Citrazinic Acid

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  • Identifiers

    CAS number
    99-11-6

    Molecular formula
    C6H5NO4

    SMILES
    C1=C(C=C(NC1=O)O)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 74.98%
    Burnt 29.2%
    Sour 27.46%
    Nutty 21.27%
    Phenolic 20.67%
    Roasted 20.49%
    Bitter 20.46%
    Cooked 20.42%
    Savory 19.41%
    Sharp 16.93%

     

    Flavor
    Odorless 56.12%
    Nutty 40.02%
    Mild 36.94%
    Phenolic 34.68%
    Sour 32.08%
    Bitter 31.27%
    Very mild 27.43%
    Faint 26.47%
    Urine 23.13%
    Yeast 21.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    9.54 (weak base)

    Molecular weight
    155.11 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    522°C

    Flash point

    • 223.61 ˚C est.

  • Synonyms

    • CITRAZINIC ACID
    • 99-11-6
    • 2,6-Dihydroxyisonicotinic acid
    • 2,6-Dihydroxy-4-carboxypyridine
    • 2,6-Dihydroxy-4-pyridinecarboxylic acid
    • 4-Pyridinecarboxylic acid, 1,2-dihydro-6-hydroxy-2-oxo-
    • N8Q4XFV86A
    • Isonicotinic acid, 1,2-dihydro-6-hydroxy-2-oxo-
    • NSC-5214
    • NSC-41334
    • DTXSID3059185
    • RefChem:577454
    • DTXCID8049094
    • 202-731-2
    • 2,6-Dihydroxypyridine-4-carboxylic acid
    • 2-hydroxy-6-oxo-1H-pyridine-4-carboxylic acid
    • MFCD00006274
    • Kyselina citrazinova
    • 2,6-Dihydroxyisonicotinate
    • 6-Hydroxy-2-oxo-1,2-dihydropyridine-4-carboxylic acid
    • 4-Pyridinecarboxylic acid, 2,6-dihydroxy-
    • 6-Hydroxy-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid
    • Isonicotinic acid, 2,6-dihydroxy-
    • NSC 41334
    • WLN: T6NJ BQ DVQ FQ
    • Isonicotinic acid,6-dihydroxy-
    • CitrazinicAcid
    • 4-Pyridinecarboxylic acid,6-dihydroxy-
    • 6-Hydroxy-4-carboxy-2-pyridone
    • Kyselina citrazinova [Czech]
    • EINECS 202-731-2
    • 4-Pyridinecarboxylic acid,2-dihydro-6-hydroxy-2-oxo-
    • UNII-N8Q4XFV86A
    • Citrazinc acid
    • Maybridge4_003590
    • Oprea1_725973
    • CITRAZINIC ACID [MI]
    • SCHEMBL185046
    • SCHEMBL5682960
    • SCHEMBL8957131
    • 1,2-Dihydro-6-hydroxy-2-oxo-4-pyridinecarboxylic acid
    • CHEMBL2048371
    • NSC5214
    • CHEBI:184700
    • HMS1531D04
    • BB_NC-01990
    • BBL004463
    • Isonicotinic acid, 2,6-dihydroxy-,
    • MFCD00134947
    • SBB013446
    • STK378282
    • AKOS000114790
    • AKOS000301520
    • AB00673
    • BS-3855
    • BP-30063
    • ST095444
    • SY009490
    • DB-346541
    • CS-0067136
    • NS00020127
    • EN300-00809
    • 2,6-Dihydroxypyridine-4-carboxylic acid, 97%
    • 2-hydroxy-6-oxohydropyridine-4-carboxylic acid
    • 2,6-Dihydroxy-isoNicotinic acid (Citrazinic acid)
    • AE-562/40806835
    • F056519
    • Q5122816
    • Z56855768
    • 6-Hydroxy-2-oxo-1,2-dihydro-4-pyridinecarboxylic acid
    • F2191-0236
    • 6-Hydroxy-2-oxo-1,2-dihydro-4-pyridinecarboxylic acid #
    • 99-11-6

