Dimethyl (R)-(+)-methylsuccinate

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  • Identifiers

    CAS number
    22644-27-5

    Molecular formula
    C7H12O4

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

    Safety labels

  • Odor profile

    Fragrance
    Fruity 96.98%
    Green 60.6%
    Sweet 58.68%
    Apple 56.63%
    Tropical 53.08%
    Winey 52.24%
    Pineapple 50.96%
    Ethereal 49.96%
    Rummy 38.49%
    Caramellic 34.57%

     

    Flavor
    Fruity 91.73%
    Sweet 50.43%
    Apple 41.97%
    Floral 41.96%
    Green 41.12%
    Berry 39.59%
    Tropical 38.68%
    Grape 34.77%
    Pineapple 34.36%
    Creamy 33.38%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    5.92 (weak acid)

    Molecular weight
    160.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    198°C

    Flash point

    • 74.46 ˚C est.

  • Synonyms

    • 22644-27-5
    • Dimethyl (R)-(+)-methylsuccinate
    • (R)-dimethyl 2-methylsuccinate
    • dimethyl (2R)-2-methylbutanedioate
    • (R)-PYROTARTARIC ACID DIMETHYL ESTER
    • MFCD00134573
    • (R)-(+)-Methylsuccinic Acid Dimethyl Ester
    • 1,4-DIMETHYL (2R)-2-METHYLBUTANEDIOATE
    • (r)-dimethyl methylsuccinate
    • (R)-dimethyl2-methylsuccinate
    • SCHEMBL774101
    • dimethyl (R)-2-methylsuccinate
    • NFOQJNGQQXICBY-RXMQYKEDSA-
    • DTXSID80431434
    • AKOS015840301
    • AS-38247
    • Dimethyl (R)-(+)-methylsuccinate, 99%
    • CS-0204538
    • d-I+/--MethylbernsteinsA currencyuredimethylester
    • 644M275
    • InChI=1/C7H12O4/c1-5(7(9)11-3)4-6(8)10-2/h5H,4H2,1-3H3/t5-/m1/s1
    • 22644-27-5

