Geranonitrile

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  • Identifiers

    CAS number
    5146-66-7

    Molecular formula
    C10H15N

    SMILES
    CC(=CCC/C(=C/C#N)/C)C

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Citrus 80.59%
    Fruity 71.77%
    Lemon 62.24%
    Sweet 60.19%
    Green 58.35%
    Fresh 55.25%
    Floral 52.37%
    Aldehydic 41.88%
    Metallic 40.14%
    Waxy 38.87%

     

    Flavor
    Woody 36.01%
    Herbal 34.77%
    Citrus 34.19%
    Balsam 32.14%
    Wood 32.0%
    Spicy 30.81%
    Sweet 28.36%
    Balsamic 27.14%
    Herb 25.87%
    Oriental 25.06%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    8.27 (weak base)

    Molecular weight
    149.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    224°C

    Flash point

    • 99.08 ˚C est.

  • Synonyms

    • 5146-66-7
    • Geranyl nitrile
    • 3,7-Dimethylocta-2,6-dienenitrile
    • Geranonitrile
    • Citralva
    • 3,7-Dimethyl-2,6-octadienenitrile
    • 5585-39-7
    • (E)-3,7-Dimethyl-2,6-octadienenitrile
    • 2,6-Octadienenitrile, 3,7-dimethyl-
    • (2E)-3,7-dimethylocta-2,6-dienenitrile
    • UNII-W889CV0E9F
    • 2,6-Octadienenitrile, 3,7-dimethyl-, (2E)-
    • W889CV0E9F
    • EINECS 226-982-2
    • DTXSID90884174
    • 2,6-OCTADIENENITRILE, 3,7-DIMETHYL-, (E)-
    • DIMETHYLOCTA-2,6-DIENENITRILE, (E)-3,7-
    • UNII-MS598KEL3M
    • DTXSID3036286
    • 2-Geranonitrile
    • Gerano nitrile 1
    • EINECS 225-918-0
    • MFCD00001926
    • (E)-3,7-dimethylocta-2,6-dienenitrile
    • EC 225-918-0
    • MS598KEL3M
    • SCHEMBL114124
    • DTXCID1016286
    • DTXCID60209557
    • Tox21_302113
    • NSC109052
    • STL371306
    • AKOS015899896
    • 2,6-Dimethyl-1,5-heptadienyl Cyanide
    • CS-W018170
    • NSC 109052
    • NSC-109052
    • NCGC00255691-01
    • LS-13824
    • (2E)-3,7-Dimethyl-2,6-octadienenitrile
    • CAS-5146-66-7
    • G0241
    • NS00080555
    • (2E)-3,7-Dimethyl-2,6-octadienenitrile #
    • D90734
    • Q27292453

