2-Benzylmalic acid

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  • Identifiers

    CAS number
    16947-49-2

    Molecular formula
    C11H12O5

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

    Safety labels

  • Odor profile

    Fragrance
    Sweet 63.7%
    Honey 49.02%
    Balsamic 40.82%
    Powdery 31.11%
    Fatty 30.08%
    Odorless 28.48%
    Sour 27.87%
    Floral 27.77%
    Creamy 25.27%
    Spicy 25.07%

     

    Flavor
    Odorless 60.53%
    Mild 39.51%
    Sour 36.05%
    Sweet 30.74%
    Very mild 27.6%
    Faint 22.47%
    Musty 22.16%
    Bland 21.86%
    Honeysuckle 21.82%
    Yeast 21.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    5.06 (weak acid)

    Molecular weight
    224.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    398°C

    Flash point

    • 212.05 ˚C est.

  • Synonyms

    • alpha-Benzylmalic acid
    • RefChem:909663
    • 16947-49-2
    • 2-Benzylmalic acid
    • 2-Benzylmalate
    • (2R)-2-benzyl-2-hydroxybutanedioic acid
    • (r)-2-benzylmalic acid
    • CHEBI:181931
    • C20653
    • 16947-49-2

  • Applications

    2-Benzylmalic acid (CAS 16947-49-2) is primarily used as a chiral building block and synthetic intermediate in the preparation of pharmaceutical and fine chemical compounds, supporting asymmetric transformations and downstream elaboration. It may serve as a fragrance intermediate in perfumery due to its benzyl substituent, and can be explored in cosmetics as a chiral building block for ingredient synthesis or fragrance-related components. With suitable derivatization (e.g., esterification to form diesters) it can function as a precursor for specialty polymers or polyesters for niche applications in coatings or inks. These uses are typically at research and development stages and subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 254.43
    methanol 524.28
    isopropanol 126.59
    water 16.94
    ethyl acetate 24.52
    n-propanol 137.76
    acetone 85.39
    n-butanol 81.53
    acetonitrile 11.17
    DMF 646.7
    toluene 3.25
    isobutanol 57.68
    1,4-dioxane 58.56
    methyl acetate 21.22
    THF 284.57
    2-butanone 44.25
    n-pentanol 47.53
    sec-butanol 87.52
    n-hexane 0.42
    ethylene glycol 283.49
    NMP 271.56
    cyclohexane 0.46
    DMSO 455.26
    n-butyl acetate 9.79
    n-octanol 11.65
    chloroform 0.37
    n-propyl acetate 11.31
    acetic acid 74.93
    dichloromethane 0.57
    cyclohexanone 35.01
    propylene glycol 206.29
    isopropyl acetate 18.45
    DMAc 618.56
    2-ethoxyethanol 345.57
    isopentanol 77.14
    n-heptane 0.75
    ethyl formate 17.46
    1,2-dichloroethane 1.94
    n-hexanol 37.2
    2-methoxyethanol 706.81
    isobutyl acetate 3.73
    tetrachloromethane 0.45
    n-pentyl acetate 6.15
    transcutol 110.07
    n-heptanol 17.37
    ethylbenzene 3.53
    MIBK 34.57
    2-propoxyethanol 154.79
    tert-butanol 215.36
    MTBE 33.53
    2-butoxyethanol 57.93
    propionic acid 40.38
    o-xylene 5.51
    formic acid 233.17
    diethyl ether 25.0
    m-xylene 4.74
    p-xylene 3.1
    chlorobenzene 0.87
    dimethyl carbonate 33.7
    n-octane 0.34
    formamide 406.39
    cyclopentanone 87.16
    2-pentanone 55.43
    anisole 21.89
    cyclopentyl methyl ether 55.79
    gamma-butyrolactone 86.34
    1-methoxy-2-propanol 380.59
    pyridine 15.76
    3-pentanone 22.48
    furfural 49.61
    n-dodecane 0.35
    diethylene glycol 208.93
