Ethyl levulinate

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  • Identifiers

    CAS number
    539-88-8

    Molecular formula
    C7H12O3

    SMILES
    CCOC(=O)CCC(=O)C

  • Odor profile

    Fruity 95.42%
    Caramellic 71.78%
    Sweet 68.57%
    Green 64.79%
    Winey 55.63%
    Apple 53.1%
    Pineapple 43.4%
    Tropical 41.55%
    Waxy 38.84%
    Ethereal 38.03%

    Scent© AI

  • Properties

    XLogP3-AA
    0.1

    pKa est.
    8.08 (weak base)

    Molecular weight
    144.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Melting point expt.

    • < 25 °C

    Boiling point

    • 93.00 to 94.00 °C. @ 18.00 mm Hg

    Flash point est.
    76.03 ˚C

    Solubility expt.

    • soluble in water and alcohol
    • 1 ml in 1 ml 95% alcohol (in ethanol)

  • Synonyms

    • ETHYL LEVULINATE
    • Ethyl 4-oxopentanoate
    • 539-88-8
    • Ethyl levulate
    • Ethyl laevulinate
    • Ethyl 4-ketovalerate
    • Ethyl 4-oxovalerate
    • Ethyl 3-acetylpropionate
    • Levulinic acid, ethyl ester
    • Pentanoic acid, 4-oxo-, ethyl ester
    • Ethyl ketovalerate
    • Ethyl acetylpropanoate
    • 4-oxopentanoic acid ethyl ester
    • FEMA No. 2442
    • Ethyl levulinate (natural)
    • NSC 24876
    • UNII-7BU24CSS2G
    • EINECS 208-728-2
    • 7BU24CSS2G
    • MFCD00009209
    • BRN 0507641
    • DTXSID8047058
    • 4-oxo-pentanoic acid ethyl ester
    • AI3-00677
    • NSC-24876
    • ETHYL LEVULINATE [MI]
    • ETHYL LEVULINATE [FCC]
    • ETHYL LEVULINATE [FHFI]
    • DTXCID6027058
    • GMEONFUTDYJSNV-UHFFFAOYSA-
    • 4-03-00-01562 (Beilstein Handbook Reference)
    • ethyllevulinate
    • Ethyl laevulate
    • 4-Ketovaleric Acid Ethyl Ester
    • 3-Acetylpropionic Acid Ethyl Ester
    • Ethyl4-oxopentanoate
    • Ethyl levulinate, 99%
    • Levulinic Acid Ethyl Ester
    • SCHEMBL92709
    • ethyl 4-oxidanylidenepentanoate
    • 4-Oxovaleric Acid Ethyl Ester
    • CHEMBL3182933
    • FEMA 2442
    • NSC8863
    • CHEBI:169371
    • AAA53988
    • BCP30245
    • NSC-8863
    • NSC24876
    • Tox21_302292
    • BBL009708
    • STL141073
    • AKOS005716867
    • CS-W011009
    • DS-4184
    • Ethyl levulinate, >=98%, FCC, FG
    • Ethyl levulinate, natural, >=98%, FG
    • NCGC00256288-01
    • CAS-539-88-8
    • DB-052448
    • CS-0204023
    • L0120
    • NS00012425
    • EN300-59517
    • D77713
    • A829891
    • doi:10.14272/GMEONFUTDYJSNV-UHFFFAOYSA-N.1
    • Q27268032
    • F0001-1401
    • BKQ
    • Levulinic acid ethyl ester 4-oxopentanoate; 4-Oxopentanoic acid ethyl ester; Ethyl laevulinate;Ethyl 4-oxovalerate; Ethyl 4-ketovalerate; Ethyl 3-acetylpropionate

