Ethyl 2-methyl-4-pentenoate

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  • Identifiers

    CAS number
    53399-81-8

    Molecular formula
    C8H14O2

    SMILES
    CCOC(=O)C(C)CC=C

    Safety labels

    Flammable
    Flammable

  • Odor profile

    Fragrance
    Fruity 96.05%
    Green 75.46%
    Pineapple 64.45%
    Tropical 63.26%
    Sweet 52.47%
    Apple 52.28%
    Berry 40.58%
    Banana 40.36%
    Pear 38.23%
    Fresh 36.51%

     

    Flavor
    Fruity 83.17%
    Tropical 44.39%
    Pineapple 40.43%
    Berry 37.77%
    Apple 36.26%
    Sweet 35.41%
    Green 32.84%
    Floral 27.4%
    Cheese 25.25%
    Pear 24.73%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.9 (neutral)

    Molecular weight
    142.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point

    • 153.00 to 155.00 °C. @ 760.00 mm Hg

    Flash point

    • 43.2 ˚C est.

    Solubility expt.

    • insoluble in water, soluble in alcohol and fixed oils

  • Synonyms

    • Ethyl 2-methyl-4-pentenoate
    • 53399-81-8
    • Ethyl 2-methylpent-4-enoate
    • 2-Methyl-4-pentenoic Acid Ethyl Ester
    • 4-Pentenoic acid, 2-methyl-, ethyl ester
    • Ethyl 2-methylpent-4-en-1-oate
    • FEMA No. 3489
    • Ethyl 2-methyl 4-pentenoate
    • UNII-F7GX41R904
    • F7GX41R904
    • EINECS 258-520-0
    • Ethyl 2-methyl-4-pentanoate
    • DTXSID00866320
    • ETHYL 2-METHYL-4-PENTENOATE [FHFI]
    • 2-Methyl-4-pentenoic Acid Ethyl Ester;
    • MFCD00010235
    • SCHEMBL356446
    • FEMA 3489
    • DTXCID10814615
    • CHEBI:180289
    • ETHYL-2-METHYL-4-PENTENOATE
    • Ethyl 2-methyl-4-pentenoate, 98%
    • LMFA07010859
    • AKOS015915881
    • Ethyl (+/-)-2-methyl-4-pentenoate
    • 2-methyl-pent-4-enoic acid ethyl ester
    • AS-77425
    • DB-071675
    • CS-0197267
    • E0717
    • Ethyl 2-methyl-4-pentenoate, >=98%, FG
    • NS00012434
    • D90556
    • Q27277765

