2-Hexenoic acid, (2E)-

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  • Identifiers

    CAS number
    13419-69-7

    Molecular formula
    C6H10O2

    SMILES
    CCC/C=C/C(=O)O

    Safety labels

    Corrosive
    Corrosive

    Retention indicies (RI)

    • Carbowax: 1979.0

  • Odor profile

    Fruity 88.77%
    Fatty 79.78%
    Cheesy 78.17%
    Sour 62.78%
    Dairy 58.05%
    Green 53.94%
    Caramellic 47.13%
    Sweet 45.6%
    Sweaty 42.85%
    Waxy 42.6%

    Scent© AI

  • Properties

    XLogP3-AA
    1.6

    pKa est.
    7.44 (neutral)

    Molecular weight
    114.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 28.00 to 34.00 °C. @ 760.00 mm Hg

    Boiling point

    • 217.00 °C. @ 760.00 mm Hg

    Flash point est.
    105.46 ˚C

    Solubility expt.

    • slightly
    • Soluble in ether, propylene glycol, and most fixed oils; Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • trans-2-Hexenoic acid
    • 13419-69-7
    • trans-Hex-2-enoic acid
    • (E)-hex-2-enoic acid
    • 2-Hexenoic acid, (2E)-
    • hex-2-enoic acid
    • 1191-04-4
    • (E)-2-Hexenoic acid
    • 2-HEXENOIC ACID
    • (2E)-2-Hexenoic acid
    • Hexenoic acid
    • (2E)-hex-2-enoic acid
    • 2-Hexenoic acid, (E)-
    • 3-Propylacrylic acid
    • FEMA No. 3169
    • 2-Hexenoic acid, trans-
    • Propylacrylic acid, beta-
    • 2E-hexenoic acid
    • Isohydrosorbic acid
    • UNII-VQ24908VRU
    • (2E)-HEXENOIC ACID
    • VQ24908VRU
    • beta-propyl acrylic acid
    • EINECS 236-528-5
    • AI3-36119
    • CHEBI:87721
    • HEXENOIC ACID, TRANS 2-
    • DTXSID60884601
    • 1289-40-3
    • C6:1n-4
    • UNII-BXY1L20879
    • hex-2-enoicacid
    • Hex-2-ensaeure
    • (E)-hexenoic acid
    • EINECS 214-727-8
    • MFCD00002705
    • alpha.beta-Hexensaeure
    • beta-propylacrylic acid
    • alpha,beta-hexenoic acid
    • SCHEMBL23614
    • SCHEMBL23615
    • trans-2-Hexenoic acid, 99%
    • QSPL 013
    • CHEMBL2252747
    • CHEBI:61206
    • NIONDZDPPYHYKY-SNAWJCMRSA-
    • DTXCID90210873
    • BXY1L20879
    • LMFA01030008
    • AKOS000121254
    • TRANS-2-HEXENOIC ACID [FHFI]
    • C6:1, n-4
    • CS-W011247
    • HY-W010531
    • trans-2-Hexenoic acid, >=98%, FG
    • BS-19492
    • CS-17340
    • DB-002108
    • H0383
    • NS00087231
    • EN300-21643
    • (E)-2-Hexenoic Acid; trans-2-Hexenoic Acid;
    • EN300-304058
    • Q27130883
    • Q27159869
    • Z104506794
    • InChI=1/C6H10O2/c1-2-3-4-5-6(7)8/h4-5H,2-3H2,1H3,(H,7,8)/b5-4+
    • 236-528-5

