6-O-Demethylnigerone

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  • Identifiers

    CAS number
    76045-68-6

    Molecular formula
    C31H24O10

    SMILES
    CC1=CC(=O)C2=C(C3=C(C=C(C=C3O)OC)C(=C2O1)C4=C5C(=C(C6=C4C=C(C=C6OC)OC)O)C(=O)C=C(O5)C)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 48.82%
    Fruity 33.87%
    Odorless 32.7%
    Burnt 31.18%
    Woody 29.76%
    Spicy 29.1%
    Sweet 28.9%
    Dry 26.25%
    Smoky 26.0%
    Powdery 24.81%

     

    Flavor
    Bitter 92.84%
    Odorless 23.58%
    Bland 22.58%
    Parsley 20.21%
    Cedarleaf 19.92%
    Sweet-like 19.62%
    Lovage 19.05%
    Indole 18.88%
    Very strong 18.81%
    Eugenol 18.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.0

    pKa est.
    9.0 (weak base)

    Molecular weight
    556.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3112°C

    Melting point expt.

    • 330 °C

    Flash point

    • 322.75 ˚C est.

  • Synonyms

    • 6'-O-demethylnigerone
    • 6-O-Demethylnigerone
    • CHEBI:205520
    • DTXSID001112903
    • (10S)-5,5a(2),6-Trihydroxy-6a(2),8,8a(2)-trimethoxy-2,2a(2)-dimethyl[10,10a(2)-bi-4H-naphtho[2,3-b]pyran]-4,4a(2)-dione
    • 5,5',6-Trihydroxy-6',8,8'-trimethoxy-2,2'-dimethyl-4H,4'H-[10,10'-binaphtho[2,3-b]pyran]-4,4'-dione
    • 5,6-dihydroxy-10-(5-hydroxy-6,8-dimethoxy-2-methyl-4-oxobenzo[g]chromen-10-yl)-8-methoxy-2-methylbenzo[g]chromen-4-one
    • 76045-68-6
    • 76045-68-6

