Alpha-Naphthoflavone

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  • Identifiers

    CAS number
    604-59-1

    Molecular formula
    C19H12O2

    SMILES
    C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3

    Safety labels

  • Odor profile

    Fragrance
    Floral 57.27%
    Sweet 44.6%
    Phenolic 35.94%
    Fruity 35.52%
    Powdery 34.9%
    Neroli 33.64%
    Balsamic 32.59%
    Animal 32.21%
    Coumarinic 31.43%
    Bitter 28.3%

     

    Flavor
    Bitter 92.43%
    Very strong 21.1%
    Moth ball 21.07%
    Naphthelene 20.88%
    Indole 20.51%
    Tar 20.21%
    Animal 19.89%
    Tarry 19.83%
    Nitrile 19.68%
    Lovage 18.46%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.8

    pKa est.
    6.96 (neutral)

    Molecular weight
    272.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    538°C

    Flash point

    • 207.68 ˚C est.

  • Synonyms

    • alpha-Naphthoflavone
    • 7,8-Benzoflavone
    • 604-59-1
    • alpha-Naphthylflavone
    • 2-phenylbenzo[h]chromen-4-one
    • Benzo(h)flavone
    • 2-Phenyl-4H-naphtho(1,2-b)pyran-4-one
    • 7,8-BF
    • 2-Phenylbenzo(h)chromen-4-one
    • FML65D8PY5
    • DTXSID2040650
    • NSC-407011
    • benzo[h]flavone
    • CCRIS-3607
    • CHEBI:76995
    • 2-Phenyl-4H-naphtho[1,2-b]pyran-4-one
    • RefChem:111352
    • DTXCID0020650
    • 210-071-1
    • 2-Phenyl-4H-benzo[h]chromen-4-one
    • 4H-Naphtho[1,2-b]pyran-4-one, 2-phenyl-
    • .alpha.-Naphthoflavone
    • 2-Phenyl-benzo[h]chromen-4-one
    • MFCD00004985
    • .alpha.-Naphthylflavone
    • A-NAPHTHYLFLAVONE
    • 4H-NAPHTHO(1,2-b)PYRAN-4-ONE, 2-PHENYL-
    • MLS003171601
    • CHEMBL283196
    • BHF
    • 2-PHENYL-4H-BENZO(H)CHROMEN-4-ONE
    • CCRIS 3607
    • EINECS 210-071-1
    • NSC 407011
    • BRN 0210862
    • Naphthoflavon
    • a-naphthoflavone
    • alpha -Naphthoflavone
    • UNII-FML65D8PY5
    • Oprea1_054595
    • Oprea1_802803
    • 4H-Naphtho[1, 2-phenyl-
    • 5-17-10-00726 (Beilstein Handbook Reference)
    • BENZOFLAVONE, 7,8-
    • BIDD:ER0569
    • SCHEMBL121594
    • orb1304733
    • SCHEMBL29351090
    • HMS3740O15
    • TNP00080
    • BDBM50014323
    • NSC407011
    • 2-phenyl-4-benzo[h][1]benzopyranone
    • AKOS000505579
    • CCG-267182
    • CS-W014028
    • DB07453
    • EBC-459081
    • FB09432
    • PS-7270
    • 2-Phenyl-4H-benzo[h]chromen-4-one #
    • NCGC00017210-01
    • NCGC00017210-02
    • NCGC00142408-01
    • DA-60547
    • SMR000112233
    • ST055359
    • SY012881
    • HY-125833
    • B0056
    • NS00043017
    • S5158
    • 7,8-BENZOFLAVONE; ALPHA-NAPHTHOFLAVONE
    • EN300-122288
    • F16466
    • N-1500
    • A832737
    • AR-683/40897030
    • Q4734915
    • 604-59-1

