4-Pentenoic acid

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  • Identifiers

    CAS number
    591-80-0

    Molecular formula
    C5H8O2

    SMILES
    C=CCCC(=O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Cheesy 65.08%
    Fruity 58.32%
    Sour 52.54%
    Pungent 40.71%
    Caramellic 38.61%
    Sharp 37.81%
    Buttery 34.16%
    Dairy 32.18%
    Sweaty 29.14%
    Green 27.75%

     

    Flavor
    Sour 35.58%
    Odorless 35.56%
    Acidic 29.08%
    Pungent 28.51%
    Cheese 23.41%
    Rancid 22.89%
    Sweat 21.47%
    Soy 21.27%
    Vinegar 21.2%
    Mousy 20.68%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    8.05 (weak base)

    Molecular weight
    100.12 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    188°C

    Melting point expt.

    • -22.5 °C

    Flash point

    • 80.32 ˚C est.

    Solubility expt.

    • slightly soluble in water; soluble in alcohol and ether

  • Synonyms

    • 4-PENTENOIC ACID
    • Pent-4-enoic acid
    • 591-80-0
    • Allylacetic acid
    • Allyl acetic acid
    • 3-Vinylpropionic acid
    • 4 PA
    • delta 4-Pentenoic acid
    • FEMA No. 2843
    • Allylessigsaeure
    • 4-Pentensaeure
    • 4-pentenic acid
    • NSC 9000
    • EINECS 209-732-7
    • MFCD00004408
    • NSC 20944
    • BRN 1633696
    • D4S77Y29FB
    • DTXSID0044448
    • CHEBI:35936
    • 4-penten-1-oic acid
    • C5:1n-1
    • NSC-9000
    • Delta(4)-pentenoic acid
    • NSC-20944
    • .DELTA.4-Pentenoic acid
    • DTXCID8024448
    • 4-PENTENOIC ACID [FHFI]
    • 4-02-00-01542 (Beilstein Handbook Reference)
    • WLN: QV3U1
    • UNII-D4S77Y29FB
    • Allylacetic Acid; NSC 20944; NSC 9000; delta4-Pentenoic Acid
    • Pent-4-enoicacid
    • delta4-Pentenoic acid
    • 4-Pentenoic acid, 97%
    • 3-Butene-1-carboxylic acid
    • SCHEMBL115342
    • CHEMBL3185583
    • SCHEMBL13341412
    • FEMA 2843
    • NSC9000
    • HY-Y0624
    • NSC20944
    • Tox21_302069
    • BBL027458
    • LMFA01030007
    • s6268
    • STL280305
    • 4-Pentenoic acid; Pent-4-enoic acid
    • AKOS006221010
    • CS-W009138
    • FP63379
    • NCGC00188966-01
    • NCGC00255889-01
    • AS-11763
    • CAS-591-80-0
    • PD124022
    • 4-Pentenoic acid, >=98%, stabilized, FG
    • NS00021234
    • P0645
    • EN300-64825
    • O12040
    • Q27116641
    • F2190-0007
    • Z995028722
    • InChI=1/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7
    • 209-732-7

