Daphnoretin methyl ether

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  • Identifiers

    CAS number
    3749-38-0

    Molecular formula
    C20H14O7

    SMILES
    COC1=C(C=C2C(=C1)C=C(C(=O)O2)OC3=CC4=C(C=C3)C=CC(=O)O4)OC

    Safety labels

  • Odor profile

    Fragrance
    Sweet 51.84%
    Fruity 48.56%
    Vanilla 44.82%
    Powdery 36.88%
    Phenolic 35.54%
    Balsamic 33.36%
    Creamy 33.27%
    Berry 29.6%
    Burnt 29.37%
    Caramellic 28.74%

     

    Flavor
    Bitter 85.1%
    Sweet 22.04%
    Tonka 20.85%
    Parsley 20.07%
    Eugenol 19.34%
    Heliotropin 18.98%
    Aniseed 18.92%
    Sweet-like 18.87%
    Lovage 18.86%
    Cedarleaf 18.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    7.11 (neutral)

    Molecular weight
    366.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    543°C

    Melting point expt.

    • 240 °C

    Flash point

    • 232.42 ˚C est.

  • Synonyms

    • Daphnoretin methyl ether
    • Isodaphnoretin (incorr.)
    • 6,7-dimethoxy-3-(2-oxochromen-7-yl)oxychromen-2-one
    • 3749-38-0
    • 6,7-dimethoxy-3-[(2-oxo-2H-chromen-7-yl)oxy]-2H-chromen-2-one
    • 6,7-dimethoxy-3-((2-oxo-2H-chromen-7-yl)oxy)-2H-chromen-2-one
    • RefChem:130944
    • SCHEMBL13784421
    • CHEBI:172597
    • DTXSID501313166
    • 6,7-Dimethoxy-3-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-2H-1-benzopyran-2-one
    • 3749-38-0