  • Applications

    Alpha-Naphthoflavone is primarily used in academic and pharmaceutical-related research as a selective inhibitor of certain cytochrome P450 enzymes, notably CYP1A1/1A2, and as an antagonist/modulator of the aryl hydrocarbon receptor (AhR). It serves as a tool compound in in vitro enzyme assays and receptor signaling studies, including the ethoxyresorufin-O-deethylase (EROD) assay, to probe enzyme activity and AhR pathways. It also functions as an organic synthesis building block for flavonoid derivatives and related heterocycles, enabling structure–activity studies. In addition, it may be evaluated as a research reagent or analytical probe in chemical analysis. Applications in consumer products or therapies are not asserted; usage is typically restricted to laboratories and subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.72
    methanol 3.85
    isopropanol 2.44
    water 0.01
    ethyl acetate 18.55
    n-propanol 4.17
    acetone 20.0
    n-butanol 4.23
    acetonitrile 7.49
    DMF 82.06
    toluene 27.42
    isobutanol 3.48
    1,4-dioxane 52.34
    methyl acetate 26.61
    THF 87.78
    2-butanone 24.92
    n-pentanol 4.04
    sec-butanol 2.84
    n-hexane 0.44
    ethylene glycol 1.85
    NMP 70.12
    cyclohexane 0.88
    DMSO 37.27
    n-butyl acetate 19.99
    n-octanol 2.65
    chloroform 64.31
    n-propyl acetate 18.67
    acetic acid 15.06
    dichloromethane 108.02
    cyclohexanone 46.18
    propylene glycol 1.88
    isopropyl acetate 18.08
    DMAc 104.43
    2-ethoxyethanol 10.6
    isopentanol 5.5
    n-heptane 0.76
    ethyl formate 13.26
    1,2-dichloroethane 104.81
    n-hexanol 5.61
    2-methoxyethanol 18.9
    isobutyl acetate 16.59
    tetrachloromethane 2.75
    n-pentyl acetate 14.34
    transcutol 106.1
    n-heptanol 3.87
    ethylbenzene 14.85
    MIBK 18.63
    2-propoxyethanol 18.25
    tert-butanol 3.69
    MTBE 7.09
    2-butoxyethanol 12.34
    propionic acid 10.29
    o-xylene 14.64
    formic acid 4.83
    diethyl ether 10.76
    m-xylene 13.88
    p-xylene 15.57
    chlorobenzene 32.71
    dimethyl carbonate 29.95
    n-octane 0.53
    formamide 15.03
    cyclopentanone 68.9
    2-pentanone 17.58
    anisole 31.42
    cyclopentyl methyl ether 24.64
    gamma-butyrolactone 87.72
    1-methoxy-2-propanol 12.86
    pyridine 88.66
    3-pentanone 18.79
    furfural 90.08
    n-dodecane 0.59
    diethylene glycol 14.59
    diisopropyl ether 4.52
    tert-amyl alcohol 3.83
    acetylacetone 45.4
    n-hexadecane 0.71
    acetophenone 34.17
    methyl propionate 22.64
    isopentyl acetate 24.29
    trichloroethylene 192.47
    n-nonanol 3.51
    cyclohexanol 5.79
    benzyl alcohol 18.48
    2-ethylhexanol 6.23
    isooctanol 4.36
    dipropyl ether 11.57
    1,2-dichlorobenzene 38.71
    ethyl lactate 10.78
    propylene carbonate 42.27
    n-methylformamide 19.24
    2-pentanol 3.0
    n-pentane 0.33
    1-propoxy-2-propanol 12.27
    1-methoxy-2-propyl acetate 34.58
    2-(2-methoxypropoxy) propanol 23.34
    mesitylene 7.99
    ε-caprolactone 43.7
    p-cymene 9.04
    epichlorohydrin 146.85
    1,1,1-trichloroethane 25.6
    2-aminoethanol 3.68
    morpholine-4-carbaldehyde 77.28
    sulfolane 79.92
    2,2,4-trimethylpentane 0.63
    2-methyltetrahydrofuran 32.3
    n-hexyl acetate 14.87
    isooctane 0.48
    2-(2-butoxyethoxy)ethanol 24.85
    sec-butyl acetate 17.42
    tert-butyl acetate 22.45
    decalin 1.72
    glycerin 5.19
    diglyme 71.04
    acrylic acid 16.88
    isopropyl myristate 9.21
    n-butyric acid 13.28
    acetyl acetate 24.33
    di(2-ethylhexyl) phthalate 11.96
    ethyl propionate 19.02
    nitromethane 46.22
    1,2-diethoxyethane 32.55
    benzonitrile 26.3
    trioctyl phosphate 6.36
    1-bromopropane 20.1
    gamma-valerolactone 96.96
    n-decanol 3.07
    triethyl phosphate 16.15
    4-methyl-2-pentanol 3.74
    propionitrile 9.94
    vinylene carbonate 49.98
    1,1,2-trichlorotrifluoroethane 52.68
    DMS 38.52
    cumene 9.63
    2-octanol 2.54
    2-hexanone 17.06
    octyl acetate 9.47
    limonene 9.56
    1,2-dimethoxyethane 39.85
    ethyl orthosilicate 14.49
    tributyl phosphate 9.43
    diacetone alcohol 21.7
    N,N-dimethylaniline 20.41
    acrylonitrile 22.16
    aniline 22.28
    1,3-propanediol 5.94
    bromobenzene 36.89
    dibromomethane 47.68
    1,1,2,2-tetrachloroethane 104.97
    2-methyl-cyclohexyl acetate 21.94
    tetrabutyl urea 13.08
    diisobutyl methanol 6.04
    2-phenylethanol 19.71
    styrene 18.56
    dioctyl adipate 16.96
    dimethyl sulfate 46.77
    ethyl butyrate 20.65
    methyl lactate 13.46
    butyl lactate 12.39
    diethyl carbonate 18.21
    propanediol butyl ether 8.56
    triethyl orthoformate 17.82
    p-tert-butyltoluene 8.11
    methyl 4-tert-butylbenzoate 26.6
    morpholine 43.74
    tert-butylamine 2.37
    n-dodecanol 2.73
    dimethoxymethane 45.12
    ethylene carbonate 33.64
    cyrene 22.92
    2-ethoxyethyl acetate 31.27
    2-ethylhexyl acetate 19.65
    1,2,4-trichlorobenzene 48.87
    4-methylpyridine 52.02
    dibutyl ether 9.35
    2,6-dimethyl-4-heptanol 6.04
    DEF 32.72
    dimethyl isosorbide 55.79
    tetrachloroethylene 66.55
    eugenol 25.39
    triacetin 29.17
    span 80 15.69
    1,4-butanediol 2.12
    1,1-dichloroethane 25.2
    2-methyl-1-pentanol 6.39
    methyl formate 19.86
    2-methyl-1-butanol 5.11
    n-decane 0.79
    butyronitrile 8.07
    3,7-dimethyl-1-octanol 5.03
    1-chlorooctane 3.77
    1-chlorotetradecane 2.27
    n-nonane 0.6
    undecane 0.67
    tert-butylcyclohexane 1.48
    cyclooctane 0.46
    cyclopentanol 6.82
    tetrahydropyran 27.59
    tert-amyl methyl ether 7.95
    2,5,8-trioxanonane 49.27
    1-hexene 3.16
    2-isopropoxyethanol 9.0
    2,2,2-trifluoroethanol 8.62
    methyl butyrate 23.21

    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