  • Applications

    Dimethyl (R)-(+)-methylsuccinate (CAS 22644-27-5) is primarily used as an enantioenriched intermediate in organic synthesis, enabling the production of chiral pharmaceutical and agrochemical candidates. It also serves as a precursor or co-monomer for biodegradable polyesters and related polymers, including polybutylene succinate (PBS) type materials. In fragrance and flavor chemistry, it can be employed as a chiral building block for the synthesis of aroma compounds; in cosmetics and personal care, it is used as an intermediate in esterification-based formulation work. It may also find utility as a specialty intermediate in coatings, inks, and other industrial formulations, depending on regulatory constraints and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 570.33
    methanol 963.69
    isopropanol 552.32
    water 73.79
    ethyl acetate 651.95
    n-propanol 453.43
    acetone 1031.15
    n-butanol 359.52
    acetonitrile 1194.74
    DMF 1666.71
    toluene 285.35
    isobutanol 393.95
    1,4-dioxane 1186.24
    methyl acetate 869.18
    THF 1147.0
    2-butanone 705.37
    n-pentanol 259.01
    sec-butanol 487.11
    n-hexane 33.9
    ethylene glycol 189.1
    NMP 1861.65
    cyclohexane 57.04
    DMSO 1344.03
    n-butyl acetate 172.51
    n-octanol 82.95
    chloroform 1290.13
    n-propyl acetate 287.59
    acetic acid 1546.58
    dichloromethane 1331.47
    cyclohexanone 790.91
    propylene glycol 145.83
    isopropyl acetate 359.42
    DMAc 1826.79
    2-ethoxyethanol 729.39
    isopentanol 362.16
    n-heptane 13.07
    ethyl formate 538.9
    1,2-dichloroethane 856.31
    n-hexanol 133.65
    2-methoxyethanol 1194.83
    isobutyl acetate 167.95
    tetrachloromethane 258.7
    n-pentyl acetate 129.75
    transcutol 728.68
    n-heptanol 81.64
    ethylbenzene 157.65
    MIBK 257.34
    2-propoxyethanol 344.46
    tert-butanol 919.96
    MTBE 680.6
    2-butoxyethanol 220.96
    propionic acid 636.62
    o-xylene 231.19
    formic acid 1152.01
    diethyl ether 510.71
    m-xylene 178.79
    p-xylene 233.47
    chlorobenzene 378.99
    dimethyl carbonate 342.63
    n-octane 8.46
    formamide 1872.84
    cyclopentanone 1000.82
    2-pentanone 424.83
    anisole 452.45
    cyclopentyl methyl ether 545.49
    gamma-butyrolactone 1409.84
    1-methoxy-2-propanol 618.89
    pyridine 941.59
    3-pentanone 401.13
    furfural 1395.45
    n-dodecane 7.1
    diethylene glycol 338.65
    diisopropyl ether 133.55
    tert-amyl alcohol 737.79
    acetylacetone 616.56
    n-hexadecane 8.13
    acetophenone 433.71
    methyl propionate 535.7
    isopentyl acetate 174.12
    trichloroethylene 1784.99
    n-nonanol 74.59
    cyclohexanol 405.73
    benzyl alcohol 361.07
    2-ethylhexanol 87.44
    isooctanol 70.62
    dipropyl ether 111.79
    1,2-dichlorobenzene 360.76
    ethyl lactate 150.46
    propylene carbonate 614.38
    n-methylformamide 1131.1
    2-pentanol 257.49
    n-pentane 36.54
    1-propoxy-2-propanol 176.58
    1-methoxy-2-propyl acetate 216.05
    2-(2-methoxypropoxy) propanol 206.05
    mesitylene 102.2
    ε-caprolactone 731.27
    p-cymene 63.89
    epichlorohydrin 1421.59
    1,1,1-trichloroethane 792.08
    2-aminoethanol 363.79
    morpholine-4-carbaldehyde 1476.65
    sulfolane 1374.29
    2,2,4-trimethylpentane 30.82
    2-methyltetrahydrofuran 990.9
    n-hexyl acetate 184.71
    isooctane 14.62
    2-(2-butoxyethoxy)ethanol 242.5
    sec-butyl acetate 216.65
    tert-butyl acetate 389.3
    decalin 33.9
    glycerin 305.44
    diglyme 630.62
    acrylic acid 668.89
    isopropyl myristate 69.49
    n-butyric acid 639.11
    acetyl acetate 512.46
    di(2-ethylhexyl) phthalate 80.91
    ethyl propionate 287.68
    nitromethane 2916.04
    1,2-diethoxyethane 226.79
    benzonitrile 441.35
    trioctyl phosphate 49.21
    1-bromopropane 354.69
    gamma-valerolactone 1515.17
    n-decanol 50.41
    triethyl phosphate 119.61
    4-methyl-2-pentanol 146.08
    propionitrile 563.03
    vinylene carbonate 633.47
    1,1,2-trichlorotrifluoroethane 1074.42
    DMS 232.9
    cumene 108.98
    2-octanol 59.87
    2-hexanone 273.36
    octyl acetate 88.5
    limonene 85.66
    1,2-dimethoxyethane 1038.9
    ethyl orthosilicate 113.62
    tributyl phosphate 71.15
    diacetone alcohol 409.53
    N,N-dimethylaniline 310.42
    acrylonitrile 801.15
    aniline 467.36
    1,3-propanediol 503.78
    bromobenzene 337.33
    dibromomethane 690.27
    1,1,2,2-tetrachloroethane 1240.15
    2-methyl-cyclohexyl acetate 160.74
    tetrabutyl urea 100.73
    diisobutyl methanol 60.12
    2-phenylethanol 192.36
    styrene 205.94
    dioctyl adipate 111.36
    dimethyl sulfate 613.6
    ethyl butyrate 168.2
    methyl lactate 247.06
    butyl lactate 99.63
    diethyl carbonate 138.62
    propanediol butyl ether 156.22
    triethyl orthoformate 129.24
    p-tert-butyltoluene 59.62
    methyl 4-tert-butylbenzoate 227.34
    morpholine 1354.33
    tert-butylamine 501.82
    n-dodecanol 37.58
    dimethoxymethane 797.45
    ethylene carbonate 485.28
    cyrene 307.62
    2-ethoxyethyl acetate 203.34
    2-ethylhexyl acetate 136.63
    1,2,4-trichlorobenzene 480.8
    4-methylpyridine 994.71
    dibutyl ether 101.44
    2,6-dimethyl-4-heptanol 60.12
    DEF 778.83
    dimethyl isosorbide 398.84
    tetrachloroethylene 917.06
    eugenol 209.86
    triacetin 225.19
    span 80 133.28
    1,4-butanediol 196.89
    1,1-dichloroethane 809.24
    2-methyl-1-pentanol 274.69
    methyl formate 871.27
    2-methyl-1-butanol 369.64
    n-decane 12.25
    butyronitrile 441.53
    3,7-dimethyl-1-octanol 89.01
    1-chlorooctane 54.43
    1-chlorotetradecane 21.93
    n-nonane 11.62
    undecane 8.81
    tert-butylcyclohexane 30.01
    cyclooctane 17.05
    cyclopentanol 490.48
    tetrahydropyran 730.63
    tert-amyl methyl ether 479.67
    2,5,8-trioxanonane 375.4
    1-hexene 118.67
    2-isopropoxyethanol 416.46
    2,2,2-trifluoroethanol 808.79
    methyl butyrate 407.86

    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