  • Applications

    Trans-2-Hexenoic acid (CAS 13419-69-7) is a straight-chain unsaturated fatty acid widely employed as a building block in flavour and fragrance formulations (imparting fresh-cut grass, cucumber and green fruity notes), as an intermediate that can be esterified to produce highly volatile flavour esters for confectionery, beverages and cosmetics; in medicinal chemistry it acts as a key synthon for the preparation of antifungal and antibacterial agents, lipoxygenase modulators, as well as a semifinished product for agrochemicals, plant growth regulators and insect pheromone derivatives used in sustainable pest management; moreover, owing to its carboxyl group and trans double bond the compound is applied in polymer modification, surface grafting on natural fibres to enhance adhesion, is used as a GC-MS analytical standard to monitor oxidation in edible oils, and is investigated as a corrosion inhibitor for metals in acidic media.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 204.53
    methanol 233.3
    isopropanol 122.51
    water 2.44
    ethyl acetate 80.56
    n-propanol 128.99
    acetone 166.69
    n-butanol 157.28
    acetonitrile 34.42
    DMF 698.93
    toluene 10.38
    isobutanol 96.37
    1,4-dioxane 146.67
    methyl acetate 62.47
    THF 339.4
    2-butanone 83.88
    n-pentanol 93.99
    sec-butanol 95.07
    n-hexane 5.81
    ethylene glycol 120.32
    NMP 526.41
    cyclohexane 5.01
    DMSO 668.27
    n-butyl acetate 110.99
    n-octanol 63.4
    chloroform 38.82
    n-propyl acetate 48.87
    acetic acid 224.48
    dichloromethane 61.92
    cyclohexanone 172.03
    propylene glycol 144.47
    isopropyl acetate 62.49
    DMAc 286.39
    2-ethoxyethanol 136.25
    isopentanol 137.06
    n-heptane 7.68
    ethyl formate 82.2
    1,2-dichloroethane 59.25
    n-hexanol 138.76
    2-methoxyethanol 329.71
    isobutyl acetate 36.35
    tetrachloromethane 7.99
    n-pentyl acetate 59.0
    transcutol 398.56
    n-heptanol 67.04
    ethylbenzene 12.53
    MIBK 76.0
    2-propoxyethanol 237.99
    tert-butanol 174.65
    MTBE 60.71
    2-butoxyethanol 124.33
    propionic acid 132.97
    o-xylene 18.15
    formic acid 111.75
    diethyl ether 38.76
    m-xylene 21.22
    p-xylene 15.07
    chlorobenzene 26.49
    dimethyl carbonate 50.19
    n-octane 3.09
    formamide 125.65
    cyclopentanone 264.63
    2-pentanone 102.63
    anisole 46.56
    cyclopentyl methyl ether 103.74
    gamma-butyrolactone 316.51
    1-methoxy-2-propanol 284.34
    pyridine 66.1
    3-pentanone 48.98
    furfural 246.21
    n-dodecane 3.83
    diethylene glycol 220.32
    diisopropyl ether 19.55
    tert-amyl alcohol 130.89
    acetylacetone 144.92
    n-hexadecane 4.12
    acetophenone 57.25
    methyl propionate 83.52
    isopentyl acetate 102.43
    trichloroethylene 105.11
    n-nonanol 55.97
    cyclohexanol 101.58
    benzyl alcohol 55.81
    2-ethylhexanol 77.13
    isooctanol 52.27
    dipropyl ether 50.18
    1,2-dichlorobenzene 36.66
    ethyl lactate 58.1
    propylene carbonate 175.82
    n-methylformamide 211.99
    2-pentanol 91.11
    n-pentane 4.54
    1-propoxy-2-propanol 188.25
    1-methoxy-2-propyl acetate 133.25
    2-(2-methoxypropoxy) propanol 135.79
    mesitylene 19.1
    ε-caprolactone 164.08
    p-cymene 22.58
