8-Methoxy-6,7-methylenedioxycoumarin

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  • Identifiers

    CAS number
    81558-03-4

    Molecular formula
    C11H8O5

    SMILES
    COC1=C2C(=CC3=C1OCO3)C=CC(=O)O2

    Safety labels

  • Odor profile

    Fragrance
    Sweet 49.02%
    Vanilla 37.21%
    Fruity 34.06%
    Powdery 34.05%
    Creamy 33.95%
    Phenolic 31.9%
    Spicy 30.3%
    Coumarinic 29.93%
    Floral 26.76%
    Balsamic 26.23%

     

    Flavor
    Bitter 86.13%
    Tonka 25.37%
    Sweet 23.31%
    Parsley 20.33%
    Eugenol 19.78%
    Naphthalic 19.72%
    Cedarleaf 19.03%
    Sweet-like 18.99%
    Heliotropin 18.91%
    Lovage 18.73%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    6.0 (neutral)

    Molecular weight
    220.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    368°C

    Melting point expt.

    • 200 - 202 °C

    Flash point

    • 186.15 ˚C est.

  • Synonyms

    • 8-Methoxy-6,7-methylenedioxycoumarin
    • 6,7-methylenedioxy-8-methoxycoumarin
    • 81558-03-4
    • 4-methoxy-2H,6H-[1,3]dioxolo[4,5-g]chromen-6-one
    • CHEMBL596030
    • 4-Methoxy-6H-1,3-dioxolo[4,5-g][1]benzopyran-6-one
    • CHEBI:178385
    • DTXSID401227750
    • 4-methoxy-[1,3]dioxolo[4,5-g]chromen-6-one
    • 4-Methoxy-2H,6H-[1,3]dioxolo[4,5-g][1]benzopyran-6-one
    • 81558-03-4