  • Applications

    4-Pentenoic acid (CAS 591-80-0) is an unsaturated carboxylic acid bearing a terminal C=C bond that serves as a versatile synthetic intermediate for installing alkene or carboxyl functions during the manufacture of pharmaceuticals, prodrugs and biochemical reagents, acts as a building block for functional monomers used in heat-resistant polymers, coatings, adhesives and 3-D printing resins, participates in cross-metathesis and thiol-ene “click” reactions to anchor ligands, fluorescently label proteins, surface-modify nanoparticles and construct smart hydrogel networks; in flavor and agrochemical industries it helps generate fruity esters, plant growth regulators and selective pesticide precursors, and it can also be employed as a corrosion-inhibiting additive for light metals and as a GC/MS analytical standard owing to the easily detectable double bond.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 176.46
    methanol 280.48
    isopropanol 135.87
    water 78.93
    ethyl acetate 31.81
    n-propanol 124.39
    acetone 89.6
    n-butanol 98.91
    acetonitrile 27.7
    DMF 532.59
    toluene 6.48
    isobutanol 91.88
    1,4-dioxane 75.98
    methyl acetate 44.31
    THF 166.64
    2-butanone 56.0
    n-pentanol 89.11
    sec-butanol 100.4
    n-hexane 6.63
    ethylene glycol 174.49
    NMP 247.62
    cyclohexane 2.14
    DMSO 296.57
    n-butyl acetate 37.4
    n-octanol 56.5
    chloroform 18.73
    n-propyl acetate 29.84
    acetic acid 104.47
    dichloromethane 15.87
    cyclohexanone 68.64
    propylene glycol 190.46
    isopropyl acetate 28.08
    DMAc 310.54
    2-ethoxyethanol 135.75
    isopentanol 84.9
    n-heptane 4.56
    ethyl formate 53.89
    1,2-dichloroethane 16.95
    n-hexanol 99.49
    2-methoxyethanol 237.1
    isobutyl acetate 23.06
    tetrachloromethane 7.26
    n-pentyl acetate 32.22
    transcutol 183.8
    n-heptanol 57.26
    ethylbenzene 11.72
    MIBK 43.85
    2-propoxyethanol 158.36
    tert-butanol 152.99
    MTBE 52.29
    2-butoxyethanol 100.56
    propionic acid 103.06
    o-xylene 13.34
    formic acid 116.73
    diethyl ether 21.01
    m-xylene 13.51
    p-xylene 14.65
    chlorobenzene 11.05
    dimethyl carbonate 30.35
    n-octane 2.78
    formamide 92.81
    cyclopentanone 122.54
    2-pentanone 51.33
    anisole 36.46
    cyclopentyl methyl ether 51.56
    gamma-butyrolactone 127.32
    1-methoxy-2-propanol 201.01
    pyridine 29.76
    3-pentanone 28.79
    furfural 110.26
    n-dodecane 3.15
    diethylene glycol 169.55
    diisopropyl ether 11.23
    tert-amyl alcohol 116.1
    acetylacetone 63.06
    n-hexadecane 3.35
    acetophenone 40.53
    methyl propionate 45.23
    isopentyl acetate 36.8
    trichloroethylene 29.12
    n-nonanol 48.17
    cyclohexanol 55.94
    benzyl alcohol 47.8
    2-ethylhexanol 47.42
    isooctanol 45.55
    dipropyl ether 24.5
    1,2-dichlorobenzene 16.08
    ethyl lactate 47.18
    propylene carbonate 67.77
    n-methylformamide 178.88
    2-pentanol 63.93
    n-pentane 3.54
    1-propoxy-2-propanol 107.22
    1-methoxy-2-propyl acetate 53.18
    2-(2-methoxypropoxy) propanol 102.84
    mesitylene 11.35
    ε-caprolactone 67.47
    p-cymene 13.21
    epichlorohydrin 84.54
    1,1,1-trichloroethane 16.36
    2-aminoethanol 212.19
    morpholine-4-carbaldehyde 202.97
    sulfolane 187.97
    2,2,4-trimethylpentane 4.34
    2-methyltetrahydrofuran 79.0
    n-hexyl acetate 51.19
    isooctane 4.05
    2-(2-butoxyethoxy)ethanol 123.33
    sec-butyl acetate 22.51
    tert-butyl acetate 41.07
    decalin 4.62
    glycerin 239.15
    diglyme 160.72
    acrylic acid 97.22
    isopropyl myristate 24.1
    n-butyric acid 89.07
    acetyl acetate 22.82
    di(2-ethylhexyl) phthalate 32.25
    ethyl propionate 31.49
    nitromethane 117.95
    1,2-diethoxyethane 36.88
    benzonitrile 30.77
    trioctyl phosphate 29.23
    1-bromopropane 11.02
    gamma-valerolactone 149.75
    n-decanol 38.14
    triethyl phosphate 22.13
    4-methyl-2-pentanol 46.61
    propionitrile 33.17
    vinylene carbonate 56.82
    1,1,2-trichlorotrifluoroethane 105.81
    DMS 34.83
    cumene 14.85
    2-octanol 38.07
    2-hexanone 43.55
    octyl acetate 33.59
    limonene 17.81
    1,2-dimethoxyethane 155.68
    ethyl orthosilicate 21.65
    tributyl phosphate 28.32
    diacetone alcohol 103.88
    N,N-dimethylaniline 42.24
    acrylonitrile 50.36
    aniline 24.01
    1,3-propanediol 179.48
    bromobenzene 7.56
    dibromomethane 10.87
    1,1,2,2-tetrachloroethane 33.67
    2-methyl-cyclohexyl acetate 32.63
    tetrabutyl urea 47.22
    diisobutyl methanol 27.85
    2-phenylethanol 51.07
    styrene 10.68
    dioctyl adipate 35.28
    dimethyl sulfate 72.25
    ethyl butyrate 28.61
    methyl lactate 81.53
    butyl lactate 49.17
    diethyl carbonate 20.19
    propanediol butyl ether 117.91
    triethyl orthoformate 24.9
    p-tert-butyltoluene 13.44
    methyl 4-tert-butylbenzoate 60.83
    morpholine 106.29
    tert-butylamine 73.34
    n-dodecanol 29.34
    dimethoxymethane 128.24
    ethylene carbonate 42.9
    cyrene 84.46
    2-ethoxyethyl acetate 38.26
    2-ethylhexyl acetate 26.21
    1,2,4-trichlorobenzene 20.22
    4-methylpyridine 39.73
    dibutyl ether 24.57
    2,6-dimethyl-4-heptanol 27.85
    DEF 93.31
    dimethyl isosorbide 111.19
    tetrachloroethylene 25.13
    eugenol 79.41
    triacetin 46.19
    span 80 90.85
    1,4-butanediol 113.83
    1,1-dichloroethane 16.09
    2-methyl-1-pentanol 76.17
    methyl formate 118.8
    2-methyl-1-butanol 80.34
    n-decane 4.35
    butyronitrile 38.48
    3,7-dimethyl-1-octanol 46.75
    1-chlorooctane 16.66
    1-chlorotetradecane 8.32
    n-nonane 3.98
    undecane 3.63
    tert-butylcyclohexane 6.49
    cyclooctane 1.48
    cyclopentanol 96.81
    tetrahydropyran 42.98
    tert-amyl methyl ether 43.28
    2,5,8-trioxanonane 140.12
    1-hexene 18.68
    2-isopropoxyethanol 91.26
    2,2,2-trifluoroethanol 51.87
    methyl butyrate 51.08

    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