Dioscorine

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  • Identifiers

    CAS number
    3329-91-7

    Molecular formula
    C13H19NO2

    SMILES
    CC1=CC(=O)O[C@@]2(C1)C[C@H]3CC[C@@H]2CN3C

    Safety labels

  • Odor profile

    Fragrance
    Nutty 35.56%
    Spicy 33.22%
    Odorless 28.87%
    Sweet 28.63%
    Coconut 28.61%
    Roasted 28.3%
    Lactonic 25.46%
    Woody 24.06%
    Coumarinic 22.82%
    Animal 22.77%

     

    Flavor
    Bitter 60.49%
    Fatty 28.31%
    Cedarleaf 21.84%
    Ripe apricot 20.64%
    Shrimp 20.61%
    Lovage 20.53%
    Alkaline 20.46%
    Minty 20.09%
    Red fruit 19.99%
    Basil 19.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    9.59 (weak base)

    Molecular weight
    221.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    504°C

    Melting point expt.

    • 54-55 °C

    Flash point

    • 138.27 ˚C est.

    Solubility expt.

    • SOLUBLE IN WATER, ALCOHOL, ACETONE, CHLOROFORM, SLIGHTLY SOL IN ETHER, BENZENE, PETROLEUM ETHER

  • Synonyms

    • DIOSCORINE
    • UNII-Q4HFK9JJ1M
    • Q4HFK9JJ1M
    • DIOSCOREINUM
    • HSDB 3481
    • 3329-91-7
    • NSC 107662
    • DTXSID00877299
    • NSC-107662
    • Spiro(2-azabicyclo(2.2.2)octane-5,2'-(2H)pyran)-6'(3'H)-one, 2,4'-dimethyl-, (1R-(1alpha,4alpha,5alpha))-
    • RefChem:56905
    • DTXCID701015378
    • (1R-(1alpha,4alpha,5alpha))-2,4'-DIMETHYLSPIRO(2-AZABICYCLO(2.2.2)OCTANE-5,2'-(2H)PYRAN)-6'(3'H)-ONE
    • NSC107662
    • C10142
    • DIOSCORINE [MI]
    • DIOSCORINE [HSDB]
    • DIOSCOREINUM [HPUS]
    • CHEBI:4628
    • SCHEMBL4899363
    • FD71733
    • Q27106423
    • (1R,2S,4R)-4',5-Dimethylspiro[5-azabicyclo[2.2.2]octane-2,2'-pyran]-6'(3'H)-one
    • (1R-(1.ALPHA.,4.ALPHA.,5.ALPHA.))-2,4'-DIMETHYLSPIRO(2-AZABICYCLO(2.2.2)OCTANE-5,2'-(2H)PYRAN)-6'(3'H)-ONE
    • 3329-91-7

