1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridinone

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  • Identifiers

    CAS number
    86680-32-2

    Molecular formula
    C16H15NO5

    SMILES
    CN1C2=C(C=CC=C2O)C(=O)C3=C1C(=C(C=C3O)OC)OC

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 56.76%
    Odorless 37.53%
    Burnt 35.24%
    Smoky 34.45%
    Spicy 34.1%
    Vanilla 32.58%
    Woody 30.49%
    Sweet 29.38%
    Dry 28.27%
    Fruity 27.39%

     

    Flavor
    Bitter 91.85%
    Odorless 26.48%
    Bland 24.72%
    Parsley 20.81%
    Sweet-like 20.73%
    Cedarleaf 20.26%
    Eugenol 19.88%
    Lovage 19.6%
    Very strong 19.39%
    Indole 19.21%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    8.83 (weak base)

    Molecular weight
    301.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    768°C

    Melting point expt.

    • 206 - 207 °C

    Flash point

    • 254.34 ˚C est.

  • Synonyms

    • Citrusinine I
    • 86680-32-2
    • 9(10H)-Acridinone, 1,5-dihydroxy-3,4-dimethoxy-10-methyl-
    • 1,5-dihydroxy-3,4-dimethoxy-10-methylacridin-9-one
    • DTXSID10235760
    • 1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-Acridinone
    • 1,5-DIHYDROXY-3,4-DIMETHOXY-10-METHYL-9,10-DIHYDROACRIDIN-9-ONE
    • RefChem:126609
    • DTXCID40158251
    • Citrusinine-I
    • CHEMBL451705
    • 1,5-dihydroxy-3,4-dimethoxy-10-methyl-acridin-9-one
    • orb1680478
    • SCHEMBL30093820
    • CHEBI:184245
    • LDA68032
    • BDBM50336481
    • AKOS040763313
    • 1,5-Dihydroxy-3,4-dimethoxy-10-methylacridone
    • 1,5-Dihydroxy-3,4-dimethoxy-10-methylacridin-9(10H)-one
    • 86680-32-2

