Naphtho[1,8-bc]pyran-7,8-dione, 2,3-dihydro-4-hydroxy-3,6,9-trimethyl-

Overview IFRA Request a quote

  • Identifiers

    CAS number
    13383-59-0

    Molecular formula
    C15H14O4

    SMILES
    CC1COC2=C(C(=O)C(=O)C3=C2C1=C(C=C3C)O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 53.8%
    Burnt 38.48%
    Caramellic 38.48%
    Phenolic 38.34%
    Powdery 32.33%
    Spicy 30.92%
    Vanilla 30.92%
    Dry 27.25%
    Woody 26.54%
    Creamy 25.96%

     

    Flavor
    Bitter 83.64%
    Lovage 20.56%
    Parsley 20.18%
    Cedarleaf 20.01%
    Ripe apricot 19.52%
    Red fruit 19.52%
    Sweet-like 19.51%
    Fenugreek 19.33%
    Basil 19.33%
    Leaves 19.19%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    7.25 (neutral)

    Molecular weight
    258.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1134°C

    Flash point

    • 219.2 ˚C est.

  • Synonyms

    • 13383-59-0
    • CHEMBL3892391
    • SCHEMBL31238210
    • VMUMUNGCHYCMDR-UHFFFAOYSA-N
    • Naphtho[1,8-bc]pyran-7,8-dione, 2,3-dihydro-4-hydroxy-3,6,9-trimethyl-
    • 4-Hydroxy-3,6,9-trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione
    • 4-Hydroxy-3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione #
    • 13383-59-0

