2,4-Hexadienal

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  • Identifiers

    CAS number
    80466-34-8

    Molecular formula
    C6H8O

    SMILES
    C/C=C/C=C/C=O

    Safety labels

    Flammable
    Flammable

    Acute Toxic
    Acute Toxic

    Retention indicies (RI)

    • DB5: 919.0
    • Carbowax: 1380.5

  • Odor profile

    Green 87.95%
    Fruity 82.39%
    Spicy 73.49%
    Sweet 70.63%
    Fatty 63.91%
    Pungent 58.46%
    Aldehydic 56.03%
    Vegetable 51.79%
    Herbal 49.98%
    Cinnamon 49.28%

    Scent© AI

    Odor threshold>

    • 0.0018 mg/cu m

  • Properties

    XLogP3-AA
    1.2

    Molecular weight
    96.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point

    • 174 °C; 76 °C @ 30 mm Hg

    Flash point est.
    49.28 ˚C

    Solubility expt.

    • In water, 8.1X10+3 mg/L @ 25 °C /Estimated/
    • Slightly soluble in water; miscible in oils
    • soluble (in ethanol)

  • Synonyms

    • 2,4-HEXADIENAL
    • 142-83-6
    • Sorbaldehyde
    • Sorbic aldehyde
    • (E,E)-2,4-hexadienal
    • trans,trans-2,4-Hexadienal
    • (2E,4E)-hexa-2,4-dienal
    • 2,4-Hexadienal, (2E,4E)-
    • Hexa-2,4-dienal
    • 80466-34-8
    • 2,4-Hexadienal, (E,E)-
    • (2E,4E)-2,4-Hexadienal
    • 2-Propyleneacrolein
    • 3-Propyleneacrolein
    • FEMA No. 3429
    • 1,3-Pentadiene-1-carboxaldehyde
    • CCRIS 4030
    • 2,4-Hexadienal, trans,trans-
    • HSDB 7239
    • 2,4-(e-e)-hexadienal
    • EINECS 205-564-3
    • trans,trans-Hexa-2,4-dienal
    • BRN 1698401
    • CHEBI:82334
    • AI3-31142
    • 878K4I6N7T
    • MFCD00007004
    • 73506-81-7
    • Hexadienal
    • DTXSID2025391
    • 2,4-HEXADIENAL [HSDB]
    • 4-01-00-03545 (Beilstein Handbook Reference)
    • NSC-16184
    • NSC-68096
    • CCRIS 5124
    • (E,E)-2,4-Hexadien-1-al
    • TRANS,TRANS-2,4-HEXADIENAL [FHFI]
    • NSC 16184
    • NSC 68096
    • 2,4-Hexadienal (89% trans,trans-, 11% cis,trans-)
    • 2-Propylene acrolein
    • (2E,4E)-Hexadienal
    • 2,4-Hexadien-1-al
    • trans,trans-4-Hexadienal
    • (E,E)-hexa-2,4-dienal
    • UNII-878K4I6N7T
    • (E)-2,(E)-4-Hexadienal
    • 3Propyleneacrolein
    • trans,trans-2,4-Hexadien-1-al
    • e,e-2,4-hexadienal
    • trans-2,4-hexadienal
    • t,t-2,4-Hexadienal
    • (2E,4E) hexadienal
    • hexadienal (2e,4e-)
    • trans,trans2,4Hexadienal
    • 2,4-(E,E)-Hexadienal
    • 2,4Hexadienal, (E,E)
    • 1,3Pentadiene1carboxaldehyde
    • DTXCID205391
    • CHEMBL1576086
    • Hexa-2,4-dienal, (E,E)-
    • (2E,4E)-2,4-Hexadienal #
    • 1,3,-pentadiene-1-carboxaldehyde
    • n-Hex-2,4-dienal, trans,trans-
    • 2,4-Hexadien-1-al, (E,E)-
    • 2,4-Hexadienal, (trans, trans)-
    • trans,trans-2,4-Hexadienal, 95%
    • Tox21_200834
    • LMFA06000006
    • AKOS015915466
    • HY-W068035
    • trans,trans-2,4-Hexadienal, >=95%
    • NCGC00090786-01
    • NCGC00090786-02
    • NCGC00090786-03
    • NCGC00258388-01
    • CAS-142-83-6
    • 2,4-Hexadienal, predominantly trans,trans
    • DB-003137
    • CS-0067535
    • H0581
    • C19249
    • D90909
    • EN300-113666
    • trans,trans-2,4-Hexadienal, analytical standard
    • A807974
    • Q27155883
    • 617-079-8