  • Applications

    Geranonitrile (CAS 5146-66-7) is primarily used as a chemical intermediate in the synthesis of fragrance and aroma compounds. It acts as a building block for downstream nitrile- and aldehyde-derived aroma materials and can feed into the production of ionone- and other terpene-derived fragrances. In the flavor and fragrance industries it is commonly evaluated as a precursor or raw material for fragrance ingredients. In cosmetics and personal care it may be used as a fragrance ingredient or precursor in formulated products, within regulatory and formulation limits. In industrial manufacturing it serves as a chemical building block for specialty polymers and coatings that incorporate nitrile functionalities, and may be used as a processing aid or intermediate in related chemical syntheses, all subject to local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 303.74
    methanol 365.23
    isopropanol 240.5
    water 1.13
    ethyl acetate 378.56
    n-propanol 250.25
    acetone 627.43
    n-butanol 232.65
    acetonitrile 413.37
    DMF 724.6
    toluene 235.16
    isobutanol 175.65
    1,4-dioxane 749.66
    methyl acetate 337.22
    THF 1007.44
    2-butanone 406.65
    n-pentanol 153.99
    sec-butanol 203.83
    n-hexane 118.75
    ethylene glycol 88.46
    NMP 655.56
    cyclohexane 265.65
    DMSO 557.39
    n-butyl acetate 376.81
    n-octanol 147.78
    chloroform 1089.25
    n-propyl acetate 231.92
    acetic acid 405.13
    dichloromethane 653.38
    cyclohexanone 642.64
    propylene glycol 154.4
    isopropyl acetate 224.21
    DMAc 544.93
    2-ethoxyethanol 197.32
    isopentanol 160.62
    n-heptane 134.36
    ethyl formate 220.82
    1,2-dichloroethane 369.78
    n-hexanol 322.63
    2-methoxyethanol 344.84
    isobutyl acetate 155.92
    tetrachloromethane 222.1
    n-pentyl acetate 185.48
    transcutol 796.56
    n-heptanol 141.42
    ethylbenzene 114.06
    MIBK 175.19
    2-propoxyethanol 353.83
    tert-butanol 294.71
    MTBE 272.06
    2-butoxyethanol 198.62
    propionic acid 288.97
    o-xylene 135.92
    formic acid 120.9
    diethyl ether 358.89
    m-xylene 149.12
    p-xylene 167.25
    chlorobenzene 308.3
    dimethyl carbonate 153.69
    n-octane 37.78
    formamide 171.09
    cyclopentanone 722.9
    2-pentanone 335.12
    anisole 225.38
    cyclopentyl methyl ether 424.6
    gamma-butyrolactone 676.24
    1-methoxy-2-propanol 288.07
    pyridine 588.01
    3-pentanone 286.81
    furfural 525.0
    n-dodecane 26.2
    diethylene glycol 241.12
    diisopropyl ether 123.97
    tert-amyl alcohol 208.97
    acetylacetone 401.19
    n-hexadecane 30.22
    acetophenone 207.55
    methyl propionate 282.03
    isopentyl acetate 287.61
    trichloroethylene 758.06
    n-nonanol 131.92
    cyclohexanol 299.15
    benzyl alcohol 157.21
    2-ethylhexanol 191.89
    isooctanol 108.31
    dipropyl ether 324.71
    1,2-dichlorobenzene 251.73
    ethyl lactate 124.44
    propylene carbonate 416.27
    n-methylformamide 285.87
    2-pentanol 168.22
    n-pentane 99.56
    1-propoxy-2-propanol 314.78
    1-methoxy-2-propyl acetate 315.51
    2-(2-methoxypropoxy) propanol 215.26
    mesitylene 101.9
    ε-caprolactone 430.55
    p-cymene 106.67
    epichlorohydrin 506.47
    1,1,1-trichloroethane 523.24
    2-aminoethanol 164.12
    morpholine-4-carbaldehyde 517.55
    sulfolane 657.76
    2,2,4-trimethylpentane 33.95
    2-methyltetrahydrofuran 637.61
    n-hexyl acetate 278.86
    isooctane 26.74
    2-(2-butoxyethoxy)ethanol 275.63
    sec-butyl acetate 158.58
    tert-butyl acetate 244.2
    decalin 66.7
    glycerin 164.69
    diglyme 550.6
    acrylic acid 272.92
    isopropyl myristate 128.24
    n-butyric acid 369.22
    acetyl acetate 297.59
    di(2-ethylhexyl) phthalate 117.0
    ethyl propionate 199.52
    nitromethane 600.84
    1,2-diethoxyethane 335.8
    benzonitrile 263.42
    trioctyl phosphate 88.0
    1-bromopropane 282.05
    gamma-valerolactone 657.83
    n-decanol 99.49
    triethyl phosphate 133.73
    4-methyl-2-pentanol 88.89
    propionitrile 297.21
    vinylene carbonate 360.36
    1,1,2-trichlorotrifluoroethane 488.49
    DMS 248.87
    cumene 79.54
    2-octanol 96.36
    2-hexanone 239.06
    octyl acetate 161.77
    limonene 191.41
    1,2-dimethoxyethane 401.16
    ethyl orthosilicate 131.66
    tributyl phosphate 105.68
    diacetone alcohol 244.0
    N,N-dimethylaniline 152.71
    acrylonitrile 305.3
    aniline 245.05
    1,3-propanediol 175.32
    bromobenzene 326.25
    dibromomethane 479.3
    1,1,2,2-tetrachloroethane 680.77
    2-methyl-cyclohexyl acetate 218.64
    tetrabutyl urea 135.53
    diisobutyl methanol 119.99
    2-phenylethanol 200.12
    styrene 153.32
    dioctyl adipate 179.14
    dimethyl sulfate 216.15
    ethyl butyrate 269.19
    methyl lactate 172.77
    butyl lactate 152.9
    diethyl carbonate 190.77
    propanediol butyl ether 205.07
    triethyl orthoformate 206.4
    p-tert-butyltoluene 109.98
    methyl 4-tert-butylbenzoate 202.31
    morpholine 721.02
    tert-butylamine 219.08
    n-dodecanol 80.2
    dimethoxymethane 329.19
    ethylene carbonate 312.32
    cyrene 195.35
    2-ethoxyethyl acetate 244.75
    2-ethylhexyl acetate 251.99
    1,2,4-trichlorobenzene 310.64
    4-methylpyridine 445.98
    dibutyl ether 221.03
    2,6-dimethyl-4-heptanol 119.99
    DEF 322.12
    dimethyl isosorbide 385.73
    tetrachloroethylene 450.33
    eugenol 189.01
    triacetin 297.27
    span 80 237.61
    1,4-butanediol 82.24
    1,1-dichloroethane 455.36
    2-methyl-1-pentanol 118.19
    methyl formate 221.26
    2-methyl-1-butanol 154.34
    n-decane 44.97
    butyronitrile 306.7
    3,7-dimethyl-1-octanol 137.93
    1-chlorooctane 131.68
    1-chlorotetradecane 57.7
    n-nonane 47.44
    undecane 32.23
    tert-butylcyclohexane 56.21
    cyclooctane 78.76
    cyclopentanol 316.81
    tetrahydropyran 795.83
    tert-amyl methyl ether 189.04
    2,5,8-trioxanonane 381.0
    1-hexene 222.32
    2-isopropoxyethanol 156.88
    2,2,2-trifluoroethanol 151.24
    methyl butyrate 254.45

    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
Geranyl nitrile should not be used as a fragrance ingredient.