  • Applications

    Ethyl levulinate (CAS 539-88-8) is a bio-based ester with a pleasant caramel-like aroma derived from cellulose-origin levulinic acid, making it a cornerstone molecule of the emerging biorefinery economy; in the energy sector it is blended up to 20 % into biodiesel and jet fuel to raise cetane number, lower viscosity and pour point, and to curb NOx, CO and soot emissions during combustion; because of its polar yet clean-evaporating nature EL also serves as a green solvent replacing NMP or DMF in water-borne paints, offset inks, metal degreasing and oil-field extraction fluids; in food and flavor formulations it imparts a mild brûléed fruit nuance to beverages, confectionery, baked goods and chewing tobacco under FEMA/GRAS approval; in cosmetics the molecule functions as a plasticizer, fragrance solvent, humectant and bio-active carrier in perfumes, creams and lotions; synthetically, EL is an intermediate toward γ-valerolactone, pyrrolidones, ketals, biodegradable polyesters, flexible epoxies, analgesic pharmaceuticals and next-generation agrochemicals; owing to its compatibility with cellulose and PVC it is also adopted as a plasticizer, injection-molding aid and binder for engineered wood composites.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1130.37
    methanol 1911.24
    isopropanol 797.26
    water 71.14
    ethyl acetate 304.63
    n-propanol 610.43
    acetone 784.96
    n-butanol 509.78
    acetonitrile 926.7
    DMF 1822.6
    toluene 150.48
    isobutanol 451.37
    1,4-dioxane 836.43
    methyl acetate 497.93
    THF 697.83
    2-butanone 494.87
    n-pentanol 336.43
    sec-butanol 554.64
    n-hexane 33.89
    ethylene glycol 345.05
    NMP 1159.44
    cyclohexane 27.92
    DMSO 1298.99
    n-butyl acetate 147.43
    n-octanol 103.44
    chloroform 845.66
    n-propyl acetate 165.9
    acetic acid 1362.58
    dichloromethane 817.15
    cyclohexanone 527.32
    propylene glycol 330.71
    isopropyl acetate 172.42
    DMAc 1789.94
    2-ethoxyethanol 731.77
    isopentanol 417.65
    n-heptane 9.78
    ethyl formate 423.81
    1,2-dichloroethane 435.1
    n-hexanol 176.46
    2-methoxyethanol 1279.62
    isobutyl acetate 98.82
    tetrachloromethane 103.24
    n-pentyl acetate 102.01
    transcutol 1097.78
    n-heptanol 73.58
    ethylbenzene 105.3
    MIBK 170.99
    2-propoxyethanol 395.84
    tert-butanol 852.77
    MTBE 449.6
    2-butoxyethanol 193.25
    propionic acid 597.68
    o-xylene 123.29
    formic acid 1006.28
    diethyl ether 306.34
    m-xylene 98.51
    p-xylene 156.61
    chlorobenzene 241.76
    dimethyl carbonate 134.35
    n-octane 6.06
    formamide 1165.66
    cyclopentanone 555.38
    2-pentanone 294.81
    anisole 298.5
    cyclopentyl methyl ether 265.07
    gamma-butyrolactone 692.65
    1-methoxy-2-propanol 667.16
    pyridine 591.71
    3-pentanone 203.11
    furfural 840.59
    n-dodecane 6.64
    diethylene glycol 415.64
    diisopropyl ether 60.32
    tert-amyl alcohol 643.87
    acetylacetone 342.16
    n-hexadecane 7.34
    acetophenone 289.36
    methyl propionate 264.17
    isopentyl acetate 147.43
    trichloroethylene 806.39
    n-nonanol 85.76
    cyclohexanol 348.87
    benzyl alcohol 305.9
    2-ethylhexanol 93.48
    isooctanol 60.47