  • Applications

    1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridinone (CAS 86680-32-2) is primarily viewed as an intermediate and scaffold for the synthesis of acridinone compounds in pharmaceutical research and SAR studies, supporting the development of bioactive lead structures. It is also explored as a basis for fluorescent sensing and fluorescence-based labeling in chemical research. Additionally, this acridinone derivative may be evaluated for materials applications, including organic electronics or photonic materials, and as a precursor for coatings or inks with optical properties, depending on regulatory and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.92
    methanol 2.66
    isopropanol 1.15
    water 0.04
    ethyl acetate 5.13
    n-propanol 1.64
    acetone 4.01
    n-butanol 1.59
    acetonitrile 3.4
    DMF 18.81
    toluene 0.45
    isobutanol 1.39
    1,4-dioxane 4.13
    methyl acetate 5.12
    THF 10.28
    2-butanone 5.05
    n-pentanol 1.72
    sec-butanol 1.36
    n-hexane 0.09
    ethylene glycol 2.65
    NMP 26.31
    cyclohexane 0.15
    DMSO 30.84
    n-butyl acetate 6.36
    n-octanol 1.88
    chloroform 5.87
    n-propyl acetate 4.91
    acetic acid 10.18
    dichloromethane 8.81
    cyclohexanone 10.27
    propylene glycol 0.91
    isopropyl acetate 3.13
    DMAc 25.5
    2-ethoxyethanol 6.71
    isopentanol 1.85
    n-heptane 0.15
    ethyl formate 5.39
    1,2-dichloroethane 8.15
    n-hexanol 3.02
    2-methoxyethanol 12.0
    isobutyl acetate 2.78
    tetrachloromethane 1.71
    n-pentyl acetate 5.23
    transcutol 8.95
    n-heptanol 2.75
    ethylbenzene 0.69
    MIBK 3.11
    2-propoxyethanol 11.93
    tert-butanol 1.85
    MTBE 1.09
    2-butoxyethanol 8.29
    propionic acid 4.32
    o-xylene 0.84
    formic acid 10.2
    diethyl ether 1.55
    m-xylene 0.6
    p-xylene 0.97
    chlorobenzene 1.82
    dimethyl carbonate 7.68
    n-octane 0.1
    formamide 16.38
    cyclopentanone 13.93
    2-pentanone 4.05
    anisole 2.18
    cyclopentyl methyl ether 3.49
    gamma-butyrolactone 20.38
    1-methoxy-2-propanol 6.53
    pyridine 5.92
    3-pentanone 4.11
    furfural 20.8
    n-dodecane 0.11
    diethylene glycol 16.2
    diisopropyl ether 0.5
    tert-amyl alcohol 2.03
    acetylacetone 6.32
    n-hexadecane 0.14
    acetophenone 5.63
    methyl propionate 6.82
    isopentyl acetate 5.81
    trichloroethylene 13.2
    n-nonanol 2.06
    cyclohexanol 2.38
    benzyl alcohol 3.5
    2-ethylhexanol 2.72
    isooctanol 2.34
    dipropyl ether 1.88
    1,2-dichlorobenzene 3.48
    ethyl lactate 5.15
    propylene carbonate 10.51
    n-methylformamide 10.21
    2-pentanol 1.06
    n-pentane 0.08
    1-propoxy-2-propanol 6.76
    1-methoxy-2-propyl acetate 8.92
    2-(2-methoxypropoxy) propanol 7.33
    mesitylene 0.49
    ε-caprolactone 11.04
    p-cymene 1.54
    epichlorohydrin 19.11
    1,1,1-trichloroethane 3.45
    2-aminoethanol 2.56
    morpholine-4-carbaldehyde 21.92
    sulfolane 33.29
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 4.91
    n-hexyl acetate 4.92
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 7.62
    sec-butyl acetate 2.67
    tert-butyl acetate 3.79
    decalin 0.19
    glycerin 5.36
    diglyme 16.17
    acrylic acid 6.56
    isopropyl myristate 1.97
    n-butyric acid 5.53
    acetyl acetate 4.73
    di(2-ethylhexyl) phthalate 3.84
    ethyl propionate 5.01
    nitromethane 20.14
    1,2-diethoxyethane 3.52
    benzonitrile 4.53
    trioctyl phosphate 3.19
    1-bromopropane 2.22
    gamma-valerolactone 19.61
    n-decanol 1.55
    triethyl phosphate 5.59
    4-methyl-2-pentanol 1.02
    propionitrile 3.82
    vinylene carbonate 11.07
    1,1,2-trichlorotrifluoroethane 25.03
    DMS 7.81
    cumene 0.83
    2-octanol 1.61
    2-hexanone 4.51
    octyl acetate 3.01
    limonene 1.92
    1,2-dimethoxyethane 12.1
    ethyl orthosilicate 4.54
    tributyl phosphate 3.67
    diacetone alcohol 7.47
    N,N-dimethylaniline 2.48
    acrylonitrile 6.92
    aniline 1.97
    1,3-propanediol 4.21
    bromobenzene 1.42
    dibromomethane 4.73
    1,1,2,2-tetrachloroethane 10.21
    2-methyl-cyclohexyl acetate 5.62
    tetrabutyl urea 5.35
    diisobutyl methanol 1.42
    2-phenylethanol 5.9
    styrene 0.65
    dioctyl adipate 3.72
    dimethyl sulfate 18.49
    ethyl butyrate 5.07
    methyl lactate 7.74
    butyl lactate 5.34
    diethyl carbonate 4.82
    propanediol butyl ether 4.48
    triethyl orthoformate 4.54
    p-tert-butyltoluene 1.21
    methyl 4-tert-butylbenzoate 7.46
    morpholine 6.59
    tert-butylamine 0.83
    n-dodecanol 1.15
    dimethoxymethane 10.49
    ethylene carbonate 9.04
    cyrene 10.96
    2-ethoxyethyl acetate 7.59
    2-ethylhexyl acetate 5.07
    1,2,4-trichlorobenzene 4.58
    4-methylpyridine 4.1
    dibutyl ether 1.58
    2,6-dimethyl-4-heptanol 1.42
    DEF 9.81
    dimethyl isosorbide 14.86
    tetrachloroethylene 9.89
    eugenol 8.48
    triacetin 6.35
    span 80 5.08
    1,4-butanediol 1.89
    1,1-dichloroethane 2.78
    2-methyl-1-pentanol 2.17
    methyl formate 9.29
    2-methyl-1-butanol 1.81
    n-decane 0.18
    butyronitrile 3.18
    3,7-dimethyl-1-octanol 1.8
    1-chlorooctane 1.1
    1-chlorotetradecane 0.49
    n-nonane 0.14
    undecane 0.14
    tert-butylcyclohexane 0.13
    cyclooctane 0.07
    cyclopentanol 2.93
    tetrahydropyran 2.71
    tert-amyl methyl ether 1.55
    2,5,8-trioxanonane 11.71
    1-hexene 0.4
    2-isopropoxyethanol 4.53
    2,2,2-trifluoroethanol 11.27
    methyl butyrate 6.75

    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