  • Applications

    Daphnoretin methyl ether (CAS 3749-38-0) is primarily encountered as a specialized synthetic building block and natural-product-derived intermediate in organic synthesis and medicinal chemistry. In practice, it is often evaluated as a scaffold for the development of derivatives in pharmaceutical research and as an intermediate for further functionalization in synthetic routes. It can also be used in academic and industrial settings as a reference compound for structure-activity studies of furanocoumarin-like frameworks. Additionally, the compound has been explored for its photochemical properties and may be used as a tool in materials science research related to conjugated systems and chromophores. In formulation and analytical work, it can serve as a standard or calibration reference in certain assays, with use governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.29
    methanol 0.23
    isopropanol 0.43
    water 0.0
    ethyl acetate 1.86
    n-propanol 0.52
    acetone 3.6
    n-butanol 0.47
    acetonitrile 1.79
    DMF 8.85
    toluene 0.63
    isobutanol 0.52
    1,4-dioxane 6.88
    methyl acetate 3.44
    THF 19.71
    2-butanone 5.2
    n-pentanol 0.52
    sec-butanol 0.76
    n-hexane 0.04
    ethylene glycol 0.25
    NMP 9.2
    cyclohexane 0.06
    DMSO 25.07
    n-butyl acetate 1.47
    n-octanol 0.35
    chloroform 3.42
    n-propyl acetate 1.67
    acetic acid 2.17
    dichloromethane 5.91
    cyclohexanone 6.43
    propylene glycol 0.19
    isopropyl acetate 1.39
    DMAc 20.18
    2-ethoxyethanol 2.48
    isopentanol 0.61
    n-heptane 0.07
    ethyl formate 1.06
    1,2-dichloroethane 4.51
    n-hexanol 0.4
    2-methoxyethanol 3.14
    isobutyl acetate 0.94
    tetrachloromethane 0.21
    n-pentyl acetate 1.29
    transcutol 7.78
    n-heptanol 0.41
    ethylbenzene 0.4
    MIBK 1.46
    2-propoxyethanol 2.94
    tert-butanol 0.79
    MTBE 1.39
    2-butoxyethanol 2.07
    propionic acid 1.28
    o-xylene 0.59
    formic acid 0.81
    diethyl ether 1.61
    m-xylene 0.35
    p-xylene 0.65
    chlorobenzene 0.73
    dimethyl carbonate 2.22
    n-octane 0.04
    formamide 2.12
    cyclopentanone 9.95
    2-pentanone 2.31
    anisole 1.41
    cyclopentyl methyl ether 2.71
    gamma-butyrolactone 10.22
    1-methoxy-2-propanol 2.0
    pyridine 5.86
    3-pentanone 3.17
    furfural 6.72
    n-dodecane 0.05
    diethylene glycol 2.5
    diisopropyl ether 0.43
    tert-amyl alcohol 1.08
    acetylacetone 4.16
    n-hexadecane 0.06
    acetophenone 2.19
    methyl propionate 2.41
    isopentyl acetate 1.73
    trichloroethylene 8.23
    n-nonanol 0.48
    cyclohexanol 0.91
    benzyl alcohol 1.22
    2-ethylhexanol 0.56
    isooctanol 0.51
    dipropyl ether 1.55
    1,2-dichlorobenzene 0.95
    ethyl lactate 1.04
    propylene carbonate 2.36
    n-methylformamide 2.19
    2-pentanol 0.44
    n-pentane 0.03
    1-propoxy-2-propanol 2.08
    1-methoxy-2-propyl acetate 2.86
    2-(2-methoxypropoxy) propanol 3.85
    mesitylene 0.22
    ε-caprolactone 4.69
    p-cymene 0.47
    epichlorohydrin 14.72
    1,1,1-trichloroethane 1.51
    2-aminoethanol 0.35
    morpholine-4-carbaldehyde 10.36
    sulfolane 17.37
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 5.8
    n-hexyl acetate 1.37
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 3.64
    sec-butyl acetate 1.16
    tert-butyl acetate 1.75
    decalin 0.06
    glycerin 0.84
    diglyme 9.75
    acrylic acid 1.53
    isopropyl myristate 0.95
    n-butyric acid 1.19
    acetyl acetate 1.41
    di(2-ethylhexyl) phthalate 1.18
    ethyl propionate 1.96
    nitromethane 7.97
    1,2-diethoxyethane 3.9
    benzonitrile 1.34
    trioctyl phosphate 0.7
    1-bromopropane 1.44
    gamma-valerolactone 12.42
    n-decanol 0.4
    triethyl phosphate 1.73
    4-methyl-2-pentanol 0.34
    propionitrile 1.69
    vinylene carbonate 2.28
    1,1,2-trichlorotrifluoroethane 6.89
    DMS 2.45
    cumene 0.34
    2-octanol 0.32
    2-hexanone 2.23
    octyl acetate 1.08
    limonene 0.58
    1,2-dimethoxyethane 8.65
    ethyl orthosilicate 1.6
    tributyl phosphate 1.01
    diacetone alcohol 2.59
    N,N-dimethylaniline 1.3
    acrylonitrile 2.76
    aniline 1.26
    1,3-propanediol 0.83
    bromobenzene 0.68
    dibromomethane 2.46
    1,1,2,2-tetrachloroethane 5.83
    2-methyl-cyclohexyl acetate 1.78
    tetrabutyl urea 1.83
    diisobutyl methanol 0.51
    2-phenylethanol 1.32
    styrene 0.42
    dioctyl adipate 1.85
    dimethyl sulfate 5.54
    ethyl butyrate 1.79
    methyl lactate 1.51
    butyl lactate 1.2
    diethyl carbonate 1.54
    propanediol butyl ether 1.0
    triethyl orthoformate 2.09
    p-tert-butyltoluene 0.4
    methyl 4-tert-butylbenzoate 2.78
    morpholine 7.03
    tert-butylamine 0.37
    n-dodecanol 0.34
    dimethoxymethane 5.47
    ethylene carbonate 1.9
    cyrene 3.51
    2-ethoxyethyl acetate 2.95
    2-ethylhexyl acetate 1.48
    1,2,4-trichlorobenzene 1.58
    4-methylpyridine 3.02
    dibutyl ether 1.3
    2,6-dimethyl-4-heptanol 0.51
    DEF 3.87
    dimethyl isosorbide 7.34
    tetrachloroethylene 3.27
    eugenol 2.71
    triacetin 2.78
    span 80 1.94
    1,4-butanediol 0.39
    1,1-dichloroethane 1.63
    2-methyl-1-pentanol 0.76
    methyl formate 2.05
    2-methyl-1-butanol 0.67
    n-decane 0.08
    butyronitrile 0.99
    3,7-dimethyl-1-octanol 0.52
    1-chlorooctane 0.34
    1-chlorotetradecane 0.19
    n-nonane 0.06
    undecane 0.06
    tert-butylcyclohexane 0.05
    cyclooctane 0.02
    cyclopentanol 1.27
    tetrahydropyran 3.96
    tert-amyl methyl ether 1.47
    2,5,8-trioxanonane 7.85
    1-hexene 0.25
    2-isopropoxyethanol 1.97
    2,2,2-trifluoroethanol 1.29
    methyl butyrate 2.22

    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