    epichlorohydrin 237.09
    1,1,1-trichloroethane 33.95
    2-aminoethanol 173.4
    morpholine-4-carbaldehyde 319.69
    sulfolane 537.34
    2,2,4-trimethylpentane 5.84
    2-methyltetrahydrofuran 169.26
    n-hexyl acetate 91.83
    isooctane 6.04
    2-(2-butoxyethoxy)ethanol 186.93
    sec-butyl acetate 35.48
    tert-butyl acetate 87.3
    decalin 6.73
    glycerin 205.8
    diglyme 244.39
    acrylic acid 127.55
    isopropyl myristate 41.66
    n-butyric acid 195.62
    acetyl acetate 58.88
    di(2-ethylhexyl) phthalate 57.33
    ethyl propionate 49.6
    nitromethane 242.68
    1,2-diethoxyethane 78.57
    benzonitrile 55.22
    trioctyl phosphate 49.64
    1-bromopropane 24.69
    gamma-valerolactone 347.08
    n-decanol 44.63
    triethyl phosphate 42.28
    4-methyl-2-pentanol 65.05
    propionitrile 40.0
    vinylene carbonate 130.58
    1,1,2-trichlorotrifluoroethane 183.39
    DMS 68.5
    cumene 15.76
    2-octanol 42.21
    2-hexanone 56.71
    octyl acetate 59.97
    limonene 37.6
    1,2-dimethoxyethane 181.13
    ethyl orthosilicate 38.96
    tributyl phosphate 53.88
    diacetone alcohol 181.81
    N,N-dimethylaniline 45.69
    acrylonitrile 63.97
    aniline 40.22
    1,3-propanediol 216.77
    bromobenzene 21.31
    dibromomethane 34.74
    1,1,2,2-tetrachloroethane 89.05
    2-methyl-cyclohexyl acetate 65.99
    tetrabutyl urea 76.2
    diisobutyl methanol 49.81
    2-phenylethanol 78.72
    styrene 12.83
    dioctyl adipate 73.38
    dimethyl sulfate 118.8
    ethyl butyrate 68.54
    methyl lactate 111.3
    butyl lactate 79.5
    diethyl carbonate 46.52
    propanediol butyl ether 156.61
    triethyl orthoformate 52.65
    p-tert-butyltoluene 24.43
    methyl 4-tert-butylbenzoate 99.63
    morpholine 203.46
    tert-butylamine 85.12
    n-dodecanol 34.72
    dimethoxymethane 199.81
    ethylene carbonate 101.51
    cyrene 130.01
    2-ethoxyethyl acetate 82.3
    2-ethylhexyl acetate 69.71
    1,2,4-trichlorobenzene 48.71
    4-methylpyridine 70.69
    dibutyl ether 39.48
    2,6-dimethyl-4-heptanol 49.81
    DEF 155.67
    dimethyl isosorbide 225.68
    tetrachloroethylene 53.56
    eugenol 102.34
    triacetin 85.46
    span 80 149.79
    1,4-butanediol 85.69
    1,1-dichloroethane 36.03
    2-methyl-1-pentanol 87.86
    methyl formate 141.22
    2-methyl-1-butanol 108.75
    n-decane 4.83
    butyronitrile 63.51
    3,7-dimethyl-1-octanol 62.96
    1-chlorooctane 22.37
    1-chlorotetradecane 11.55
    n-nonane 4.25
    undecane 4.29
    tert-butylcyclohexane 7.94
    cyclooctane 2.53
    cyclopentanol 145.63
    tetrahydropyran 100.95
    tert-amyl methyl ether 57.97
    2,5,8-trioxanonane 212.32
    1-hexene 19.19
    2-isopropoxyethanol 92.13
    2,2,2-trifluoroethanol 63.77
    methyl butyrate 74.66

    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
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.03%
Zizyphus jujuba fruit (Malaysia) Zizyphus jujuba Mill. var. inermis, fam. Rhamnaceae 0.01%
Jasmine rose absolute (India) Gardenia jasminoides Ellis, fam. Rubiaceae 0.1%
Spearmint, scotch (Japan) Mentha gracilis Sole, fam. Lamiaceae (Labiatae) 4.98%
Carob bean powder 2a raw 9000-40-2 Ceratonia siliqua L., fam. Leguminoseae 0.02%
Carob bean powder 2b roasted 9000-40-2 Ceratonia siliqua L., fam. Leguminoseae 0.02%