Tetrahydroalstonine

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  • Identifiers

    CAS number
    6474-90-4

    Molecular formula
    C21H24N2O3

    SMILES
    C[C@H]1[C@@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 37.71%
    Sweet 26.79%
    Floral 26.38%
    Nutty 25.58%
    Animal 21.54%
    Green 20.79%
    Fresh 20.05%
    Roasted 19.51%
    Popcorn 18.9%
    Earthy 18.37%

     

    Flavor
    Bitter 93.63%
    Cedarleaf 20.09%
    Sweet-like 19.75%
    Cereal 19.2%
    Bland 19.06%
    Alkaline 18.86%
    Indole 18.83%
    Very strong 18.8%
    Lovage 18.65%
    Nitrile 18.42%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    7.19 (neutral)

    Molecular weight
    352.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    666°C

    Flash point

    • 242.49 ˚C est.

  • Synonyms

    • Tetrahydroalstonine
    • 6474-90-4
    • Alstonine, 3,4,5,6-tetrahydro-
    • 6U62R2Y5Y2
    • Alstonine, 3,4,5,6-tetrahydro-, (3alpha)-
    • CHEBI:9479
    • DTXSID201020629
    • NSC-72115
    • methyl (1S,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
    • tetrahydro-alstonine
    • methyl (1S,15S,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo(11.8.0.02,10.04,9.015,20)henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
    • RefChem:50885
    • DTXCID301478396
    • 229-331-0
    • Alstonine, tetrahydro-
    • EINECS 229-331-0
    • NSC 72115
    • BRN 0097270
    • (-)-Tetrahydroalstonine
    • methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate
    • Alstonine, 3,4,5,6-tetrahydro-, (3.alpha.)-
    • Methyl (19alpha,20alpha)-16,17-didehydro-19-methyloxayohimban-16-carboxylate
    • 4-27-00-07926 (Beilstein Handbook Reference)
    • SCHEMBL564502
    • UNII-6U62R2Y5Y2
    • CHEMBL498734
    • orb1684181
    • SCHEMBL29664999
    • Alstonine, 3,4,5,6-tetrahydro
    • HY-N1163
    • BDBM50407156
    • PDSP2_001642
    • AKOS037515397
    • CCG-208423
    • FT74459
    • NCGC00163632-01
    • NCGC00163632-02
    • DA-58436
    • MS-25467
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-alpha,20-alpha)-
    • Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19.alpha.,20.alpha.)-
    • CS-0016454
    • NS00082054
    • (3.ALPHA.)-3,4,5,6-TETRAHYDROALSTONINE
    • Q27108406
    • 815B4D52-2710-4B1D-B671-7CCBD7EC8A81
    • 16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid, methyl ester
    • methyl (19alpha,20alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
    • Methyl 19alpha-methyl-20alpha-16,17-didehydro-18-oxayohimban-16-carboxylate
    • 4H-INDOLO(2,3-A)PYRANO(3,4-G)QUINOLIZINE-1-CARBOXYLIC ACID, 4A,5,7,8,13,13B,14,14A-OCTAHYDRO-4-METHYL-, METHYL ESTER, (4S,4AS,13BS,14AS)-
    • 6474-90-4

