Vincamine

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  • Identifiers

    CAS number
    1617-90-9

    Molecular formula
    C21H26N2O3

    SMILES
    CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@](C2)(C(=O)OC)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 50.06%
    Animal 25.4%
    Cooling 20.4%
    Nutty 19.37%
    Sweet 19.35%
    Fresh 18.3%
    Roasted 17.41%
    Milky 17.39%
    Popcorn 17.17%
    Earthy 16.82%

     

    Flavor
    Bitter 92.13%
    Bland 24.4%
    Odorless 23.42%
    Cedarleaf 21.01%
    Sweet-like 20.91%
    Cereal 19.19%
    Very strong 18.93%
    Indole 18.82%
    Nitrile 18.72%
    Alkaline 18.62%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    6.56 (neutral)

    Molecular weight
    354.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    471°C

    Melting point expt.

    • 232-233 °C

    Flash point

    • 246.01 ˚C est.

    Solubility expt.

    • In water, 62 mg/L @ 25 °C /Estimated/

  • Synonyms

    • vincamine
    • 1617-90-9
    • Pervincamine
    • Arteriovinca
    • Angiopac
    • Vincafor
    • Vincamidol
    • Novicet
    • Methyl vincaminate
    • Oxygeron
    • Vincagil
    • Equipur
    • Vincafolina
    • Tripervan
    • Vincadar
    • Ocu-vinc
    • Vincamina
    • Vincimax
    • Perval
    • Pervone
    • Vincaminum
    • Vraap
    • Cetal retard
    • Vinodrel retard
    • DTXSID9040134
    • 996XVD0JHT
    • NSC-91998
    • CHEBI:9985
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
    • DTXCID7020134
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • methyl 14beta-hydroxy-14,15-dihydro-3alpha,16alpha-eburnamenine-14alpha-carboxylate
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.0^(2,7).0^(8,18).0^(15,19))nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo(9.6.2.02,7.08,18.015,19)nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
    • RefChem:194264
    • C04AX07
    • 216-576-3
    • Devincan
    • Minorine
    • (+)-Vincamine
    • Vincamin
    • Anasclerol
    • Monorin
    • Devinkan
    • Vincasaunier
    • Decincan
    • Vincapront
    • Vinkametrin
    • Minorin
    • MFCD00078054
    • Vincachron
    • Vincapan
    • Vinca-Ecobi
    • Vinca-Minor
    • Alkaloid obtained from Vinca minor
    • Anasclerol (base)
    • 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
    • Vincamine (INN)
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methylester, (3a,14b,16a)-
    • VINCAMINE [INN]
    • Methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
    • Vincamina [DCIT]
    • Vincamine base
    • Vincaminum [INN-Latin]
    • Vincamine [INN:BAN:DCF]
    • HSDB 7150
    • EINECS 216-576-3
    • NSC 91998
    • UNII-996XVD0JHT
    • Pervincamine;
    • Vincamarine;
    • Minorine;
    • Vincamine CRS
    • NCGC00094824-01
    • Prestwick_495
    • CAS-1617-90-9
    • Vincamine for system suitability CRS
    • Cetal retard (TN)
    • Vincamine, 98%
    • Vincamine (Standard)
    • VINCAMINE [MI]
    • VINCAMINE [HSDB]
    • Prestwick0_000271
    • Prestwick1_000271
    • Prestwick2_000271
    • Prestwick3_000271
    • VINCAMINE [MART.]
    • VINCAMINE [WHO-DD]
    • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.)
    • BSPBio_000142
    • GTPL349
    • MLS002154249
    • SCHEMBL147179
    • SPBio_002361
    • BPBio1_000158
    • CHEMBL1165342
    • SCHEMBL29710919
    • VINCAMINE [EP MONOGRAPH]
    • BCBcMAP01_000080
    • HY-B1021R
    • HMS1568H04
    • HMS2095H04
    • HMS2268C20
    • HMS3712H04
    • HY-B1021
    • Tox21_111342
    • Tox21_301968
    • s3891
    • AKOS015896471
    • Tox21_111342_1
    • CCG-208544
    • CS-4536
    • DB13374
    • EBC-618387
    • FV65205
    • KS-5179
    • SMP1_000314
    • Vincamine, analytical reference material
    • NCGC00184983-01
    • NCGC00184983-03
    • NCGC00255542-01
    • AC-22625
    • SMR000112509
    • SY057985
    • NS00006858
    • C09251
    • 1617-90-9