  • Applications

    Dioscorine (CAS 3329-91-7) is predominantly encountered in academic and industrial research as an indolizidine alkaloid isolated from Dioscorea species; in practice, it is commonly evaluated as a chemical probe and reference standard in natural products and pharmaceutical research, used as an intermediate in the synthesis of related alkaloids, and studied in toxicology and mechanism studies to understand its biosynthesis and biological roles in plants; it may also serve as a marker compound for quality control of yam-derived extracts in analytical laboratories.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 36.63
    methanol 77.68
    isopropanol 27.3
    water 9.74
    ethyl acetate 44.6
    n-propanol 37.86
    acetone 45.22
    n-butanol 32.73
    acetonitrile 30.95
    DMF 103.88
    toluene 27.02
    isobutanol 31.97
    1,4-dioxane 73.23
    methyl acetate 48.55
    THF 81.45
    2-butanone 47.38
    n-pentanol 16.73
    sec-butanol 21.43
    n-hexane 0.33
    ethylene glycol 46.55
    NMP 97.5
    cyclohexane 1.59
    DMSO 96.86
    n-butyl acetate 38.48
    n-octanol 13.86
    chloroform 389.18
    n-propyl acetate 23.33
    acetic acid 122.52
    dichloromethane 237.56
    cyclohexanone 92.47
    propylene glycol 37.93
    isopropyl acetate 29.58
    DMAc 95.29
    2-ethoxyethanol 42.75
    isopentanol 32.78
    n-heptane 0.43
    ethyl formate 53.21
    1,2-dichloroethane 95.3
    n-hexanol 28.01
    2-methoxyethanol 107.39
    isobutyl acetate 21.28
    tetrachloromethane 28.28
    n-pentyl acetate 28.66
    transcutol 200.78
    n-heptanol 18.28
    ethylbenzene 9.52
    MIBK 29.07
    2-propoxyethanol 86.79
    tert-butanol 27.29
    MTBE 9.22
    2-butoxyethanol 55.71
    propionic acid 73.4
    o-xylene 20.57
    formic acid 138.23
    diethyl ether 10.16
    m-xylene 26.88
    p-xylene 14.09
    chlorobenzene 57.9
    dimethyl carbonate 34.91
    n-octane 0.3
    formamide 116.85
    cyclopentanone 98.37
    2-pentanone 37.23
    anisole 22.24
    cyclopentyl methyl ether 29.91
    gamma-butyrolactone 141.79
    1-methoxy-2-propanol 70.94
    pyridine 81.95
    3-pentanone 29.09
    furfural 170.77
    n-dodecane 0.44
    diethylene glycol 111.98
    diisopropyl ether 4.29
    tert-amyl alcohol 20.0
    acetylacetone 56.56
    n-hexadecane 0.52
    acetophenone 37.67
    methyl propionate 46.45
    isopentyl acetate 38.82
    trichloroethylene 303.59
    n-nonanol 13.17
    cyclohexanol 35.81
    benzyl alcohol 41.6
    2-ethylhexanol 16.38
    isooctanol 15.68
    dipropyl ether 6.36
    1,2-dichlorobenzene 59.84
    ethyl lactate 29.98
    propylene carbonate 89.64
    n-methylformamide 90.69
    2-pentanol 16.03
    n-pentane 0.59
    1-propoxy-2-propanol 50.9
    1-methoxy-2-propyl acetate 57.77
    2-(2-methoxypropoxy) propanol 55.16
    mesitylene 14.67
    ε-caprolactone 90.33
    p-cymene 10.83
    epichlorohydrin 144.67
    1,1,1-trichloroethane 79.32
    2-aminoethanol 56.5
    morpholine-4-carbaldehyde 123.56
    sulfolane 132.33
    2,2,4-trimethylpentane 0.77
    2-methyltetrahydrofuran 46.44
    n-hexyl acetate 36.18
    isooctane 0.67
    2-(2-butoxyethoxy)ethanol 73.6
    sec-butyl acetate 18.18
    tert-butyl acetate 28.11
    decalin 1.2
    glycerin 87.54
    diglyme 106.71
    acrylic acid 91.16
    isopropyl myristate 12.08
    n-butyric acid 86.23
    acetyl acetate 48.18
    di(2-ethylhexyl) phthalate 26.54
    ethyl propionate 21.39
    nitromethane 144.99
    1,2-diethoxyethane 27.29
    benzonitrile 58.59
    trioctyl phosphate 17.31
    1-bromopropane 27.63
    gamma-valerolactone 162.58
    n-decanol 9.55
    triethyl phosphate 19.25
    4-methyl-2-pentanol 15.27
    propionitrile 31.91
    vinylene carbonate 110.57
    1,1,2-trichlorotrifluoroethane 165.39
    DMS 48.43
    cumene 8.91
    2-octanol 9.95
    2-hexanone 19.86
    octyl acetate 17.81
    limonene 10.98
    1,2-dimethoxyethane 45.38
    ethyl orthosilicate 17.02
    tributyl phosphate 21.32
    diacetone alcohol 47.6
    N,N-dimethylaniline 17.1
    acrylonitrile 59.05
    aniline 52.2
    1,3-propanediol 71.45
    bromobenzene 51.47
    dibromomethane 117.08
    1,1,2,2-tetrachloroethane 213.2
    2-methyl-cyclohexyl acetate 26.87
    tetrabutyl urea 25.35
    diisobutyl methanol 9.54
    2-phenylethanol 50.45
    styrene 10.23
    dioctyl adipate 22.07
    dimethyl sulfate 60.11
    ethyl butyrate 22.78
    methyl lactate 49.81
    butyl lactate 39.79
    diethyl carbonate 21.99
    propanediol butyl ether 57.55
    triethyl orthoformate 20.24
    p-tert-butyltoluene 9.45
    methyl 4-tert-butylbenzoate 43.0
    morpholine 75.39
    tert-butylamine 10.53
    n-dodecanol 6.83
    dimethoxymethane 57.2
    ethylene carbonate 84.92
    cyrene 59.06
    2-ethoxyethyl acetate 51.6
    2-ethylhexyl acetate 29.9
    1,2,4-trichlorobenzene 80.11
    4-methylpyridine 75.81
    dibutyl ether 6.65
    2,6-dimethyl-4-heptanol 9.54
    DEF 40.74
    dimethyl isosorbide 83.54
    tetrachloroethylene 138.45
    eugenol 53.78
    triacetin 49.43
    span 80 43.91
    1,4-butanediol 25.98
    1,1-dichloroethane 87.05
    2-methyl-1-pentanol 20.96
    methyl formate 77.93
    2-methyl-1-butanol 29.94
    n-decane 0.62
    butyronitrile 32.37
    3,7-dimethyl-1-octanol 16.74
    1-chlorooctane 4.97
    1-chlorotetradecane 2.14
    n-nonane 0.47
    undecane 0.51
    tert-butylcyclohexane 1.02
    cyclooctane 0.67
    cyclopentanol 40.07
    tetrahydropyran 40.93
    tert-amyl methyl ether 9.65
    2,5,8-trioxanonane 76.77
    1-hexene 1.86
    2-isopropoxyethanol 30.03
    2,2,2-trifluoroethanol 91.79
    methyl butyrate 28.03

    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