Cinchonine

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  • Identifiers

    CAS number
    118-10-5

    Molecular formula
    C19H22N2O

    SMILES
    C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 50.08%
    Nutty 24.37%
    Animal 23.45%
    Roasted 21.98%
    Bitter 21.54%
    Popcorn 21.52%
    Burnt 19.43%
    Fishy 18.76%
    Cooked 17.66%
    Savory 17.43%

     

    Flavor
    Bitter 83.38%
    Odorless 22.66%
    Alkaline 20.53%
    Cedarleaf 20.46%
    Sweet-like 20.34%
    Nitrile 20.13%
    Very strong 19.77%
    Cereal 19.71%
    Indole 19.66%
    Shrimp 18.91%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    6.9 (neutral)

    Molecular weight
    294.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    578°C

    Flash point

    • 235.86 ˚C est.

  • Synonyms

    • cinchonine
    • 118-10-5
    • D-Cinchonine
    • (9S)-Cinchonan-9-ol
    • Cinchonan-9-ol, (9S)-
    • (8R,9S)-Cinchonine
    • (+)-Cinconine
    • DTXSID6045082
    • NSC-6176
    • V43X79NZCD
    • CHEBI:27509
    • DTXCID801474963
    • 2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-
    • alpha-(5-Vinyl-2-quinuclidinyl)-4-quinolinemethanol
    • (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
    • (S)-((2R,4S,5R)-5-ethenyl-1-azabicyclo(2.2.2)octan-2-yl)-quinolin-4-ylmethanol
    • LA-40221
    • RefChem:126196
    • 204-234-6
    • (+)-Cinchonine
    • (1S)-Quinolin-4-yl((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
    • cinchonin
    • (+)-cinchonin
    • (S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol
    • MFCD00064372
    • 2-Quinuclidinemethanol, .alpha.-(5-vinyl-2-quinolyl)-
    • NSC6176
    • .alpha.-Quinidine
    • (S)-4-quinolyl-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol
    • (S)-Quinolin-4-yl-(5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol
    • UNII-V43X79NZCD
    • (S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol
    • (9S)-Cinchonan-9-ol; Cinchonine (8CI); (+)-Cinchonine; (8R,9S)-Cinchonine; NSC 6176; d-Cinchonine
    • CAS-118-10-5
    • NSC 6176
    • EINECS 204-234-6
    • CINCHORINE
    • Cinchonine (Standard)
    • CINCHONINE [MI]
    • AI3-09058
    • Prestwick3_000608
    • 2-Quinuclidinemethanol, .alpha.-4-quinolyl-5-vinyl-
    • (+)-Cinchonine, 85%
    • CINCHONINE [WHO-DD]
    • (+)-Cinchonine; >99%
    • BSPBio_000516
    • MLS002153907
    • SCHEMBL158394
    • SCHEMBL158395
    • (5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)methanol
    • BPBio1_000568
    • CHEMBL588619
    • MEGxp0_001905
    • orb1311022
    • SCHEMBL29364855
    • ACon0_001352
    • ACon1_000336
    • GTPL13363
    • HY-Y0152R
    • Quinidine Sulfate EP Impurity B
    • HMS2096J18
    • HMS2235N18
    • HY-Y0152
    • Tox21_110009
    • (+)-Cinchonine, analytical standard
    • BDBM50370411
    • EBC-69053
    • MSK159057
    • AKOS015895982
    • FC11047
    • NCGC00013067-01
    • NCGC00169174-01
    • NCGC00169174-02
    • NCGC00262542-03
    • NCGC00262542-10
    • DS-15267
    • NCI60_005298
    • SMR001233256
    • Cinchonine, crystallized, >=98.0% (NT)
    • AB00374715
    • CS-0008420
    • O10016
    • WLN: T66 BNJ EYQ-DT66 A B CNTJ A1U1
    • AL-466/21162039
    • AM-331/20711019
    • F121600
    • Q2972710
    • BRD-K90268819-001-03-4
    • 118-10-5