    diisopropyl ether 6.56
    tert-amyl alcohol 141.7
    acetylacetone 51.82
    n-hexadecane 0.38
    acetophenone 22.83
    methyl propionate 43.21
    isopentyl acetate 10.6
    trichloroethylene 2.28
    n-nonanol 11.65
    cyclohexanol 32.17
    benzyl alcohol 29.17
    2-ethylhexanol 13.81
    isooctanol 12.9
    dipropyl ether 13.85
    1,2-dichlorobenzene 1.56
    ethyl lactate 27.31
    propylene carbonate 24.53
    n-methylformamide 281.07
    2-pentanol 54.06
    n-pentane 0.51
    1-propoxy-2-propanol 74.22
    1-methoxy-2-propyl acetate 30.67
    2-(2-methoxypropoxy) propanol 50.43
    mesitylene 3.75
    ε-caprolactone 33.17
    p-cymene 3.42
    epichlorohydrin 64.1
    1,1,1-trichloroethane 0.94
    2-aminoethanol 406.87
    morpholine-4-carbaldehyde 196.29
    sulfolane 146.86
    2,2,4-trimethylpentane 0.63
    2-methyltetrahydrofuran 86.88
    n-hexyl acetate 10.33
    isooctane 0.46
    2-(2-butoxyethoxy)ethanol 70.97
    sec-butyl acetate 8.49
    tert-butyl acetate 29.92
    decalin 0.56
    glycerin 310.31
    diglyme 114.43
    acrylic acid 38.05
    isopropyl myristate 5.07
    n-butyric acid 39.41
    acetyl acetate 8.79
    di(2-ethylhexyl) phthalate 8.59
    ethyl propionate 16.78
    nitromethane 98.63
    1,2-diethoxyethane 15.88
    benzonitrile 5.89
    trioctyl phosphate 6.7
    1-bromopropane 0.97
    gamma-valerolactone 110.9
    n-decanol 8.93
    triethyl phosphate 9.37
    4-methyl-2-pentanol 29.24
    propionitrile 10.57
    vinylene carbonate 14.2
    1,1,2-trichlorotrifluoroethane 67.54
    DMS 10.86
    cumene 3.19
    2-octanol 8.35
    2-hexanone 17.57
    octyl acetate 7.45
    limonene 4.74
    1,2-dimethoxyethane 206.12
    ethyl orthosilicate 8.83
    tributyl phosphate 5.77
    diacetone alcohol 118.55
    N,N-dimethylaniline 22.2
    acrylonitrile 16.09
    aniline 11.38
    1,3-propanediol 328.82
    bromobenzene 0.63
    dibromomethane 0.39
    1,1,2,2-tetrachloroethane 3.37
    2-methyl-cyclohexyl acetate 10.91
    tetrabutyl urea 13.75
    diisobutyl methanol 9.3
    2-phenylethanol 22.58
    styrene 3.0
    dioctyl adipate 9.13
    dimethyl sulfate 68.85
    ethyl butyrate 11.18
    methyl lactate 73.49
    butyl lactate 13.92
    diethyl carbonate 7.31
    propanediol butyl ether 50.43
    triethyl orthoformate 9.92
    p-tert-butyltoluene 3.46
    methyl 4-tert-butylbenzoate 26.85
    morpholine 139.68
    tert-butylamine 48.35
    n-dodecanol 6.1
    dimethoxymethane 269.18
    ethylene carbonate 12.25
    cyrene 75.87
    2-ethoxyethyl acetate 12.37
    2-ethylhexyl acetate 6.37
    1,2,4-trichlorobenzene 2.57
    4-methylpyridine 15.7
    dibutyl ether 4.69
    2,6-dimethyl-4-heptanol 9.3
    DEF 99.91
    dimethyl isosorbide 74.13
    tetrachloroethylene 2.92
    eugenol 31.25
    triacetin 14.01
    span 80 32.84
    1,4-butanediol 132.97
    1,1-dichloroethane 0.61
    2-methyl-1-pentanol 41.59
    methyl formate 114.76
    2-methyl-1-butanol 64.95
    n-decane 0.54
    butyronitrile 10.26
    3,7-dimethyl-1-octanol 11.66
    1-chlorooctane 1.85
    1-chlorotetradecane 0.95
    n-nonane 0.44
    undecane 0.43
    tert-butylcyclohexane 0.54
    cyclooctane 0.32
    cyclopentanol 61.77
    tetrahydropyran 27.6
    tert-amyl methyl ether 40.49
    2,5,8-trioxanonane 88.55
    1-hexene 2.29
    2-isopropoxyethanol 132.76
    2,2,2-trifluoroethanol 33.49
    methyl butyrate 23.17

    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