(-)-Dihydroquinine

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  • Identifiers

    CAS number
    522-66-7

    Molecular formula
    C20H26N2O2

    SMILES
    CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 47.44%
    Animal 30.11%
    Roasted 24.27%
    Sweet 23.44%
    Nutty 23.03%
    Vanilla 22.53%
    Cooling 22.32%
    Savory 20.3%
    Earthy 18.8%
    Popcorn 18.58%

     

    Flavor
    Bitter 83.98%
    Odorless 23.19%
    Bland 23.1%
    Sweet-like 21.81%
    Cedarleaf 21.13%
    Cereal 19.53%
    Alkaline 19.35%
    Very strong 18.92%
    Indole 18.86%
    Nitrile 18.82%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    8.3 (weak base)

    Molecular weight
    326.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    650°C

    Flash point

    • 242.43 ˚C est.

  • Synonyms

    • HYDROQUININE
    • 522-66-7
    • (-)-Dihydroquinine
    • 10,11-dihydroquinine
    • (-)-hydroquinine
    • (-)-10,11-dihydroquinine
    • 31J3Q51T6L
    • NSC-41799
    • DTXSID70878516
    • Cinchonan-9-ol, 10,11-dihydro-6'-methoxy-, (8alpha,9R)-
    • RefChem:147104
    • DTXCID301016562
    • (R)-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo(2.2.2)octan-2-yl)(6-methoxyquinolin-4-yl)methanol
    • 208-334-0
    • Dihydroquinine
    • (1R)-((2S,4S,5R)-5-Ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol
    • MFCD00151107
    • C20H26N2O2
    • Quinine Sulfate EP Impurity C
    • (R)-((1S,2S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methanol
    • (8alpha,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
    • (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
    • (R)-[(2S,4S,5R)-5-ethylquinuclidin-2-yl]-(6-methoxy-4-quinolyl)methanol
    • 23495-98-9
    • Hydrochinin
    • Quinine, 10,11-dihydro-
    • Cinchonan-9-ol, 10,11-dihydro-6'-methoxy-, (8.alpha.,9R)-
    • NSC41799
    • UNII-31J3Q51T6L
    • EINECS 208-334-0
    • NSC 41799
    • Hydroquinine, 98%
    • Hydroquinine (Standard)
    • Dihydroquinidine;(+)-Hydroquinidine;Hydroconquinine
    • HYDROQUININE [MI]
    • HYDROQUININE [WHO-DD]
    • SCHEMBL109600
    • SCHEMBL109601
    • CHEMBL588934
    • MEGxp0_001893
    • orb1300047
    • SCHEMBL7905453
    • DIHYDROQUININE [WHO-IP]
    • ACon1_002104
    • CHEBI:135994
    • EBC-44323
    • HY-42034R
    • AKOS015920285
    • DB13718
    • FH30590
    • (R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
    • NCGC00179825-01
    • NCGC00385355-01
    • AC-30190
    • SY009729
    • QUINIDINE SULFATE IMPURITY C [WHO-IP]
    • QUININE BISULFATE IMPURITY C [WHO-IP]
    • D70296
    • EN300-1710087
    • QUININE SULFATE IMPURITY C [EP IMPURITY]
    • F093441
    • (8a,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
    • Q5276450
    • (8|A,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
    • BRD-K13794225-001-01-5
    • QUININE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
    • (9R)-6'-Methoxy-8alpha-10,11-dihydrocinchonan-9-ol
    • Z3234911758
    • QUININE BISULFATE HEPTAHYDRATE IMPURITY C [WHO-IP]
    • (8.ALPHA.,9R)-10,11-DIHYDRO-6'-METHOXYCINCHONAN-9-OL
    • (R)-((2S,4S,5R)-5-ETHYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(6-METHOXYQUINOLIN-4-YL)METHANOL [WHO-IP]
    • 522-66-7

