2-Butenoic acid, 2-methyl-, propyl ester, (Z)-

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  • Identifiers

    CAS number
    53082-57-8

    Molecular formula
    C8H14O2

    SMILES
    CCCOC(=O)/C(=C\C)/C

    Retention indicies (RI)

    • DB5: 1030.0

  • Odor profile

    Fruity 86.33%
    Sweet 73.53%
    Floral 63.28%
    Herbal 62.95%
    Green 60.54%
    Chamomile 58.41%
    Apple 52.16%
    Winey 49.24%
    Rose 41.69%
    Ethereal 41.11%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    Molecular weight
    142.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    171°C

    Flash point est.
    50.87 ˚C

  • Synonyms

    • Propyl 2-methylisocrotonate
    • propyl angelate
    • 53082-57-8
    • propyl (Z)-2-methylbut-2-enoate
    • 2-Butenoic acid, 2-methyl-, propyl ester, (Z)-
    • n-Propyl angelate
    • EINECS 258-349-1
    • SCHEMBL2351899
    • DTXSID501317118
    • propyl (z)-2-methyl-2-butenoate
    • DB-321420
    • NS00089266

  • Applications

    2-Butenoic acid, 2-methyl-, propyl ester, (Z)- (commonly called propyl angelate; CAS 53082-57-8) is an unsaturated ester with a fruity–green, softly herbaceous odor, used mainly in fragrance/flavor design and research to add fresh apple/pear, leafy-green and mild herbal facets to top and heart notes and to fine-tune citrus/green/herbal accords; in food flavoring it may be dosed at trace levels in beverages, confectionery and baked goods to boost juiciness; in organic synthesis this α,β-unsaturated ester serves as a convenient dienophile/Michael acceptor for 1,4-addition, Diels–Alder, transesterification and amidation, making it a versatile intermediate to access angelate/tiglate derivatives, an analytical GC/LC reference and a stereochemical probe (Z/E odor/reactivity studies), as well as a hydrolyzable carrier in controlled-release aroma systems; practical use typically requires assessing stability (oxidation, isomerization), formulation compatibility and compliance with local safety and flavor–fragrance standards.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3203.63
    methanol 3329.68
    isopropanol 3105.86
    water 5.57
    ethyl acetate 1928.55
    n-propanol 2735.08
    acetone 2593.89
    n-butanol 2768.11
    acetonitrile 3345.49
    DMF 2543.17
    toluene 1335.28
    isobutanol 2402.56
    1,4-dioxane 2984.76
    methyl acetate 2016.93
    THF 2585.26
    2-butanone 2427.86
    n-pentanol 2371.95
    sec-butanol 3292.81
    n-hexane 818.3
    ethylene glycol 366.35
    NMP 2191.19
    cyclohexane 1066.93
    DMSO 1770.5
    n-butyl acetate 2270.3
    n-octanol 1574.62
    chloroform 8715.22
    n-propyl acetate 1740.95
    acetic acid 2948.54
    dichloromethane 6906.25
    cyclohexanone 3047.56
    propylene glycol 609.27
    isopropyl acetate 1107.21
    DMAc 2073.53
    2-ethoxyethanol 1867.33
    isopentanol 2416.49
    n-heptane 403.55
    ethyl formate 1796.33
    1,2-dichloroethane 3368.66
    n-hexanol 2179.34
    2-methoxyethanol 2199.35
    isobutyl acetate 994.59
    tetrachloromethane 1625.97
    n-pentyl acetate 1471.75
    transcutol 3673.25
    n-heptanol 1320.26
    ethylbenzene 1111.68
    MIBK 1062.64
    2-propoxyethanol 1944.88
    tert-butanol 3615.09
    MTBE 2591.01
    2-butoxyethanol 1484.87
    propionic acid 1975.64
    o-xylene 957.5
    formic acid 697.36
    diethyl ether 2175.97
    m-xylene 865.24
    p-xylene 1608.26
    chlorobenzene 2290.89
    dimethyl carbonate 470.74
    n-octane 234.64
    formamide 1031.71
    cyclopentanone 2553.27
    2-pentanone 1834.08
    anisole 1656.08
    cyclopentyl methyl ether 1551.38
    gamma-butyrolactone 2710.4
    1-methoxy-2-propanol 1573.9
    pyridine 3618.0
    3-pentanone 1300.59
    furfural 2785.55
    n-dodecane 186.46
    diethylene glycol 1010.27
    diisopropyl ether 695.49
    tert-amyl alcohol 3629.41
    acetylacetone 1324.16
    n-hexadecane 205.96
    acetophenone 1533.61
    methyl propionate 1243.53
    isopentyl acetate 1848.79
    trichloroethylene 6937.03
    n-nonanol 1227.14
    cyclohexanol 2506.83
    benzyl alcohol 1512.31
    2-ethylhexanol 1489.24
