3-Mercaptopyruvic acid

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  • Identifiers

    CAS number
    2464-23-5

    Molecular formula
    C3H4O3S

    SMILES
    C(C(=O)C(=O)O)S

  • Odor profile

    Fragrance
    Sulfurous 78.86%
    Meaty 57.31%
    Roasted 47.4%
    Savory 42.26%
    Burnt 36.41%
    Cheesy 36.12%
    Odorless 34.63%
    Cooked 33.39%
    Onion 31.37%
    Alliaceous 30.35%

     

    Flavor
    Odorless 56.12%
    Sour 36.96%
    Very mild 33.12%
    Caramellic 28.33%
    Nutty 28.09%
    Mild 22.68%
    Musty 22.62%
    Yeast 22.2%
    Acidic 22.13%
    Faint 21.79%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.0

    pKa est.
    7.34 (neutral)

    Molecular weight
    120.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    272°C

    Flash point

    • 120.46 ˚C est.

  • Synonyms

    • 3-mercaptopyruvic acid
    • 2464-23-5
    • 2-oxo-3-sulfanylpropanoic acid
    • 3-mercaptopyruvate
    • beta-mercaptopyruvate
    • mercaptopyruvate
    • Mercaptopyruvic acid
    • beta-Thiopyruvic acid
    • propanoic acid, 3-mercapto-2-oxo-
    • 3-Mercapto-2-oxopropanoic acid
    • Pyruvic acid, 3-mercapto-
    • beta-Mercaptopyruvic acid
    • beta-thiopyruvate
    • 5Z1F5OW4YB
    • BRN 1747058
    • .BETA.-THIOPYRUVIC ACID
    • PYRUVIC ACID, MERCAPTO-
    • CHEBI:16208
    • DTXSID20862960
    • 4-03-00-01936 (Beilstein Handbook Reference)
    • 3-MERCAPTO-2-OXOPROPIONIC ACID
    • 3-mercapto-pyruvic acid
    • UNII-5Z1F5OW4YB
    • 3-MERCAPTO-PYRUVATE
    • thiopyruvate
    • 2-oxo-3-sulfanylpropanoicacid
    • SCHEMBL188201
    • GTPL5118
    • DTXCID90198809
    • beta-3-mercapto-2-oxo-propanoate
    • OJOLFAIGOXZBCI-UHFFFAOYSA-N
    • beta-3-mercapto-2-oxo-propanoic acid
    • AKOS006223734
    • PD051014
    • Pyruvic acid, mercapto- (6CI,7CI,8CI)
    • Propanoic acid, 3-mercapto-2-oxo- (9CI)
    • C00957
    • EN300-1166901
    • Q4634163