  • Applications

    Citrazinic Acid (CAS 99-11-6) is used primarily as an intermediate in the synthesis of heterocyclic compounds and colorants; it commonly serves as a chelating agent or ligand in metal complexes; in plastics, polymers, and coatings sectors it is employed as a building block for functional derivatives and as a precursor for compounds used in inks and coatings; in research and development, it is evaluated as a starting point for the synthesis of heterocyclic organic materials and metal-binding or fluorescent compounds; its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.28
    methanol 1.18
    isopropanol 0.2
    water 1.8
    ethyl acetate 0.02
    n-propanol 0.29
    acetone 0.23
    n-butanol 0.23
    acetonitrile 0.12
    DMF 39.37
    toluene 0.02
    isobutanol 0.18
    1,4-dioxane 0.33
    methyl acetate 0.13
    THF 3.09
    2-butanone 0.19
    n-pentanol 0.3
    sec-butanol 0.18
    n-hexane 0.02
    ethylene glycol 3.15
    NMP 13.53
    cyclohexane 0.0
    DMSO 168.43
    n-butyl acetate 0.38
    n-octanol 0.43
    chloroform 0.09
    n-propyl acetate 0.18
    acetic acid 0.24
    dichloromethane 0.16
    cyclohexanone 0.29
    propylene glycol 1.03
    isopropyl acetate 0.04
    DMAc 19.99
    2-ethoxyethanol 2.89
    isopentanol 0.31
    n-heptane 0.03
    ethyl formate 0.42
    1,2-dichloroethane 0.14
    n-hexanol 0.49
    2-methoxyethanol 5.25
    isobutyl acetate 0.11
    tetrachloromethane 0.1
    n-pentyl acetate 0.26
    transcutol 1.56
    n-heptanol 0.65
    ethylbenzene 0.04
    MIBK 0.19
    2-propoxyethanol 4.65
    tert-butanol 0.65
    MTBE 0.11
    2-butoxyethanol 3.64
    propionic acid 0.2
    o-xylene 0.05
    formic acid 2.72
    diethyl ether 0.04
    m-xylene 0.04
    p-xylene 0.07
    chlorobenzene 0.02
    dimethyl carbonate 0.6
    n-octane 0.02
    formamide 3.88
    cyclopentanone 1.27
    2-pentanone 0.11
    anisole 0.29
    cyclopentyl methyl ether 0.26
    gamma-butyrolactone 2.0
    1-methoxy-2-propanol 2.85
    pyridine 0.19
    3-pentanone 0.09
    furfural 3.86
    n-dodecane 0.02
    diethylene glycol 8.14
    diisopropyl ether 0.02
    tert-amyl alcohol 0.49
    acetylacetone 0.24
    n-hexadecane 0.02
    acetophenone 0.52
    methyl propionate 0.12
    isopentyl acetate 0.5
    trichloroethylene 0.18
    n-nonanol 0.45
    cyclohexanol 0.12
    benzyl alcohol 0.41
    2-ethylhexanol 0.39
    isooctanol 0.58
    dipropyl ether 0.29
    1,2-dichlorobenzene 0.07
    ethyl lactate 1.18
    propylene carbonate 0.81
    n-methylformamide 5.66
    2-pentanol 0.09
    n-pentane 0.01
    1-propoxy-2-propanol 2.92
    1-methoxy-2-propyl acetate 0.77
    2-(2-methoxypropoxy) propanol 3.91
    mesitylene 0.05
    ε-caprolactone 0.37
    p-cymene 0.12
    epichlorohydrin 1.87
    1,1,1-trichloroethane 0.07
    2-aminoethanol 2.44
    morpholine-4-carbaldehyde 8.85
    sulfolane 16.81
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.36
    n-hexyl acetate 0.34
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 3.29
    sec-butyl acetate 0.08
    tert-butyl acetate 0.19
    decalin 0.01
    glycerin 5.41
    diglyme 7.51
    acrylic acid 0.38
    isopropyl myristate 0.26
    n-butyric acid 0.17
    acetyl acetate 0.04
    di(2-ethylhexyl) phthalate 0.79
    ethyl propionate 0.17
    nitromethane 1.33
    1,2-diethoxyethane 0.25
    benzonitrile 0.27
    trioctyl phosphate 0.86
    1-bromopropane 0.05
    gamma-valerolactone 2.54
    n-decanol 0.37
    triethyl phosphate 1.35
    4-methyl-2-pentanol 0.15
    propionitrile 0.18
    vinylene carbonate 0.66
    1,1,2-trichlorotrifluoroethane 4.64
    DMS 0.28
    cumene 0.07
    2-octanol 0.31
    2-hexanone 0.33
    octyl acetate 0.35
    limonene 0.11
    1,2-dimethoxyethane 7.94
    ethyl orthosilicate 1.08
    tributyl phosphate 0.72
    diacetone alcohol 1.32
    N,N-dimethylaniline 0.86
    acrylonitrile 0.45
    aniline 0.07
    1,3-propanediol 1.7
    bromobenzene 0.02
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.28
    2-methyl-cyclohexyl acetate 0.65
    tetrabutyl urea 1.87
    diisobutyl methanol 0.38
    2-phenylethanol 0.64
    styrene 0.03
    dioctyl adipate 0.62
    dimethyl sulfate 5.99
    ethyl butyrate 0.4
    methyl lactate 1.43
    butyl lactate 1.03
    diethyl carbonate 0.48
    propanediol butyl ether 2.21
    triethyl orthoformate 0.73
    p-tert-butyltoluene 0.14
    methyl 4-tert-butylbenzoate 2.42
    morpholine 0.67
    tert-butylamine 0.24
    n-dodecanol 0.28
    dimethoxymethane 3.63
    ethylene carbonate 0.39
    cyrene 5.82
    2-ethoxyethyl acetate 0.3
    2-ethylhexyl acetate 0.35
    1,2,4-trichlorobenzene 0.1
    4-methylpyridine 0.23
    dibutyl ether 0.17
    2,6-dimethyl-4-heptanol 0.38
    DEF 0.86
    dimethyl isosorbide 9.07
    tetrachloroethylene 0.2
    eugenol 3.5
    triacetin 0.48
    span 80 1.57
    1,4-butanediol 1.36
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 0.35
    methyl formate 3.44
    2-methyl-1-butanol 0.24
    n-decane 0.02
    butyronitrile 0.16
    3,7-dimethyl-1-octanol 0.38
    1-chlorooctane 0.08
    1-chlorotetradecane 0.05
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.02
    cyclooctane 0.0
    cyclopentanol 0.38
    tetrahydropyran 0.09
    tert-amyl methyl ether 0.16
    2,5,8-trioxanonane 7.62
    1-hexene 0.04
    2-isopropoxyethanol 1.37
    2,2,2-trifluoroethanol 0.78
    methyl butyrate 0.42

    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