    dipropyl ether 74.96
    1,2-dichlorobenzene 222.64
    ethyl lactate 121.98
    propylene carbonate 346.06
    n-methylformamide 1004.98
    2-pentanol 273.04
    n-pentane 26.76
    1-propoxy-2-propanol 212.91
    1-methoxy-2-propyl acetate 161.09
    2-(2-methoxypropoxy) propanol 258.43
    mesitylene 54.5
    ε-caprolactone 482.57
    p-cymene 44.81
    epichlorohydrin 682.01
    1,1,1-trichloroethane 341.17
    2-aminoethanol 619.56
    morpholine-4-carbaldehyde 1093.67
    sulfolane 774.02
    2,2,4-trimethylpentane 20.99
    2-methyltetrahydrofuran 549.15
    n-hexyl acetate 179.88
    isooctane 9.44
    2-(2-butoxyethoxy)ethanol 316.97
    sec-butyl acetate 117.23
    tert-butyl acetate 183.33
    decalin 24.87
    glycerin 488.52
    diglyme 579.57
    acrylic acid 553.59
    isopropyl myristate 61.92
    n-butyric acid 585.09
    acetyl acetate 211.01
    di(2-ethylhexyl) phthalate 87.1
    ethyl propionate 159.24
    nitromethane 1711.26
    1,2-diethoxyethane 223.2
    benzonitrile 389.9
    trioctyl phosphate 49.14
    1-bromopropane 238.23
    gamma-valerolactone 917.4
    n-decanol 58.17
    triethyl phosphate 76.1
    4-methyl-2-pentanol 135.14
    propionitrile 476.53
    vinylene carbonate 372.04
    1,1,2-trichlorotrifluoroethane 651.87
    DMS 166.79
    cumene 72.91
    2-octanol 55.61
    2-hexanone 208.5
    octyl acetate 78.93
    limonene 63.35
    1,2-dimethoxyethane 946.78
    ethyl orthosilicate 72.77
    tributyl phosphate 76.69
    diacetone alcohol 283.64
    N,N-dimethylaniline 225.07
    acrylonitrile 644.96
    aniline 322.36
    1,3-propanediol 723.19
    bromobenzene 210.02
    dibromomethane 453.93
    1,1,2,2-tetrachloroethane 623.06
    2-methyl-cyclohexyl acetate 111.85
    tetrabutyl urea 103.27
    diisobutyl methanol 54.34
    2-phenylethanol 164.75
    styrene 148.99
    dioctyl adipate 113.66
    dimethyl sulfate 286.23
    ethyl butyrate 109.37
    methyl lactate 207.93
    butyl lactate 105.18
    diethyl carbonate 94.07
    propanediol butyl ether 243.29
    triethyl orthoformate 86.02
    p-tert-butyltoluene 43.07
    methyl 4-tert-butylbenzoate 168.59
    morpholine 1034.3
    tert-butylamine 458.46
    n-dodecanol 42.59
    dimethoxymethane 493.39
    ethylene carbonate 291.8
    cyrene 243.54
    2-ethoxyethyl acetate 169.34
    2-ethylhexyl acetate 111.91
    1,2,4-trichlorobenzene 279.4
    4-methylpyridine 719.05
    dibutyl ether 102.49
    2,6-dimethyl-4-heptanol 54.34
    DEF 544.44
    dimethyl isosorbide 312.65
    tetrachloroethylene 411.1
    eugenol 189.48
    triacetin 214.02
    span 80 177.73
    1,4-butanediol 280.68
    1,1-dichloroethane 447.94
    2-methyl-1-pentanol 293.81
    methyl formate 645.05
    2-methyl-1-butanol 403.15
    n-decane 11.2
    butyronitrile 433.47
    3,7-dimethyl-1-octanol 106.77
    1-chlorooctane 51.99
    1-chlorotetradecane 20.51
    n-nonane 10.64
    undecane 8.21
    tert-butylcyclohexane 23.76
    cyclooctane 7.79
    cyclopentanol 423.46
    tetrahydropyran 464.98
    tert-amyl methyl ether 308.27
    2,5,8-trioxanonane 403.71
    1-hexene 126.19
    2-isopropoxyethanol 369.15
    2,2,2-trifluoroethanol 443.96
    methyl butyrate 255.77

    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