(-)-Dehydrogriseofulvin

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  • Identifiers

    CAS number
    3573-90-8

    Molecular formula
    C17H15ClO6

    SMILES
    CC1=CC(=O)C=C([C@]12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 47.04%
    Sweet 46.37%
    Fruity 44.06%
    Burnt 33.83%
    Spicy 28.41%
    Vanilla 26.7%
    Powdery 24.02%
    Creamy 23.88%
    Roasted 23.78%
    Phenolic 23.62%

     

    Flavor
    Bitter 73.58%
    Parsley 21.17%
    Bland 20.35%
    Cedarleaf 20.29%
    Lovage 20.23%
    Ripe apricot 19.87%
    Odorless 19.71%
    Seedy 19.68%
    Sweet-like 19.68%
    Cotton candy 19.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    5.56 (weak acid)

    Molecular weight
    350.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    696°C

    Flash point

    • 172.89 ˚C est.

  • Synonyms

    • Dehydrogriseofulvin
    • 3573-90-8
    • 2S5ET7TN92
    • (2S)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohexa-2,5-diene]-1',3-dione
    • (-)-DEHYDROGRISEOFULVIN
    • Spiro(benzofuran-2(3H),1'-(2,5)cyclohexadiene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (S)-
    • (2S)-7-CHLORO-3',4,6-TRIMETHOXY-5'-METHYLSPIRO(1-BENZOFURAN-2,4'-CYCLOHEXA-2,5-DIENE)-1',3-DIONE
    • Spiro[benzofuran-2(3H),1'-[2,5]cyclohexadiene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (S)-
    • RefChem:131514
    • Amudene
    • (-)-Dehydro Griseofulvin
    • Dehydro Griseofulvin
    • Griseofulvin, dehydro-
    • UNII-2S5ET7TN92
    • (?)-dehydro Griseofulvin
    • C17H15ClO6
    • CHEMBL4127442
    • CHEBI:81999
    • DTXSID00957141
    • ISLYVROQSJYFAZ-KRWDZBQOSA-N
    • MFCD24386705
    • HY-W741556
    • GRISEOFULVIN IMPURITY C [EP IMPURITY]
    • C18838
    • Q27155679
    • (1'S)-7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYL-3H-SPIRO(1-BENZOFURAN-2,1'-CYCLOHEXA(2,5)DIENE)-3,4'-DIONE
    • (1'S)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[[1]benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione
    • (2S)-7-chloro-3',4,6-trimethoxy-5'-methyl-spiro[benzofuran-2,4'-cyclohexa-2,5-diene]-1',3-dione
    • (S)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione
    • 7-Chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione
    • SPIRO(BENZOFURAN-2(3H),1'-(2,5)CYCLOHEXADIENE)-3,4'-DIONE, 7-CHLORO-2',4,6-TRIMETHOXY-6'-METHYL-, (1'S)-
    • Spiro[benzofuran-2(3H),1'-[2,5]cyclohexadiene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-
    • 3573-90-8

