Lupinine

Overview IFRA Request a quote

  • Identifiers

    CAS number
    486-70-4

    Molecular formula
    C10H19NO

    SMILES
    C1CCN2CCC[C@H]([C@H]2C1)CO

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fishy 58.34%
    Animal 47.01%
    Floral 39.01%
    Sweet 36.52%
    Cheesy 33.11%
    Nutty 27.01%
    Ripe 25.0%
    Popcorn 24.03%
    Odorless 23.06%
    Oily 23.01%

     

    Flavor
    Bitter 54.47%
    Sweet 42.54%
    Animal 35.21%
    Floral 33.21%
    Alkaline 27.73%
    Amine 25.98%
    Ammoniacal 24.12%
    Shrimp 23.55%
    Cauliflower 22.99%
    Sweet-like 22.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    8.47 (weak base)

    Molecular weight
    169.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    266°C

    Flash point

    • 119.06 ˚C est.

  • Synonyms

    • Lupinine
    • (-)-Lupinine
    • 486-70-4
    • [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
    • Octahydroquinolizine-1-methanol
    • 33BAJ73U1F
    • NSC-21723
    • CHEBI:28012
    • DTXSID00197565
    • 1S-cis-octahydro-2H-quinolizine-1-methanol
    • ((1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl)methanol
    • RefChem:924995
    • DTXCID60120056
    • 207-638-0
    • ((1R,9aR)-Octahydro-1H-quinolizin-1-yl)methanol
    • (+/-)-Lupinine
    • 10248-30-3
    • NSC 21723
    • Lupinine DL-form [MI]
    • Lupinine, (+/-)-
    • (1R-trans)-Octahydro-2H-quinolizine-1-methanol
    • F74RAC8A5Q
    • (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol
    • (trans-Octahydro-1H-quinolizin-1-yl)methanol
    • MFCD00213431
    • 2H-Quinolizine-1-methanol, octahydro-, (1R,9aR)-rel-
    • 2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-(+/-)-
    • (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE)
    • ((1R,9aR)-octahydro-2H-quinolizin-1-yl)methanol
    • [(1R,9aR)-octahydro-1H-quinolizin-1-yl]methanol
    • ((1R,2R)-6-azabicyclo[4.4.0]dec-2-yl)methan-1-ol
    • l-lupinine
    • 2H-Quinolizine-1-methanol, octahydro-, (1R-trans)-
    • (R,R)-1-(Hydroxymethyl)octahydroindolizine
    • [(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methanol
    • EINECS 207-638-0
    • UNII-F74RAC8A5Q
    • BRN 0080447
    • UNII-33BAJ73U1F
    • (1R,9AR)-octahydro-2h-quinolizine-1-methanol
    • Spectrum_001736
    • SpecPlus_000606
    • LUPININE [MI]
    • Spectrum2_000499
    • Spectrum3_001094
    • Spectrum4_001921
    • Spectrum5_000773
    • (-)-Lupinine, AldrichCPR
    • BSPBio_002768
    • KBioGR_002262
    • KBioSS_002216
    • 5-21-01-00338 (Beilstein Handbook Reference)
    • DivK1c_006702
    • SCHEMBL177708
    • SPECTRUM1504021
    • SPBio_000397
    • CHEMBL459397
    • orb1311047
    • KBio1_001646
    • KBio2_002216
    • KBio2_004784
    • KBio2_007352
    • KBio3_001988
    • DTXSID80871679
    • HMS1922N13
    • NSC21723
    • CCG-38712
    • SBB000161
    • STK050782
    • AKOS004120072
    • EBC-616647
    • FL61612
    • SDCCGMLS-0066745.P001
    • BS-35956
    • DA-76298
    • ST018409
    • 2H-Quinolizine-1-methanol, (1R-trans)-
    • HY-121219
    • CS-0081248
    • NS00031813
    • F77309
    • (1R,9aR)-1-(Octahydroquinolizin-1-yl)methanol
    • 486L704
    • F234394
    • Q412589
    • (1R,9aR)-1-(octahydro-quinolizin-1-yl)-methanol
    • BRD-K45978015-001-03-6
    • 486-70-4

