Evodiamine

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  • Identifiers

    CAS number
    518-17-2

    Molecular formula
    C19H17N3O

    SMILES
    CN1[C@@H]2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 43.46%
    Animal 28.21%
    Bitter 24.92%
    Burnt 24.74%
    Grape 22.18%
    Musty 20.4%
    Neroli 19.87%
    Fruity 19.82%
    Sweet 19.44%
    Cooked 18.97%

     

    Flavor
    Bitter 96.88%
    Odorless 19.11%
    Very strong 18.67%
    Indole 18.38%
    Cedarleaf 18.05%
    Nitrile 17.83%
    Cereal 17.68%
    Sweet-like 17.52%
    Alkaline 17.15%
    Moth ball 16.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    6.62 (neutral)

    Molecular weight
    303.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    818°C

    Flash point

    • 264.1 ˚C est.

  • Synonyms

    • Evodiamine
    • d-Evodiamine
    • Evodiamine, (+)-
    • C01825BVNL
    • (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
    • (1S)-21-methyl-3,13,21-triazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-2(10),4,6,8,15,17,19-heptaen-14-one
    • RefChem:596968
    • 637-111-4
    • 518-17-2
    • (+)-Evodiamine
    • C19H17N3O
    • CHEBI:4948
    • CHEMBL463165
    • (S)-14-methyl-7,8,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(13H)-one
    • (S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
    • (13bS)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
    • UNII-C01825BVNL
    • Evodiamine CRS
    • S-(+)-evodiamine
    • Evodiamine (Standard)
    • EVODIAMINE [MI]
    • EVODIAMINE [WHO-DD]
    • MLS006011787
    • SCHEMBL682158
    • orb1304910
    • HY-N0114R
    • DTXSID10966123
    • GLXC-10981
    • BB_NC-01930
    • HY-N0114
    • MSK40309
    • BBL033833
    • BDBM50560847
    • STK801981
    • AKOS005622478
    • CS-6161
    • EBC-469130
    • FE09940
    • SMR001934404
    • VS-12304
    • C09187
    • 518E172
    • Q27894193
    • Evodiamine, European Pharmacopoeia (EP) Reference Standard
    • (+)-Evodiamine; D-Evodiamine; (S)-14-methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one
    • (1S)-21-METHYL-3,13,21-TRIAZAPENTACYCLO[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]HENICOSA-2(10),4,6,8,15,17,19-HEPTAEN-14-ONE
    • (1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7,15(20),16,18-heptaen-14-one
    • Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (13bS)-
    • Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (S)-
    • INDOLO(2',3':3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE, 8,13,13B,14-TETRAHYDRO-14-METHYL-, (13BS)-
    • 518-17-2

