(+)-Dicentrine

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  • Identifiers

    CAS number
    517-66-8

    Molecular formula
    C20H21NO4

    SMILES
    CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC(=C(C=C54)OC)OC)OCO3

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 32.37%
    Phenolic 31.78%
    Sweet 30.54%
    Spicy 30.38%
    Odorless 29.41%
    Animal 28.43%
    Powdery 27.93%
    Musk 26.24%
    Smoky 22.98%
    Floral 22.89%

     

    Flavor
    Bitter 95.98%
    Bland 22.71%
    Cedarleaf 19.21%
    Sweet-like 19.14%
    Parsley 18.52%
    Cereal 17.57%
    Indole 17.52%
    Very strong 17.51%
    Eugenol 17.11%
    Lovage 17.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    6.54 (neutral)

    Molecular weight
    339.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    626°C

    Flash point

    • 215.58 ˚C est.

  • Synonyms

    • Dicentrine
    • 517-66-8
    • d-Dicentrine
    • Eximine
    • (+)-dicentrine
    • O,N-Dimethyllitseferine
    • J2ZGT5M0N7
    • NSC-406035
    • DTXSID10199651
    • (12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
    • (12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo(10.7.1.02,6.08,20.014,19)icosa-1(20),2(6),7,14,16,18-hexaene
    • RefChem:132995
    • DTXCID70122142
    • 5H-1,3-Benzodioxolo(6,5,4-de)benzo(g)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (7aS)-
    • Dicentrin
    • Dicentrine-(+)
    • CHEMBL464748
    • NSC406035
    • 9,10-Dimethoxy-1,2-(methylenedioxy)-6a.alpha.-aporphine
    • 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
    • 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)- (9CI)
    • CCRIS 3806
    • 9,10-Dimethoxy-1,2-(methylenedioxy)aporphine
    • UNII-J2ZGT5M0N7
    • NSC 406035
    • BRN 0095476
    • 1,2-Methylenedioxy-9,10-dimethoxyaporphine
    • 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
    • DICENTRINE [MI]
    • (R)-(-)-Dicentrine; L-Dicentrine; NSC 251699
    • DICENTRINE, (+)-
    • 4-27-00-06486 (Beilstein Handbook Reference)
    • 9,2-(methylenedioxy)aporphine
    • orb1684647
    • SCHEMBL6369440
    • DICENTRINE D-FORM [MI]
    • SCHEMBL30475130
    • CHEBI:81079
    • 6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
    • YJWBWQWUHVXPNC-AWEZNQCLSA-N
    • 6a-alpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
    • HY-N6969
    • BDBM50306885
    • MFCD00210492
    • AKOS037514612
    • DA-72736
    • MS-25168
    • CS-0026026
    • NS00094624
    • C17426
    • Q15410930
    • 6a.alpha.-Aporphine,10-dimethoxy-1,2-(methylenedioxy)-
    • 5H-Benzo[g]-1,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
    • (7aS)-10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline
    • 10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-, (S)-
    • 5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE, 6,7,7A,8-TETRAHYDRO-10,11-DIMETHOXY-7-METHYL-, (7AS)-
    • 517-66-8