  • Applications

    Lupinine is primarily used as a chiral amine building block and intermediate in organic synthesis, where it serves as a starting material or precursor for the development of pharmaceutical compounds bearing amine functionality. It is also evaluated as an intermediate in the synthesis of other lupine alkaloids and related agrochemical ingredients, supporting research and development in agrochemistry. In industrial and academic settings, lupinine and its derivatives are employed as starting materials, ligands, or auxiliaries in asymmetric synthesis to enable enantioselective transformations. Additionally, it is encountered in natural-product synthesis studies and alkaloid chemistry research, with handling and use typically governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 246.17
    methanol 372.16
    isopropanol 184.88
    water 7.42
    ethyl acetate 149.6
    n-propanol 235.39
    acetone 180.4
    n-butanol 198.11
    acetonitrile 193.95
    DMF 275.87
    toluene 85.96
    isobutanol 175.12
    1,4-dioxane 474.34
    methyl acetate 153.96
    THF 414.33
    2-butanone 142.77
    n-pentanol 99.68
    sec-butanol 117.6
    n-hexane 3.21
    ethylene glycol 135.04
    NMP 288.29
    cyclohexane 18.22
    DMSO 604.57
    n-butyl acetate 153.66
    n-octanol 54.31
    chloroform 876.79
    n-propyl acetate 87.1
    acetic acid 416.61
    dichloromethane 836.75
    cyclohexanone 346.42
    propylene glycol 110.87
    isopropyl acetate 79.81
    DMAc 143.87
    2-ethoxyethanol 176.76
    isopentanol 151.91
    n-heptane 9.09
    ethyl formate 242.89
    1,2-dichloroethane 342.19
    n-hexanol 145.59
    2-methoxyethanol 407.75
    isobutyl acetate 59.67
    tetrachloromethane 137.77
    n-pentyl acetate 77.79
    transcutol 469.9
    n-heptanol 70.68
    ethylbenzene 29.18
    MIBK 72.11
    2-propoxyethanol 266.63
    tert-butanol 167.06
    MTBE 63.87
    2-butoxyethanol 147.66
    propionic acid 296.79
    o-xylene 62.32
    formic acid 239.89
    diethyl ether 77.14
    m-xylene 68.36
    p-xylene 37.85
    chlorobenzene 196.12
    dimethyl carbonate 55.31
    n-octane 4.09
    formamide 259.25
    cyclopentanone 398.14
    2-pentanone 112.03
    anisole 67.23
    cyclopentyl methyl ether 150.93
    gamma-butyrolactone 611.92
    1-methoxy-2-propanol 237.21
    pyridine 328.27
    3-pentanone 85.02
    furfural 543.48
    n-dodecane 3.95
    diethylene glycol 254.42
    diisopropyl ether 22.74
    tert-amyl alcohol 93.05
    acetylacetone 149.27
    n-hexadecane 4.57
    acetophenone 86.13
    methyl propionate 121.05
    isopentyl acetate 115.13
    trichloroethylene 721.64
    n-nonanol 46.45
    cyclohexanol 174.04
    benzyl alcohol 103.53
    2-ethylhexanol 75.14
    isooctanol 55.39
    dipropyl ether 61.51
    1,2-dichlorobenzene 173.25
    ethyl lactate 65.99
    propylene carbonate 318.39
    n-methylformamide 336.78
    2-pentanol 87.39
    n-pentane 6.65
    1-propoxy-2-propanol 178.19
    1-methoxy-2-propyl acetate 142.85
    2-(2-methoxypropoxy) propanol 104.36
    mesitylene 44.01
    ε-caprolactone 296.11
    p-cymene 41.92
    epichlorohydrin 551.48
    1,1,1-trichloroethane 267.37
    2-aminoethanol 207.36
    morpholine-4-carbaldehyde 341.89
    sulfolane 598.06
    2,2,4-trimethylpentane 6.03
    2-methyltetrahydrofuran 258.37
    n-hexyl acetate 87.58
    isooctane 5.77
    2-(2-butoxyethoxy)ethanol 159.14
    sec-butyl acetate 50.22
    tert-butyl acetate 80.03
    decalin 7.78
    glycerin 201.68
    diglyme 309.21
    acrylic acid 282.17
    isopropyl myristate 34.25
    n-butyric acid 372.18
    acetyl acetate 117.56
    di(2-ethylhexyl) phthalate 51.98
    ethyl propionate 67.72
    nitromethane 546.92
    1,2-diethoxyethane 128.56
    benzonitrile 191.97
    trioctyl phosphate 38.42
    1-bromopropane 133.52
    gamma-valerolactone 548.18
    n-decanol 34.91
    triethyl phosphate 52.7
    4-methyl-2-pentanol 51.82
    propionitrile 178.25
    vinylene carbonate 347.4
    1,1,2-trichlorotrifluoroethane 396.0
    DMS 75.13
    cumene 24.99
    2-octanol 37.12
    2-hexanone 67.67
    octyl acetate 45.92
    limonene 55.75
    1,2-dimethoxyethane 205.04
    ethyl orthosilicate 47.31
    tributyl phosphate 48.17
    diacetone alcohol 114.38
    N,N-dimethylaniline 43.66
    acrylonitrile 284.76
    aniline 168.39
    1,3-propanediol 298.27
    bromobenzene 189.9
    dibromomethane 440.38
    1,1,2,2-tetrachloroethane 472.59
    2-methyl-cyclohexyl acetate 77.84
    tetrabutyl urea 54.59
    diisobutyl methanol 45.17
    2-phenylethanol 121.4
    styrene 35.64
    dioctyl adipate 56.08
    dimethyl sulfate 102.94
    ethyl butyrate 101.59
    methyl lactate 93.85
    butyl lactate 80.73
    diethyl carbonate 70.22
    propanediol butyl ether 117.72
    triethyl orthoformate 75.19
    p-tert-butyltoluene 38.99
    methyl 4-tert-butylbenzoate 96.54
    morpholine 419.84
    tert-butylamine 79.48
    n-dodecanol 26.96
    dimethoxymethane 160.73
    ethylene carbonate 295.47
    cyrene 116.52
    2-ethoxyethyl acetate 114.96
    2-ethylhexyl acetate 89.44
    1,2,4-trichlorobenzene 210.37
    4-methylpyridine 230.61
    dibutyl ether 46.8
    2,6-dimethyl-4-heptanol 45.17
    DEF 136.67
    dimethyl isosorbide 186.74
    tetrachloroethylene 356.44
    eugenol 96.41
    triacetin 100.26
    span 80 104.69
    1,4-butanediol 94.68
    1,1-dichloroethane 283.06
    2-methyl-1-pentanol 75.63
    methyl formate 272.66
    2-methyl-1-butanol 131.92
    n-decane 6.47
    butyronitrile 191.41
    3,7-dimethyl-1-octanol 53.83
    1-chlorooctane 32.38
    1-chlorotetradecane 12.68
    n-nonane 5.82
    undecane 4.9
    tert-butylcyclohexane 7.35
    cyclooctane 7.18
    cyclopentanol 226.56
    tetrahydropyran 268.45
    tert-amyl methyl ether 46.16
    2,5,8-trioxanonane 186.46
    1-hexene 14.17
    2-isopropoxyethanol 101.07
    2,2,2-trifluoroethanol 186.2
    methyl butyrate 102.74

    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