  • Applications

    2,4‑Hexadienal (CAS 80466-34-8) is a conjugated unsaturated aldehyde widely used in flavor, fragrance, and organic synthesis: at trace levels it imparts fresh green, slightly fatty, herbal or fruity notes and serves as a modifier to boost brightness and diffusion in citrus, leafy-green, and vegetable accords for foods, beverages, personal-care, and home-care products; in synthesis it acts as a versatile building block for Michael additions and condensation chemistry (Schiff base/imine formation, aldol, Knoevenagel) as well as chain extension to polyenes, enabling access to fragrance intermediates, fine chemicals for pharma/agro, and functional materials; additionally, 2,4‑hexadienal is used as an analytical reference standard to monitor unsaturated aldehydes from lipid oxidation by GC/MS, in sensory studies of rancidity, and as a mild crosslinking agent with biological nucleophiles in protein/peptide research, with appropriate precautions due to its reactivity and irritancy.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1073.73
    methanol 759.36
    isopropanol 719.71
    water 0.74
    ethyl acetate 1252.98
    n-propanol 726.01
    acetone 1874.89
    n-butanol 702.78
    acetonitrile 1025.15
    DMF 1731.08
    toluene 256.32
    isobutanol 497.66
    1,4-dioxane 1083.23
    methyl acetate 1029.23
    THF 1987.64
    2-butanone 1229.28
    n-pentanol 400.54
    sec-butanol 568.32
    n-hexane 126.55
    ethylene glycol 198.14
    NMP 1677.87
    cyclohexane 162.78
    DMSO 2258.33
    n-butyl acetate 817.87
    n-octanol 221.91
    chloroform 1561.1
    n-propyl acetate 548.02
    acetic acid 1010.68
    dichloromethane 2075.22
    cyclohexanone 1379.56
    propylene glycol 249.81
    isopropyl acetate 514.28
    DMAc 780.15
    2-ethoxyethanol 446.0
    isopentanol 483.61
    n-heptane 111.49
    ethyl formate 547.19
    1,2-dichloroethane 1381.05
    n-hexanol 558.01
    2-methoxyethanol 904.87
    isobutyl acetate 294.96
    tetrachloromethane 261.8
    n-pentyl acetate 315.61
    transcutol 2168.01
    n-heptanol 180.25
    ethylbenzene 151.99
    MIBK 424.3
    2-propoxyethanol 724.96
    tert-butanol 701.13
    MTBE 589.27
    2-butoxyethanol 328.02
    propionic acid 784.58
    o-xylene 158.98
    formic acid 196.47
    diethyl ether 878.94
    m-xylene 189.28
    p-xylene 179.14
    chlorobenzene 481.22
    dimethyl carbonate 282.71
    n-octane 34.79
    formamide 356.07
    cyclopentanone 1987.2
    2-pentanone 1009.8
    anisole 356.59
    cyclopentyl methyl ether 858.41
    gamma-butyrolactone 2057.26
    1-methoxy-2-propanol 698.74
    pyridine 987.19
    3-pentanone 665.82
    furfural 1056.88
    n-dodecane 27.88
    diethylene glycol 489.01
    diisopropyl ether 201.94
    tert-amyl alcohol 528.1
    acetylacetone 919.32
    n-hexadecane 31.55
    acetophenone 328.33
    methyl propionate 851.52
    isopentyl acetate 545.33
    trichloroethylene 2254.92
    n-nonanol 182.85
    cyclohexanol 562.25
    benzyl alcohol 240.21
    2-ethylhexanol 307.53
    isooctanol 143.83
    dipropyl ether 473.73
    1,2-dichlorobenzene 407.79
    ethyl lactate 210.72
    propylene carbonate 880.31
    n-methylformamide 812.03
    2-pentanol 476.98
    n-pentane 123.45
    1-propoxy-2-propanol 566.66
    1-methoxy-2-propyl acetate 565.06
    2-(2-methoxypropoxy) propanol 373.3
    mesitylene 127.11
    ε-caprolactone 976.5
    p-cymene 128.81
    epichlorohydrin 1692.4
    1,1,1-trichloroethane 1064.58
    2-aminoethanol 351.72
    morpholine-4-carbaldehyde 1035.95
    sulfolane 2243.5
    2,2,4-trimethylpentane 47.98
    2-methyltetrahydrofuran 1577.6
    n-hexyl acetate 500.71
    isooctane 46.06
    2-(2-butoxyethoxy)ethanol 523.15
    sec-butyl acetate 318.44
    tert-butyl acetate 496.27
    decalin 69.94
    glycerin 295.78
    diglyme 916.89
    acrylic acid 616.83
    isopropyl myristate 182.93
    n-butyric acid 1014.44
    acetyl acetate 516.62
    di(2-ethylhexyl) phthalate 154.02
    ethyl propionate 470.52
    nitromethane 1757.62
    1,2-diethoxyethane 681.95
    benzonitrile 417.47
    trioctyl phosphate 127.48
    1-bromopropane 865.61
    gamma-valerolactone 1551.55
    n-decanol 140.95
    triethyl phosphate 173.95
    4-methyl-2-pentanol 214.45
    propionitrile 676.4
    vinylene carbonate 671.82
    1,1,2-trichlorotrifluoroethane 861.2
    DMS 413.38
    cumene 104.67
    2-octanol 139.71
    2-hexanone 583.87
    octyl acetate 228.15
    limonene 229.66
    1,2-dimethoxyethane 800.1
    ethyl orthosilicate 166.75
    tributyl phosphate 167.93
    diacetone alcohol 566.55
    N,N-dimethylaniline 213.63
    acrylonitrile 834.36
    aniline 342.59
    1,3-propanediol 505.72
    bromobenzene 535.22
    dibromomethane 1325.7
    1,1,2,2-tetrachloroethane 1419.38
    2-methyl-cyclohexyl acetate 304.55
    tetrabutyl urea 218.14
    diisobutyl methanol 186.24
    2-phenylethanol 294.72
    styrene 218.11
    dioctyl adipate 265.17
    dimethyl sulfate 471.18
    ethyl butyrate 511.08
    methyl lactate 298.13
    butyl lactate 238.94
    diethyl carbonate 303.31
    propanediol butyl ether 355.74
    triethyl orthoformate 281.16
    p-tert-butyltoluene 122.64
    methyl 4-tert-butylbenzoate 278.31
    morpholine 1331.99
    tert-butylamine 442.78
    n-dodecanol 111.49
    dimethoxymethane 779.24
    ethylene carbonate 526.49
    cyrene 295.87
    2-ethoxyethyl acetate 457.26
    2-ethylhexyl acetate 409.52
    1,2,4-trichlorobenzene 454.99
    4-methylpyridine 795.99
    dibutyl ether 351.77
    2,6-dimethyl-4-heptanol 186.24
    DEF 914.75
    dimethyl isosorbide 633.0
    tetrachloroethylene 884.92
    eugenol 287.4
    triacetin 418.43
    span 80 353.09
    1,4-butanediol 180.02
    1,1-dichloroethane 1313.28
    2-methyl-1-pentanol 324.85
    methyl formate 626.37
    2-methyl-1-butanol 466.69
    n-decane 44.63
    butyronitrile 737.77
    3,7-dimethyl-1-octanol 227.66
    1-chlorooctane 185.39
    1-chlorotetradecane 74.59
    n-nonane 47.05
    undecane 34.72
    tert-butylcyclohexane 67.73
    cyclooctane 50.58
    cyclopentanol 761.18
    tetrahydropyran 1360.11
    tert-amyl methyl ether 409.64
    2,5,8-trioxanonane 613.59
    1-hexene 390.17
    2-isopropoxyethanol 335.94
    2,2,2-trifluoroethanol 247.77
    methyl butyrate 656.49

