7,8-Dihydro-8,8-dimethyl-2H,6H-benzo(1,2-b:5,4-b')dipyran-2,6-dione

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  • Identifiers

    CAS number
    16499-05-1

    Molecular formula
    C14H12O4

    SMILES
    CC1(CC(=O)C2=C(O1)C=C3C(=C2)C=CC(=O)O3)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 64.86%
    Coumarinic 59.6%
    Coconut 45.97%
    Tobacco 44.39%
    Hay 42.56%
    Nutty 39.02%
    Powdery 37.59%
    Herbal 34.75%
    Phenolic 34.35%
    Creamy 34.05%

     

    Flavor
    Bitter 77.51%
    Sweet 35.26%
    Tonka 28.83%
    Tobacco 24.56%
    Balsam 21.59%
    Herbal 20.27%
    Woody 20.22%
    Coumarin 19.8%
    Naphthalic 19.71%
    Ripe apricot 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    7.64 (neutral)

    Molecular weight
    244.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    447°C

    Melting point expt.

    • 177.5 - 178 °C

    Flash point

    • 195.45 ˚C est.

  • Synonyms

    • Graveolone
    • 16499-05-1
    • 2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
    • DTXSID10167830
    • 8,8-dimethyl-2H,6H,7H,8H-pyrano[3,2-g]chromene-2,6-dione
    • 2,2-dimethyl-3H-pyrano(3,2-g)chromene-4,8-dione
    • 8,8-dimethyl-2H,6H,7H,8H-pyrano(3,2-g)chromene-2,6-dione
    • RefChem:1074266
    • DTXCID1090321
    • 7,8-Dihydro-8,8-dimethyl-2H,6H-benzo(1,2-b:5,4-b')dipyran-2,6-dione
    • 7,8-Dihydro-8,8-dimethyl-2H,6H-benzo[1,2-b
    • 8,8-Dimethyl-7,8-dihydro-pyrano[3,2-g]chromene-2,6-dione
    • 6,7-Dihydro-8,8-dimethyl-2h,8h-benzo(1,2-b:5,4-b')dipyran-2,6-dione
    • 6,7-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2,6-dione
    • orb2563975
    • CHEBI:174258
    • 2H,6H-Benzo[1,2-b:5,4-b']dipyran-2,6-dione, 7,8-dihydro-8,8-dimethyl-
    • XG163695
    • 2,2-dimethyl-3H-pyrano[5,6-g]chromene-4,8-quinone
    • 8,8-dimethyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione
    • 8,8-Dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromene-2,6-dione
    • 6,7-Dihydro-8,8-dimethyl-2H,8H-benzo-(1,2b:5,4')-dipyran-2,6-dione
    • 8,8-Dimethyl-7,8-dihydro-2H,6H-benzo[1,2-b:5,4-b']dipyran-2,6-dione
    • 8,8-Dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromene-2,6-dione #
    • InChI=1/C14H12O4/c1-14(2)7-10(15)9-5-8-3-4-13(16)17-11(8)6-12(9)18-14/h3-6H,7H2,1-2H
    • 16499-05-1

