(2S)-2-(Benzoyloxy)butanedioic acid

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  • Identifiers

    CAS number
    22138-51-8

    Molecular formula
    C11H10O6

    SMILES
    C1=CC=C(C=C1)C(=O)O[C@@H](CC(=O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 48.02%
    Sour 38.85%
    Winey 32.14%
    Balsamic 31.77%
    Caramellic 28.96%
    Burnt 27.46%
    Nutty 25.51%
    Sweet 24.4%
    Cooked 23.35%
    Clean 23.27%

     

    Flavor
    Odorless 59.3%
    Very mild 37.97%
    Sour 36.72%
    Mild 32.88%
    Faint 27.63%
    Musty 24.19%
    Nutty 23.75%
    Yeast 22.85%
    Bland 22.69%
    Caramellic 21.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    4.34 (weak acid)

    Molecular weight
    238.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    364°C

    Flash point

    • 223.59 ˚C est.

  • Synonyms

    • 22138-51-8
    • (2S)-2-(BENZOYLOXY)BUTANEDIOIC ACID
    • (-)-2-O-Benzoyl-L-malic acid
    • O-Benzoyl-L-malic acid
    • Benzoyl (S)-(-)-malic acid
    • orb1991464
    • SCHEMBL11890496
    • DTXSID401314416
    • HY-N13713
    • AKOS040735304
    • H50809
    • 22138-51-8

