Liriodenine

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  • Identifiers

    CAS number
    475-75-2

    Molecular formula
    C17H9NO3

    SMILES
    C1OC2=C(O1)C3=C4C(=C2)C=CN=C4C(=O)C5=CC=CC=C53

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Floral 43.18%
    Fruity 31.34%
    Powdery 28.85%
    Odorless 28.59%
    Neroli 28.0%
    Sweet 27.1%
    Phenolic 25.45%
    Animal 23.43%
    Spicy 22.04%
    Balsamic 21.18%

     

    Flavor
    Bitter 98.54%
    Very strong 16.77%
    Indole 16.47%
    Cedarleaf 16.44%
    Lovage 16.04%
    Nitrile 15.89%
    Cereal 15.81%
    Sweet-like 15.69%
    Rotten 15.48%
    Moth ball 15.42%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    5.46 (weak acid)

    Molecular weight
    275.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    556°C

    Flash point

    • 249.43 ˚C est.

  • Synonyms

    • Liriodenine
    • 475-75-2
    • Micheline B
    • Oxoushinsunine
    • Spermatheridine
    • Spermatheridin
    • Oxoushinsunin
    • Ushinsunine, oxo-
    • 8H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one
    • Noraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)-
    • E134R7X4O9
    • 8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-one
    • NSC-93681
    • NSC-215254
    • CHEBI:70649
    • DTXSID40197165
    • 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one
    • 8H-(1,3)benzodioxolo(6,5,4-de)benzo(g)quinolin-8-one
    • RefChem:153652
    • DTXCID50119656
    • NSC93681
    • NSC215254
    • Spermatheridine; VLT 045
    • CHEMBL37736
    • 3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one
    • 8H-Benzo[g]-1,5,4-de]quinolin-8-one
    • CCRIS 1549
    • NSC 93681
    • NSC 215254
    • BRN 0273167
    • liriodemine
    • Hiriodenine
    • Noraporphin-7-one,5,6,6a-tetradehydro-1,2-(methylenedioxy)-
    • 4-27-00-06585 (Beilstein Handbook Reference)
    • SCHEMBL165803
    • UNII-E134R7X4O9
    • MEGxp0_001521
    • orb1684452
    • SCHEMBL29381388
    • AAA47575
    • HY-N3376
    • BDBM50202301
    • AKOS028108460
    • FS-9911
    • DA-54951
    • NCI60_001798
    • NCI60_042088
    • CS-0024041
    • C09567
    • AK-693/21087012
    • Q5976903
    • 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one #
    • 2H,8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one
    • 3,5-dioxa-11-azapentacyclo[10.7.1.0^{2,6.0^{8,20.0^{14,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one
    • 475-75-2

