Salicylhydroxamic Acid

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  • Identifiers

    CAS number
    89-73-6

    Molecular formula
    C7H7NO3

    SMILES
    C1=CC=C(C(=C1)C(=O)NO)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 50.91%
    Sweet 43.38%
    Bitter 34.67%
    Phenolic 29.82%
    Savory 24.74%
    Vanilla 24.61%
    Burnt 23.83%
    Almond 23.21%
    Spicy 22.88%
    Caramellic 21.67%

     

    Flavor
    Odorless 52.67%
    Bitter 40.43%
    Mild 40.29%
    Phenolic 32.54%
    Very mild 26.7%
    Faint 24.82%
    Nutty 24.71%
    Bland 22.47%
    Sweet-like 21.9%
    Urine 21.81%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    9.44 (weak base)

    Molecular weight
    153.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    364°C

    Melting point expt.

    • 168 °C

    Flash point

    • 176.11 ˚C est.

  • Synonyms

    • Salicylhydroxamic acid
    • N,2-Dihydroxybenzamide
    • 89-73-6
    • 2-Hydroxybenzohydroxamic acid
    • SHAM
    • Salicylohydroximic acid
    • 2-Hydroxybenzhydroxamic acid
    • O-Hydroxybenzohydroxamic acid
    • 2-hydroxybenzenecarbohydroxamic acid
    • DTXSID5075365
    • NSC-5088
    • 8Q07182D0T
    • NSC-193440
    • CHEBI:45615
    • RefChem:884393
    • DTXCID7048665
    • 201-934-3
    • Salicylohydroxamic acid
    • Benzamide, N,2-dihydroxy-
    • MFCD00002110
    • SHA
    • NSC 5088
    • NSC 193440
    • Saliaylhydroxamic acid
    • 2,N-Dihydroxy-benzamide
    • MLS000069410
    • CHEMBL309339
    • Benzamide,2-dihydroxy-
    • SMR000059099
    • SalicylhydroxaMicacid
    • 1-hydroxybenzene-2-carbohydroxamic acid
    • N-Salicylhydroxamic acid
    • EINECS 201-934-3
    • UNII-8Q07182D0T
    • NSC5088
    • N-Hydroxysalicylamide
    • salicyl hydroximic acid
    • Opera_ID_592
    • N,2-Dihydroxy-benzamide
    • Salicylic Hydroxamic Acid
    • N,2-Dihydroxybenzamide #
    • bmse000772
    • Oprea1_838400
    • Salicylhydroxamic acid, 99%
    • MLS001076305
    • SCHEMBL144849
    • 2-Hydroxybenzenehydroxamic acid
    • orb2941085
    • SALICYLOYLHYDROXAMIC ACID
    • SCHEMBL5928967
    • SCHEMBL21530845
    • benzohydroxamic acid, 2-hydroxy-
    • HMS2234D15
    • HMS3372H11
    • SALICYLHYDROXAMIC ACID [MI]
    • BDBM50015089
    • EBC-03222
    • NSC193440
    • SBB043988
    • STK387225
    • 2-HYDROXYPHENYLHYDROXAMIC ACID
    • AKOS000120047
    • AKOS004905639
    • AKOS005260023
    • DB03819
    • FS-3250
    • FS27783
    • SALICYLHYDROXAMIC ACID [WHO-DD]
    • NCGC00018115-01
    • NCGC00018115-02
    • NCGC00018115-03
    • HY-18721
    • SY046520
    • CS-0014188
    • NS00015042
    • S0008
    • ST50115655
    • EN300-18305
    • O11999
    • F079691
    • Q7404461
    • Z57842350
    • InChI=1/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10
    • 89-73-6