  • Applications

    7,8-Dihydro-8,8-dimethyl-2H,6H-benzo(1,2-b:5,4-b')dipyran-2,6-dione (CAS 16499-05-1) is primarily used as a synthetic intermediate in organic synthesis. In real-world applications, it is commonly evaluated as a building block in the manufacture of pharmaceuticals and agrochemicals, as well as in the synthesis of dyes and pigments. It can also serve as a precursor for specialty polymers and resins, enabling functionalization or crosslinking in polymer chemistry. In coatings and inks, it may be used as a reactive intermediate or additive to introduce specific functional groups. Additionally, in research and development settings, it is used as a substrate for reaction development and process optimization.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.24
    methanol 10.04
    isopropanol 5.82
    water 0.19
    ethyl acetate 28.07
    n-propanol 6.35
    acetone 42.56
    n-butanol 6.08
    acetonitrile 33.98
    DMF 219.68
    toluene 4.78
    isobutanol 6.81
    1,4-dioxane 49.59
    methyl acetate 49.05
    THF 91.02
    2-butanone 32.89
    n-pentanol 6.32
    sec-butanol 5.32
    n-hexane 0.15
    ethylene glycol 11.78
    NMP 210.35
    cyclohexane 0.16
    DMSO 155.75
    n-butyl acetate 26.24
    n-octanol 9.28
    chloroform 36.24
    n-propyl acetate 27.06
    acetic acid 48.33
    dichloromethane 35.67
    cyclohexanone 48.51
    propylene glycol 12.77
    isopropyl acetate 22.17
    DMAc 250.31
    2-ethoxyethanol 36.09
    isopentanol 9.44
    n-heptane 0.26
    ethyl formate 25.06
    1,2-dichloroethane 24.96
    n-hexanol 7.06
    2-methoxyethanol 66.89
    isobutyl acetate 24.31
    tetrachloromethane 1.87
    n-pentyl acetate 18.95
    transcutol 209.91
    n-heptanol 6.95
    ethylbenzene 4.05
    MIBK 23.64
    2-propoxyethanol 55.84
    tert-butanol 11.66
    MTBE 9.39
    2-butoxyethanol 28.28
    propionic acid 28.21
    o-xylene 5.1
    formic acid 32.99
    diethyl ether 6.78
    m-xylene 5.97
    p-xylene 7.06
    chlorobenzene 13.0
    dimethyl carbonate 49.27
    n-octane 0.25
    formamide 44.74
    cyclopentanone 83.71
    2-pentanone 24.51
    anisole 24.53
    cyclopentyl methyl ether 25.03
    gamma-butyrolactone 132.54
    1-methoxy-2-propanol 53.52
    pyridine 31.97
    3-pentanone 20.33
    furfural 120.72
    n-dodecane 0.64
    diethylene glycol 70.56
    diisopropyl ether 3.55
    tert-amyl alcohol 9.34
    acetylacetone 58.57
    n-hexadecane 0.75
    acetophenone 36.53
    methyl propionate 41.25
    isopentyl acetate 29.92
    trichloroethylene 68.45
    n-nonanol 9.72
    cyclohexanol 8.77
    benzyl alcohol 24.08
    2-ethylhexanol 8.45
    isooctanol 7.53
    dipropyl ether 9.51
    1,2-dichlorobenzene 18.52
    ethyl lactate 32.42
    propylene carbonate 70.45
    n-methylformamide 62.68
    2-pentanol 4.42
    n-pentane 0.1
    1-propoxy-2-propanol 39.24
    1-methoxy-2-propyl acetate 55.43
    2-(2-methoxypropoxy) propanol 60.45
    mesitylene 4.36
    ε-caprolactone 58.77
    p-cymene 6.33
    epichlorohydrin 115.61
    1,1,1-trichloroethane 18.42
    2-aminoethanol 13.33
    morpholine-4-carbaldehyde 191.2
    sulfolane 158.36
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 37.39
    n-hexyl acetate 28.79
    isooctane 0.32
    2-(2-butoxyethoxy)ethanol 64.02
    sec-butyl acetate 20.2
    tert-butyl acetate 27.86
    decalin 0.6
    glycerin 40.36
    diglyme 111.24
    acrylic acid 39.82
    isopropyl myristate 14.96
    n-butyric acid 26.55
    acetyl acetate 29.89
    di(2-ethylhexyl) phthalate 22.32
    ethyl propionate 28.35
    nitromethane 152.06
    1,2-diethoxyethane 39.3
    benzonitrile 33.13
    trioctyl phosphate 14.5
    1-bromopropane 6.05
    gamma-valerolactone 148.15
    n-decanol 8.11
    triethyl phosphate 22.29
    4-methyl-2-pentanol 5.97
    propionitrile 18.83
    vinylene carbonate 73.58
    1,1,2-trichlorotrifluoroethane 95.79
    DMS 60.25
    cumene 4.67
    2-octanol 5.67
    2-hexanone 23.45
    octyl acetate 18.41
    limonene 7.08
    1,2-dimethoxyethane 71.49
    ethyl orthosilicate 19.04
    tributyl phosphate 20.11
    diacetone alcohol 44.37
    N,N-dimethylaniline 20.94
    acrylonitrile 37.85
    aniline 14.77
    1,3-propanediol 19.22
    bromobenzene 10.66
    dibromomethane 14.34
    1,1,2,2-tetrachloroethane 51.0
    2-methyl-cyclohexyl acetate 26.35
    tetrabutyl urea 29.03
    diisobutyl methanol 7.2
    2-phenylethanol 24.23
    styrene 4.86
    dioctyl adipate 27.28
    dimethyl sulfate 107.45
    ethyl butyrate 23.64
    methyl lactate 50.7
    butyl lactate 26.04
    diethyl carbonate 22.94
    propanediol butyl ether 37.3
    triethyl orthoformate 23.37
    p-tert-butyltoluene 5.99
    methyl 4-tert-butylbenzoate 39.31
    morpholine 55.85
    tert-butylamine 4.1
    n-dodecanol 6.73
    dimethoxymethane 80.38
    ethylene carbonate 54.69
    cyrene 65.85
    2-ethoxyethyl acetate 39.76
    2-ethylhexyl acetate 23.23
    1,2,4-trichlorobenzene 28.95
    4-methylpyridine 40.0
    dibutyl ether 12.4
    2,6-dimethyl-4-heptanol 7.2
    DEF 48.17
    dimethyl isosorbide 99.29
    tetrachloroethylene 21.37
    eugenol 42.89
    triacetin 56.17
    span 80 36.56
    1,4-butanediol 10.12
    1,1-dichloroethane 17.62
    2-methyl-1-pentanol 8.78
    methyl formate 66.45
    2-methyl-1-butanol 7.49
    n-decane 0.83
    butyronitrile 15.22
    3,7-dimethyl-1-octanol 12.04
    1-chlorooctane 4.67
    1-chlorotetradecane 2.85
    n-nonane 0.6
    undecane 0.73
    tert-butylcyclohexane 0.66
    cyclooctane 0.11
    cyclopentanol 13.95
    tetrahydropyran 17.1
    tert-amyl methyl ether 9.58
    2,5,8-trioxanonane 93.13
    1-hexene 1.04
    2-isopropoxyethanol 28.37
    2,2,2-trifluoroethanol 33.99
    methyl butyrate 35.4

    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