2-Thiomalic acid

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  • Identifiers

    CAS number
    70-49-5

    Molecular formula
    C4H6O4S

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

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sulfurous 73.21%
    Meaty 54.82%
    Odorless 44.13%
    Savory 43.33%
    Roasted 43.29%
    Cooked 31.48%
    Cheesy 30.81%
    Onion 23.3%
    Alliaceous 23.26%
    Burnt 21.8%

     

    Flavor
    Odorless 73.38%
    Sour 33.65%
    Mild 32.97%
    Very mild 31.89%
    Bland 25.69%
    Yeast 24.6%
    Acidic 23.47%
    Faint 23.02%
    Sweet-like 21.52%
    Caramellic 21.09%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    6.95 (neutral)

    Molecular weight
    150.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    325°C

    Flash point

    • 161.41 ˚C est.

  • Synonyms

    • Mercaptosuccinic acid
    • Thiomalic acid
    • 70-49-5
    • 2-sulfanylbutanedioic acid
    • 2-Mercaptosuccinic acid
    • 2-Thiomalic acid
    • DL-Mercaptosuccinic acid
    • Butanedioic acid, mercapto-
    • Monomercaptosuccinic acid
    • Malic acid, 2-thio-
    • Mercaptosuccinate
    • USAF EK-P-6297
    • SUCCINIC ACID, MERCAPTO-
    • USAF M-2
    • 2-Sulfanylsuccinic acid
    • NSC 7302
    • butanedioic acid, 2-mercapto-
    • (1)-Mercaptosuccinic acid
    • EINECS 200-736-4
    • EINECS 211-423-7
    • BRN 1099858
    • AI3-22956
    • DL-THIOMALIC ACID
    • NSC-7302
    • MFCD00004860
    • alpha-Mercaptosuccinic acid
    • 94239W5L4H
    • THIOMALIC ACID [MI]
    • .alpha.-Mercaptosuccinic acid
    • (+/-)-Mercaptosuccinic acid
    • CHEBI:38705
    • 4-03-00-01130 (Beilstein Handbook Reference)
    • SODIUM AUROTHIOMALATE IMPURITY C [EP IMPURITY]
    • NSC41809
    • mercaptobutanedioic acid
    • SODIUM AUROTHIOMALATE IMPURITY C (EP IMPURITY)
    • UNII-94239W5L4H
    • Malic acid, 2thio
    • HSTM
    • 2Mercaptosuccinic acid
    • Succinic acid, mercapto
    • WLN: SHYVQ1VQ
    • (1)Mercaptosuccinic acid
    • 2-Mercapto-succinic acid
    • Butanedioic acid, mercapto
    • 2-Sulfanylsuccinic acid #
    • Butanedioic acid, 2mercapto
    • Mercaptosuccinic acid, 97%
    • MLS006011445
    • SCHEMBL133541
    • CHEMBL4303414
    • DTXSID20861615
    • NSC7302
    • 2-Sulphanylbutane-1,4-dioic acid
    • STR07420
    • BBL011516
    • STL146632
    • AKOS000120969
    • AKOS016042329
    • CS-W010986
    • SB45438
    • 1-Sulfanylethane-1,2-dicarboxylic acid
    • NCI60_003949
    • PD062592
    • SMR001826671
    • M0064
    • NS00020699
    • EN300-20552
    • D70319
    • SBI-0653860.0001
    • SR-01000945206
    • Q7784684
    • SR-01000945206-1
    • BRD-A43435802-001-01-2
    • BRD-A43435802-001-02-0
    • Mercaptosuccinic acid, Vetec(TM) reagent grade, 97%
    • F2191-0218
    • Z104478826
    • Mercaptosuccinic acid, ReagentPlus(R), >=99.0% (HPLC)
    • 200-736-4