  • Applications

    3-Mercaptopyruvic acid (CAS 2464-23-5) is used as a specialty building block in organic synthesis; it serves as a sulfur-containing intermediate for the preparation of amino acid derivatives and related biochemically relevant compounds. It is also employed as a chelating agent/ligand in metal-catalyzed processes and as a precursor to sulfur-containing heterocycles. In industrial and pharmaceutical contexts, it is often evaluated as an intermediate for the synthesis of fine chemicals and drugs. In research settings, it can function as a biochemical substrate or reference reagent for studies of metabolism and enzyme activity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 115.8
    methanol 262.65
    isopropanol 57.93
    water 101.8
    ethyl acetate 13.15
    n-propanol 45.91
    acetone 210.62
    n-butanol 31.54
    acetonitrile 14.39
    DMF 541.79
    toluene 1.44
    isobutanol 18.99
    1,4-dioxane 34.76
    methyl acetate 20.53
    THF 70.53
    2-butanone 36.62
    n-pentanol 24.0
    sec-butanol 22.2
    n-hexane 1.1
    ethylene glycol 130.21
    NMP 223.4
    cyclohexane 1.15
    DMSO 775.23
    n-butyl acetate 10.36
    n-octanol 18.91
    chloroform 1.77
    n-propyl acetate 10.83
    acetic acid 108.48
    dichloromethane 4.36
    cyclohexanone 30.36
    propylene glycol 46.03
    isopropyl acetate 12.43
    DMAc 215.35
    2-ethoxyethanol 116.2
    isopentanol 25.64
    n-heptane 1.99
    ethyl formate 25.06
    1,2-dichloroethane 8.39
    n-hexanol 16.54
    2-methoxyethanol 216.75
    isobutyl acetate 3.68
    tetrachloromethane 0.95
    n-pentyl acetate 16.95
    transcutol 252.94
    n-heptanol 16.9
    ethylbenzene 1.53
    MIBK 24.33
    2-propoxyethanol 60.71
    tert-butanol 64.87
    MTBE 16.12
    2-butoxyethanol 50.3
    propionic acid 30.29
    o-xylene 2.7
    formic acid 234.69
    diethyl ether 16.29
    m-xylene 2.9
    p-xylene 1.82
    chlorobenzene 1.57
    dimethyl carbonate 17.35
    n-octane 1.22
    formamide 330.19
    cyclopentanone 57.63
    2-pentanone 41.55
    anisole 8.52
    cyclopentyl methyl ether 15.73
    gamma-butyrolactone 59.08
    1-methoxy-2-propanol 117.46
    pyridine 12.46
    3-pentanone 17.49
    furfural 67.02
    n-dodecane 1.07
    diethylene glycol 106.96
    diisopropyl ether 6.03
    tert-amyl alcohol 29.82
    acetylacetone 68.87
    n-hexadecane 1.11
    acetophenone 15.49
    methyl propionate 17.82
    isopentyl acetate 8.4
    trichloroethylene 8.55
    n-nonanol 17.44
    cyclohexanol 13.01
    benzyl alcohol 15.37
    2-ethylhexanol 8.52
    isooctanol 12.93
    dipropyl ether 10.06
    1,2-dichlorobenzene 2.24
    ethyl lactate 13.99
    propylene carbonate 17.1
    n-methylformamide 193.32
    2-pentanol 20.11
    n-pentane 1.82
    1-propoxy-2-propanol 37.85
    1-methoxy-2-propyl acetate 20.39
    2-(2-methoxypropoxy) propanol 54.64
    mesitylene 3.35
    ε-caprolactone 23.41
    p-cymene 3.03
    epichlorohydrin 39.12
    1,1,1-trichloroethane 2.01
    2-aminoethanol 101.55
    morpholine-4-carbaldehyde 159.51
    sulfolane 135.02
    2,2,4-trimethylpentane 0.77
    2-methyltetrahydrofuran 21.72
    n-hexyl acetate 20.84
    isooctane 0.97
    2-(2-butoxyethoxy)ethanol 86.24
    sec-butyl acetate 5.43
    tert-butyl acetate 19.56
    decalin 0.73
    glycerin 96.48
    diglyme 142.48
    acrylic acid 42.18
    isopropyl myristate 9.77
    n-butyric acid 28.39
    acetyl acetate 10.2
    di(2-ethylhexyl) phthalate 12.54
    ethyl propionate 8.18
    nitromethane 186.99
    1,2-diethoxyethane 33.9
    benzonitrile 5.59
    trioctyl phosphate 10.87
    1-bromopropane 2.64
    gamma-valerolactone 94.95
    n-decanol 13.77
    triethyl phosphate 5.56
    4-methyl-2-pentanol 13.32
    propionitrile 6.0
    vinylene carbonate 15.0
    1,1,2-trichlorotrifluoroethane 47.96
    DMS 13.41
    cumene 2.06
    2-octanol 12.06
    2-hexanone 18.06
    octyl acetate 13.52
    limonene 4.88
    1,2-dimethoxyethane 109.13
    ethyl orthosilicate 5.24
    tributyl phosphate 10.42
    diacetone alcohol 62.97
    N,N-dimethylaniline 12.68
    acrylonitrile 12.91
    aniline 7.21
    1,3-propanediol 106.16
    bromobenzene 0.88
    dibromomethane 2.65
    1,1,2,2-tetrachloroethane 7.43
    2-methyl-cyclohexyl acetate 8.44
    tetrabutyl urea 24.43
    diisobutyl methanol 8.3
    2-phenylethanol 13.39
    styrene 1.72
    dioctyl adipate 16.74
    dimethyl sulfate 49.93
    ethyl butyrate 8.5
    methyl lactate 32.75
    butyl lactate 20.41
    diethyl carbonate 4.4
    propanediol butyl ether 59.64
    triethyl orthoformate 6.96
    p-tert-butyltoluene 3.39
    methyl 4-tert-butylbenzoate 32.8
    morpholine 47.84
    tert-butylamine 22.83
    n-dodecanol 10.46
    dimethoxymethane 146.21
    ethylene carbonate 10.58
    cyrene 49.21
    2-ethoxyethyl acetate 30.66
    2-ethylhexyl acetate 5.31
    1,2,4-trichlorobenzene 3.09
    4-methylpyridine 10.56
    dibutyl ether 10.73
    2,6-dimethyl-4-heptanol 8.3
    DEF 62.61
    dimethyl isosorbide 63.23
    tetrachloroethylene 8.85
    eugenol 38.04
    triacetin 27.21
    span 80 41.91
    1,4-butanediol 51.59
    1,1-dichloroethane 2.61
    2-methyl-1-pentanol 15.97
    methyl formate 132.36
    2-methyl-1-butanol 16.85
    n-decane 1.54
    butyronitrile 7.09
    3,7-dimethyl-1-octanol 14.27
    1-chlorooctane 4.43
    1-chlorotetradecane 2.39
    n-nonane 1.45
    undecane 1.27
    tert-butylcyclohexane 0.74
    cyclooctane 0.76
    cyclopentanol 20.52
    tetrahydropyran 12.11
    tert-amyl methyl ether 13.31
    2,5,8-trioxanonane 111.94
    1-hexene 2.74
    2-isopropoxyethanol 54.81
    2,2,2-trifluoroethanol 48.2
    methyl butyrate 14.98

    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