Gentianine

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  • Identifiers

    CAS number
    439-89-4

    Molecular formula
    C10H9NO2

    SMILES
    C=CC1=CN=CC2=C1CCOC2=O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 47.31%
    Nutty 43.21%
    Spicy 41.97%
    Coumarinic 36.19%
    Herbal 34.31%
    Tobacco 32.63%
    Burnt 31.05%
    Mint 30.26%
    Bitter 29.44%
    Coconut 29.17%

     

    Flavor
    Bitter 82.03%
    Lovage 21.03%
    Nitrile 19.68%
    Cedarleaf 19.5%
    Odorless 19.47%
    Parsley 19.28%
    Ripe apricot 19.07%
    Basil 19.05%
    Bread crust 18.92%
    Red fruit 18.88%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    5.62 (weak acid)

    Molecular weight
    175.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    439°C

    Flash point

    • 151.24 ˚C est.

  • Synonyms

    • Gentianine
    • 439-89-4
    • 5-ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
    • C2PD310UXB
    • 5-ethenyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one
    • NSC-606848
    • CHEBI:28981
    • DTXSID00963141
    • 5-Ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-one
    • 1H-Pyrano(3,4-c)pyridin-1-one, 5-ethenyl-3,4-dihydro-
    • 1H-Pyrano[3,4-c]pyridin-1-one, 5-ethenyl-3,4-dihydro-
    • 5-ethenyl-3,4-dihydropyrano(3,4-c)pyridin-1-one
    • RefChem:36996
    • DTXCID501390910
    • Gentiannine
    • 5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one
    • NSC606848
    • Erythricine
    • 5-vinyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one
    • 4-(2-hydroxyethyl)-5-vinylnicotinic acid gamma-lactone
    • 5-vinyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
    • UNII-C2PD310UXB
    • 5-VINYL-3,4-DIHYDROPYRANO(3,4-C)PYRIDIN-1-ONE
    • Gencianina
    • BRN 0137011
    • GENTIANINE [MI]
    • C06525
    • 4-27-00-02817 (Beilstein Handbook Reference)
    • orb1684578
    • SCHEMBL2216852
    • CHEMBL4753058
    • Nicotinic acid, 4-(2-hydroxyethyl)-5-vinyl-, gamma-lactone
    • BB_NC-03270
    • HY-N6039
    • BBL036668
    • MFCD00801129
    • STL559047
    • AKOS005266580
    • DA-63738
    • ST023290
    • VS-13618
    • CS-0032220
    • 4-(2-Hydroxyethyl)-5-vinylnicotinic lactone;
    • G12658
    • From Schultesia guianensis malme (Mata-Zombando)
    • 5-vinyl-3-hydro-4H-pyrano[3,4-c]pyridin-1-one
    • Q27104004
    • 1H-Pyrano(3,4-c)pyridin-1-one, 3,4-dihydro-5-vinyl-
    • NICOTINIC ACID, 4-(2-HYDROXYETHYL)-5-VINYL-, .DELTA.-LACTONE
    • Gentianine

