(S)-2-Ethyl-3-oxobutanoic acid ethyl ester

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  • Identifiers

    CAS number
    130606-81-4

    Molecular formula
    C8H14O3

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

  • Odor profile

    Fragrance
    Fruity 97.08%
    Green 77.53%
    Apple 67.44%
    Sweet 53.4%
    Winey 52.64%
    Herbal 50.81%
    Pineapple 45.7%
    Tropical 45.32%
    Caramellic 44.65%
    Berry 38.71%

     

    Flavor
    Fruity 89.48%
    Berry 40.16%
    Apple 35.97%
    Grape 35.85%
    Fruit 35.62%
    Pineapple 34.87%
    Creamy 34.85%
    Fatty 34.51%
    Tropical 34.39%
    Green 33.39%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    7.96 (neutral)

    Molecular weight
    158.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    191°C

    Flash point

    • 72.61 ˚C est.

  • Synonyms

    • 130606-81-4
    • (S)-2-Ethyl-3-oxobutanoic acid ethyl ester
    • QA38U73JGE
    • Ethyl alpha-acetylbutyrate, (S)-
    • ethyl (2S)-2-ethyl-3-oxobutanoate
    • 2-ethyl-3-oxo-butanoic acid ethyl ester
    • Butanoic acid, 2-ethyl-3-oxo-, ethyl ester, (S)-