  • Applications

    (-)-Dehydrogriseofulvin is primarily used as an intermediate in pharmaceutical synthesis and as a chiral building block for asymmetric synthesis; in medicinal chemistry research, it is evaluated as a scaffold for developing novel antifungal agents and related polyketide derivatives; it may be employed as a specialty intermediate in complex industrial synthesis workflows and as a research reagent for stereochemical investigations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.13
    methanol 1.43
    isopropanol 1.22
    water 0.0
    ethyl acetate 24.98
    n-propanol 1.56
    acetone 22.56
    n-butanol 2.07
    acetonitrile 18.8
    DMF 24.27
    toluene 10.95
    isobutanol 1.82
    1,4-dioxane 31.77
    methyl acetate 26.73
    THF 60.56
    2-butanone 22.28
    n-pentanol 2.32
    sec-butanol 1.86
    n-hexane 0.29
    ethylene glycol 0.97
    NMP 106.28
    cyclohexane 1.0
    DMSO 45.56
    n-butyl acetate 20.05
    n-octanol 2.87
    chloroform 73.27
    n-propyl acetate 17.45
    acetic acid 12.85
    dichloromethane 67.87
    cyclohexanone 50.7
    propylene glycol 0.9
    isopropyl acetate 17.36
    DMAc 67.19
    2-ethoxyethanol 8.95
    isopentanol 3.53
    n-heptane 0.4
    ethyl formate 13.47
    1,2-dichloroethane 46.87
    n-hexanol 3.87
    2-methoxyethanol 12.17
    isobutyl acetate 14.33
    tetrachloromethane 7.76
    n-pentyl acetate 12.4
    transcutol 21.22
    n-heptanol 3.52
    ethylbenzene 7.35
    MIBK 14.67
    2-propoxyethanol 17.81
    tert-butanol 3.24
    MTBE 5.76
    2-butoxyethanol 11.63
    propionic acid 7.53
    o-xylene 8.83
    formic acid 4.62
    diethyl ether 6.4
    m-xylene 7.41
    p-xylene 10.45
    chlorobenzene 27.2
    dimethyl carbonate 22.42
    n-octane 0.24
    formamide 8.77
    cyclopentanone 62.43
    2-pentanone 17.83
    anisole 18.96
    cyclopentyl methyl ether 20.76
    gamma-butyrolactone 78.05
    1-methoxy-2-propanol 9.34
    pyridine 40.48
    3-pentanone 18.76
    furfural 70.9
    n-dodecane 0.37
    diethylene glycol 15.75
    diisopropyl ether 3.07
    tert-amyl alcohol 3.94
    acetylacetone 43.05
    n-hexadecane 0.47
    acetophenone 28.35
    methyl propionate 22.45
    isopentyl acetate 21.92
    trichloroethylene 101.63
    n-nonanol 3.53
    cyclohexanol 7.34
    benzyl alcohol 14.11
    2-ethylhexanol 5.88
    isooctanol 3.85
    dipropyl ether 6.85
    1,2-dichlorobenzene 30.53
    ethyl lactate 12.77
    propylene carbonate 44.55
    n-methylformamide 10.12
    2-pentanol 1.84
    n-pentane 0.2
    1-propoxy-2-propanol 13.24
    1-methoxy-2-propyl acetate 30.71
    2-(2-methoxypropoxy) propanol 22.48
    mesitylene 4.63
    ε-caprolactone 46.88
    p-cymene 7.05
    epichlorohydrin 78.9
    1,1,1-trichloroethane 42.46
    2-aminoethanol 1.42
    morpholine-4-carbaldehyde 64.87
    sulfolane 100.2
    2,2,4-trimethylpentane 0.4
    2-methyltetrahydrofuran 31.98
    n-hexyl acetate 13.93
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 17.44
    sec-butyl acetate 14.51
    tert-butyl acetate 20.3
    decalin 1.26
    glycerin 4.33
    diglyme 36.45
    acrylic acid 11.25
    isopropyl myristate 9.03
    n-butyric acid 11.41
    acetyl acetate 31.41
    di(2-ethylhexyl) phthalate 13.95
    ethyl propionate 20.25
    nitromethane 48.57
    1,2-diethoxyethane 12.24
    benzonitrile 25.75
    trioctyl phosphate 8.76
    1-bromopropane 13.25
    gamma-valerolactone 75.83
    n-decanol 2.89
    triethyl phosphate 19.1
    4-methyl-2-pentanol 2.56
    propionitrile 11.52
    vinylene carbonate 41.76
    1,1,2-trichlorotrifluoroethane 65.25
    DMS 28.56
    cumene 5.41
    2-octanol 2.48
    2-hexanone 16.56
    octyl acetate 10.76
    limonene 8.56
    1,2-dimethoxyethane 25.2
    ethyl orthosilicate 15.79
    tributyl phosphate 11.3
    diacetone alcohol 20.65
    N,N-dimethylaniline 14.32
    acrylonitrile 20.69
    aniline 16.32
    1,3-propanediol 3.29
    bromobenzene 29.67
    dibromomethane 38.03
    1,1,2,2-tetrachloroethane 72.22
    2-methyl-cyclohexyl acetate 25.22
    tetrabutyl urea 16.99
    diisobutyl methanol 4.09
    2-phenylethanol 18.82
    styrene 8.87
    dioctyl adipate 17.03
    dimethyl sulfate 44.48
    ethyl butyrate 19.63
    methyl lactate 14.99
    butyl lactate 10.84
    diethyl carbonate 18.66
    propanediol butyl ether 7.06
    triethyl orthoformate 17.51
    p-tert-butyltoluene 5.93
    methyl 4-tert-butylbenzoate 24.45
    morpholine 27.61
    tert-butylamine 1.75
    n-dodecanol 2.41
    dimethoxymethane 21.83
    ethylene carbonate 33.66
    cyrene 39.77
    2-ethoxyethyl acetate 20.7
    2-ethylhexyl acetate 20.22
    1,2,4-trichlorobenzene 40.1
    4-methylpyridine 36.21
    dibutyl ether 5.1
    2,6-dimethyl-4-heptanol 4.09
    DEF 26.45
    dimethyl isosorbide 51.9
    tetrachloroethylene 44.4
    eugenol 23.86
    triacetin 24.66
    span 80 14.45
    1,4-butanediol 1.76
    1,1-dichloroethane 29.09
    2-methyl-1-pentanol 4.38
    methyl formate 14.69
    2-methyl-1-butanol 3.18
    n-decane 0.51
    butyronitrile 9.53
    3,7-dimethyl-1-octanol 4.44
    1-chlorooctane 3.09
    1-chlorotetradecane 1.97
    n-nonane 0.36
    undecane 0.42
    tert-butylcyclohexane 0.78
    cyclooctane 0.39
    cyclopentanol 8.3
    tetrahydropyran 19.23
    tert-amyl methyl ether 7.26
    2,5,8-trioxanonane 33.31
    1-hexene 1.53
    2-isopropoxyethanol 9.0
    2,2,2-trifluoroethanol 11.46
    methyl butyrate 22.0

    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