  • Applications

    Gentianine (CAS 439-89-4) can serve as an intermediate in organic synthesis, particularly for building heterocyclic frameworks of interest in pharmaceutical and fine chemical research. It is commonly evaluated as a versatile starting material or building block for related compounds and as an analytical reference standard in laboratories. In industrial R&D, it may be used to prepare specialty chemicals and as a precursor in academic studies on reaction mechanisms and catalysis. Its applications are typically limited to laboratory- or pilot-scale contexts and are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.2
    methanol 12.93
    isopropanol 7.07
    water 0.1
    ethyl acetate 47.74
    n-propanol 8.1
    acetone 58.7
    n-butanol 8.79
    acetonitrile 38.63
    DMF 150.88
    toluene 35.57
    isobutanol 8.04
    1,4-dioxane 95.73
    methyl acetate 52.08
    THF 123.77
    2-butanone 49.33
    n-pentanol 9.85
    sec-butanol 6.42
    n-hexane 0.45
    ethylene glycol 7.44
    NMP 167.94
    cyclohexane 0.95
    DMSO 174.39
    n-butyl acetate 34.59
    n-octanol 6.52
    chloroform 105.59
    n-propyl acetate 31.94
    acetic acid 28.81
    dichloromethane 189.18
    cyclohexanone 95.31
    propylene glycol 3.82
    isopropyl acetate 29.91
    DMAc 127.8
    2-ethoxyethanol 35.03
    isopentanol 13.5
    n-heptane 1.16
    ethyl formate 35.84
    1,2-dichloroethane 136.72
    n-hexanol 13.26
    2-methoxyethanol 56.68
    isobutyl acetate 21.66
    tetrachloromethane 14.19
    n-pentyl acetate 22.11
    transcutol 136.7
    n-heptanol 8.8
    ethylbenzene 14.08
    MIBK 31.95
    2-propoxyethanol 45.36
    tert-butanol 16.18
    MTBE 16.06
    2-butoxyethanol 28.01
    propionic acid 18.8
    o-xylene 25.2
    formic acid 16.59
    diethyl ether 16.75
    m-xylene 27.19
    p-xylene 22.42
    chlorobenzene 56.63
    dimethyl carbonate 41.39
    n-octane 0.62
    formamide 41.69
    cyclopentanone 139.07
    2-pentanone 41.43
    anisole 38.49
    cyclopentyl methyl ether 45.2
    gamma-butyrolactone 171.97
    1-methoxy-2-propanol 36.66
    pyridine 94.93
    3-pentanone 37.3
    furfural 179.97
    n-dodecane 0.84
    diethylene glycol 51.34
    diisopropyl ether 7.66
    tert-amyl alcohol 12.76
    acetylacetone 80.42
    n-hexadecane 1.02
    acetophenone 47.21
    methyl propionate 47.51
    isopentyl acetate 33.22
    trichloroethylene 261.52
    n-nonanol 7.22
    cyclohexanol 13.73
    benzyl alcohol 30.79
    2-ethylhexanol 12.47
    isooctanol 9.33
    dipropyl ether 14.6
    1,2-dichlorobenzene 59.22
    ethyl lactate 20.33
    propylene carbonate 75.42
    n-methylformamide 61.5
    2-pentanol 6.82
    n-pentane 0.47
    1-propoxy-2-propanol 28.46
    1-methoxy-2-propyl acetate 49.86
    2-(2-methoxypropoxy) propanol 39.52
    mesitylene 17.2
    ε-caprolactone 76.37
    p-cymene 14.13
    epichlorohydrin 226.82
    1,1,1-trichloroethane 77.27
    2-aminoethanol 8.93
    morpholine-4-carbaldehyde 148.44
    sulfolane 203.51
    2,2,4-trimethylpentane 1.04
    2-methyltetrahydrofuran 66.63
    n-hexyl acetate 25.0
    isooctane 0.98
    2-(2-butoxyethoxy)ethanol 44.08
    sec-butyl acetate 22.84
    tert-butyl acetate 36.75
    decalin 2.12
    glycerin 15.61
    diglyme 98.99
    acrylic acid 26.16
    isopropyl myristate 13.69
    n-butyric acid 27.27
    acetyl acetate 39.17
    di(2-ethylhexyl) phthalate 20.1
    ethyl propionate 31.9
    nitromethane 106.38
    1,2-diethoxyethane 38.65
    benzonitrile 58.03
    trioctyl phosphate 12.45
    1-bromopropane 29.76
    gamma-valerolactone 164.62
    n-decanol 6.32
    triethyl phosphate 23.12
    4-methyl-2-pentanol 8.24
    propionitrile 33.24
    vinylene carbonate 77.85
    1,1,2-trichlorotrifluoroethane 95.95
    DMS 47.53
    cumene 12.48
    2-octanol 5.82
    2-hexanone 30.5
    octyl acetate 16.87
    limonene 16.47
    1,2-dimethoxyethane 71.74
    ethyl orthosilicate 20.23
    tributyl phosphate 16.09
    diacetone alcohol 43.31
    N,N-dimethylaniline 28.91
    acrylonitrile 62.0
    aniline 36.01
    1,3-propanediol 16.64
    bromobenzene 63.77
    dibromomethane 81.63
    1,1,2,2-tetrachloroethane 139.26
    2-methyl-cyclohexyl acetate 29.65
    tetrabutyl urea 23.05
    diisobutyl methanol 10.26
    2-phenylethanol 34.35
    styrene 16.61
    dioctyl adipate 23.24
    dimethyl sulfate 93.33
    ethyl butyrate 30.0
    methyl lactate 28.42
    butyl lactate 19.95
    diethyl carbonate 26.48
    propanediol butyl ether 20.19
    triethyl orthoformate 24.34
    p-tert-butyltoluene 13.04
    methyl 4-tert-butylbenzoate 40.76
    morpholine 75.91
    tert-butylamine 8.2
    n-dodecanol 5.46
    dimethoxymethane 83.31
    ethylene carbonate 60.14
    cyrene 53.73
    2-ethoxyethyl acetate 43.57
    2-ethylhexyl acetate 27.3
    1,2,4-trichlorobenzene 73.01
    4-methylpyridine 82.47
    dibutyl ether 10.67
    2,6-dimethyl-4-heptanol 10.26
    DEF 54.57
    dimethyl isosorbide 87.03
    tetrachloroethylene 84.35
    eugenol 41.83
    triacetin 39.12
    span 80 25.05
    1,4-butanediol 8.46
    1,1-dichloroethane 71.14
    2-methyl-1-pentanol 14.02
    methyl formate 63.72
    2-methyl-1-butanol 10.27
    n-decane 1.05
    butyronitrile 28.02
    3,7-dimethyl-1-octanol 10.24
    1-chlorooctane 6.29
    1-chlorotetradecane 3.86
    n-nonane 0.83
    undecane 0.94
    tert-butylcyclohexane 2.08
    cyclooctane 0.63
    cyclopentanol 18.14
    tetrahydropyran 43.83
    tert-amyl methyl ether 15.78
    2,5,8-trioxanonane 71.0
    1-hexene 2.96
    2-isopropoxyethanol 26.71
    2,2,2-trifluoroethanol 24.48
    methyl butyrate 39.73

    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