Homogentisic Acid

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  • Identifiers

    CAS number
    451-13-8

    Molecular formula
    C8H8O4

    SMILES
    C1=CC(=C(C=C1O)CC(=O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 58.1%
    Phenolic 56.17%
    Vanilla 29.46%
    Burnt 29.26%
    Balsamic 28.39%
    Creamy 24.54%
    Smoky 23.69%
    Milky 23.56%
    Savory 22.5%
    Medicinal 22.27%

     

    Flavor
    Odorless 56.33%
    Mild 52.55%
    Phenolic 49.64%
    Nutty 35.97%
    Sour 35.5%
    Faint 27.01%
    Very mild 26.67%
    Musty 25.35%
    Bland 24.55%
    Cadaverous 22.54%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    8.55 (weak base)

    Molecular weight
    168.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    368°C

    Melting point expt.

    • 153 °C

    Flash point

    • 199.64 ˚C est.

    Solubility expt.

    • 850 mg/mL at 25 °C

  • Synonyms

    • Homogentisic acid
    • 451-13-8
    • 2,5-Dihydroxyphenylacetic acid
    • 2-(2,5-dihydroxyphenyl)acetic acid
    • Alcapton
    • Homogentisate acid
    • Homogentisinic acid
    • homogentisate
    • 2,5-Dihydroxybenzeneacetic acid
    • 2,5-Dihydroxy-alpha-toluic acid
    • Benzeneacetic acid, 2,5-dihydroxy-
    • 2,5-Dihydroxyphenylacetate
    • NP8UE6VF08
    • NSC-88940
    • DTXSID1060005
    • CHEBI:44747
    • CHEBI:16169
    • Acid, Homogentisic
    • RefChem:788461
    • DTXCID6040375
    • 207-192-7
    • (2,5-Dihydroxyphenyl)acetic acid
    • MFCD00004324
    • 2,5-DHPOP
    • Acetic acid, (2,5-dihydroxyphenyl)-
    • BRN 2692860
    • 2-(3,6-DIHYDROXYPHENYL)ACETIC ACID
    • 2,5-Dihydroxy-.alpha.-toluic acid
    • 71694-00-3
    • 2,5-dihydroxy-benzeneacetic acid
    • Melanic acid
    • EINECS 207-192-7
    • NSC 88940
    • UNII-NP8UE6VF08
    • Homogentisinate
    • 1ajp
    • 4aq6
    • 2,5-Dihydroxy-a-toluate
    • bmse000200
    • Homogentisic acid (Standard)
    • 2,5-Dihydroxy-alpha-toluate
    • 2,5-Dihydroxy-benzeneacetate
    • 4-10-00-01506 (Beilstein Handbook Reference)
    • 2,5-Dihydroxy-a-toluic acid
    • Homogentisic acid, crystalline
    • SCHEMBL155333
    • HOMOGENTISIC ACID [MI]
    • (2,5-dihydroxyphenyl)-Acetate
    • orb1297717
    • Benzeneacetic acid,5-dihydroxy-
    • SCHEMBL29354171
    • Acetic acid,5-dihydroxyphenyl)-
    • 2-(2,5-dihydroxyphenyl)aceticacid
    • (2,5-dihydroxyphenyl)-Acetic acid
    • MSK40047
    • NSC88940
    • RYB46848
    • s9352
    • Homogentisic acid, analytical standard
    • AKOS004910342
    • DB08327
    • EBC-616850
    • FH23844
    • HY-113283R
    • AS-19326
    • SY051598
    • DB-020087
    • HY-113283
    • CS-0059508
    • D1050
    • NS00015132
    • ST50406743
    • C00544
    • T70932
    • Q416054
    • 5A20D3D5-DF92-400D-AB62-07CC3E7DBFBB
    • HQ9
    • InChI=1/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12
    • 451-13-8