  • Applications

    The compound (S)-2-Ethyl-3-oxobutanoic acid ethyl ester (CAS 130606-81-4) is a versatile building block in organic synthesis, commonly used as an enolate partner for C-C bond-forming reactions such as Michael additions and Robinson annulations; it serves as an intermediate in medicinal-chemistry programs to access chiral scaffolds and alpha-alkylated derivatives; it is also employed in agrochemical research as a precursor to more complex chiral molecules; in industrial manufacturing it functions as a starting material for beta-keto ester libraries and heterocyclic frameworks; its beta-keto ester motif makes it a useful precursor for preparing related polymers or specialty chemicals under controlled conditions.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1059.58
    methanol 1584.74
    isopropanol 975.1
    water 9.03
    ethyl acetate 697.85
    n-propanol 880.7
    acetone 1204.86
    n-butanol 721.85
    acetonitrile 1331.43
    DMF 1816.95
    toluene 397.43
    isobutanol 653.64
    1,4-dioxane 1678.3
    methyl acetate 784.05
    THF 1897.5
    2-butanone 754.21
    n-pentanol 561.11
    sec-butanol 803.04
    n-hexane 142.25
    ethylene glycol 311.82
    NMP 1851.94
    cyclohexane 330.39
    DMSO 1409.42
    n-butyl acetate 393.04
    n-octanol 327.83
    chloroform 2994.69
    n-propyl acetate 399.9
    acetic acid 1741.23
    dichloromethane 2660.95
    cyclohexanone 1426.9
    propylene glycol 436.81
    isopropyl acetate 377.28
    DMAc 1241.8
    2-ethoxyethanol 611.45
    isopentanol 525.68
    n-heptane 76.1
    ethyl formate 673.01
    1,2-dichloroethane 1203.15
    n-hexanol 543.77
    2-methoxyethanol 1185.41
    isobutyl acetate 237.71
    tetrachloromethane 396.53
    n-pentyl acetate 309.16
    transcutol 1030.4
    n-heptanol 213.69
    ethylbenzene 274.02
    MIBK 338.29
    2-propoxyethanol 698.23
    tert-butanol 1068.2
    MTBE 519.14
    2-butoxyethanol 309.4
    propionic acid 902.21
    o-xylene 298.67
    formic acid 505.59
    diethyl ether 572.56
    m-xylene 279.49
    p-xylene 382.72
    chlorobenzene 751.97
    dimethyl carbonate 316.4
    n-octane 40.17
    formamide 594.71
    cyclopentanone 1465.73
    2-pentanone 585.6
    anisole 500.32
    cyclopentyl methyl ether 774.2
    gamma-butyrolactone 1930.6
    1-methoxy-2-propanol 831.71
    pyridine 1205.57
    3-pentanone 480.21
    furfural 1463.2
    n-dodecane 39.51
    diethylene glycol 618.28
    diisopropyl ether 168.89
    tert-amyl alcohol 806.84
    acetylacetone 698.43
    n-hexadecane 45.3
    acetophenone 475.83
    methyl propionate 618.65
    isopentyl acetate 338.61
    trichloroethylene 2441.45
    n-nonanol 267.79
    cyclohexanol 981.74
    benzyl alcohol 510.36
    2-ethylhexanol 277.0
    isooctanol 182.31
    dipropyl ether 263.22
    1,2-dichlorobenzene 683.16
    ethyl lactate 280.95
    propylene carbonate 970.52
    n-methylformamide 975.68
    2-pentanol 493.67
    n-pentane 133.8
    1-propoxy-2-propanol 449.11
    1-methoxy-2-propyl acetate 390.22
    2-(2-methoxypropoxy) propanol 356.06
    mesitylene 197.07
    ε-caprolactone 1158.95
    p-cymene 166.6
    epichlorohydrin 1631.66
    1,1,1-trichloroethane 1270.51
    2-aminoethanol 532.11
    morpholine-4-carbaldehyde 1361.21
    sulfolane 2030.72
    2,2,4-trimethylpentane 65.34
    2-methyltetrahydrofuran 1187.2
    n-hexyl acetate 545.96
    isooctane 46.03
    2-(2-butoxyethoxy)ethanol 458.51
    sec-butyl acetate 243.4
    tert-butyl acetate 406.46
    decalin 119.06
    glycerin 525.6
    diglyme 792.16
    acrylic acid 849.1
    isopropyl myristate 199.05
    n-butyric acid 1005.14
    acetyl acetate 526.51
    di(2-ethylhexyl) phthalate 211.57
    ethyl propionate 397.25
    nitromethane 2143.01
    1,2-diethoxyethane 384.3
    benzonitrile 802.42
    trioctyl phosphate 161.26
    1-bromopropane 728.17
    gamma-valerolactone 1710.38
    n-decanol 189.35
    triethyl phosphate 197.23
    4-methyl-2-pentanol 248.59
    propionitrile 905.5
    vinylene carbonate 1039.66
    1,1,2-trichlorotrifluoroethane 1074.84
    DMS 397.9
    cumene 194.51
    2-octanol 210.33
    2-hexanone 420.7
    octyl acetate 269.15
    limonene 260.7
    1,2-dimethoxyethane 1089.63
    ethyl orthosilicate 171.56
    tributyl phosphate 192.09
    diacetone alcohol 495.73
    N,N-dimethylaniline 349.28
    acrylonitrile 1124.42
    aniline 554.47
    1,3-propanediol 700.2
    bromobenzene 778.93
    dibromomethane 1704.95
    1,1,2,2-tetrachloroethane 1827.38
    2-methyl-cyclohexyl acetate 318.62
    tetrabutyl urea 264.63
    diisobutyl methanol 160.68
    2-phenylethanol 407.71
    styrene 346.33
    dioctyl adipate 299.6
    dimethyl sulfate 519.55
    ethyl butyrate 347.1
    methyl lactate 385.33
    butyl lactate 263.24
    diethyl carbonate 272.63
    propanediol butyl ether 397.54
    triethyl orthoformate 235.59
    p-tert-butyltoluene 160.56
    methyl 4-tert-butylbenzoate 395.08
    morpholine 1573.92
    tert-butylamine 628.58
    n-dodecanol 144.06
    dimethoxymethane 853.6
    ethylene carbonate 808.0
    cyrene 457.6
    2-ethoxyethyl acetate 348.82
    2-ethylhexyl acetate 263.96
    1,2,4-trichlorobenzene 802.04
    4-methylpyridine 1140.88
    dibutyl ether 291.77
    2,6-dimethyl-4-heptanol 160.68
    DEF 769.2
    dimethyl isosorbide 635.03
    tetrachloroethylene 1164.1
    eugenol 369.32
    triacetin 462.23
    span 80 368.23
    1,4-butanediol 339.51
    1,1-dichloroethane 1293.5
    2-methyl-1-pentanol 445.18
    methyl formate 889.8
    2-methyl-1-butanol 548.6
    n-decane 63.85
    butyronitrile 859.25
    3,7-dimethyl-1-octanol 266.99
    1-chlorooctane 234.28
    1-chlorotetradecane 97.16
    n-nonane 66.17
    undecane 48.83
    tert-butylcyclohexane 95.91
    cyclooctane 78.37
    cyclopentanol 1111.77
    tetrahydropyran 1350.59
    tert-amyl methyl ether 388.63
    2,5,8-trioxanonane 588.25
    1-hexene 370.87
    2-isopropoxyethanol 382.75
    2,2,2-trifluoroethanol 447.78
    methyl butyrate 564.63

    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