(+)-Lycopsamine

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  • Identifiers

    CAS number
    10285-07-1

    Molecular formula
    C15H25NO5

    SMILES
    C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 66.82%
    Cooling 28.19%
    Sweet 23.86%
    Milky 23.74%
    Savory 20.86%
    Buttery 20.23%
    Mint 20.16%
    Nutty 16.97%
    Alcoholic 15.61%
    Creamy 15.49%

     

    Flavor
    Bitter 79.65%
    Odorless 37.44%
    Bland 29.92%
    Sweet-like 25.06%
    Very mild 21.64%
    Cedarleaf 19.28%
    Mild 18.58%
    Heather 18.18%
    Parsley 18.15%
    Broom 18.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.4

    pKa est.
    7.74 (neutral)

    Molecular weight
    299.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    547°C

    Flash point

    • 222.04 ˚C est.

  • Synonyms

    • Lycopsamine
    • 10285-07-1
    • (+)-Lycopsamine
    • UER4ET3OHI
    • DTXSID60145542
    • Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3S*),7abeta))-
    • [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
    • ((7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S)-2-hydroxy-2-((1S)-1-hydroxyethyl)-3-methyl-butanoate
    • ((7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S)-2-hydroxy-2-((1S)-1-hydroxyethyl)-3-methylbutanoate
    • [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methyl-butanoate
    • RefChem:41791
    • DTXCID9068033
    • CCIRS 9199
    • Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S,3S)-
    • [(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
    • ((1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3S)-2,3-dihydroxy-2-isopropylbutanoate
    • C15H25NO5
    • CCRIS 9199
    • MFCD09260181
    • Lycopsamine Impurity 1
    • UNII-UER4ET3OHI
    • 9-Viridiflorylretronecine
    • Lycopsamine, HPLC Grade
    • 3'-EPI-INTERMEDINE
    • (1R-(1alpha,7(2S*,3S*),7abeta))-(2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-(1-methylethyl)butanoate
    • CHEBI:6598
    • orb1696251
    • SFVVQRJOGUKCEG-ZGFBFQLVSA-N
    • MSK14171
    • Lycopsamine 100 microg/mL in Water
    • AKOS040752803
    • DA-55120
    • FL161608
    • HY-124916
    • RETRONECINE 9-((-)-VIRIDIFLORATE)
    • CS-0089560
    • NS00098507
    • Q27107262
    • [(1R,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S,3S)-2,3-dihydroxy-2-(propan-2-yl)butanoate
    • BUTANOIC ACID, 2,3-DIHYDROXY-2-(1-METHYLETHYL)-, (2,3,5,7A-TETRAHYDRO-1-HYDROXY-1H-PYRROLIZIN-7-YL)METHYL ESTER, (1R-(1.ALPHA.,7(2S*,3S*),7A.BETA.))-
    • 10285-07-1