  • Applications

    2-Thiomalic acid (CAS 70-49-5) is typically used as an intermediate in organic synthesis to access sulfur-containing compounds and thioesters; it also serves as a chelating agent or ligand for metal ions in analytical chemistry, catalysis, and materials research; in polymer and plastics applications it can function as a functional building block or crosslinking junction via thiol-ene chemistry or related condensation processes; it is a precursor for the synthesis of sulfur-containing heterocycles; and it is evaluated for coatings and inks formulations to improve metal stability and substrate adhesion, depending on local regulations and formulation specifics.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 645.43
    methanol 958.75
    isopropanol 404.32
    water 1358.86
    ethyl acetate 91.2
    n-propanol 376.88
    acetone 443.0
    n-butanol 305.79
    acetonitrile 145.48
    DMF 2189.6
    toluene 14.99
    isobutanol 188.12
    1,4-dioxane 362.39
    methyl acetate 118.95
    THF 469.64
    2-butanone 173.47
    n-pentanol 168.7
    sec-butanol 235.03
    n-hexane 10.0
    ethylene glycol 837.11
    NMP 393.57
    cyclohexane 6.86
    DMSO 1649.49
    n-butyl acetate 30.19
    n-octanol 58.69
    chloroform 24.02
    n-propyl acetate 52.07
    acetic acid 189.04
    dichloromethane 44.5
    cyclohexanone 100.55
    propylene glycol 367.16
    isopropyl acetate 50.35
    DMAc 881.84
    2-ethoxyethanol 661.63
    isopentanol 177.04
    n-heptane 7.94
    ethyl formate 237.85
    1,2-dichloroethane 69.6
    n-hexanol 88.3
    2-methoxyethanol 1237.74
    isobutyl acetate 14.98
    tetrachloromethane 14.99
    n-pentyl acetate 28.74
    transcutol 232.07
    n-heptanol 59.66
    ethylbenzene 15.06
    MIBK 72.18
    2-propoxyethanol 284.88
    tert-butanol 388.79
    MTBE 109.08
    2-butoxyethanol 163.08
    propionic acid 114.58
    o-xylene 20.92
    formic acid 673.79
    diethyl ether 143.89
    m-xylene 17.15
    p-xylene 14.3
    chlorobenzene 8.7
    dimethyl carbonate 122.92
    n-octane 4.76
    formamide 909.52
    cyclopentanone 191.42
    2-pentanone 160.91
    anisole 66.13
    cyclopentyl methyl ether 109.5
    gamma-butyrolactone 196.16
    1-methoxy-2-propanol 603.03
    pyridine 71.38
    3-pentanone 90.02
    furfural 230.44
    n-dodecane 3.83
    diethylene glycol 475.17
    diisopropyl ether 26.87
    tert-amyl alcohol 227.43
    acetylacetone 154.14
    n-hexadecane 3.98
    acetophenone 56.87
    methyl propionate 110.45
    isopentyl acetate 20.87
    trichloroethylene 49.76
    n-nonanol 51.71
    cyclohexanol 91.47
    benzyl alcohol 85.1
    2-ethylhexanol 32.84
    isooctanol 37.05
    dipropyl ether 46.97
    1,2-dichlorobenzene 10.51
    ethyl lactate 64.81
    propylene carbonate 69.36
    n-methylformamide 900.13
    2-pentanol 147.4
    n-pentane 12.66
    1-propoxy-2-propanol 134.98
    1-methoxy-2-propyl acetate 52.61
    2-(2-methoxypropoxy) propanol 109.41
    mesitylene 13.8
    ε-caprolactone 85.11
    p-cymene 9.5
    epichlorohydrin 243.9
    1,1,1-trichloroethane 23.09
    2-aminoethanol 750.86
    morpholine-4-carbaldehyde 561.49
    sulfolane 270.56
    2,2,4-trimethylpentane 3.54
    2-methyltetrahydrofuran 160.54
    n-hexyl acetate 38.73
    isooctane 3.16
    2-(2-butoxyethoxy)ethanol 161.48
    sec-butyl acetate 24.39
    tert-butyl acetate 55.0
    decalin 3.77
    glycerin 608.42
    diglyme 316.96
    acrylic acid 115.03
    isopropyl myristate 18.56
    n-butyric acid 123.7
    acetyl acetate 40.19
    di(2-ethylhexyl) phthalate 21.51
    ethyl propionate 55.6
    nitromethane 375.31
    1,2-diethoxyethane 70.14
    benzonitrile 27.27
    trioctyl phosphate 23.78
    1-bromopropane 30.17
    gamma-valerolactone 298.27
    n-decanol 41.32
    triethyl phosphate 21.95
    4-methyl-2-pentanol 62.29
    propionitrile 83.22
    vinylene carbonate 70.12
    1,1,2-trichlorotrifluoroethane 213.07
    DMS 26.94
    cumene 12.3
    2-octanol 36.77
    2-hexanone 74.03
    octyl acetate 28.2
    limonene 12.44
    1,2-dimethoxyethane 784.16
    ethyl orthosilicate 20.64
    tributyl phosphate 19.89
    diacetone alcohol 161.78
    N,N-dimethylaniline 75.04
    acrylonitrile 114.6
    aniline 46.67
    1,3-propanediol 673.79
    bromobenzene 5.82
    dibromomethane 26.42
    1,1,2,2-tetrachloroethane 54.28
    2-methyl-cyclohexyl acetate 20.46
    tetrabutyl urea 47.96
    diisobutyl methanol 23.19
    2-phenylethanol 53.72
    styrene 14.42
    dioctyl adipate 26.75
    dimethyl sulfate 218.99
    ethyl butyrate 32.55
    methyl lactate 155.62
    butyl lactate 37.7
    diethyl carbonate 20.86
    propanediol butyl ether 128.86
    triethyl orthoformate 25.33
    p-tert-butyltoluene 10.76
    methyl 4-tert-butylbenzoate 62.14
    morpholine 413.22
    tert-butylamine 162.61
    n-dodecanol 33.05
    dimethoxymethane 862.51
    ethylene carbonate 64.46
    cyrene 111.58
    2-ethoxyethyl acetate 42.64
    2-ethylhexyl acetate 14.19
    1,2,4-trichlorobenzene 11.71
    4-methylpyridine 75.78
    dibutyl ether 30.38
    2,6-dimethyl-4-heptanol 23.19
    DEF 293.75
    dimethyl isosorbide 117.83
    tetrachloroethylene 47.97
    eugenol 82.31
    triacetin 31.36
    span 80 66.28
    1,4-butanediol 349.71
    1,1-dichloroethane 35.33
    2-methyl-1-pentanol 92.68
    methyl formate 692.63
    2-methyl-1-butanol 158.56
    n-decane 5.7
    butyronitrile 94.74
    3,7-dimethyl-1-octanol 35.4
    1-chlorooctane 15.76
    1-chlorotetradecane 7.75
    n-nonane 5.66
    undecane 4.56
    tert-butylcyclohexane 3.51
    cyclooctane 4.07
    cyclopentanol 159.63
    tetrahydropyran 134.12
    tert-amyl methyl ether 86.0
    2,5,8-trioxanonane 233.36
    1-hexene 24.18
    2-isopropoxyethanol 255.68
    2,2,2-trifluoroethanol 193.04
    methyl butyrate 89.29

    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