate 1.52
    tert-butyl acetate 8.69
    decalin 0.16
    glycerin 16.79
    diglyme 28.11
    acrylic acid 2.66
    isopropyl myristate 2.61
    n-butyric acid 3.69
    acetyl acetate 2.06
    di(2-ethylhexyl) phthalate 3.61
    ethyl propionate 2.89
    nitromethane 13.36
    1,2-diethoxyethane 3.66
    benzonitrile 1.43
    trioctyl phosphate 4.1
    1-bromopropane 0.36
    gamma-valerolactone 27.29
    n-decanol 3.76
    triethyl phosphate 4.06
    4-methyl-2-pentanol 3.93
    propionitrile 0.81
    vinylene carbonate 3.56
    1,1,2-trichlorotrifluoroethane 20.29
    DMS 2.72
    cumene 0.88
    2-octanol 4.56
    2-hexanone 4.28
    octyl acetate 3.97
    limonene 1.86
    1,2-dimethoxyethane 32.23
    ethyl orthosilicate 3.79
    tributyl phosphate 2.79
    diacetone alcohol 24.0
    N,N-dimethylaniline 4.29
    acrylonitrile 1.62
    aniline 0.99
    1,3-propanediol 10.72
    bromobenzene 0.24
    dibromomethane 0.31
    1,1,2,2-tetrachloroethane 2.5
    2-methyl-cyclohexyl acetate 4.08
    tetrabutyl urea 5.51
    diisobutyl methanol 4.08
    2-phenylethanol 6.88
    styrene 0.38
    dioctyl adipate 3.34
    dimethyl sulfate 20.4
    ethyl butyrate 3.95
    methyl lactate 8.77
    butyl lactate 4.96
    diethyl carbonate 2.41
    propanediol butyl ether 8.1
    triethyl orthoformate 3.7
    p-tert-butyltoluene 1.69
    methyl 4-tert-butylbenzoate 11.72
    morpholine 8.75
    tert-butylamine 3.31
    n-dodecanol 2.77
    dimethoxymethane 30.53
    ethylene carbonate 2.79
    cyrene 17.66
    2-ethoxyethyl acetate 5.21
    2-ethylhexyl acetate 2.88
    1,2,4-trichlorobenzene 1.07
    4-methylpyridine 1.99
    dibutyl ether 1.91
    2,6-dimethyl-4-heptanol 4.08
    DEF 10.49
    dimethyl isosorbide 25.21
    tetrachloroethylene 3.08
    eugenol 12.24
    triacetin 4.27
    span 80 9.02
    1,4-butanediol 5.59
    1,1-dichloroethane 0.48
    2-methyl-1-pentanol 3.72
    methyl formate 10.64
    2-methyl-1-butanol 2.46
    n-decane 0.31
    butyronitrile 1.12
    3,7-dimethyl-1-octanol 3.77
    1-chlorooctane 1.27
    1-chlorotetradecane 0.63
    n-nonane 0.26
    undecane 0.25
    tert-butylcyclohexane 0.25
    cyclooctane 0.06
    cyclopentanol 4.74
    tetrahydropyran 1.86
    tert-amyl methyl ether 4.83
    2,5,8-trioxanonane 24.66
    1-hexene 0.51
    2-isopropoxyethanol 12.26
    2,2,2-trifluoroethanol 8.17
    methyl butyrate 4.07

    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