  • Applications

    Ethyl 2-methyl-4-pentenoate is a short-chain allylic ester with a soft fruity odor that is mainly employed as an intermediate for the preparation of flavor and fragrance ingredients—especially green, pear and apple notes—and for perfumery formulations; its reactive C=C bond and ester group make it an important building block in medicinal chemistry, enabling the incorporation of heterocycles, halogens or chiral centers to afford precursors of anti-inflammatory and antimicrobial drugs; in agrochemistry it is used to synthesize insect pheromone precursors and plant-growth regulators; in organic chemistry research it serves as a model substrate for allylation, metathesis, free-radical polymerization and asymmetric catalysis studies, and it is also exploited as a functional monomer for producing biodegradable copolymers.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1429.67
    methanol 2099.93
    isopropanol 1253.24
    water 4.61
    ethyl acetate 813.61
    n-propanol 1195.45
    acetone 1091.18
    n-butanol 1190.82
    acetonitrile 1131.85
    DMF 1284.59
    toluene 524.53
    isobutanol 1029.47
    1,4-dioxane 1460.9
    methyl acetate 829.65
    THF 1496.82
    2-butanone 1049.45
    n-pentanol 1091.55
    sec-butanol 1281.94
    n-hexane 369.11
    ethylene glycol 246.51
    NMP 1233.99
    cyclohexane 382.86
    DMSO 998.36
    n-butyl acetate 962.39
    n-octanol 616.46
    chloroform 2734.06
    n-propyl acetate 678.93
    acetic acid 1298.27
    dichloromethane 2337.7
    cyclohexanone 1414.01
    propylene glycol 333.55
    isopropyl acetate 510.72
    DMAc 1208.7
    2-ethoxyethanol 996.52
    isopentanol 1091.69
    n-heptane 174.5
    ethyl formate 688.0
    1,2-dichloroethane 1283.06
    n-hexanol 1124.59
    2-methoxyethanol 1243.24
    isobutyl acetate 447.92
    tetrachloromethane 557.67
    n-pentyl acetate 601.25
    transcutol 1873.48
    n-heptanol 503.51
    ethylbenzene 458.47
    MIBK 552.16
    2-propoxyethanol 1162.66
    tert-butanol 1477.25
    MTBE 1179.18
    2-butoxyethanol 639.57
    propionic acid 872.86
    o-xylene 423.08
    formic acid 396.94
    diethyl ether 1015.4
    m-xylene 405.21
    p-xylene 620.95
    chlorobenzene 841.93
    dimethyl carbonate 238.72
    n-octane 91.19
    formamide 411.09
    cyclopentanone 1293.86
    2-pentanone 836.16
    anisole 677.01
    cyclopentyl methyl ether 852.33
    gamma-butyrolactone 1370.34
    1-methoxy-2-propanol 841.94
    pyridine 1198.02
    3-pentanone 649.25
    furfural 1219.57
    n-dodecane 75.0
    diethylene glycol 685.85
    diisopropyl ether 338.57
    tert-amyl alcohol 1458.95
    acetylacetone 652.1
    n-hexadecane 83.1
    acetophenone 667.19
    methyl propionate 580.06
    isopentyl acetate 810.14
    trichloroethylene 2358.56
    n-nonanol 477.25
    cyclohexanol 1100.45
    benzyl alcohol 651.65
    2-ethylhexanol 662.23
    isooctanol 413.14
    dipropyl ether 528.17
    1,2-dichlorobenzene 769.62
    ethyl lactate 300.87
    propylene carbonate 805.31
    n-methylformamide 734.19
    2-pentanol 890.36
    n-pentane 287.91
    1-propoxy-2-propanol 774.82
    1-methoxy-2-propyl acetate 540.89
    2-(2-methoxypropoxy) propanol 574.71
    mesitylene 294.09
    ε-caprolactone 1203.29
    p-cymene 297.01
    epichlorohydrin 1407.3
    1,1,1-trichloroethane 1354.4
    2-aminoethanol 515.06
    morpholine-4-carbaldehyde 1193.36
    sulfolane 1382.65
    2,2,4-trimethylpentane 171.23
    2-methyltetrahydrofuran 1466.45
    n-hexyl acetate 907.38
    isooctane 118.26
    2-(2-butoxyethoxy)ethanol 713.12
    sec-butyl acetate 469.95
    tert-butyl acetate 577.0
    decalin 205.16
    glycerin 399.82
    diglyme 1196.09
    acrylic acid 729.81
    isopropyl myristate 313.97
    n-butyric acid 1157.05
    acetyl acetate 478.72
    di(2-ethylhexyl) phthalate 300.86
    ethyl propionate 542.38
    nitromethane 1345.09
    1,2-diethoxyethane 846.0
    benzonitrile 940.78
    trioctyl phosphate 235.34
    1-bromopropane 1040.16
    gamma-valerolactone 1459.39
    n-decanol 332.93
    triethyl phosphate 284.76
    4-methyl-2-pentanol 497.42
    propionitrile 1034.29
    vinylene carbonate 820.18
    1,1,2-trichlorotrifluoroethane 957.28
    DMS 471.52
    cumene 331.47
    2-octanol 426.5
    2-hexanone 811.84
    octyl acetate 410.26
    limonene 428.11
    1,2-dimethoxyethane 1473.13
    ethyl orthosilicate 291.45
    tributyl phosphate 301.27
    diacetone alcohol 589.06
    N,N-dimethylaniline 513.26
    acrylonitrile 1084.46
    aniline 617.02
    1,3-propanediol 761.93
    bromobenzene 922.09
    dibromomethane 1636.81
    1,1,2,2-tetrachloroethane 1881.41
    2-methyl-cyclohexyl acetate 502.09
    tetrabutyl urea 364.91
    diisobutyl methanol 334.05
    2-phenylethanol 622.45
    styrene 578.81
    dioctyl adipate 420.52
    dimethyl sulfate 372.32
    ethyl butyrate 587.96
    methyl lactate 302.82
    butyl lactate 429.08
    diethyl carbonate 421.69
    propanediol butyl ether 582.31
    triethyl orthoformate 386.7
    p-tert-butyltoluene 274.93
    methyl 4-tert-butylbenzoate 501.03
    morpholine 1607.27
    tert-butylamine 1084.4
    n-dodecanol 252.85
    dimethoxymethane 689.95
    ethylene carbonate 676.65
    cyrene 483.61
    2-ethoxyethyl acetate 594.12
    2-ethylhexyl acetate 643.6
    1,2,4-trichlorobenzene 813.24
    4-methylpyridine 1359.15
    dibutyl ether 598.81
    2,6-dimethyl-4-heptanol 334.05
    DEF 1010.59
    dimethyl isosorbide 771.35
    tetrachloroethylene 1307.99
    eugenol 516.09
    triacetin 543.72
    span 80 519.61
    1,4-butanediol 463.71
    1,1-dichloroethane 1478.89
    2-methyl-1-pentanol 1081.45
    methyl formate 588.59
    2-methyl-1-butanol 1121.58
    n-decane 126.46
    butyronitrile 1211.65
    3,7-dimethyl-1-octanol 533.24
    1-chlorooctane 412.31
    1-chlorotetradecane 161.61
    n-nonane 135.39
    undecane 93.13
    tert-butylcyclohexane 208.84
    cyclooctane 124.37
    cyclopentanol 988.39
    tetrahydropyran 1547.5
    tert-amyl methyl ether 867.85
    2,5,8-trioxanonane 793.91
    1-hexene 915.88
    2-isopropoxyethanol 711.03
    2,2,2-trifluoroethanol 343.25
    methyl butyrate 829.14

    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