  • Applications

    (+)-Dicentrine, CAS number: 517-66-8, is an aporphine alkaloid primarily regarded as a synthetic intermediate and structural scaffold for aporphine-type alkaloids in pharmaceutical research; it is commonly used as a chiral building block in asymmetric synthesis; it also serves as a basis for structure–activity studies in early-stage drug development; in analytical chemistry, it is used as a reference standard for alkaloid profiling and quantification in natural product extracts; it is employed as a research reagent in natural product chemistry and in synthetic chemistry workflows; use is subject to local regulations and formulation/development constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.9
    methanol 6.59
    isopropanol 4.24
    water 0.25
    ethyl acetate 20.44
    n-propanol 5.35
    acetone 15.64
    n-butanol 6.24
    acetonitrile 11.78
    DMF 34.38
    toluene 2.89
    isobutanol 5.34
    1,4-dioxane 17.46
    methyl acetate 18.16
    THF 16.12
    2-butanone 15.0
    n-pentanol 5.82
    sec-butanol 3.25
    n-hexane 0.19
    ethylene glycol 7.31
    NMP 30.65
    cyclohexane 0.57
    DMSO 39.66
    n-butyl acetate 22.59
    n-octanol 4.17
    chloroform 86.05
    n-propyl acetate 21.91
    acetic acid 43.25
    dichloromethane 75.43
    cyclohexanone 28.55
    propylene glycol 2.4
    isopropyl acetate 16.32
    DMAc 51.43
    2-ethoxyethanol 27.41
    isopentanol 9.35
    n-heptane 0.35
    ethyl formate 24.64
    1,2-dichloroethane 39.15
    n-hexanol 8.12
    2-methoxyethanol 32.7
    isobutyl acetate 17.42
    tetrachloromethane 14.65
    n-pentyl acetate 18.96
    transcutol 53.34
    n-heptanol 7.4
    ethylbenzene 2.68
    MIBK 13.9
    2-propoxyethanol 36.69
    tert-butanol 6.12
    MTBE 3.8
    2-butoxyethanol 29.18
    propionic acid 15.88
    o-xylene 3.74
    formic acid 29.73
    diethyl ether 5.38
    m-xylene 3.55
    p-xylene 4.39
    chlorobenzene 11.4
    dimethyl carbonate 23.39
    n-octane 0.29
    formamide 38.41
    cyclopentanone 24.47
    2-pentanone 13.5
    anisole 8.08
    cyclopentyl methyl ether 7.44
    gamma-butyrolactone 40.1
    1-methoxy-2-propanol 19.12
    pyridine 16.74
    3-pentanone 11.75
    furfural 55.64
    n-dodecane 0.35
    diethylene glycol 45.72
    diisopropyl ether 2.7
    tert-amyl alcohol 4.95
    acetylacetone 24.95
    n-hexadecane 0.41
    acetophenone 18.53
    methyl propionate 18.44
    isopentyl acetate 22.36
    trichloroethylene 86.9
    n-nonanol 5.27
    cyclohexanol 7.2
    benzyl alcohol 14.27
    2-ethylhexanol 7.54
    isooctanol 7.66
    dipropyl ether 5.56
    1,2-dichlorobenzene 20.1
    ethyl lactate 19.43
    propylene carbonate 34.73
    n-methylformamide 23.82
    2-pentanol 3.72
    n-pentane 0.26
    1-propoxy-2-propanol 20.83
    1-methoxy-2-propyl acetate 32.72
    2-(2-methoxypropoxy) propanol 26.19
    mesitylene 2.89
    ε-caprolactone 31.98
    p-cymene 5.46
    epichlorohydrin 47.51
    1,1,1-trichloroethane 32.42
    2-aminoethanol 6.75
    morpholine-4-carbaldehyde 52.97
    sulfolane 48.74
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 9.29
    n-hexyl acetate 14.84
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 29.89
    sec-butyl acetate 14.64
    tert-butyl acetate 15.93
    decalin 0.59
    glycerin 14.28
    diglyme 56.68
    acrylic acid 24.03
    isopropyl myristate 7.78
    n-butyric acid 25.36
    acetyl acetate 27.38
    di(2-ethylhexyl) phthalate 14.14
    ethyl propionate 17.21
    nitromethane 69.8
    1,2-diethoxyethane 17.53
    benzonitrile 19.79
    trioctyl phosphate 9.59
    1-bromopropane 9.39
    gamma-valerolactone 57.0
    n-decanol 4.12
    triethyl phosphate 17.97
    4-methyl-2-pentanol 4.95
    propionitrile 11.9
    vinylene carbonate 45.16
    1,1,2-trichlorotrifluoroethane 80.95
    DMS 25.78
    cumene 3.17
    2-octanol 3.89
    2-hexanone 14.07
    octyl acetate 10.07
    limonene 5.49
    1,2-dimethoxyethane 33.63
    ethyl orthosilicate 15.83
    tributyl phosphate 11.93
    diacetone alcohol 20.86
    N,N-dimethylaniline 7.76
    acrylonitrile 20.3
    aniline 8.17
    1,3-propanediol 14.23
    bromobenzene 10.66
    dibromomethane 35.86
    1,1,2,2-tetrachloroethane 60.05
    2-methyl-cyclohexyl acetate 19.8
    tetrabutyl urea 14.91
    diisobutyl methanol 5.09
    2-phenylethanol 19.38
    styrene 2.99
    dioctyl adipate 14.49
    dimethyl sulfate 40.85
    ethyl butyrate 18.9
    methyl lactate 20.04
    butyl lactate 20.15
    diethyl carbonate 20.33
    propanediol butyl ether 15.33
    triethyl orthoformate 17.55
    p-tert-butyltoluene 4.38
    methyl 4-tert-butylbenzoate 24.66
    morpholine 18.85
    tert-butylamine 2.82
    n-dodecanol 3.25
    dimethoxymethane 28.38
    ethylene carbonate 39.22
    cyrene 32.35
    2-ethoxyethyl acetate 34.24
    2-ethylhexyl acetate 19.02
    1,2,4-trichlorobenzene 23.82
    4-methylpyridine 14.2
    dibutyl ether 4.64
    2,6-dimethyl-4-heptanol 5.09
    DEF 23.78
    dimethyl isosorbide 41.53
    tetrachloroethylene 50.74
    eugenol 28.3
    triacetin 26.78
    span 80 17.18
    1,4-butanediol 7.72
    1,1-dichloroethane 21.98
    2-methyl-1-pentanol 8.23
    methyl formate 26.01
    2-methyl-1-butanol 6.66
    n-decane 0.51
    butyronitrile 11.24
    3,7-dimethyl-1-octanol 5.77
    1-chlorooctane 2.71
    1-chlorotetradecane 1.54
    n-nonane 0.37
    undecane 0.41
    tert-butylcyclohexane 0.45
    cyclooctane 0.26
    cyclopentanol 6.1
    tetrahydropyran 8.26
    tert-amyl methyl ether 3.98
    2,5,8-trioxanonane 43.39
    1-hexene 1.0
    2-isopropoxyethanol 20.72
    2,2,2-trifluoroethanol 42.58
    methyl butyrate 22.92

    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