  • Applications

    8-Methoxy-6,7-methylenedioxycoumarin, CAS number: 81558-03-4, is a coumarin derivative primarily used as an intermediate and building block for the synthesis of related compounds in pharmaceutical and chemical research. In the fragrance industry, it is considered a potential fragrance ingredient or fixative for perfumery and personal care products. In cosmetics and personal care, it may function as a fragrance component in formulations. In industrial manufacturing, it is evaluated as a starting material for the synthesis of more complex coumarin derivatives and related chemical transformations. In coatings and inks, it can be explored as a specialty additive with scent-related or functional roles depending on formulation. Additionally, it is regarded as a precursor in pharmaceutical and agrochemical research, subject to regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 10.65
    methanol 16.36
    isopropanol 6.72
    water 0.39
    ethyl acetate 37.97
    n-propanol 7.06
    acetone 65.46
    n-butanol 6.65
    acetonitrile 43.27
    DMF 136.54
    toluene 9.96
    isobutanol 6.09
    1,4-dioxane 55.01
    methyl acetate 50.07
    THF 61.33
    2-butanone 41.9
    n-pentanol 7.55
    sec-butanol 6.68
    n-hexane 0.47
    ethylene glycol 16.72
    NMP 120.74
    cyclohexane 1.65
    DMSO 218.63
    n-butyl acetate 33.19
    n-octanol 13.27
    chloroform 43.22
    n-propyl acetate 33.96
    acetic acid 30.08
    dichloromethane 83.89
    cyclohexanone 64.76
    propylene glycol 4.59
    isopropyl acetate 23.69
    DMAc 132.75
    2-ethoxyethanol 38.84
    isopentanol 8.55
    n-heptane 1.61
    ethyl formate 46.19
    1,2-dichloroethane 64.0
    n-hexanol 12.3
    2-methoxyethanol 58.89
    isobutyl acetate 18.88
    tetrachloromethane 8.26
    n-pentyl acetate 26.5
    transcutol 52.62
    n-heptanol 12.27
    ethylbenzene 9.59
    MIBK 19.95
    2-propoxyethanol 41.72
    tert-butanol 10.85
    MTBE 9.0
    2-butoxyethanol 32.9
    propionic acid 18.53
    o-xylene 12.32
    formic acid 29.11
    diethyl ether 12.0
    m-xylene 9.58
    p-xylene 15.02
    chlorobenzene 25.54
    dimethyl carbonate 39.96
    n-octane 1.33
    formamide 70.55
    cyclopentanone 78.13
    2-pentanone 29.18
    anisole 25.31
    cyclopentyl methyl ether 22.28
    gamma-butyrolactone 102.45
    1-methoxy-2-propanol 28.22
    pyridine 60.16
    3-pentanone 27.59
    furfural 121.24
    n-dodecane 1.94
    diethylene glycol 57.51
    diisopropyl ether 4.86
    tert-amyl alcohol 9.75
    acetylacetone 57.82
    n-hexadecane 2.3
    acetophenone 43.93
    methyl propionate 38.39
    isopentyl acetate 27.31
    trichloroethylene 100.07
    n-nonanol 13.13
    cyclohexanol 12.15
    benzyl alcohol 26.8
    2-ethylhexanol 12.62
    isooctanol 11.38
    dipropyl ether 12.06
    1,2-dichlorobenzene 32.6
    ethyl lactate 26.45
    propylene carbonate 59.66
    n-methylformamide 65.62
    2-pentanol 4.95
    n-pentane 0.49
    1-propoxy-2-propanol 26.19
    1-methoxy-2-propyl acetate 39.26
    2-(2-methoxypropoxy) propanol 33.34
    mesitylene 7.1
    ε-caprolactone 59.49
    p-cymene 12.11
    epichlorohydrin 103.12
    1,1,1-trichloroethane 28.13
    2-aminoethanol 11.84
    morpholine-4-carbaldehyde 117.33
    sulfolane 133.29
    2,2,4-trimethylpentane 0.61
    2-methyltetrahydrofuran 34.22
    n-hexyl acetate 29.19
    isooctane 0.47
    2-(2-butoxyethoxy)ethanol 35.77
    sec-butyl acetate 19.75
    tert-butyl acetate 21.72
    decalin 1.73
    glycerin 19.55
    diglyme 79.95
    acrylic acid 25.84
    isopropyl myristate 14.29
    n-butyric acid 21.3
    acetyl acetate 32.12
    di(2-ethylhexyl) phthalate 19.0
    ethyl propionate 29.33
    nitromethane 110.44
    1,2-diethoxyethane 23.67
    benzonitrile 44.06
    trioctyl phosphate 15.57
    1-bromopropane 15.61
    gamma-valerolactone 108.68
    n-decanol 11.06
    triethyl phosphate 24.14
    4-methyl-2-pentanol 5.1
    propionitrile 26.37
    vinylene carbonate 64.73
    1,1,2-trichlorotrifluoroethane 81.58
    DMS 39.08
    cumene 8.8
    2-octanol 9.29
    2-hexanone 28.97
    octyl acetate 19.35
    limonene 13.34
    1,2-dimethoxyethane 85.58
    ethyl orthosilicate 18.74
    tributyl phosphate 17.9
    diacetone alcohol 31.83
    N,N-dimethylaniline 23.06
    acrylonitrile 52.08
    aniline 17.81
    1,3-propanediol 17.56
    bromobenzene 25.78
    dibromomethane 41.94
    1,1,2,2-tetrachloroethane 68.17
    2-methyl-cyclohexyl acetate 26.21
    tetrabutyl urea 26.31
    diisobutyl methanol 8.24
    2-phenylethanol 30.8
    styrene 10.91
    dioctyl adipate 23.51
    dimethyl sulfate 75.99
    ethyl butyrate 29.08
    methyl lactate 30.68
    butyl lactate 23.02
    diethyl carbonate 27.3
    propanediol butyl ether 23.36
    triethyl orthoformate 22.08
    p-tert-butyltoluene 9.85
    methyl 4-tert-butylbenzoate 36.88
    morpholine 46.85
    tert-butylamine 5.37
    n-dodecanol 9.37
    dimethoxymethane 65.78
    ethylene carbonate 52.71
    cyrene 48.05
    2-ethoxyethyl acetate 37.87
    2-ethylhexyl acetate 24.26
    1,2,4-trichlorobenzene 39.26
    4-methylpyridine 47.7
    dibutyl ether 12.6
    2,6-dimethyl-4-heptanol 8.24
    DEF 55.25
    dimethyl isosorbide 56.47
    tetrachloroethylene 53.9
    eugenol 39.3
    triacetin 36.07
    span 80 22.77
    1,4-butanediol 11.08
    1,1-dichloroethane 28.34
    2-methyl-1-pentanol 9.59
    methyl formate 75.91
    2-methyl-1-butanol 7.29
    n-decane 2.57
    butyronitrile 21.74
    3,7-dimethyl-1-octanol 12.13
    1-chlorooctane 10.18
    1-chlorotetradecane 5.7
    n-nonane 2.13
    undecane 2.21
    tert-butylcyclohexane 1.21
    cyclooctane 0.88
    cyclopentanol 14.55
    tetrahydropyran 24.78
    tert-amyl methyl ether 9.84
    2,5,8-trioxanonane 57.27
    1-hexene 2.6
    2-isopropoxyethanol 27.28
    2,2,2-trifluoroethanol 30.77
    methyl butyrate 41.56

    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