  • Applications

    (2S)-2-(Benzoyloxy)butanedioic acid, CAS 22138-51-8, is predominantly used as an enantioenriched intermediate in the synthesis of chiral building blocks for pharmaceuticals and agrochemicals. It can function as a protected/activated diacid derivative, enabling selective transformations at the stereocenter. The compound also serves as a precursor for chiral ligands and catalysts in asymmetric synthesis and can be used as a building block for specialty polyesters or other polymeric materials. Additionally, it is employed in protecting-group strategies in multistep syntheses and is studied as a chiral scaffold for material and chemical development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 150.76
    methanol 259.44
    isopropanol 81.58
    water 5.77
    ethyl acetate 9.4
    n-propanol 81.28
    acetone 78.19
    n-butanol 43.52
    acetonitrile 12.72
    DMF 910.25
    toluene 0.95
    isobutanol 27.67
    1,4-dioxane 71.21
    methyl acetate 30.02
    THF 135.04
    2-butanone 45.77
    n-pentanol 25.0
    sec-butanol 64.29
    n-hexane 0.12
    ethylene glycol 100.42
    NMP 261.3
    cyclohexane 0.14
    DMSO 947.1
    n-butyl acetate 5.06
    n-octanol 7.1
    chloroform 0.48
    n-propyl acetate 7.07
    acetic acid 42.12
    dichloromethane 1.23
    cyclohexanone 21.38
    propylene glycol 71.56
    isopropyl acetate 5.82
    DMAc 801.99
    2-ethoxyethanol 232.33
    isopentanol 28.27
    n-heptane 0.15
    ethyl formate 12.62
    1,2-dichloroethane 2.85
    n-hexanol 10.03
    2-methoxyethanol 462.3
    isobutyl acetate 1.72
    tetrachloromethane 0.13
    n-pentyl acetate 3.69
    transcutol 130.34
    n-heptanol 6.81
    ethylbenzene 1.58
    MIBK 9.48
    2-propoxyethanol 74.42
    tert-butanol 106.0
    MTBE 22.18
    2-butoxyethanol 31.69
    propionic acid 24.44
    o-xylene 2.2
    formic acid 130.55
    diethyl ether 14.51
    m-xylene 0.93
    p-xylene 1.78
    chlorobenzene 0.51
    dimethyl carbonate 23.62
    n-octane 0.11
    formamide 376.6
    cyclopentanone 48.92
    2-pentanone 18.73
    anisole 17.61
    cyclopentyl methyl ether 18.03
    gamma-butyrolactone 55.35
    1-methoxy-2-propanol 201.54
    pyridine 20.18
    3-pentanone 12.31
    furfural 42.44
    n-dodecane 0.16
    diethylene glycol 106.63
    diisopropyl ether 1.9
    tert-amyl alcohol 91.05
    acetylacetone 23.49
    n-hexadecane 0.18
    acetophenone 15.92
    methyl propionate 24.39
    isopentyl acetate 5.01
    trichloroethylene 2.96
    n-nonanol 6.99
    cyclohexanol 15.4
    benzyl alcohol 19.81
    2-ethylhexanol 4.25
    isooctanol 4.84
    dipropyl ether 5.92
    1,2-dichlorobenzene 0.92
    ethyl lactate 14.12
    propylene carbonate 11.76
    n-methylformamide 218.14
    2-pentanol 18.24
    n-pentane 0.11
    1-propoxy-2-propanol 35.82
    1-methoxy-2-propyl acetate 14.61
    2-(2-methoxypropoxy) propanol 42.93
    mesitylene 0.84
    ε-caprolactone 22.26
    p-cymene 1.23
    epichlorohydrin 58.49
    1,1,1-trichloroethane 0.54
    2-aminoethanol 174.2
    morpholine-4-carbaldehyde 193.4
    sulfolane 120.51
    2,2,4-trimethylpentane 0.16
    2-methyltetrahydrofuran 48.16
    n-hexyl acetate 6.78
    isooctane 0.07
    2-(2-butoxyethoxy)ethanol 56.17
    sec-butyl acetate 3.76
    tert-butyl acetate 11.12
    decalin 0.2
    glycerin 126.07
    diglyme 106.73
    acrylic acid 25.7
    isopropyl myristate 3.11
    n-butyric acid 14.89
    acetyl acetate 4.21
    di(2-ethylhexyl) phthalate 5.67
    ethyl propionate 7.74
    nitromethane 106.87
    1,2-diethoxyethane 18.22
    benzonitrile 4.75
    trioctyl phosphate 3.83
    1-bromopropane 0.93
    gamma-valerolactone 82.96
    n-decanol 5.4
    triethyl phosphate 5.86
    4-methyl-2-pentanol 6.69
    propionitrile 8.49
    vinylene carbonate 9.63
    1,1,2-trichlorotrifluoroethane 48.0
    DMS 9.5
    cumene 1.31
    2-octanol 4.01
    2-hexanone 11.82
    octyl acetate 4.9
    limonene 1.67
    1,2-dimethoxyethane 205.82
    ethyl orthosilicate 5.48
    tributyl phosphate 4.11
    diacetone alcohol 48.53
    N,N-dimethylaniline 17.19
    acrylonitrile 15.14
    aniline 8.3
    1,3-propanediol 156.09
    bromobenzene 0.33
    dibromomethane 0.51
    1,1,2,2-tetrachloroethane 3.93
    2-methyl-cyclohexyl acetate 5.98
    tetrabutyl urea 10.88
    diisobutyl methanol 3.23
    2-phenylethanol 10.79
    styrene 1.78
    dioctyl adipate 6.7
    dimethyl sulfate 62.27
    ethyl butyrate 5.3
    methyl lactate 38.47
    butyl lactate 8.7
    diethyl carbonate 4.62
    propanediol butyl ether 32.22
    triethyl orthoformate 6.43
    p-tert-butyltoluene 1.21
    methyl 4-tert-butylbenzoate 16.78
    morpholine 154.06
    tert-butylamine 19.76
    n-dodecanol 3.79
    dimethoxymethane 207.71
    ethylene carbonate 7.39
    cyrene 46.39
    2-ethoxyethyl acetate 9.21
    2-ethylhexyl acetate 3.25
    1,2,4-trichlorobenzene 1.96
    4-methylpyridine 15.87
    dibutyl ether 4.51
    2,6-dimethyl-4-heptanol 3.23
    DEF 71.73
    dimethyl isosorbide 46.94
    tetrachloroethylene 2.21
    eugenol 20.26
    triacetin 11.85
    span 80 21.32
    1,4-butanediol 58.25
    1,1-dichloroethane 0.61
    2-methyl-1-pentanol 19.18
    methyl formate 97.83
    2-methyl-1-butanol 34.07
    n-decane 0.25
    butyronitrile 6.5
    3,7-dimethyl-1-octanol 5.53
    1-chlorooctane 1.04
    1-chlorotetradecane 0.57
    n-nonane 0.19
    undecane 0.2
    tert-butylcyclohexane 0.15
    cyclooctane 0.08
    cyclopentanol 25.87
    tetrahydropyran 21.61
    tert-amyl methyl ether 24.46
    2,5,8-trioxanonane 83.43
    1-hexene 0.85
    2-isopropoxyethanol 80.14
    2,2,2-trifluoroethanol 21.34
    methyl butyrate 12.63

    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