  • Applications

    (+)-Lycopsamine, CAS 10285-07-1, is mainly regarded as a precursor and scaffold for the synthesis of complex alkaloids in organic chemistry and pharmaceutical research; it is commonly used as a chiral building block in asymmetric synthesis and as a reference sample for analytical method development (HPLC/GC) in laboratory work; it is also evaluated as an intermediate for synthesizing alkaloid families and serves as a reference material for natural product libraries in research programs; its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 227.97
    methanol 562.63
    isopropanol 99.76
    water 23.16
    ethyl acetate 67.68
    n-propanol 127.17
    acetone 83.46
    n-butanol 112.4
    acetonitrile 34.82
    DMF 278.32
    toluene 8.46
    isobutanol 70.6
    1,4-dioxane 124.35
    methyl acetate 47.16
    THF 213.24
    2-butanone 51.81
    n-pentanol 47.16
    sec-butanol 68.57
    n-hexane 1.16
    ethylene glycol 167.86
    NMP 171.65
    cyclohexane 2.22
    DMSO 498.49
    n-butyl acetate 31.18
    n-octanol 24.61
    chloroform 138.1
    n-propyl acetate 25.59
    acetic acid 572.09
    dichloromethane 117.93
    cyclohexanone 94.96
    propylene glycol 122.16
    isopropyl acetate 46.28
    DMAc 201.48
    2-ethoxyethanol 207.57
    isopentanol 78.59
    n-heptane 1.19
    ethyl formate 69.75
    1,2-dichloroethane 72.05
    n-hexanol 47.81
    2-methoxyethanol 509.44
    isobutyl acetate 16.76
    tetrachloromethane 18.2
    n-pentyl acetate 31.92
    transcutol 402.26
    n-heptanol 33.98
    ethylbenzene 5.3
    MIBK 51.44
    2-propoxyethanol 191.16
    tert-butanol 92.61
    MTBE 28.77
    2-butoxyethanol 121.99
    propionic acid 117.53
    o-xylene 8.76
    formic acid 910.23
    diethyl ether 40.85
    m-xylene 9.6
    p-xylene 6.09
    chlorobenzene 16.98
    dimethyl carbonate 45.94
    n-octane 0.89
    formamide 794.04
    cyclopentanone 120.58
    2-pentanone 68.51
    anisole 17.31
    cyclopentyl methyl ether 52.47
    gamma-butyrolactone 168.29
    1-methoxy-2-propanol 297.43
    pyridine 50.09
    3-pentanone 37.33
    furfural 170.77
    n-dodecane 0.76
    diethylene glycol 243.15
    diisopropyl ether 10.63
    tert-amyl alcohol 68.95
    acetylacetone 100.38
    n-hexadecane 0.86
    acetophenone 30.21
    methyl propionate 61.09
    isopentyl acetate 33.08
    trichloroethylene 151.47
    n-nonanol 24.1
    cyclohexanol 58.32
    benzyl alcohol 38.42
    2-ethylhexanol 18.74
    isooctanol 25.71
    dipropyl ether 13.95
    1,2-dichlorobenzene 22.15
    ethyl lactate 40.51
    propylene carbonate 81.31
    n-methylformamide 245.26
    2-pentanol 55.31
    n-pentane 2.0
    1-propoxy-2-propanol 95.91
    1-methoxy-2-propyl acetate 70.87
    2-(2-methoxypropoxy) propanol 79.91
    mesitylene 6.48
    ε-caprolactone 109.14
    p-cymene 6.52
    epichlorohydrin 204.15
    1,1,1-trichloroethane 38.89
    2-aminoethanol 251.45
    morpholine-4-carbaldehyde 237.35
    sulfolane 238.13
    2,2,4-trimethylpentane 1.61
    2-methyltetrahydrofuran 74.9
    n-hexyl acetate 39.43
    isooctane 1.27
    2-(2-butoxyethoxy)ethanol 134.79
    sec-butyl acetate 18.83
    tert-butyl acetate 50.26
    decalin 1.25
    glycerin 282.29
    diglyme 216.9
    acrylic acid 142.39
    isopropyl myristate 12.54
    n-butyric acid 172.17
    acetyl acetate 52.46
    di(2-ethylhexyl) phthalate 22.5
    ethyl propionate 26.61
    nitromethane 425.31
    1,2-diethoxyethane 47.71
    benzonitrile 27.8
    trioctyl phosphate 17.35
    1-bromopropane 24.83
    gamma-valerolactone 252.48
    n-decanol 15.81
    triethyl phosphate 16.86
    4-methyl-2-pentanol 33.93
    propionitrile 27.18
    vinylene carbonate 81.24
    1,1,2-trichlorotrifluoroethane 297.16
    DMS 40.51
    cumene 5.06
    2-octanol 18.53
    2-hexanone 24.77
    octyl acetate 19.17
    limonene 9.15
    1,2-dimethoxyethane 154.39
    ethyl orthosilicate 15.85
    tributyl phosphate 18.65
    diacetone alcohol 109.31
    N,N-dimethylaniline 14.57
    acrylonitrile 46.83
    aniline 28.65
    1,3-propanediol 310.74
    bromobenzene 13.38
    dibromomethane 63.21
    1,1,2,2-tetrachloroethane 123.51
    2-methyl-cyclohexyl acetate 23.38
    tetrabutyl urea 24.98
    diisobutyl methanol 13.39
    2-phenylethanol 44.16
    styrene 5.15
    dioctyl adipate 22.83
    dimethyl sulfate 94.54
    ethyl butyrate 22.94
    methyl lactate 94.34
    butyl lactate 48.86
    diethyl carbonate 15.39
    propanediol butyl ether 113.03
    triethyl orthoformate 20.81
    p-tert-butyltoluene 6.34
    methyl 4-tert-butylbenzoate 50.02
    morpholine 174.64
    tert-butylamine 29.84
    n-dodecanol 10.33
    dimethoxymethane 212.27
    ethylene carbonate 65.58
    cyrene 88.48
    2-ethoxyethyl acetate 65.87
    2-ethylhexyl acetate 21.32
    1,2,4-trichlorobenzene 29.13
    4-methylpyridine 35.65
    dibutyl ether 12.0
    2,6-dimethyl-4-heptanol 13.39
    DEF 85.45
    dimethyl isosorbide 116.44
    tetrachloroethylene 95.76
    eugenol 61.25
    triacetin 53.58
    span 80 68.05
    1,4-butanediol 95.5
    1,1-dichloroethane 46.18
    2-methyl-1-pentanol 38.27
    methyl formate 174.54
    2-methyl-1-butanol 69.47
    n-decane 1.39
    butyronitrile 31.84
    3,7-dimethyl-1-octanol 22.72
    1-chlorooctane 7.39
    1-chlorotetradecane 2.7
    n-nonane 1.19
    undecane 0.98
    tert-butylcyclohexane 1.06
    cyclooctane 1.05
    cyclopentanol 71.13
    tetrahydropyran 59.6
    tert-amyl methyl ether 27.14
    2,5,8-trioxanonane 140.8
    1-hexene 4.27
    2-isopropoxyethanol 94.7
    2,2,2-trifluoroethanol 268.6
    methyl butyrate 35.87

    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