  • Applications

    6-O-Demethylnigerone (CAS 76045-68-6) is primarily used as an intermediate in organic synthesis and as a building block for natural-product type workflows, supporting pharmaceutical and agrochemical research and SAR studies of Nigerone-class compounds; it is commonly employed as an analytical reference standard to aid method development and compound identification in research laboratories; additionally, it is considered a research reagent for studies of Nigerone-family chemistry and may be evaluated as a chromophore or redox-active component in dye/pigment research or electronic-material development, with potential explorations in polymer or coating formulations under appropriate regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.67
    methanol 4.96
    isopropanol 1.7
    water 0.02
    ethyl acetate 3.38
    n-propanol 3.0
    acetone 4.96
    n-butanol 1.8
    acetonitrile 2.3
    DMF 53.96
    toluene 0.25
    isobutanol 1.66
    1,4-dioxane 5.55
    methyl acetate 6.65
    THF 13.24
    2-butanone 7.06
    n-pentanol 1.13
    sec-butanol 1.91
    n-hexane 0.03
    ethylene glycol 4.57
    NMP 74.27
    cyclohexane 0.04
    DMSO 64.64
    n-butyl acetate 2.37
    n-octanol 0.38
    chloroform 6.94
    n-propyl acetate 2.65
    acetic acid 20.59
    dichloromethane 7.1
    cyclohexanone 8.35
    propylene glycol 5.45
    isopropyl acetate 1.55
    DMAc 68.25
    2-ethoxyethanol 8.03
    isopentanol 1.05
    n-heptane 0.03
    ethyl formate 4.74
    1,2-dichloroethane 4.01
    n-hexanol 0.6
    2-methoxyethanol 20.44
    isobutyl acetate 1.14
    tetrachloromethane 0.49
    n-pentyl acetate 1.61
    transcutol 8.28
    n-heptanol 0.55
    ethylbenzene 0.14
    MIBK 1.2
    2-propoxyethanol 8.58
    tert-butanol 1.1
    MTBE 0.59
    2-butoxyethanol 4.21
    propionic acid 10.35
    o-xylene 0.21
    formic acid 14.64
    diethyl ether 0.99
    m-xylene 0.13
    p-xylene 0.19
    chlorobenzene 0.6
    dimethyl carbonate 8.29
    n-octane 0.01
    formamide 19.03
    cyclopentanone 16.51
    2-pentanone 3.24
    anisole 0.88
    cyclopentyl methyl ether 1.88
    gamma-butyrolactone 28.67
    1-methoxy-2-propanol 12.67
    pyridine 5.24
    3-pentanone 3.15
    furfural 20.34
    n-dodecane 0.01
    diethylene glycol 10.65
    diisopropyl ether 0.13
    tert-amyl alcohol 1.37
    acetylacetone 5.07
    n-hexadecane 0.01
    acetophenone 2.25
    methyl propionate 7.33
    isopentyl acetate 1.63
    trichloroethylene 12.01
    n-nonanol 0.44
    cyclohexanol 1.38
    benzyl alcohol 1.9
    2-ethylhexanol 0.41
    isooctanol 0.45
    dipropyl ether 0.88
    1,2-dichlorobenzene 0.78
    ethyl lactate 4.3
    propylene carbonate 9.4
    n-methylformamide 22.79
    2-pentanol 0.79
    n-pentane 0.03
    1-propoxy-2-propanol 5.44
    1-methoxy-2-propyl acetate 5.39
    2-(2-methoxypropoxy) propanol 4.67
    mesitylene 0.07
    ε-caprolactone 9.84
    p-cymene 0.14
    epichlorohydrin 21.42
    1,1,1-trichloroethane 1.68
    2-aminoethanol 5.96
    morpholine-4-carbaldehyde 41.75
    sulfolane 55.22
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 3.99
    n-hexyl acetate 1.31
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 4.65
    sec-butyl acetate 1.21
    tert-butyl acetate 1.21
    decalin 0.02
    glycerin 16.41
    diglyme 9.71
    acrylic acid 15.79
    isopropyl myristate 0.44
    n-butyric acid 6.94
    acetyl acetate 2.78
    di(2-ethylhexyl) phthalate 1.14
    ethyl propionate 2.57
    nitromethane 37.72
    1,2-diethoxyethane 1.94
    benzonitrile 1.35
    trioctyl phosphate 0.78
    1-bromopropane 1.13
    gamma-valerolactone 39.11
    n-decanol 0.31
    triethyl phosphate 1.76
    4-methyl-2-pentanol 0.31
    propionitrile 2.47
    vinylene carbonate 10.45
    1,1,2-trichlorotrifluoroethane 43.37
    DMS 3.54
    cumene 0.1
    2-octanol 0.29
    2-hexanone 2.35
    octyl acetate 0.82
    limonene 0.22
    1,2-dimethoxyethane 10.23
    ethyl orthosilicate 1.26
    tributyl phosphate 0.93
    diacetone alcohol 4.17
    N,N-dimethylaniline 0.86
    acrylonitrile 5.29
    aniline 1.55
    1,3-propanediol 7.03
    bromobenzene 0.42
    dibromomethane 2.78
    1,1,2,2-tetrachloroethane 9.44
    2-methyl-cyclohexyl acetate 1.78
    tetrabutyl urea 1.66
    diisobutyl methanol 0.21
    2-phenylethanol 1.41
    styrene 0.18
    dioctyl adipate 1.43
    dimethyl sulfate 25.57
    ethyl butyrate 2.07
    methyl lactate 13.33
    butyl lactate 3.15
    diethyl carbonate 1.71
    propanediol butyl ether 3.37
    triethyl orthoformate 1.87
    p-tert-butyltoluene 0.12
    methyl 4-tert-butylbenzoate 2.64
    morpholine 11.33
    tert-butylamine 0.33
    n-dodecanol 0.21
    dimethoxymethane 14.65
    ethylene carbonate 6.99
    cyrene 10.26
    2-ethoxyethyl acetate 3.87
    2-ethylhexyl acetate 1.27
    1,2,4-trichlorobenzene 1.53
    4-methylpyridine 3.12
    dibutyl ether 0.43
    2,6-dimethyl-4-heptanol 0.21
    DEF 9.39
    dimethyl isosorbide 8.88
    tetrachloroethylene 4.8
    eugenol 3.35
    triacetin 3.95
    span 80 3.51
    1,4-butanediol 2.5
    1,1-dichloroethane 2.03
    2-methyl-1-pentanol 0.86
    methyl formate 16.41
    2-methyl-1-butanol 1.51
    n-decane 0.02
    butyronitrile 1.59
    3,7-dimethyl-1-octanol 0.33
    1-chlorooctane 0.13
    1-chlorotetradecane 0.05
    n-nonane 0.02
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 2.87
    tetrahydropyran 2.39
    tert-amyl methyl ether 0.75
    2,5,8-trioxanonane 6.88
    1-hexene 0.14
    2-isopropoxyethanol 3.9
    2,2,2-trifluoroethanol 12.21
    methyl butyrate 3.92

    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