  • Applications

    Vincamine is used in pharmaceuticals as a vasodilatory component in formulations aimed at cerebral blood flow, and it serves as a precursor in the industrial synthesis of vinpocetine. In chemical research and natural product synthesis, it is treated as a reference material and a starting point for the synthesis of indole alkaloids; in industrial manufacturing, it is used as a building block for related alkaloid compounds. Additionally, it is sometimes evaluated as a versatile intermediate in alkaloid chemistry development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.2
    methanol 6.13
    isopropanol 2.6
    water 0.04
    ethyl acetate 6.79
    n-propanol 4.07
    acetone 10.04
    n-butanol 5.36
    acetonitrile 2.36
    DMF 27.63
    toluene 7.13
    isobutanol 3.91
    1,4-dioxane 15.23
    methyl acetate 7.29
    THF 21.06
    2-butanone 13.12
    n-pentanol 3.59
    sec-butanol 1.95
    n-hexane 0.06
    ethylene glycol 3.49
    NMP 49.55
    cyclohexane 0.35
    DMSO 12.9
    n-butyl acetate 11.39
    n-octanol 1.86
    chloroform 36.66
    n-propyl acetate 6.61
    acetic acid 15.81
    dichloromethane 29.53
    cyclohexanone 45.47
    propylene glycol 1.89
    isopropyl acetate 7.19
    DMAc 38.62
    2-ethoxyethanol 10.55
    isopentanol 7.23
    n-heptane 0.08
    ethyl formate 9.23
    1,2-dichloroethane 17.56
    n-hexanol 5.06
    2-methoxyethanol 19.29
    isobutyl acetate 7.49
    tetrachloromethane 4.69
    n-pentyl acetate 12.83
    transcutol 23.08
    n-heptanol 4.54
    ethylbenzene 2.43
    MIBK 9.69
    2-propoxyethanol 22.39
    tert-butanol 2.83
    MTBE 1.42
    2-butoxyethanol 18.86
    propionic acid 8.28
    o-xylene 4.45
    formic acid 13.49
    diethyl ether 2.18
    m-xylene 4.82
    p-xylene 3.95
    chlorobenzene 14.14
    dimethyl carbonate 10.22
    n-octane 0.06
    formamide 14.77
    cyclopentanone 42.61
    2-pentanone 11.28
    anisole 4.42
    cyclopentyl methyl ether 6.85
    gamma-butyrolactone 41.85
    1-methoxy-2-propanol 12.69
    pyridine 27.77
    3-pentanone 9.09
    furfural 55.14
    n-dodecane 0.08
    diethylene glycol 23.13
    diisopropyl ether 0.84
    tert-amyl alcohol 2.23
    acetylacetone 16.83
    n-hexadecane 0.1
    acetophenone 12.73
    methyl propionate 8.38
    isopentyl acetate 14.58
    trichloroethylene 55.29
    n-nonanol 2.36
    cyclohexanol 7.22
    benzyl alcohol 12.77
    2-ethylhexanol 3.72
    isooctanol 4.44
    dipropyl ether 1.56
    1,2-dichlorobenzene 16.36
    ethyl lactate 7.9
    propylene carbonate 26.17
    n-methylformamide 14.46
    2-pentanol 2.36
    n-pentane 0.1
    1-propoxy-2-propanol 11.99
    1-methoxy-2-propyl acetate 18.16
    2-(2-methoxypropoxy) propanol 13.88
    mesitylene 2.57
    ε-caprolactone 31.44
    p-cymene 3.2
    epichlorohydrin 38.99
    1,1,1-trichloroethane 11.36
    2-aminoethanol 4.39
    morpholine-4-carbaldehyde 45.58
    sulfolane 48.01
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 8.27
    n-hexyl acetate 9.23
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 16.31
    sec-butyl acetate 5.51
    tert-butyl acetate 7.59
    decalin 0.23
    glycerin 9.07
    diglyme 29.37
    acrylic acid 13.24
    isopropyl myristate 3.59
    n-butyric acid 15.47
    acetyl acetate 9.62
    di(2-ethylhexyl) phthalate 9.62
    ethyl propionate 5.39
    nitromethane 21.39
    1,2-diethoxyethane 6.35
    benzonitrile 15.84
    trioctyl phosphate 6.45
    1-bromopropane 4.2
    gamma-valerolactone 72.23
    n-decanol 1.7
    triethyl phosphate 7.05
    4-methyl-2-pentanol 2.82
    propionitrile 4.75
    vinylene carbonate 35.02
    1,1,2-trichlorotrifluoroethane 50.68
    DMS 14.5
    cumene 2.11
    2-octanol 2.05
    2-hexanone 7.35
    octyl acetate 5.0
    limonene 3.1
    1,2-dimethoxyethane 13.21
    ethyl orthosilicate 6.16
    tributyl phosphate 6.72
    diacetone alcohol 12.47
    N,N-dimethylaniline 4.19
    acrylonitrile 10.01
    aniline 12.14
    1,3-propanediol 9.36
    bromobenzene 12.0
    dibromomethane 13.84
    1,1,2,2-tetrachloroethane 34.05
    2-methyl-cyclohexyl acetate 11.29
    tetrabutyl urea 9.24
    diisobutyl methanol 2.2
    2-phenylethanol 16.9
    styrene 2.78
    dioctyl adipate 7.15
    dimethyl sulfate 19.87
    ethyl butyrate 7.1
    methyl lactate 12.47
    butyl lactate 15.29
    diethyl carbonate 6.37
    propanediol butyl ether 10.25
    triethyl orthoformate 7.14
    p-tert-butyltoluene 2.63
    methyl 4-tert-butylbenzoate 16.01
    morpholine 15.74
    tert-butylamine 1.05
    n-dodecanol 1.2
    dimethoxymethane 14.9
    ethylene carbonate 26.44
    cyrene 25.6
    2-ethoxyethyl acetate 20.97
    2-ethylhexyl acetate 12.0
    1,2,4-trichlorobenzene 22.44
    4-methylpyridine 21.75
    dibutyl ether 1.3
    2,6-dimethyl-4-heptanol 2.2
    DEF 13.64
    dimethyl isosorbide 27.39
    tetrachloroethylene 32.23
    eugenol 21.0
    triacetin 13.85
    span 80 11.52
    1,4-butanediol 4.3
    1,1-dichloroethane 10.04
    2-methyl-1-pentanol 4.77
    methyl formate 15.07
    2-methyl-1-butanol 5.14
    n-decane 0.11
    butyronitrile 4.93
    3,7-dimethyl-1-octanol 2.71
    1-chlorooctane 0.87
    1-chlorotetradecane 0.44
    n-nonane 0.07
    undecane 0.09
    tert-butylcyclohexane 0.16
    cyclooctane 0.12
    cyclopentanol 6.81
    tetrahydropyran 9.12
    tert-amyl methyl ether 1.58
    2,5,8-trioxanonane 20.69
    1-hexene 0.4
    2-isopropoxyethanol 7.99
    2,2,2-trifluoroethanol 13.63
    methyl butyrate 8.18

    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