  • Applications

    Liriodenine (CAS 475-75-2) is an aporphine alkaloid isolated from Liriodendron and related plant sources, and is primarily of interest in natural products chemistry and synthetic chemistry. It serves as a building block and scaffold for the synthesis of aporphine alkaloid derivatives. In biomedical research, liriodenine has been evaluated for in vitro biological activities, including antimicrobial and cytotoxic effects in laboratory systems. In analytical chemistry, it can be used as a reference material or screening target for alkaloid profiling in plant extracts (LC-MS/GC-MS). It also provides an educational example for alkaloid isolation and structure elucidation in natural product chemistry.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.28
    methanol 0.25
    isopropanol 0.2
    water 0.0
    ethyl acetate 1.45
    n-propanol 0.24
    acetone 2.3
    n-butanol 0.27
    acetonitrile 1.05
    DMF 6.93
    toluene 1.79
    isobutanol 0.23
    1,4-dioxane 2.85
    methyl acetate 1.54
    THF 4.97
    2-butanone 2.0
    n-pentanol 0.41
    sec-butanol 0.16
    n-hexane 0.01
    ethylene glycol 0.43
    NMP 10.72
    cyclohexane 0.06
    DMSO 5.71
    n-butyl acetate 3.38
    n-octanol 1.88
    chloroform 2.03
    n-propyl acetate 2.36
    acetic acid 1.8
    dichloromethane 3.68
    cyclohexanone 6.93
    propylene glycol 0.15
    isopropyl acetate 1.98
    DMAc 10.86
    2-ethoxyethanol 1.8
    isopentanol 0.54
    n-heptane 0.08
    ethyl formate 2.03
    1,2-dichloroethane 3.54
    n-hexanol 1.03
    2-methoxyethanol 2.54
    isobutyl acetate 2.52
    tetrachloromethane 0.38
    n-pentyl acetate 5.55
    transcutol 8.71
    n-heptanol 2.07
    ethylbenzene 1.4
    MIBK 2.39
    2-propoxyethanol 4.31
    tert-butanol 0.42
    MTBE 0.3
    2-butoxyethanol 5.62
    propionic acid 0.83
    o-xylene 1.77
    formic acid 1.29
    diethyl ether 0.38
    m-xylene 1.68
    p-xylene 2.17
    chlorobenzene 2.99
    dimethyl carbonate 3.17
    n-octane 0.09
    formamide 2.78
    cyclopentanone 7.69
    2-pentanone 1.85
    anisole 2.79
    cyclopentyl methyl ether 1.68
    gamma-butyrolactone 7.4
    1-methoxy-2-propanol 1.53
    pyridine 7.82
    3-pentanone 1.53
    furfural 15.12
    n-dodecane 0.2
    diethylene glycol 5.38
    diisopropyl ether 0.31
    tert-amyl alcohol 0.3
    acetylacetone 5.26
    n-hexadecane 0.25
    acetophenone 6.59
    methyl propionate 1.7
    isopentyl acetate 4.71
    trichloroethylene 7.95
    n-nonanol 2.31
    cyclohexanol 0.62
    benzyl alcohol 3.23
    2-ethylhexanol 1.55
    isooctanol 2.18
    dipropyl ether 1.02
    1,2-dichlorobenzene 4.44
    ethyl lactate 2.26
    propylene carbonate 4.76
    n-methylformamide 2.16
    2-pentanol 0.18
    n-pentane 0.02
    1-propoxy-2-propanol 2.89
    1-methoxy-2-propyl acetate 5.38
    2-(2-methoxypropoxy) propanol 6.74
    mesitylene 1.26
    ε-caprolactone 5.74
    p-cymene 2.5
    epichlorohydrin 8.43
    1,1,1-trichloroethane 1.79
    2-aminoethanol 0.42
    morpholine-4-carbaldehyde 11.22
    sulfolane 12.17
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.88
    n-hexyl acetate 5.46
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 7.33
    sec-butyl acetate 1.87
    tert-butyl acetate 2.56
    decalin 0.14
    glycerin 1.05
    diglyme 14.24
    acrylic acid 1.69
    isopropyl myristate 3.26
    n-butyric acid 1.37
    acetyl acetate 2.56
    di(2-ethylhexyl) phthalate 4.95
    ethyl propionate 2.07
    nitromethane 4.5
    1,2-diethoxyethane 3.44
    benzonitrile 6.76
    trioctyl phosphate 3.61
    1-bromopropane 0.71
    gamma-valerolactone 12.89
    n-decanol 1.85
    triethyl phosphate 3.68
    4-methyl-2-pentanol 0.43
    propionitrile 1.25
    vinylene carbonate 6.71
    1,1,2-trichlorotrifluoroethane 9.25
    DMS 6.0
    cumene 1.42
    2-octanol 1.38
    2-hexanone 2.78
    octyl acetate 3.83
    limonene 2.1
    1,2-dimethoxyethane 5.3
    ethyl orthosilicate 3.41
    tributyl phosphate 3.8
    diacetone alcohol 3.48
    N,N-dimethylaniline 3.06
    acrylonitrile 2.99
    aniline 2.09
    1,3-propanediol 0.84
    bromobenzene 3.19
    dibromomethane 1.74
    1,1,2,2-tetrachloroethane 5.02
    2-methyl-cyclohexyl acetate 4.98
    tetrabutyl urea 6.64
    diisobutyl methanol 1.33
    2-phenylethanol 5.69
    styrene 1.46
    dioctyl adipate 5.08
    dimethyl sulfate 5.95
    ethyl butyrate 2.98
    methyl lactate 2.24
    butyl lactate 4.76
    diethyl carbonate 3.15
    propanediol butyl ether 3.24
    triethyl orthoformate 3.31
    p-tert-butyltoluene 1.9
    methyl 4-tert-butylbenzoate 9.07
    morpholine 2.62
    tert-butylamine 0.21
    n-dodecanol 1.52
    dimethoxymethane 3.82
    ethylene carbonate 4.46
    cyrene 7.71
    2-ethoxyethyl acetate 7.38
    2-ethylhexyl acetate 4.05
    1,2,4-trichlorobenzene 5.54
    4-methylpyridine 5.46
    dibutyl ether 1.87
    2,6-dimethyl-4-heptanol 1.33
    DEF 3.65
    dimethyl isosorbide 13.12
    tetrachloroethylene 4.52
    eugenol 10.31
    triacetin 7.06
    span 80 4.64
    1,4-butanediol 0.48
    1,1-dichloroethane 1.05
    2-methyl-1-pentanol 0.73
    methyl formate 2.56
    2-methyl-1-butanol 0.33
    n-decane 0.26
    butyronitrile 1.17
    3,7-dimethyl-1-octanol 2.01
    1-chlorooctane 1.43
    1-chlorotetradecane 0.84
    n-nonane 0.16
    undecane 0.23
    tert-butylcyclohexane 0.11
    cyclooctane 0.04
    cyclopentanol 0.68
    tetrahydropyran 1.41
    tert-amyl methyl ether 0.39
    2,5,8-trioxanonane 12.38
    1-hexene 0.12
    2-isopropoxyethanol 1.68
    2,2,2-trifluoroethanol 1.65
    methyl butyrate 2.79

    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