(-)-Eburnamonine

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  • Identifiers

    CAS number
    4880-88-0

    Molecular formula
    C19H22N2O

    SMILES
    CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2

    Safety labels

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 38.0%
    Animal 34.78%
    Roasted 22.89%
    Nutty 22.12%
    Earthy 20.59%
    Popcorn 19.99%
    Burnt 19.87%
    Spicy 18.68%
    Musty 18.45%
    Cooling 17.5%

     

    Flavor
    Bitter 91.83%
    Cedarleaf 20.43%
    Cereal 19.11%
    Very strong 18.97%
    Indole 18.68%
    Nitrile 18.43%
    Alkaline 18.41%
    Sweet-like 18.23%
    Lovage 18.04%
    Shrimp 17.6%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    7.27 (neutral)

    Molecular weight
    294.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    541°C

    Flash point

    • 231.94 ˚C est.

  • Synonyms

    • Vinburnine
    • (-)-Eburnamonine
    • 4880-88-0
    • Eburnal
    • Vinburnina
    • Vinburninum
    • 3alpha,16alpha-Eburnamonine
    • NSC-322920
    • G54D0HMY25
    • DTXSID6045119
    • (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one
    • DTXCID4025119
    • (15S,19S)-15-ethyl-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraen-17-one
    • Eburnamonine (-)-
    • RefChem:905548
    • C04AX17
    • 225-490-5
    • Vincamone
    • Eburnamonine (-)
    • Vinburnine [INN]
    • Vincanorine
    • DL-Eburnamonine
    • Eburnamonine (-)-form
    • (+/-)-Vincamone
    • (+/-)-Eburnamonine
    • Vinburnine, (+/-)-
    • 2580-88-3
    • Eburnamonine (+/-)-form [MI]
    • NSC322920
    • (41S,13aS)-13a-Ethyl-2,3,5,6,13,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41H)-one
    • l-Eburnamonine
    • Eburnamenin-14(15H)-one, (+/-)-
    • Eburnal ritardo
    • cis-Vincamone
    • 3.alpha.,16.alpha.-eburnamonine
    • 64UB2942IE
    • Vinburnine (INN)
    • Vincamona [Spanish]
    • Vincamona
    • Vinburninum [INN-Latin]
    • Vinburnina [INN-Spanish]
    • (-)-Eburnamonina
    • CH-846
    • (-)-Eburnamonina [Spanish]
    • 3-alpha,16-alpha-Eburnamonine
    • MLS000758467
    • EINECS 225-490-5
    • CH 846
    • NSC 322920
    • UNII-G54D0HMY25
    • UNII-64UB2942IE
    • (3alpha,16alpha)-Eburnamenin-14(15H)-one
    • (3-alpha,16-alpha)-Eburnamin-14(15H)-one
    • Eburnamin-14(15H)-one, (3-alpha,16-alpha)-
    • NCGC00014750-02
    • Cervoxan (TN)
    • Prestwick_189
    • CAS-4880-88-0
    • Vinburnine (Standard)
    • Spectrum_000379
    • Vinpocetine Impurity 13
    • Vinpocetine Impurity 31
    • Prestwick0_000607
    • Prestwick1_000607
    • Prestwick2_000607
    • Prestwick3_000607
    • Spectrum2_001504
    • Spectrum3_001199
    • Spectrum4_000751
    • Spectrum5_000938
    • VINBURNINE [MART.]
    • NCIStruc1_000941
    • NCIStruc2_000870
    • VINBURNINE [WHO-DD]
    • BSPBio_000514
    • BSPBio_002877
    • GTPL345
    • KBioGR_001102
    • KBioSS_000859
    • MLS002153906
    • DivK1c_000411
    • SCHEMBL456385
    • SPBio_001547
    • SPBio_002733
    • BPBio1_000566
    • CHEBI:4740
    • MEGxp0_001871
    • orb1306330
    • CHEMBL1892145
    • SCHEMBL29391038
    • ACon1_000004
    • HMS501E13
    • HY-B1180R
    • KBio1_000411
    • KBio2_000859
    • KBio2_003427
    • KBio2_005995
    • KBio3_002377
    • NINDS_000411
    • WYJAPUKIYAZSEM-MOPGFXCFSA-N
    • GLXC-06666
    • HMS1569J16
    • HMS2096J16
    • HMS2233K13
    • HMS3713J16
    • HY-B1180
    • Tox21_110060
    • CCG-36740
    • EBURNAMONINE (-)-FORM [MI]
    • NCI322920
    • s5681
    • AKOS015896486
    • Tox21_110060_1
    • CS-4789
    • DB13793
    • EBC-615989
    • FD10193
    • FE65898
    • IDI1_000411
    • NCGC00262533-02
    • NCGC00262533-03
    • AC-26459
    • BS-16859
    • NCI60_002800
    • SMR001233255
    • SBI-0051740.P002
    • NS00003481
    • 4880-88-0