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0 %
Category 2
Products applied to the axillae
 0 % Category 7B
Leave-on products applied to the hair with some hand contact
 0 %
Category 3
Products applied to the face/body using fingertips
 0 % Category 8
Products with significant anogenital exposure
 0 %
Category 4
Products related to fine fragrance
 0 % Category 9
Products with body and hand exposure, primarily rinse off
 0 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0 % Category 10A
Household care products with mostly hand contact
 0 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0 %
Category 5D
Baby Creams, baby Oils and baby talc
 0 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0 %
Category 6
Products with oral and lip exposure
 0 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 0 %

Prohibition
2,4-Dienals should not be used as a fragrance ingredient.

Botanical

Name CAS Botanical Proportion
Chervil (France) 8000-44-0 Anthriscus cerefolium (L.) Hoffm. (Cerefolium sativum Lam.), fam. Apiaceae 0.1%
Zizyphus jujuba fruit (Malaysia) Zizyphus jujuba Mill. var. inermis, fam. Rhamnaceae 0.04%
Cyphomandra betacea fruit Cyphomandra betacea Sendtn., fam. Solanaceae (tree tomato, tamarillo) 0.1%
Guava fruit headspace (Reunion island) 91770-12-6 Psidium guajava L., fam. Myrtaceae 2.2%