  • Applications

    Tetrahydroalstonine (CAS 6474-90-4) is principally encountered in pharmaceutical and chemical synthesis contexts as an intermediate and building block for indole alkaloid derivatives; it is used in medicinal chemistry research to explore structure-activity relationships and receptor interactions related to serotonin biology. It also appears as a chiral building block in asymmetric synthesis workflows and, in academic and contract research settings, as a reference compound for natural product isolation and method development. Where applicable, its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.66
    methanol 3.0
    isopropanol 1.51
    water 0.01
    ethyl acetate 3.28
    n-propanol 1.9
    acetone 4.86
    n-butanol 2.79
    acetonitrile 1.14
    DMF 9.01
    toluene 1.93
    isobutanol 1.97
    1,4-dioxane 6.34
    methyl acetate 3.35
    THF 6.0
    2-butanone 6.39
    n-pentanol 2.15
    sec-butanol 1.05
    n-hexane 0.03
    ethylene glycol 1.02
    NMP 8.13
    cyclohexane 0.07
    DMSO 8.3
    n-butyl acetate 4.87
    n-octanol 0.91
    chloroform 15.93
    n-propyl acetate 4.23
    acetic acid 8.49
    dichloromethane 11.5
    cyclohexanone 13.55
    propylene glycol 0.55
    isopropyl acetate 3.34
    DMAc 22.22
    2-ethoxyethanol 9.98
    isopentanol 3.82
    n-heptane 0.04
    ethyl formate 4.09
    1,2-dichloroethane 5.89
    n-hexanol 2.01
    2-methoxyethanol 12.13
    isobutyl acetate 4.41
    tetrachloromethane 1.71
    n-pentyl acetate 5.95
    transcutol 27.33
    n-heptanol 2.07
    ethylbenzene 0.82
    MIBK 4.71
    2-propoxyethanol 13.63
    tert-butanol 1.47
    MTBE 0.83
    2-butoxyethanol 12.42
    propionic acid 2.75
    o-xylene 1.28
    formic acid 6.14
    diethyl ether 1.05
    m-xylene 1.47
    p-xylene 1.4
    chlorobenzene 3.5
    dimethyl carbonate 3.68
    n-octane 0.04
    formamide 7.67
    cyclopentanone 9.46
    2-pentanone 5.4
    anisole 2.13
    cyclopentyl methyl ether 2.25
    gamma-butyrolactone 9.06
    1-methoxy-2-propanol 7.39
    pyridine 8.56
    3-pentanone 4.11
    furfural 17.65
    n-dodecane 0.04
    diethylene glycol 14.08
    diisopropyl ether 0.46
    tert-amyl alcohol 1.24
    acetylacetone 7.77
    n-hexadecane 0.05
    acetophenone 5.54
    methyl propionate 3.44
    isopentyl acetate 6.53
    trichloroethylene 19.33
    n-nonanol 1.26
    cyclohexanol 2.1
    benzyl alcohol 5.26
    2-ethylhexanol 1.48
    isooctanol 2.19
    dipropyl ether 0.85
    1,2-dichlorobenzene 4.0
    ethyl lactate 3.99
    propylene carbonate 6.52
    n-methylformamide 4.74
    2-pentanol 1.14
    n-pentane 0.04
    1-propoxy-2-propanol 6.67
    1-methoxy-2-propyl acetate 8.54
    2-(2-methoxypropoxy) propanol 10.16
    mesitylene 0.83
    ε-caprolactone 10.12
    p-cymene 1.02
    epichlorohydrin 14.47
    1,1,1-trichloroethane 4.65
    2-aminoethanol 1.56
    morpholine-4-carbaldehyde 16.27
    sulfolane 12.03
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 2.67
    n-hexyl acetate 4.34
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 13.56
    sec-butyl acetate 3.12
    tert-butyl acetate 3.39
    decalin 0.08
    glycerin 3.17
    diglyme 23.09
    acrylic acid 4.1
    isopropyl myristate 1.81
    n-butyric acid 6.73
    acetyl acetate 3.96
    di(2-ethylhexyl) phthalate 4.99
    ethyl propionate 3.04
    nitromethane 12.09
    1,2-diethoxyethane 5.23
    benzonitrile 5.74
    trioctyl phosphate 2.61
    1-bromopropane 1.77
    gamma-valerolactone 26.39
    n-decanol 0.91
    triethyl phosphate 3.84
    4-methyl-2-pentanol 1.38
    propionitrile 2.21
    vinylene carbonate 9.25
    1,1,2-trichlorotrifluoroethane 21.72
    DMS 5.69
    cumene 0.77
    2-octanol 0.98
    2-hexanone 4.57
    octyl acetate 2.56
    limonene 1.0
    1,2-dimethoxyethane 11.08
    ethyl orthosilicate 3.39
    tributyl phosphate 3.05
    diacetone alcohol 6.49
    N,N-dimethylaniline 1.85
    acrylonitrile 3.81
    aniline 3.77
    1,3-propanediol 5.53
    bromobenzene 2.86
    dibromomethane 5.57
    1,1,2,2-tetrachloroethane 12.41
    2-methyl-cyclohexyl acetate 4.81
    tetrabutyl urea 4.43
    diisobutyl methanol 1.04
    2-phenylethanol 6.58
    styrene 0.88
    dioctyl adipate 4.04
    dimethyl sulfate 6.68
    ethyl butyrate 3.52
    methyl lactate 4.22
    butyl lactate 7.03
    diethyl carbonate 3.28
    propanediol butyl ether 5.99
    triethyl orthoformate 3.75
    p-tert-butyltoluene 0.86
    methyl 4-tert-butylbenzoate 8.04
    morpholine 6.54
    tert-butylamine 0.5
    n-dodecanol 0.66
    dimethoxymethane 8.43
    ethylene carbonate 7.86
    cyrene 11.6
    2-ethoxyethyl acetate 12.99
    2-ethylhexyl acetate 4.75
    1,2,4-trichlorobenzene 6.12
    4-methylpyridine 7.23
    dibutyl ether 0.94
    2,6-dimethyl-4-heptanol 1.04
    DEF 5.88
    dimethyl isosorbide 14.73
    tetrachloroethylene 10.65
    eugenol 11.21
    triacetin 7.87
    span 80 6.71
    1,4-butanediol 2.39
    1,1-dichloroethane 4.11
    2-methyl-1-pentanol 2.99
    methyl formate 4.79
    2-methyl-1-butanol 2.58
    n-decane 0.07
    butyronitrile 2.58
    3,7-dimethyl-1-octanol 1.34
    1-chlorooctane 0.43
    1-chlorotetradecane 0.21
    n-nonane 0.05
    undecane 0.05
    tert-butylcyclohexane 0.07
    cyclooctane 0.04
    cyclopentanol 1.62
    tetrahydropyran 2.89
    tert-amyl methyl ether 0.89
    2,5,8-trioxanonane 16.63
    1-hexene 0.19
    2-isopropoxyethanol 7.31
    2,2,2-trifluoroethanol 5.57
    methyl butyrate 4.61

    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