  • Applications

    (-)-Dihydroquinine (CAS 522-66-7) is used primarily as a chiral building block and ligand in asymmetric synthesis, where its cinchona-alkaloid backbone enables enantioselective transformations in pharmaceutical and fine-chemical development. It also serves as an intermediate for preparing cinchona alkaloid derivatives and related chiral amines, supporting research and process development in drug discovery. In addition, it is explored as a precursor for specialized polymers and materials where a rigid, chiral scaffold can influence stereochemical outcomes in catalytic or optoelectronic applications. These roles reflect its value as a stereochemically rich starting point for enantioselective catalysis and synthetic elaboration, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.0
    methanol 20.89
    isopropanol 8.48
    water 0.34
    ethyl acetate 17.23
    n-propanol 16.28
    acetone 10.69
    n-butanol 18.19
    acetonitrile 5.17
    DMF 16.29
    toluene 10.41
    isobutanol 11.62
    1,4-dioxane 32.74
    methyl acetate 11.48
    THF 32.85
    2-butanone 14.75
    n-pentanol 9.18
    sec-butanol 6.8
    n-hexane 0.16
    ethylene glycol 7.82
    NMP 9.96
    cyclohexane 0.69
    DMSO 35.92
    n-butyl acetate 13.7
    n-octanol 2.74
    chloroform 93.17
    n-propyl acetate 9.85
    acetic acid 63.02
    dichloromethane 89.88
    cyclohexanone 31.86
    propylene glycol 3.62
    isopropyl acetate 11.74
    DMAc 31.36
    2-ethoxyethanol 38.69
    isopentanol 17.48
    n-heptane 0.36
    ethyl formate 15.66
    1,2-dichloroethane 53.6
    n-hexanol 10.04
    2-methoxyethanol 65.02
    isobutyl acetate 7.92
    tetrachloromethane 9.0
    n-pentyl acetate 11.49
    transcutol 173.52
    n-heptanol 6.48
    ethylbenzene 2.89
    MIBK 11.46
    2-propoxyethanol 43.71
    tert-butanol 6.83
    MTBE 3.94
    2-butoxyethanol 28.29
    propionic acid 15.35
    o-xylene 5.65
    formic acid 54.33
    diethyl ether 7.77
    m-xylene 8.13
    p-xylene 3.99
    chlorobenzene 15.98
    dimethyl carbonate 8.94
    n-octane 0.19
    formamide 58.02
    cyclopentanone 24.8
    2-pentanone 15.61
    anisole 5.7
    cyclopentyl methyl ether 12.71
    gamma-butyrolactone 31.13
    1-methoxy-2-propanol 30.14
    pyridine 35.41
    3-pentanone 11.63
    furfural 52.48
    n-dodecane 0.15
    diethylene glycol 52.29
    diisopropyl ether 2.28
    tert-amyl alcohol 6.1
    acetylacetone 22.15
    n-hexadecane 0.17
    acetophenone 10.82
    methyl propionate 13.68
    isopentyl acetate 15.36
    trichloroethylene 128.79
    n-nonanol 3.55
    cyclohexanol 13.52
    benzyl alcohol 13.62
    2-ethylhexanol 5.98
    isooctanol 6.17
    dipropyl ether 4.32
    1,2-dichlorobenzene 15.58
    ethyl lactate 8.35
    propylene carbonate 18.16
    n-methylformamide 19.53
    2-pentanol 7.39
    n-pentane 0.33
    1-propoxy-2-propanol 22.24
    1-methoxy-2-propyl acetate 23.2
    2-(2-methoxypropoxy) propanol 22.77
    mesitylene 3.86
    ε-caprolactone 26.83
    p-cymene 3.71
    epichlorohydrin 73.77
    1,1,1-trichloroethane 23.38
    2-aminoethanol 14.3
    morpholine-4-carbaldehyde 39.24
    sulfolane 30.68
    2,2,4-trimethylpentane 0.3
    2-methyltetrahydrofuran 14.63
    n-hexyl acetate 9.26
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 40.8
    sec-butyl acetate 6.94
    tert-butyl acetate 10.5
    decalin 0.39
    glycerin 17.0
    diglyme 77.58
    acrylic acid 17.91
    isopropyl myristate 3.68
    n-butyric acid 32.47
    acetyl acetate 14.64
    di(2-ethylhexyl) phthalate 7.4
    ethyl propionate 7.42
    nitromethane 49.84
    1,2-diethoxyethane 22.72
    benzonitrile 13.46
    trioctyl phosphate 4.62
    1-bromopropane 11.54
    gamma-valerolactone 62.88
    n-decanol 2.66
    triethyl phosphate 7.74
    4-methyl-2-pentanol 5.84
    propionitrile 7.15
    vinylene carbonate 25.34
    1,1,2-trichlorotrifluoroethane 75.28
    DMS 12.13
    cumene 2.4
    2-octanol 2.9
    2-hexanone 7.87
    octyl acetate 5.12
    limonene 3.76
    1,2-dimethoxyethane 32.2
    ethyl orthosilicate 7.94
    tributyl phosphate 6.1
    diacetone alcohol 17.93
    N,N-dimethylaniline 4.74
    acrylonitrile 11.71
    aniline 19.25
    1,3-propanediol 37.02
    bromobenzene 14.09
    dibromomethane 37.95
    1,1,2,2-tetrachloroethane 78.94
    2-methyl-cyclohexyl acetate 10.76
    tetrabutyl urea 7.44
    diisobutyl methanol 3.75
    2-phenylethanol 16.86
    styrene 3.0
    dioctyl adipate 7.14
    dimethyl sulfate 14.27
    ethyl butyrate 9.57
    methyl lactate 11.12
    butyl lactate 13.0
    diethyl carbonate 8.14
    propanediol butyl ether 16.42
    triethyl orthoformate 9.61
    p-tert-butyltoluene 3.14
    methyl 4-tert-butylbenzoate 14.51
    morpholine 38.89
    tert-butylamine 2.78
    n-dodecanol 1.97
    dimethoxymethane 26.4
    ethylene carbonate 22.64
    cyrene 19.2
    2-ethoxyethyl acetate 28.83
    2-ethylhexyl acetate 11.21
    1,2,4-trichlorobenzene 20.34
    4-methylpyridine 20.9
    dibutyl ether 3.28
    2,6-dimethyl-4-heptanol 3.75
    DEF 17.61
    dimethyl isosorbide 36.98
    tetrachloroethylene 66.04
    eugenol 18.64
    triacetin 15.62
    span 80 14.73
    1,4-butanediol 10.47
    1,1-dichloroethane 24.44
    2-methyl-1-pentanol 10.04
    methyl formate 17.33
    2-methyl-1-butanol 13.54
    n-decane 0.25
    butyronitrile 8.97
    3,7-dimethyl-1-octanol 4.51
    1-chlorooctane 1.45
    1-chlorotetradecane 0.68
    n-nonane 0.19
    undecane 0.19
    tert-butylcyclohexane 0.3
    cyclooctane 0.32
    cyclopentanol 9.75
    tetrahydropyran 20.8
    tert-amyl methyl ether 3.98
    2,5,8-trioxanonane 48.72
    1-hexene 0.86
    2-isopropoxyethanol 21.13
    2,2,2-trifluoroethanol 28.62
    methyl butyrate 10.0

    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