  • Applications

    (-)-Eburnamonine (CAS 4880-88-0) is primarily used as a chiral building block and intermediate in medicinal-chemistry synthesis of indole alkaloid frameworks; it serves as a scaffold for semisynthetic routes to related bioactive alkaloids and can be a starting material for enantioselective syntheses. In pharmaceutical research, it is employed for structure–activity studies and as a reference substrate in alkaloid biosynthesis investigations. It may also be encountered as an analytical standard or specialty reagent in natural-product analysis and, in some cases, as a modestly scalable intermediate in organic synthesis, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.44
    methanol 3.63
    isopropanol 3.27
    water 0.01
    ethyl acetate 10.1
    n-propanol 4.65
    acetone 15.6
    n-butanol 6.3
    acetonitrile 2.83
    DMF 31.96
    toluene 12.91
    isobutanol 5.21
    1,4-dioxane 28.21
    methyl acetate 12.38
    THF 29.81
    2-butanone 19.04
    n-pentanol 4.49
    sec-butanol 2.59
    n-hexane 0.09
    ethylene glycol 2.07
    NMP 39.68
    cyclohexane 0.66
    DMSO 14.37
    n-butyl acetate 21.35
    n-octanol 3.34
    chloroform 78.43
    n-propyl acetate 12.86
    acetic acid 10.77
    dichloromethane 58.19
    cyclohexanone 59.37
    propylene glycol 1.2
    isopropyl acetate 11.91
    DMAc 43.44
    2-ethoxyethanol 10.72
    isopentanol 9.41
    n-heptane 0.14
    ethyl formate 13.39
    1,2-dichloroethane 35.61
    n-hexanol 7.59
    2-methoxyethanol 17.08
    isobutyl acetate 18.46
    tetrachloromethane 7.05
    n-pentyl acetate 23.42
    transcutol 37.28
    n-heptanol 6.84
    ethylbenzene 4.96
    MIBK 15.02
    2-propoxyethanol 26.46
    tert-butanol 3.9
    MTBE 2.71
    2-butoxyethanol 24.61
    propionic acid 7.96
    o-xylene 7.91
    formic acid 5.16
    diethyl ether 2.96
    m-xylene 8.76
    p-xylene 9.3
    chlorobenzene 30.07
    dimethyl carbonate 12.61
    n-octane 0.13
    formamide 7.28
    cyclopentanone 52.36
    2-pentanone 15.02
    anisole 9.45
    cyclopentyl methyl ether 10.51
    gamma-butyrolactone 51.04
    1-methoxy-2-propanol 11.6
    pyridine 46.54
    3-pentanone 12.99
    furfural 68.09
    n-dodecane 0.23
    diethylene glycol 25.36
    diisopropyl ether 1.6
    tert-amyl alcohol 2.88
    acetylacetone 24.91
    n-hexadecane 0.3
    acetophenone 21.06
    methyl propionate 10.79
    isopentyl acetate 28.62
    trichloroethylene 107.29
    n-nonanol 4.32
    cyclohexanol 8.94
    benzyl alcohol 16.99
    2-ethylhexanol 6.68
    isooctanol 7.37
    dipropyl ether 2.77
    1,2-dichlorobenzene 32.52
    ethyl lactate 10.41
    propylene carbonate 35.88
    n-methylformamide 11.81
    2-pentanol 2.91
    n-pentane 0.14
    1-propoxy-2-propanol 15.53
    1-methoxy-2-propyl acetate 27.7
    2-(2-methoxypropoxy) propanol 23.39