  • Applications

    Cinchonine (CAS 118-10-5) is an alkaloid from the Cinchona family that is commonly used as a chiral resolving agent for racemic compounds by forming diastereomeric salts with acids; it also serves as a chiral precursor, auxiliary, and ligand in asymmetric synthesis to improve the enantioselectivity of reactions; it is a key starting material for the synthesis of other cinchonine alkaloids and related pharmaceutical intermediates; it is used in the research and development of cinchonine-derived catalytic systems for enantioselective reactions; and it can function as a building block for pharmaceutical intermediates and other complex organic compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.62
    methanol 12.03
    isopropanol 7.54
    water 0.09
    ethyl acetate 8.68
    n-propanol 13.48
    acetone 6.58
    n-butanol 16.37
    acetonitrile 2.69
    DMF 13.28
    toluene 10.74
    isobutanol 10.16
    1,4-dioxane 27.11
    methyl acetate 5.88
    THF 43.11
    2-butanone 9.75
    n-pentanol 9.51
    sec-butanol 6.39
    n-hexane 0.2
    ethylene glycol 3.22
    NMP 6.92
    cyclohexane 0.55
    DMSO 26.46
    n-butyl acetate 11.26
    n-octanol 3.22
    chloroform 40.31
    n-propyl acetate 6.79
    acetic acid 27.31
    dichloromethane 38.77
    cyclohexanone 23.87
    propylene glycol 2.29
    isopropyl acetate 7.33
    DMAc 20.39
    2-ethoxyethanol 30.48
    isopentanol 16.67
    n-heptane 0.49
    ethyl formate 9.37
    1,2-dichloroethane 27.72
    n-hexanol 11.79
    2-methoxyethanol 45.23
    isobutyl acetate 6.33
    tetrachloromethane 4.14
    n-pentyl acetate 10.15
    transcutol 165.72
    n-heptanol 7.6
    ethylbenzene 3.02
    MIBK 10.13
    2-propoxyethanol 41.49
    tert-butanol 6.76
    MTBE 3.24
    2-butoxyethanol 27.04
    propionic acid 8.12
    o-xylene 5.39
    formic acid 19.75
    diethyl ether 6.51
    m-xylene 8.32
    p-xylene 3.71
    chlorobenzene 10.61
    dimethyl carbonate 5.34
    n-octane 0.26
    formamide 22.77
    cyclopentanone 20.81
    2-pentanone 11.19
    anisole 5.16
    cyclopentyl methyl ether 12.36
    gamma-butyrolactone 21.58
    1-methoxy-2-propanol 25.47
    pyridine 32.05
    3-pentanone 7.64
    furfural 36.94
    n-dodecane 0.19
    diethylene glycol 38.49
    diisopropyl ether 1.98
    tert-amyl alcohol 5.82
    acetylacetone 13.06
    n-hexadecane 0.22
    acetophenone 8.99
    methyl propionate 7.76
    isopentyl acetate 13.56
    trichloroethylene 65.56
    n-nonanol 4.05
    cyclohexanol 11.57
    benzyl alcohol 12.53
    2-ethylhexanol 6.99
    isooctanol 7.08
    dipropyl ether 5.29
    1,2-dichlorobenzene 9.81
    ethyl lactate 6.52
    propylene carbonate 12.0
    n-methylformamide 10.69
    2-pentanol 7.38
    n-pentane 0.37
    1-propoxy-2-propanol 23.45
    1-methoxy-2-propyl acetate 17.75
    2-(2-methoxypropoxy) propanol 21.75
    mesitylene 3.75
    ε-caprolactone 19.24
    p-cymene 3.95
    epichlorohydrin 56.16
    1,1,1-trichloroethane 10.92
    2-aminoethanol 8.17
    morpholine-4-carbaldehyde 25.62
    sulfolane 22.79
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 14.53
    n-hexyl acetate 7.99
    isooctane 0.29
    2-(2-butoxyethoxy)ethanol 40.82
    sec-butyl acetate 5.05
    tert-butyl acetate 7.54
    decalin 0.39
    glycerin 10.2
    diglyme 70.8
    acrylic acid 8.97
    isopropyl myristate 3.59
    n-butyric acid 20.0
    acetyl acetate 6.45
    di(2-ethylhexyl) phthalate 6.82
    ethyl propionate 5.04
    nitromethane 19.83
    1,2-diethoxyethane 24.06
    benzonitrile 11.33
    trioctyl phosphate 4.44
    1-bromopropane 8.43
    gamma-valerolactone 46.18
    n-decanol 3.08
    triethyl phosphate 6.1
    4-methyl-2-pentanol 6.51
    propionitrile 5.02
    vinylene carbonate 15.47
    1,1,2-trichlorotrifluoroethane 43.62
    DMS 7.92
    cumene 2.57
    2-octanol 3.57
    2-hexanone 7.29
    octyl acetate 4.79
    limonene 3.84
    1,2-dimethoxyethane 31.24
    ethyl orthosilicate 6.79
    tributyl phosphate 5.68
    diacetone alcohol 15.01
    N,N-dimethylaniline 4.6
    acrylonitrile 7.86
    aniline 16.6
    1,3-propanediol 23.49
    bromobenzene 9.21
    dibromomethane 18.6
    1,1,2,2-tetrachloroethane 42.42
    2-methyl-cyclohexyl acetate 9.3
    tetrabutyl urea 7.44
    diisobutyl methanol 4.36
    2-phenylethanol 16.76
    styrene 2.79
    dioctyl adipate 6.52
    dimethyl sulfate 8.46
    ethyl butyrate 8.16
    methyl lactate 7.29
    butyl lactate 11.98
    diethyl carbonate 5.86
    propanediol butyl ether 15.83
    triethyl orthoformate 8.31
    p-tert-butyltoluene 3.37
    methyl 4-tert-butylbenzoate 12.94
    morpholine 32.7
    tert-butylamine 2.95
    n-dodecanol 2.31
    dimethoxymethane 23.84
    ethylene carbonate 13.17
    cyrene 16.96
    2-ethoxyethyl acetate 22.41
    2-ethylhexyl acetate 9.67
    1,2,4-trichlorobenzene 12.26
    4-methylpyridine 18.8
    dibutyl ether 3.98
    2,6-dimethyl-4-heptanol 4.36
    DEF 11.47
    dimethyl isosorbide 35.55
    tetrachloroethylene 35.55
    eugenol 17.33
    triacetin 11.33
    span 80 14.54
    1,4-butanediol 7.05
    1,1-dichloroethane 12.27
    2-methyl-1-pentanol 10.72
    methyl formate 8.77
    2-methyl-1-butanol 12.53
    n-decane 0.32
    butyronitrile 6.79
    3,7-dimethyl-1-octanol 5.08
    1-chlorooctane 1.67
    1-chlorotetradecane 0.76
    n-nonane 0.25
    undecane 0.23
    tert-butylcyclohexane 0.34
    cyclooctane 0.29
    cyclopentanol 8.23
    tetrahydropyran 20.43
    tert-amyl methyl ether 3.53
    2,5,8-trioxanonane 44.12
    1-hexene 1.09
    2-isopropoxyethanol 18.74
    2,2,2-trifluoroethanol 10.31
    methyl butyrate 6.96

    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