  • Applications

    Homogentisic acid (CAS 451-13-8) is primarily used as a chemical intermediate and pigment precursor in specialty applications: it serves as a building block for pigment formulations and dyes (notably melanin- and pyomelanin-related materials) used in coatings, inks, and related colorants; it is investigated as a precursor for aromatic polymers and dye intermediates in polymer and plastics chemistry; in analytical and biochemical contexts it functions as a substrate in tyrosinase activity assays and as a reference in metabolic studies related to tyrosine degradation; its phenolic and carboxylate functionalities enable limited metal chelation and potential complexation applications; its oxidation to quinone products is studied in materials science for pigment formation and conductive or electrochromic materials; applications in pharmaceuticals or food are not standard; subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 201.91
    methanol 357.64
    isopropanol 121.4
    water 28.91
    ethyl acetate 35.52
    n-propanol 122.13
    acetone 188.36
    n-butanol 82.79
    acetonitrile 65.65
    DMF 590.88
    toluene 3.13
    isobutanol 57.7
    1,4-dioxane 133.3
    methyl acetate 53.18
    THF 278.52
    2-butanone 85.16
    n-pentanol 50.05
    sec-butanol 62.65
    n-hexane 1.08
    ethylene glycol 141.99
    NMP 186.71
    cyclohexane 0.76
    DMSO 419.34
    n-butyl acetate 14.92
    n-octanol 22.36
    chloroform 0.79
    n-propyl acetate 19.35
    acetic acid 59.15
    dichloromethane 2.47
    cyclohexanone 39.4
    propylene glycol 91.91
    isopropyl acetate 19.72
    DMAc 396.98
    2-ethoxyethanol 180.43
    isopentanol 56.58
    n-heptane 2.91
    ethyl formate 42.93
    1,2-dichloroethane 5.37
    n-hexanol 31.57
    2-methoxyethanol 328.03
    isobutyl acetate 6.8
    tetrachloromethane 0.55
    n-pentyl acetate 11.89
    transcutol 81.92
    n-heptanol 24.91
    ethylbenzene 3.93
    MIBK 27.13
    2-propoxyethanol 119.77
    tert-butanol 129.09
    MTBE 36.07
    2-butoxyethanol 60.75
    propionic acid 37.63
    o-xylene 5.48
    formic acid 123.37
    diethyl ether 41.01
    m-xylene 4.68
    p-xylene 4.58
    chlorobenzene 1.61
    dimethyl carbonate 39.04
    n-octane 1.34
    formamide 248.65
    cyclopentanone 99.56
    2-pentanone 58.49
    anisole 23.63
    cyclopentyl methyl ether 40.11
    gamma-butyrolactone 112.52
    1-methoxy-2-propanol 176.46
    pyridine 22.06
    3-pentanone 31.5
    furfural 61.1
    n-dodecane 1.32
    diethylene glycol 137.58
    diisopropyl ether 8.28
    tert-amyl alcohol 68.73
    acetylacetone 50.6
    n-hexadecane 1.41
    acetophenone 20.26
    methyl propionate 50.86
    isopentyl acetate 12.78
    trichloroethylene 4.33
    n-nonanol 21.75
    cyclohexanol 22.34
    benzyl alcohol 24.7
    2-ethylhexanol 15.47
    isooctanol 17.94
    dipropyl ether 26.25
    1,2-dichlorobenzene 2.23
    ethyl lactate 24.65
    propylene carbonate 32.04
    n-methylformamide 258.12
    2-pentanol 38.19
    n-pentane 1.12
    1-propoxy-2-propanol 56.0
    1-methoxy-2-propyl acetate 31.27
    2-(2-methoxypropoxy) propanol 48.04
    mesitylene 4.21
    ε-caprolactone 37.39
    p-cymene 5.31
    epichlorohydrin 93.66
    1,1,1-trichloroethane 2.0
    2-aminoethanol 188.3
    morpholine-4-carbaldehyde 171.15
    sulfolane 112.99
    2,2,4-trimethylpentane 0.82
    2-methyltetrahydrofuran 76.11
    n-hexyl acetate 17.47
    isooctane 0.77
    2-(2-butoxyethoxy)ethanol 66.2
    sec-butyl acetate 10.75
    tert-butyl acetate 22.34
    decalin 0.96
    glycerin 135.04
    diglyme 105.96
    acrylic acid 34.05
    isopropyl myristate 9.77
    n-butyric acid 37.75
    acetyl acetate 14.25
    di(2-ethylhexyl) phthalate 11.79
    ethyl propionate 25.13
    nitromethane 159.37
    1,2-diethoxyethane 27.05
    benzonitrile 10.77
    trioctyl phosphate 11.2
    1-bromopropane 3.1
    gamma-valerolactone 121.35
    n-decanol 17.9
    triethyl phosphate 12.39
    4-methyl-2-pentanol 19.28
    propionitrile 39.61
    vinylene carbonate 23.06
    1,1,2-trichlorotrifluoroethane 47.44
    DMS 14.11
    cumene 4.07
    2-octanol 12.99
    2-hexanone 26.63
    octyl acetate 15.15
    limonene 7.06
    1,2-dimethoxyethane 187.85
    ethyl orthosilicate 12.02
    tributyl phosphate 9.4
    diacetone alcohol 61.11
    N,N-dimethylaniline 21.27
    acrylonitrile 50.74
    aniline 10.58
    1,3-propanediol 167.59
    bromobenzene 0.99
    dibromomethane 1.28
    1,1,2,2-tetrachloroethane 4.54
    2-methyl-cyclohexyl acetate 12.92
    tetrabutyl urea 21.8
    diisobutyl methanol 10.97
    2-phenylethanol 21.33
    styrene 3.21
    dioctyl adipate 16.12
    dimethyl sulfate 55.65
    ethyl butyrate 18.08
    methyl lactate 51.23
    butyl lactate 14.89
    diethyl carbonate 12.69
    propanediol butyl ether 42.97
    triethyl orthoformate 14.4
    p-tert-butyltoluene 5.12
    methyl 4-tert-butylbenzoate 28.7
    morpholine 151.87
    tert-butylamine 40.76
    n-dodecanol 13.82
    dimethoxymethane 259.86
    ethylene carbonate 21.34
    cyrene 63.04
    2-ethoxyethyl acetate 19.35
    2-ethylhexyl acetate 9.02
    1,2,4-trichlorobenzene 3.09
    4-methylpyridine 21.55
    dibutyl ether 12.78
    2,6-dimethyl-4-heptanol 10.97
    DEF 87.54
    dimethyl isosorbide 70.34
    tetrachloroethylene 3.26
    eugenol 32.39
    triacetin 17.93
    span 80 31.36
    1,4-butanediol 84.88
    1,1-dichloroethane 2.56
    2-methyl-1-pentanol 30.3
    methyl formate 153.17
    2-methyl-1-butanol 48.01
    n-decane 1.98
    butyronitrile 35.46
    3,7-dimethyl-1-octanol 15.28
    1-chlorooctane 5.0
    1-chlorotetradecane 2.91
    n-nonane 1.77
    undecane 1.59
    tert-butylcyclohexane 0.97
    cyclooctane 0.73
    cyclopentanol 48.45
    tetrahydropyran 45.98
    tert-amyl methyl ether 28.89
    2,5,8-trioxanonane 91.42
    1-hexene 4.26
    2-isopropoxyethanol 84.44
    2,2,2-trifluoroethanol 35.61
    methyl butyrate 29.82

    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