Ethyl 3-hexenoate, (3Z)-

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  • Identifiers

    CAS number
    64187-83-3

    Molecular formula
    C8H14O2

    SMILES
    CC/C=C\CC(=O)OCC

    Retention indicies (RI)

    • Carbowax: 1303.0

  • Odor profile

    Fruity 94.63%
    Green 91.12%
    Apple 72.86%
    Tropical 72.27%
    Pineapple 66.79%
    Sweet 62.24%
    Pear 59.3%
    Fresh 57.73%
    Banana 51.28%
    Melon 49.15%

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  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    142.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    170°C

    Flash point est.
    58.64 ˚C

    Solubility expt.

    • Soluble in fats and non-polar solvents; slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • ethyl (Z)-hex-3-enoate
    • Ethyl (E)-3-hexenoate
    • Ethyl (Z)hex-3-enoate
    • 64187-83-3
    • Ethyl (Z)-3-hexenoate
    • Ethyl (3Z)-3-hexenoate
    • Ethyl 3-hexenoate, (3Z)-
    • ETHYL CIS-3-HEXENOATE
    • 3-Hexenoic acid, ethyl ester, (Z)-
    • R35DY1229O
    • Ethyl cis-hex-3-enoate
    • EINECS 264-724-0
    • 3-Hexenoic acid, ethyl ester, (3Z)-
    • FEMA NO. 4112
    • ETHYL 3-HEXENOATE, CIS-
    • DTXSID701314453
    • ETHYL (3Z)-HEX-3-ENOATE
    • ETHYL CIS-3-HEXENOATE [FHFI]
    • UNII-R35DY1229O
    • Ethyl 3Z-Hexenoate
    • Ethyl(Z)hex-3-enoate
    • (3Z)-ethyl 3-hexenoate
    • SCHEMBL148958
    • Ethyl ester(Z)-3-Hexenoic acid
    • DTXCID10911911
    • CHEBI:195733
    • LMFA07010849
    • AKOS006229067
    • DB-319284
    • Q27287731