  • Applications

    Evodiamine is a natural alkaloid isolated from Evodia rutaecarpa and is primarily used in pharmaceutical research and medicinal chemistry as a scaffold for studying mechanism of action and structure-activity relationships of indoloquinazoline alkaloids. Real-world applications include: (1) laboratory-level pharmaceutical research and drug development; (2) investigation of bioactive constituents and their incorporation into traditional herbal medicine formulations; (3) chemical analysis and quality control of botanical samples using HPLC/LC-MS, serving as a reference standard for extract normalization; (4) lead-optimization and synthesis of derivatives to expand the compound library; (5) use as a tool compound in interdisciplinary pharmacology and natural product synthesis research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.51
    methanol 0.43
    isopropanol 0.43
    water 0.0
    ethyl acetate 0.76
    n-propanol 0.44
    acetone 1.22
    n-butanol 0.62
    acetonitrile 0.22
    DMF 4.45
    toluene 0.45
    isobutanol 0.45
    1,4-dioxane 1.76
    methyl acetate 0.79
    THF 2.73
    2-butanone 1.62
    n-pentanol 0.57
    sec-butanol 0.29
    n-hexane 0.01
    ethylene glycol 0.17
    NMP 4.15
    cyclohexane 0.01
    DMSO 2.46
    n-butyl acetate 2.95
    n-octanol 0.56
    chloroform 2.99
    n-propyl acetate 1.71
    acetic acid 1.49
    dichloromethane 2.52
    cyclohexanone 3.95
    propylene glycol 0.11
    isopropyl acetate 1.25
    DMAc 7.84
    2-ethoxyethanol 2.34
    isopentanol 1.04
    n-heptane 0.02
    ethyl formate 1.22
    1,2-dichloroethane 1.69
    n-hexanol 0.85
    2-methoxyethanol 2.7
    isobutyl acetate 2.18
    tetrachloromethane 0.36
    n-pentyl acetate 4.33
    transcutol 9.32
    n-heptanol 1.19
    ethylbenzene 0.39
    MIBK 2.2
    2-propoxyethanol 5.18
    tert-butanol 0.53
    MTBE 0.35
    2-butoxyethanol 6.01
    propionic acid 0.68
    o-xylene 0.46
    formic acid 1.02
    diethyl ether 0.26
    m-xylene 0.54
    p-xylene 0.68
    chlorobenzene 1.35
    dimethyl carbonate 1.68
    n-octane 0.02
    formamide 1.59
    cyclopentanone 3.8
    2-pentanone 1.62
    anisole 1.19
    cyclopentyl methyl ether 0.8
    gamma-butyrolactone 3.9
    1-methoxy-2-propanol 2.01
    pyridine 3.02
    3-pentanone 0.98
    furfural 9.54
    n-dodecane 0.04
    diethylene glycol 4.53
    diisopropyl ether 0.18
    tert-amyl alcohol 0.43
    acetylacetone 3.2
    n-hexadecane 0.05
    acetophenone 3.17
    methyl propionate 0.94
    isopentyl acetate 4.4
    trichloroethylene 5.92
    n-nonanol 0.83
    cyclohexanol 0.46
    benzyl alcohol 2.1
    2-ethylhexanol 0.93
    isooctanol 1.43
    dipropyl ether 0.49
    1,2-dichlorobenzene 2.16
    ethyl lactate 1.83
    propylene carbonate 3.16
    n-methylformamide 1.36
    2-pentanol 0.33
    n-pentane 0.01
    1-propoxy-2-propanol 3.3
    1-methoxy-2-propyl acetate 4.89
    2-(2-methoxypropoxy) propanol 5.98
    mesitylene 0.39
    ε-caprolactone 3.38
    p-cymene 0.79
    epichlorohydrin 5.6
    1,1,1-trichloroethane 1.37
    2-aminoethanol 0.33
    morpholine-4-carbaldehyde 8.09
    sulfolane 5.9
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 0.97
    n-hexyl acetate 2.99
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 6.53
    sec-butyl acetate 1.46
    tert-butyl acetate 1.93
    decalin 0.03
    glycerin 0.65
    diglyme 13.3
    acrylic acid 1.07
    isopropyl myristate 1.71
    n-butyric acid 1.61
    acetyl acetate 1.4
    di(2-ethylhexyl) phthalate 3.89
    ethyl propionate 1.32
    nitromethane 2.69
    1,2-diethoxyethane 3.08
    benzonitrile 2.61
    trioctyl phosphate 2.34
    1-bromopropane 0.48
    gamma-valerolactone 10.55
    n-decanol 0.66
    triethyl phosphate 2.82
    4-methyl-2-pentanol 0.55
    propionitrile 0.51
    vinylene carbonate 4.78
    1,1,2-trichlorotrifluoroethane 7.7
    DMS 3.93
    cumene 0.49
    2-octanol 0.68
    2-hexanone 2.02
    octyl acetate 2.0
    limonene 0.67
    1,2-dimethoxyethane 4.79
    ethyl orthosilicate 2.6
    tributyl phosphate 2.85
    diacetone alcohol 3.25
    N,N-dimethylaniline 1.23
    acrylonitrile 1.07
    aniline 1.03
    1,3-propanediol 0.98
    bromobenzene 1.21
    dibromomethane 1.13
    1,1,2,2-tetrachloroethane 3.59
    2-methyl-cyclohexyl acetate 3.41
    tetrabutyl urea 4.34
    diisobutyl methanol 0.86
    2-phenylethanol 3.54
    styrene 0.42
    dioctyl adipate 3.26
    dimethyl sulfate 3.67
    ethyl butyrate 2.08
    methyl lactate 1.59
    butyl lactate 4.64
    diethyl carbonate 2.15
    propanediol butyl ether 2.63
    triethyl orthoformate 2.65
    p-tert-butyltoluene 0.69
    methyl 4-tert-butylbenzoate 6.47
    morpholine 1.84
    tert-butylamine 0.22
    n-dodecanol 0.51
    dimethoxymethane 2.85
    ethylene carbonate 3.19
    cyrene 6.23
    2-ethoxyethyl acetate 7.65
    2-ethylhexyl acetate 3.41
    1,2,4-trichlorobenzene 2.93
    4-methylpyridine 2.62
    dibutyl ether 0.75
    2,6-dimethyl-4-heptanol 0.86
    DEF 2.23
    dimethyl isosorbide 10.55
    tetrachloroethylene 3.2
    eugenol 8.74
    triacetin 4.71
    span 80 4.04
    1,4-butanediol 0.48
    1,1-dichloroethane 0.9
    2-methyl-1-pentanol 0.97
    methyl formate 1.43
    2-methyl-1-butanol 0.67
    n-decane 0.06
    butyronitrile 0.73
    3,7-dimethyl-1-octanol 0.9
    1-chlorooctane 0.33
    1-chlorotetradecane 0.2
    n-nonane 0.03
    undecane 0.05
    tert-butylcyclohexane 0.04
    cyclooctane 0.01
    cyclopentanol 0.44
    tetrahydropyran 0.73
    tert-amyl methyl ether 0.4
    2,5,8-trioxanonane 10.22
    1-hexene 0.07
    2-isopropoxyethanol 2.14
    2,2,2-trifluoroethanol 1.28
    methyl butyrate 1.99

    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