1,4-dimethyl (2R)-2-hydroxybutanedioate

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  • Identifiers

    CAS number
    70681-41-3

    Molecular formula
    C6H10O5

    SMILES
    COC(=O)C[C@H](C(=O)OC)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fruity 86.59%
    Caramellic 60.37%
    Winey 57.5%
    Ethereal 48.71%
    Sweet 45.82%
    Green 39.6%
    Apple 38.37%
    Rummy 37.08%
    Buttery 35.58%
    Sour 30.9%

     

    Flavor
    Fruity 70.04%
    Creamy 33.25%
    Mild 31.99%
    Odorless 31.07%
    Grape 28.67%
    Buttery 26.13%
    Wine 25.15%
    Sweet 24.6%
    Musty 24.51%
    Bitter 24.4%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    5.54 (weak acid)

    Molecular weight
    162.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    238°C

    Flash point

    • 103.23 ˚C est.

  • Synonyms

    • 1,4-Dimethyl (2R)-2-Hydroxybutanedioate
    • Butanedioic acid, hydroxy-, dimethyl ester, (2R)-
    • RefChem:416812
    • 829-455-0
    • 70681-41-3
    • (R)-Dimethyl 2-hydroxysuccinate
    • Dimethyl D-malate
    • D-(+)-Malic Acid Dimethyl Ester
    • MFCD00066216
    • dimethyl (2R)-2-hydroxybutanedioate
    • Dimethyl D-(+)-Malate
    • D-Dimethylmalate
    • dimethyl-d-malate
    • (r)-dimethyl malate
    • dimethyl (r)-malate
    • (+)-Dimethyl malate
    • (R)-2-hydroxysuccinic acid dimethyl ester
    • (R)-(+)-Dimethylmalate
    • orb2893278
    • SCHEMBL1691025
    • DTXSID30892495
    • D-(+)-Apple Acid Dimethyl Ester
    • Dimethyl (R)-(+)-malate, 98%
    • AKOS015910996
    • CS-W016123
    • (R)-2-hydroxysuccinic acid dimethylester
    • AS-60590
    • SY066757
    • M1347
    • D91488
    • EN300-183703
    • F135100
    • 70681-41-3