  • Applications

    Ethyl 3-hexenoate, (3Z)- (ethyl cis-3-hexenoate; CAS 64187-83-3) is a fruity green ester (green apple, pear, strawberry, pineapple, fresh-cut grass) used to deliver crisp, realistic top notes in flavor formulations for beverages, juices, confections, dairy and bakery; to impart natural green-leafy freshness in fine fragrances, personal care, and household air/fabric care; as a reference standard in GC/GC-MS, sensory training, quality control, and aroma research of fruits, wines, and juices; to model plant volatiles in studies of plant–insect interactions; and as a versatile ingredient in flavor technology (e.g., microencapsulation, solubilization in ethanol/propylene glycol/oils) where moderate volatility and good blendability are desired.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2050.08
    methanol 2269.35
    isopropanol 1388.0
    water 1.39
    ethyl acetate 1296.43
    n-propanol 1366.52
    acetone 2020.46
    n-butanol 1276.69
    acetonitrile 1422.85
    DMF 2628.67
    toluene 633.74
    isobutanol 975.11
    1,4-dioxane 2134.66
    methyl acetate 1040.49
    THF 2667.05
    2-butanone 1225.98
    n-pentanol 840.76
    sec-butanol 1181.22
    n-hexane 315.72
    ethylene glycol 381.69
    NMP 2431.34
    cyclohexane 536.55
    DMSO 2467.24
    n-butyl acetate 890.77
    n-octanol 402.42
    chloroform 3183.16
    n-propyl acetate 592.68
    acetic acid 2188.52
    dichloromethane 2938.88
    cyclohexanone 1972.31
    propylene glycol 471.14
    isopropyl acetate 724.63
    DMAc 1708.05
    2-ethoxyethanol 874.65
    isopentanol 978.11
    n-heptane 138.93
    ethyl formate 680.23
    1,2-dichloroethane 1734.9
    n-hexanol 902.89
    2-methoxyethanol 1660.54
    isobutyl acetate 357.49
    tetrachloromethane 468.53
    n-pentyl acetate 513.66
    transcutol 2813.36
    n-heptanol 292.4
    ethylbenzene 334.15
    MIBK 558.91
    2-propoxyethanol 1123.3
    tert-butanol 1657.84
    MTBE 1181.12
    2-butoxyethanol 498.82
    propionic acid 1180.48
    o-xylene 368.84
    formic acid 548.51
    diethyl ether 1385.39
    m-xylene 405.03
    p-xylene 409.28
    chlorobenzene 893.87
    dimethyl carbonate 340.98
    n-octane 54.67
    formamide 721.67
    cyclopentanone 1997.9
    2-pentanone 1078.69
    anisole 623.51
    cyclopentyl methyl ether 1312.02
    gamma-butyrolactone 2023.29
    1-methoxy-2-propanol 1199.6
    pyridine 1728.08
    3-pentanone 757.43
    furfural 1469.72
    n-dodecane 46.49
    diethylene glycol 790.2
    diisopropyl ether 334.79
    tert-amyl alcohol 1256.71
    acetylacetone 1150.32
    n-hexadecane 53.07
    acetophenone 543.1
    methyl propionate 868.3
    isopentyl acetate 713.13
    trichloroethylene 2923.06
    n-nonanol 343.94
    cyclohexanol 1387.78
    benzyl alcohol 538.19
    2-ethylhexanol 489.97
    isooctanol 241.51
    dipropyl ether 528.32
    1,2-dichlorobenzene 728.41
    ethyl lactate 279.73
    propylene carbonate 1028.25
    n-methylformamide 1118.61
    2-pentanol 879.5
    n-pentane 261.59
    1-propoxy-2-propanol 776.6
    1-methoxy-2-propyl acetate 676.97
    2-(2-methoxypropoxy) propanol 607.3
    mesitylene 256.92
    ε-caprolactone 1516.38
    p-cymene 201.97
    epichlorohydrin 2027.13
    1,1,1-trichloroethane 1567.96
    2-aminoethanol 731.15
    morpholine-4-carbaldehyde 1711.42
    sulfolane 2471.41
    2,2,4-trimethylpentane 107.8
    2-methyltetrahydrofuran 2076.38
    n-hexyl acetate 827.64
    isooctane 77.11
    2-(2-butoxyethoxy)ethanol 819.52
    sec-butyl acetate 414.29
    tert-butyl acetate 745.59
    decalin 178.94
    glycerin 573.17
    diglyme 1301.08
    acrylic acid 1018.52
    isopropyl myristate 285.61
    n-butyric acid 1582.47
    acetyl acetate 782.4
    di(2-ethylhexyl) phthalate 291.57
    ethyl propionate 574.0
    nitromethane 2333.26
    1,2-diethoxyethane 973.04
    benzonitrile 754.44
    trioctyl phosphate 200.99
    1-bromopropane 1227.84
    gamma-valerolactone 2107.72
    n-decanol 245.62
    triethyl phosphate 266.35
    4-methyl-2-pentanol 391.34
    propionitrile 1044.53
    vinylene carbonate 942.3
    1,1,2-trichlorotrifluoroethane 1383.04
    DMS 568.89
    cumene 208.55
    2-octanol 242.33
    2-hexanone 665.32
    octyl acetate 377.44
    limonene 372.58
    1,2-dimethoxyethane 1502.05
    ethyl orthosilicate 260.79
    tributyl phosphate 275.03
    diacetone alcohol 743.65
    N,N-dimethylaniline 429.97
    acrylonitrile 1163.99
    aniline 831.91
    1,3-propanediol 926.93
    bromobenzene 1025.3
    dibromomethane 2009.06
    1,1,2,2-tetrachloroethane 2398.42
    2-methyl-cyclohexyl acetate 450.19
    tetrabutyl urea 355.33
    diisobutyl methanol 254.38
    2-phenylethanol 522.76
    styrene 470.82
    dioctyl adipate 433.68
    dimethyl sulfate 558.7
    ethyl butyrate 536.69
    methyl lactate 430.69
    butyl lactate 372.89
    diethyl carbonate 383.96
    propanediol butyl ether 564.45
    triethyl orthoformate 365.64
    p-tert-butyltoluene 195.61
    methyl 4-tert-butylbenzoate 466.28
    morpholine 2552.13
    tert-butylamine 1141.69
    n-dodecanol 186.02
    dimethoxymethane 1107.25
    ethylene carbonate 796.23
    cyrene 495.91
    2-ethoxyethyl acetate 653.71
    2-ethylhexyl acetate 547.92
    1,2,4-trichlorobenzene 814.79
    4-methylpyridine 1636.2
    dibutyl ether 563.28
    2,6-dimethyl-4-heptanol 254.38
    DEF 1380.87
    dimethyl isosorbide 900.59
    tetrachloroethylene 1527.23
    eugenol 481.28
    triacetin 659.04
    span 80 593.66
    1,4-butanediol 366.38
    1,1-dichloroethane 1818.28
    2-methyl-1-pentanol 687.15
    methyl formate 744.8
    2-methyl-1-butanol 943.23
    n-decane 79.44
    butyronitrile 1251.2
    3,7-dimethyl-1-octanol 390.08
    1-chlorooctane 306.22
    1-chlorotetradecane 118.39
    n-nonane 80.71
    undecane 58.47
    tert-butylcyclohexane 149.17
    cyclooctane 125.96
    cyclopentanol 1329.79
    tetrahydropyran 2326.49
    tert-amyl methyl ether 837.74
    2,5,8-trioxanonane 944.13
    1-hexene 812.94
    2-isopropoxyethanol 596.08
    2,2,2-trifluoroethanol 487.75
    methyl butyrate 802.94

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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
Pistacia lentiscus (Israel) 1b leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.07%
Astrocarium vulgare fruit Astrocarium vulgare Mart., fam. Arecaceae 0.7%
Psidium cattleianum fruit (R‚union Island) Psidium cattleianum Sabine, fam. Myrtaceae 0.3%