  • Applications

    Salicylhydroxamic acid (CAS 89-73-6) is commonly used in biochemical research as an inhibitor of the mitochondrial alternative oxidase (AOX), allowing researchers to dissect respiration and energy metabolism in plants and fungi. It also functions as a chelating ligand for transition and post-transition metal ions, forming stable metal complexes that are exploited in analytical methods, coordination chemistry, and the study of catalysis and separations. Additionally, SHAM is employed as an intermediate or building block in the synthesis of metal-containing ligands and complexes for research and sensor applications, and it is evaluated for use in academic investigations of spectroscopy and ligand design, subject to formulation specifics and regulatory guidelines.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 90.86
    methanol 143.06
    isopropanol 55.37
    water 39.29
    ethyl acetate 27.07
    n-propanol 57.72
    acetone 76.24
    n-butanol 41.08
    acetonitrile 37.78
    DMF 647.38
    toluene 3.17
    isobutanol 30.23
    1,4-dioxane 61.03
    methyl acetate 37.96
    THF 147.87
    2-butanone 53.73
    n-pentanol 36.59
    sec-butanol 37.7
    n-hexane 0.69
    ethylene glycol 164.33
    NMP 240.77
    cyclohexane 0.58
    DMSO 832.95
    n-butyl acetate 14.82
    n-octanol 23.47
    chloroform 6.74
    n-propyl acetate 18.71
    acetic acid 41.26
    dichloromethane 13.66
    cyclohexanone 49.77
    propylene glycol 67.46
    isopropyl acetate 17.18
    DMAc 351.46
    2-ethoxyethanol 115.75
    isopentanol 30.51
    n-heptane 1.86
    ethyl formate 37.65
    1,2-dichloroethane 20.31
    n-hexanol 32.31
    2-methoxyethanol 225.54
    isobutyl acetate 7.86
    tetrachloromethane 2.79
    n-pentyl acetate 14.55
    transcutol 90.66
    n-heptanol 26.09
    ethylbenzene 4.71
    MIBK 27.06
    2-propoxyethanol 83.56
    tert-butanol 59.86
    MTBE 19.1
    2-butoxyethanol 50.9
    propionic acid 35.47
    o-xylene 6.57
    formic acid 96.08
    diethyl ether 13.54
    m-xylene 6.72
    p-xylene 5.44
    chlorobenzene 5.78
    dimethyl carbonate 38.79
    n-octane 1.11
    formamide 209.83
    cyclopentanone 92.67
    2-pentanone 42.49
    anisole 19.71
    cyclopentyl methyl ether 28.39
    gamma-butyrolactone 117.16
    1-methoxy-2-propanol 129.99
    pyridine 23.33
    3-pentanone 27.41
    furfural 82.8
    n-dodecane 1.4
    diethylene glycol 123.74
    diisopropyl ether 5.23
    tert-amyl alcohol 41.65
    acetylacetone 54.42
    n-hexadecane 1.51
    acetophenone 27.6
    methyl propionate 47.24
    isopentyl acetate 12.74
    trichloroethylene 25.89
    n-nonanol 21.97
    cyclohexanol 22.85
    benzyl alcohol 28.72
    2-ethylhexanol 16.5
    isooctanol 18.14
    dipropyl ether 12.9
    1,2-dichlorobenzene 8.44
    ethyl lactate 29.95
    propylene carbonate 40.89
    n-methylformamide 247.99
    2-pentanol 23.95
    n-pentane 0.74
    1-propoxy-2-propanol 48.98
    1-methoxy-2-propyl acetate 30.65
    2-(2-methoxypropoxy) propanol 41.83
    mesitylene 6.03
    ε-caprolactone 40.88
    p-cymene 6.74
    epichlorohydrin 99.66
    1,1,1-trichloroethane 8.29
    2-aminoethanol 141.95
    morpholine-4-carbaldehyde 154.56
    sulfolane 223.58
    2,2,4-trimethylpentane 0.99
    2-methyltetrahydrofuran 42.71
    n-hexyl acetate 19.7
    isooctane 1.1
    2-(2-butoxyethoxy)ethanol 56.7
    sec-butyl acetate 10.07
    tert-butyl acetate 21.23
    decalin 1.13
    glycerin 130.32
    diglyme 90.89
    acrylic acid 37.94
    isopropyl myristate 10.68
    n-butyric acid 35.24
    acetyl acetate 14.51
    di(2-ethylhexyl) phthalate 13.73
    ethyl propionate 20.78
    nitromethane 122.55
    1,2-diethoxyethane 21.11
    benzonitrile 20.63
    trioctyl phosphate 14.1
    1-bromopropane 6.95
    gamma-valerolactone 115.88
    n-decanol 17.74
    triethyl phosphate 12.69
    4-methyl-2-pentanol 15.5
    propionitrile 28.86
    vinylene carbonate 35.63
    1,1,2-trichlorotrifluoroethane 86.55
    DMS 19.83
    cumene 5.15
    2-octanol 15.44
    2-hexanone 24.3
    octyl acetate 15.68
    limonene 9.54
    1,2-dimethoxyethane 112.49
    ethyl orthosilicate 11.03
    tributyl phosphate 11.75
    diacetone alcohol 59.45
    N,N-dimethylaniline 21.82
    acrylonitrile 54.53
    aniline 13.04
    1,3-propanediol 118.7
    bromobenzene 3.93
    dibromomethane 7.38
    1,1,2,2-tetrachloroethane 25.25
    2-methyl-cyclohexyl acetate 15.09
    tetrabutyl urea 24.72
    diisobutyl methanol 11.6
    2-phenylethanol 29.1
    styrene 4.42
    dioctyl adipate 16.72
    dimethyl sulfate 93.47
    ethyl butyrate 16.15
    methyl lactate 65.72
    butyl lactate 20.28
    diethyl carbonate 11.63
    propanediol butyl ether 43.6
    triethyl orthoformate 12.1
    p-tert-butyltoluene 6.88
    methyl 4-tert-butylbenzoate 34.27
    morpholine 81.74
    tert-butylamine 20.54
    n-dodecanol 13.46
    dimethoxymethane 158.19
    ethylene carbonate 27.76
    cyrene 61.26
    2-ethoxyethyl acetate 21.17
    2-ethylhexyl acetate 8.76
    1,2,4-trichlorobenzene 10.91
    4-methylpyridine 22.53
    dibutyl ether 9.94
    2,6-dimethyl-4-heptanol 11.6
    DEF 88.27
    dimethyl isosorbide 61.06
    tetrachloroethylene 15.71
    eugenol 39.86
    triacetin 21.75
    span 80 34.01
    1,4-butanediol 72.66
    1,1-dichloroethane 9.41
    2-methyl-1-pentanol 23.2
    methyl formate 151.36
    2-methyl-1-butanol 27.45
    n-decane 1.79
    butyronitrile 25.75
    3,7-dimethyl-1-octanol 16.8
    1-chlorooctane 7.71
    1-chlorotetradecane 3.87
    n-nonane 1.51
    undecane 1.57
    tert-butylcyclohexane 1.21
    cyclooctane 0.52
    cyclopentanol 38.0
    tetrahydropyran 22.2
    tert-amyl methyl ether 18.3
    2,5,8-trioxanonane 76.82
    1-hexene 3.16
    2-isopropoxyethanol 57.54
    2,2,2-trifluoroethanol 39.67
    methyl butyrate 29.22

    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