    isooctanol 1082.58
    dipropyl ether 1096.11
    1,2-dichlorobenzene 1880.57
    ethyl lactate 615.02
    propylene carbonate 1724.83
    n-methylformamide 1673.91
    2-pentanol 2145.91
    n-pentane 584.73
    1-propoxy-2-propanol 1519.67
    1-methoxy-2-propyl acetate 988.81
    2-(2-methoxypropoxy) propanol 1015.37
    mesitylene 577.29
    ε-caprolactone 2526.67
    p-cymene 641.37
    epichlorohydrin 3158.17
    1,1,1-trichloroethane 4089.46
    2-aminoethanol 985.64
    morpholine-4-carbaldehyde 2091.89
    sulfolane 2416.23
    2,2,4-trimethylpentane 353.22
    2-methyltetrahydrofuran 2817.18
    n-hexyl acetate 2180.38
    isooctane 242.53
    2-(2-butoxyethoxy)ethanol 1440.49
    sec-butyl acetate 1060.21
    tert-butyl acetate 1167.95
    decalin 445.88
    glycerin 627.12
    diglyme 2556.51
    acrylic acid 1639.24
    isopropyl myristate 682.56
    n-butyric acid 2733.49
    acetyl acetate 1023.42
    di(2-ethylhexyl) phthalate 567.62
    ethyl propionate 1262.55
    nitromethane 3544.19
    1,2-diethoxyethane 1692.54
    benzonitrile 2705.62
    trioctyl phosphate 463.49
    1-bromopropane 2751.73
    gamma-valerolactone 2973.49
    n-decanol 840.44
    triethyl phosphate 532.78
    4-methyl-2-pentanol 1062.68
    propionitrile 2659.32
    vinylene carbonate 1884.11
    1,1,2-trichlorotrifluoroethane 2168.79
    DMS 913.98
    cumene 767.89
    2-octanol 1200.04
    2-hexanone 1891.29
    octyl acetate 941.33
    limonene 914.04
    1,2-dimethoxyethane 3019.29
    ethyl orthosilicate 544.53
    tributyl phosphate 568.94
    diacetone alcohol 1168.94
    N,N-dimethylaniline 1085.9
    acrylonitrile 2843.12
    aniline 1575.98
    1,3-propanediol 1594.59
    bromobenzene 2473.42
    dibromomethane 4970.42
    1,1,2,2-tetrachloroethane 5237.85
    2-methyl-cyclohexyl acetate 986.17
    tetrabutyl urea 700.56
    diisobutyl methanol 707.0
    2-phenylethanol 1345.36
    styrene 1486.44
    dioctyl adipate 828.6
    dimethyl sulfate 610.14
    ethyl butyrate 1345.01
    methyl lactate 539.09
    butyl lactate 951.31
    diethyl carbonate 966.37
    propanediol butyl ether 1326.78
    triethyl orthoformate 810.28
    p-tert-butyltoluene 586.68
    methyl 4-tert-butylbenzoate 1046.78
    morpholine 3400.25
    tert-butylamine 2893.92
    n-dodecanol 602.58
    dimethoxymethane 1144.83
    ethylene carbonate 1500.56
    cyrene 786.22
    2-ethoxyethyl acetate 1275.48
    2-ethylhexyl acetate 1416.06
    1,2,4-trichlorobenzene 1993.41
    4-methylpyridine 3619.1
    dibutyl ether 1498.85
    2,6-dimethyl-4-heptanol 707.0
    DEF 1982.4
    dimethyl isosorbide 1286.67
    tetrachloroethylene 3557.86
    eugenol 1096.17
    triacetin 1141.83
    span 80 1061.09
    1,4-butanediol 860.78
    1,1-dichloroethane 4483.61
    2-methyl-1-pentanol 2292.66
    methyl formate 1207.42
    2-methyl-1-butanol 2475.53
    n-decane 329.78
    butyronitrile 3399.68
    3,7-dimethyl-1-octanol 1282.41
    1-chlorooctane 1068.61
    1-chlorotetradecane 391.53
    n-nonane 357.72
    undecane 236.34
    tert-butylcyclohexane 443.34
    cyclooctane 289.33
    cyclopentanol 2226.73
    tetrahydropyran 3401.07
    tert-amyl methyl ether 1815.95
    2,5,8-trioxanonane 1523.71
    1-hexene 2086.98
    2-isopropoxyethanol 1356.15
    2,2,2-trifluoroethanol 685.17
    methyl butyrate 1997.89

    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

Botanical

Name CAS Botanical Proportion
Roman chamomile (India) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 0.83%
Roman chamomile (Italy) 1 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 5.0%
Roman chamomile (Italy) 3 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.1%
Roman chamomile (Italy) 2 (headspace) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.1%
Roman chamomile (Japan) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.33%
Roman chamomile (Germany) 1a hydrodistillate 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.04%
Roman chamomile (Germany) 1b headspace 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.58%
Roman chamomile (Italy) 6 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 1.2%