  • Applications

    1,4-dimethyl (2R)-2-hydroxybutanedioate (CAS 70681-41-3) is commonly used as a chiral building block and intermediate in organic synthesis, particularly for enantioselective transformations, and as a scaffold for converting into malate esters and related chiral derivatives. In pharmaceutical and agrochemical development, it is frequently employed as a precursor to enantioenriched intermediates and as a source for chiral ligands in asymmetric catalysis. It may also be used as a starting material in polymer and materials research for malate-derived esters and potential biobased polyesters. Additionally, it can serve as a synthetic reagent or auxiliary in stereochemical resolutions and in routes requiring a hydroxyl-bearing chiral center. Applications in fragrance and flavor research exist where derivatives may be explored as chiral aroma precursors, although such use is exploratory and governed by regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 100.6
    methanol 197.74
    isopropanol 80.26
    water 118.86
    ethyl acetate 56.96
    n-propanol 67.72
    acetone 133.89
    n-butanol 52.15
    acetonitrile 93.35
    DMF 558.26
    toluene 18.97
    isobutanol 53.23
    1,4-dioxane 205.21
    methyl acetate 94.48
    THF 222.12
    2-butanone 79.01
    n-pentanol 34.65
    sec-butanol 65.08
    n-hexane 3.4
    ethylene glycol 81.47
    NMP 654.59
    cyclohexane 7.46
    DMSO 576.58
    n-butyl acetate 16.08
    n-octanol 15.4
    chloroform 53.03
    n-propyl acetate 28.36
    acetic acid 231.46
    dichloromethane 84.08
    cyclohexanone 110.9
    propylene glycol 41.45
    isopropyl acetate 31.47
    DMAc 621.29
    2-ethoxyethanol 139.53
    isopentanol 48.86
    n-heptane 2.93
    ethyl formate 73.67
    1,2-dichloroethane 68.06
    n-hexanol 18.33
    2-methoxyethanol 286.82
    isobutyl acetate 15.14
    tetrachloromethane 13.09
    n-pentyl acetate 13.77
    transcutol 151.03
    n-heptanol 13.84
    ethylbenzene 13.63
    MIBK 30.85
    2-propoxyethanol 61.48
    tert-butanol 143.85
    MTBE 72.79
    2-butoxyethanol 40.46
    propionic acid 88.75
    o-xylene 26.24
    formic acid 409.41
    diethyl ether 52.24
    m-xylene 16.3
    p-xylene 19.19
    chlorobenzene 22.44
    dimethyl carbonate 64.71
    n-octane 1.76
    formamide 590.87
    cyclopentanone 169.36
    2-pentanone 49.25
    anisole 53.05
    cyclopentyl methyl ether 77.37
    gamma-butyrolactone 247.07
    1-methoxy-2-propanol 136.8
    pyridine 106.64
    3-pentanone 50.14
    furfural 249.93
    n-dodecane 1.53
    diethylene glycol 89.89
    diisopropyl ether 13.31
    tert-amyl alcohol 107.36
    acetylacetone 75.93
    n-hexadecane 1.68
    acetophenone 60.08
    methyl propionate 72.18
    isopentyl acetate 17.94
    trichloroethylene 107.96
    n-nonanol 14.87
    cyclohexanol 57.56
    benzyl alcohol 49.91
    2-ethylhexanol 12.82
    isooctanol 12.2
    dipropyl ether 18.02
    1,2-dichlorobenzene 27.36
    ethyl lactate 30.16
    propylene carbonate 94.5
    n-methylformamide 262.07
    2-pentanol 33.77
    n-pentane 4.64
    1-propoxy-2-propanol 33.72
    1-methoxy-2-propyl acetate 31.04
    2-(2-methoxypropoxy) propanol 52.58
    mesitylene 11.88
    ε-caprolactone 104.97
    p-cymene 8.17
    epichlorohydrin 196.94
    1,1,1-trichloroethane 35.86
    2-aminoethanol 105.87
    morpholine-4-carbaldehyde 405.17
    sulfolane 356.94
    2,2,4-trimethylpentane 3.8
    2-methyltetrahydrofuran 143.81
    n-hexyl acetate 22.03
    isooctane 1.64
    2-(2-butoxyethoxy)ethanol 57.8
    sec-butyl acetate 19.9
    tert-butyl acetate 40.09
    decalin 4.54
    glycerin 127.21
    diglyme 138.3
    acrylic acid 112.62
    isopropyl myristate 10.97
    n-butyric acid 70.62
    acetyl acetate 50.31
    di(2-ethylhexyl) phthalate 15.7
    ethyl propionate 35.47
    nitromethane 444.74
    1,2-diethoxyethane 31.85
    benzonitrile 40.69
    trioctyl phosphate 10.42
    1-bromopropane 24.0
    gamma-valerolactone 265.2
    n-decanol 11.05
    triethyl phosphate 23.01
    4-methyl-2-pentanol 20.25
    propionitrile 53.26
    vinylene carbonate 95.99
    1,1,2-trichlorotrifluoroethane 188.11
    DMS 34.99
    cumene 11.38
    2-octanol 9.89
    2-hexanone 29.79
    octyl acetate 14.46
    limonene 12.75
    1,2-dimethoxyethane 197.27
    ethyl orthosilicate 21.05
    tributyl phosphate 12.75
    diacetone alcohol 67.47
    N,N-dimethylaniline 51.8
    acrylonitrile 81.78
    aniline 54.74
    1,3-propanediol 123.84
    bromobenzene 16.23
    dibromomethane 40.98
    1,1,2,2-tetrachloroethane 87.3
    2-methyl-cyclohexyl acetate 24.63
    tetrabutyl urea 23.54
    diisobutyl methanol 10.1
    2-phenylethanol 26.02
    styrene 15.74
    dioctyl adipate 20.69
    dimethyl sulfate 154.95
    ethyl butyrate 22.27
    methyl lactate 63.45
    butyl lactate 17.01
    diethyl carbonate 20.84
    propanediol butyl ether 34.93
    triethyl orthoformate 22.12
    p-tert-butyltoluene 7.88
    methyl 4-tert-butylbenzoate 43.2
    morpholine 237.63
    tert-butylamine 70.19
    n-dodecanol 8.71
    dimethoxymethane 191.68
    ethylene carbonate 72.64
    cyrene 86.15
    2-ethoxyethyl acetate 25.75
    2-ethylhexyl acetate 14.18
    1,2,4-trichlorobenzene 40.15
    4-methylpyridine 96.95
    dibutyl ether 15.11
    2,6-dimethyl-4-heptanol 10.1
    DEF 142.35
    dimethyl isosorbide 92.67
    tetrachloroethylene 67.94
    eugenol 41.58
    triacetin 36.86
    span 80 31.97
    1,4-butanediol 45.6
    1,1-dichloroethane 39.2
    2-methyl-1-pentanol 35.41
    methyl formate 191.22
    2-methyl-1-butanol 50.6
    n-decane 2.46
    butyronitrile 41.19
    3,7-dimethyl-1-octanol 14.67
    1-chlorooctane 7.82
    1-chlorotetradecane 3.76
    n-nonane 2.27
    undecane 1.88
    tert-butylcyclohexane 3.24
    cyclooctane 3.06
    cyclopentanol 82.61
    tetrahydropyran 95.15
    tert-amyl methyl ether 64.45
    2,5,8-trioxanonane 101.29
    1-hexene 9.64
    2-isopropoxyethanol 69.01
    2,2,2-trifluoroethanol 176.61
    methyl butyrate 49.81

    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