  • Applications

    Naphtho[1,8-bc]pyran-7,8-dione, 2,3-dihydro-4-hydroxy-3,6,9-trimethyl- (CAS 13383-59-0) serves as a practical starting point in organic synthesis, functioning as a building block for pharmaceutical and agrochemical intermediates, and as a scaffold for developing quinone- and chromene-based dyes and pigments for coatings, inks, and plastics. The compound’s quinone and hydroxy functionality also makes it a candidate for antioxidant or polymer-stabilizer studies, and it serves as a building block for chromene/quinone-based systems in materials research. In R&D contexts, it may be evaluated as a redox-active component in electrochemical applications, with regulatory compliance and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.61
    methanol 2.16
    isopropanol 1.78
    water 0.01
    ethyl acetate 5.19
    n-propanol 2.31
    acetone 8.89
    n-butanol 2.19
    acetonitrile 3.45
    DMF 28.35
    toluene 8.67
    isobutanol 1.78
    1,4-dioxane 15.43
    methyl acetate 7.55
    THF 18.12
    2-butanone 9.89
    n-pentanol 3.22
    sec-butanol 1.46
    n-hexane 0.11
    ethylene glycol 1.4
    NMP 52.58
    cyclohexane 0.3
    DMSO 17.43
    n-butyl acetate 10.97
    n-octanol 4.48
    chloroform 15.51
    n-propyl acetate 7.93
    acetic acid 5.7
    dichloromethane 18.85
    cyclohexanone 27.99
    propylene glycol 0.81
    isopropyl acetate 4.91
    DMAc 33.7
    2-ethoxyethanol 7.67
    isopentanol 2.7
    n-heptane 0.18
    ethyl formate 7.79
    1,2-dichloroethane 13.33
    n-hexanol 4.8
    2-methoxyethanol 9.5
    isobutyl acetate 7.24
    tetrachloromethane 2.37
    n-pentyl acetate 13.16
    transcutol 12.35
    n-heptanol 5.32
    ethylbenzene 5.78
    MIBK 6.32
    2-propoxyethanol 14.8
    tert-butanol 2.59
    MTBE 1.56
    2-butoxyethanol 12.5
    propionic acid 4.1
    o-xylene 6.99
    formic acid 2.99
    diethyl ether 1.68
    m-xylene 6.5
    p-xylene 9.28
    chlorobenzene 14.8
    dimethyl carbonate 6.63
    n-octane 0.2
    formamide 6.24
    cyclopentanone 28.18
    2-pentanone 7.07
    anisole 9.9
    cyclopentyl methyl ether 6.2
    gamma-butyrolactone 30.53
    1-methoxy-2-propanol 6.05
    pyridine 31.0
    3-pentanone 5.79
    furfural 45.61
    n-dodecane 0.34
    diethylene glycol 14.03
    diisopropyl ether 0.9
    tert-amyl alcohol 2.02
    acetylacetone 12.88
    n-hexadecane 0.42
    acetophenone 20.07
    methyl propionate 6.35
    isopentyl acetate 11.68
    trichloroethylene 34.37
    n-nonanol 4.87
    cyclohexanol 3.66
    benzyl alcohol 13.62
    2-ethylhexanol 4.47
    isooctanol 4.91
    dipropyl ether 2.33
    1,2-dichlorobenzene 16.42
    ethyl lactate 6.03
    propylene carbonate 18.68
    n-methylformamide 9.5
    2-pentanol 1.16
    n-pentane 0.08
    1-propoxy-2-propanol 8.04
    1-methoxy-2-propyl acetate 12.46
    2-(2-methoxypropoxy) propanol 12.45
    mesitylene 3.81
    ε-caprolactone 23.87
    p-cymene 5.71
    epichlorohydrin 30.38
    1,1,1-trichloroethane 8.44
    2-aminoethanol 2.16
    morpholine-4-carbaldehyde 40.47
    sulfolane 40.35
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 9.36
    n-hexyl acetate 12.85
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 12.76
    sec-butyl acetate 5.44
    tert-butyl acetate 6.19
    decalin 0.52
    glycerin 2.72
    diglyme 25.16
    acrylic acid 6.03
    isopropyl myristate 5.79
    n-butyric acid 5.43
    acetyl acetate 5.74
    di(2-ethylhexyl) phthalate 10.92
    ethyl propionate 5.99
    nitromethane 12.48
    1,2-diethoxyethane 7.31
    benzonitrile 21.17
    trioctyl phosphate 7.43
    1-bromopropane 3.66
    gamma-valerolactone 47.16
    n-decanol 3.83
    triethyl phosphate 7.15
    4-methyl-2-pentanol 1.5
    propionitrile 4.44
    vinylene carbonate 22.27
    1,1,2-trichlorotrifluoroethane 21.84
    DMS 14.05
    cumene 4.59
    2-octanol 3.81
    2-hexanone 9.49
    octyl acetate 8.03
    limonene 5.27
    1,2-dimethoxyethane 15.71
    ethyl orthosilicate 6.31
    tributyl phosphate 7.4
    diacetone alcohol 8.97
    N,N-dimethylaniline 8.99
    acrylonitrile 8.85
    aniline 9.57
    1,3-propanediol 3.84
    bromobenzene 15.0
    dibromomethane 9.38
    1,1,2,2-tetrachloroethane 21.49
    2-methyl-cyclohexyl acetate 13.09
    tetrabutyl urea 12.61
    diisobutyl methanol 2.63
    2-phenylethanol 18.94
    styrene 6.12
    dioctyl adipate 10.11
    dimethyl sulfate 13.03
    ethyl butyrate 7.48
    methyl lactate 5.74
    butyl lactate 9.59
    diethyl carbonate 6.45
    propanediol butyl ether 8.11
    triethyl orthoformate 6.8
    p-tert-butyltoluene 4.65
    methyl 4-tert-butylbenzoate 18.75
    morpholine 14.78
    tert-butylamine 1.2
    n-dodecanol 2.94
    dimethoxymethane 12.06
    ethylene carbonate 16.22
    cyrene 22.94
    2-ethoxyethyl acetate 15.92
    2-ethylhexyl acetate 10.33
    1,2,4-trichlorobenzene 21.91
    4-methylpyridine 27.12
    dibutyl ether 3.23
    2,6-dimethyl-4-heptanol 2.63
    DEF 12.67
    dimethyl isosorbide 27.46
    tetrachloroethylene 17.18
    eugenol 20.3
    triacetin 13.69
    span 80 10.53
    1,4-butanediol 2.69
    1,1-dichloroethane 6.48
    2-methyl-1-pentanol 3.93
    methyl formate 9.88
    2-methyl-1-butanol 2.26
    n-decane 0.47
    butyronitrile 4.64
    3,7-dimethyl-1-octanol 4.21
    1-chlorooctane 2.93
    1-chlorotetradecane 1.51
    n-nonane 0.33
    undecane 0.39
    tert-butylcyclohexane 0.41
    cyclooctane 0.15
    cyclopentanol 4.3
    tetrahydropyran 7.5
    tert-amyl methyl ether 1.75
    2,5,8-trioxanonane 20.36
    1-hexene 0.77
    2-isopropoxyethanol 6.65
    2,2,2-trifluoroethanol 4.34
    methyl butyrate 9.24

    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