    mesitylene 5.19
    ε-caprolactone 42.85
    p-cymene 6.25
    epichlorohydrin 60.22
    1,1,1-trichloroethane 25.16
    2-aminoethanol 3.08
    morpholine-4-carbaldehyde 54.32
    sulfolane 50.2
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 14.04
    n-hexyl acetate 18.7
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 27.39
    sec-butyl acetate 10.88
    tert-butyl acetate 12.97
    decalin 0.52
    glycerin 5.2
    diglyme 44.98
    acrylic acid 11.72
    isopropyl myristate 9.13
    n-butyric acid 16.38
    acetyl acetate 14.7
    di(2-ethylhexyl) phthalate 19.5
    ethyl propionate 9.81
    nitromethane 20.54
    1,2-diethoxyethane 13.0
    benzonitrile 27.73
    trioctyl phosphate 11.74
    1-bromopropane 8.28
    gamma-valerolactone 91.19
    n-decanol 3.44
    triethyl phosphate 13.42
    4-methyl-2-pentanol 4.25
    propionitrile 6.69
    vinylene carbonate 47.59
    1,1,2-trichlorotrifluoroethane 50.66
    DMS 26.7
    cumene 4.63
    2-octanol 3.67
    2-hexanone 14.24
    octyl acetate 11.42
    limonene 5.95
    1,2-dimethoxyethane 19.82
    ethyl orthosilicate 11.62
    tributyl phosphate 13.95
    diacetone alcohol 16.23
    N,N-dimethylaniline 7.61
    acrylonitrile 12.22
    aniline 16.57
    1,3-propanediol 8.81
    bromobenzene 29.42
    dibromomethane 27.82
    1,1,2,2-tetrachloroethane 63.31
    2-methyl-cyclohexyl acetate 20.77
    tetrabutyl urea 19.31
    diisobutyl methanol 4.39
    2-phenylethanol 25.44
    styrene 5.65
    dioctyl adipate 14.83
    dimethyl sulfate 21.56
    ethyl butyrate 12.67
    methyl lactate 10.09
    butyl lactate 20.4
    diethyl carbonate 12.56
    propanediol butyl ether 12.22
    triethyl orthoformate 13.33
    p-tert-butyltoluene 5.21
    methyl 4-tert-butylbenzoate 26.87
    morpholine 23.48
    tert-butylamine 1.75
    n-dodecanol 2.8
    dimethoxymethane 18.58
    ethylene carbonate 36.49
    cyrene 30.03
    2-ethoxyethyl acetate 35.69
    2-ethylhexyl acetate 24.13
    1,2,4-trichlorobenzene 41.7
    4-methylpyridine 35.11
    dibutyl ether 3.43
    2,6-dimethyl-4-heptanol 4.39
    DEF 16.24
    dimethyl isosorbide 40.74
    tetrachloroethylene 49.11
    eugenol 33.48
    triacetin 24.93
    span 80 18.17
    1,4-butanediol 3.76
    1,1-dichloroethane 19.2
    2-methyl-1-pentanol 7.31
    methyl formate 14.18
    2-methyl-1-butanol 6.58
    n-decane 0.3
    butyronitrile 7.61
    3,7-dimethyl-1-octanol 5.74
    1-chlorooctane 2.29
    1-chlorotetradecane 1.35
    n-nonane 0.19
    undecane 0.26
    tert-butylcyclohexane 0.39
    cyclooctane 0.22
    cyclopentanol 7.95
    tetrahydropyran 16.63
    tert-amyl methyl ether 2.5
    2,5,8-trioxanonane 35.71
    1-hexene 0.7
    2-isopropoxyethanol 10.3
    2,2,2-trifluoroethanol 10.13
    methyl butyrate 14.9

    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