2-(4,5-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    150853-99-9

    Molecular formula
    C21H20O7

    SMILES
    CC(=CCC1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=CC(=C3O)O)OC)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 57.2%
    Spicy 42.15%
    Odorless 39.73%
    Burnt 39.18%
    Smoky 35.91%
    Woody 27.69%
    Medicinal 25.07%
    Dry 24.91%
    Balsamic 23.32%
    Vanilla 21.08%

     

    Flavor
    Bitter 88.74%
    Odorless 21.85%
    Bland 21.76%
    Parsley 20.74%
    Eugenol 20.49%
    Cedarleaf 20.3%
    Sweet-like 19.95%
    Lovage 19.64%
    Ham 19.43%
    Allspice 19.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.4

    pKa est.
    10.54 (weak base)

    Molecular weight
    384.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    912°C

    Melting point expt.

    • 216 - 218 °C

    Flash point

    • 241.8 ˚C est.

  • Synonyms

    • Uralene
    • 150853-99-9
    • 5,6,3',4'-Tetrahydroxy-3-methoxy-6'-isoprenylflavone
    • 2-[4,5-dihydroxy-2-(3-methylbut-2-enyl)phenyl]-5,6-dihydroxy-3-methoxychromen-4-one
    • 4H-1-Benzopyran-4-one, 2-(4,5-dihydroxy-2-(3-methyl-2-butenyl)phenyl)-5,6-dihydroxy-3-methoxy-
    • 2-(4,5-dihydroxy-2-(3-methylbut-2-enyl)phenyl)-5,6-dihydroxy-3-methoxychromen-4-one
    • RefChem:909258
    • 2-(4,5-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-one
    • 4',5,5',6-tetrahydroxy-3-methoxy-2'-prenylflavone
    • 2-(4,5-Dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl)-5,6-dihydroxy-3-methoxy-4H-chromen-4-one
    • 2-[4,5-dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl]-5,6-dihydroxy-3-methoxy-4H-chromen-4-one
    • SCHEMBL3977970
    • DTXSID30934107
    • CHEBI:175907
    • LMPK12111615
    • 2-[4,5-Dihydroxy-2-(3-methyl-2-butenyl)phenyl]-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-one
    • 2-[4,5-Dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl]-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-one
    • 150853-99-9

  • Applications

    Chemical name: 2-(4,5-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-5,6-dihydroxy-3-methoxy-4H-1-benzopyran-4-one; CAS number: 150853-99-9. The compound may be used as a prenylated polyphenol with potential applications as an antioxidant and stabilizer in cosmetics/personal care; as an antioxidant and stabilizer additive for coatings, inks, and plastics in industrial manufacturing; as an intermediate or scaffold for pharmaceutical synthesis or natural-product–derived drug discovery; and it may be evaluated for packaging and food-contact materials as an antioxidant or stabilizer, subject to regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.48
    methanol 1.88
    isopropanol 2.31
    water 0.0
    ethyl acetate 2.43
    n-propanol 4.74
    acetone 2.17
    n-butanol 2.75
    acetonitrile 0.89
    DMF 16.05
    toluene 0.4
    isobutanol 2.46
    1,4-dioxane 5.88
    methyl acetate 4.55
    THF 28.55
    2-butanone 7.18
    n-pentanol 1.92
    sec-butanol 4.77
    n-hexane 0.02
    ethylene glycol 1.93
    NMP 20.93
    cyclohexane 0.02
    DMSO 28.24
    n-butyl acetate 1.71
    n-octanol 1.25
    chloroform 0.77
    n-propyl acetate 1.74
    acetic acid 7.67
    dichloromethane 0.87
    cyclohexanone 6.47
    propylene glycol 4.37
    isopropyl acetate 1.76
    DMAc 38.43
    2-ethoxyethanol 10.61
    isopentanol 2.28
    n-heptane 0.03
    ethyl formate 1.31
    1,2-dichloroethane 1.04
    n-hexanol 1.6
    2-methoxyethanol 22.06
    isobutyl acetate 0.94
    tetrachloromethane 0.08
    n-pentyl acetate 2.45
    transcutol 20.91
    n-heptanol 1.58
    ethylbenzene 0.25
    MIBK 1.66
    2-propoxyethanol 11.89
    tert-butanol 3.29
    MTBE 2.02
    2-butoxyethanol 7.74
    propionic acid 5.45
    o-xylene 0.35
    formic acid 3.7
    diethyl ether 1.44
    m-xylene 0.24
    p-xylene 0.3
    chlorobenzene 0.33
    dimethyl carbonate 3.17
    n-octane 0.02
    formamide 6.78
    cyclopentanone 13.15
    2-pentanone 2.7
    anisole 1.54
    cyclopentyl methyl ether 3.93
    gamma-butyrolactone 14.76
    1-methoxy-2-propanol 16.32
    pyridine 6.57
    3-pentanone 2.51
    furfural 8.77
    n-dodecane 0.02
    diethylene glycol 9.63
    diisopropyl ether 0.28
    tert-amyl alcohol 4.99
    acetylacetone 3.91
    n-hexadecane 0.03
    acetophenone 2.37
    methyl propionate 4.85
    isopentyl acetate 1.99
    trichloroethylene 3.06
    n-nonanol 1.5
    cyclohexanol 2.59
    benzyl alcohol 2.43
    2-ethylhexanol 1.06
    isooctanol 1.4
    dipropyl ether 1.18
    1,2-dichlorobenzene 0.37
    ethyl lactate 2.74
    propylene carbonate 3.44
    n-methylformamide 5.42
    2-pentanol 1.88
    n-pentane 0.02
    1-propoxy-2-propanol 7.63
    1-methoxy-2-propyl acetate 5.38
    2-(2-methoxypropoxy) propanol 7.89
    mesitylene 0.13
    ε-caprolactone 7.55
    p-cymene 0.36
    epichlorohydrin 15.78
    1,1,1-trichloroethane 0.44
    2-aminoethanol 4.68
    morpholine-4-carbaldehyde 19.92
    sulfolane 27.1
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 8.17
    n-hexyl acetate 2.69
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 10.19
    sec-butyl acetate 1.45
    tert-butyl acetate 2.76
    decalin 0.03
    glycerin 11.0
    diglyme 16.97
    acrylic acid 5.6
    isopropyl myristate 1.05
    n-butyric acid 4.62
    acetyl acetate 1.32
    di(2-ethylhexyl) phthalate 1.56
    ethyl propionate 1.94
    nitromethane 11.56
    1,2-diethoxyethane 3.67
    benzonitrile 1.08
    trioctyl phosphate 1.2
    1-bromopropane 0.5
    gamma-valerolactone 24.07
    n-decanol 0.99
    triethyl phosphate 1.37
    4-methyl-2-pentanol 1.07
    propionitrile 1.48
    vinylene carbonate 2.65
    1,1,2-trichlorotrifluoroethane 18.68
    DMS 3.6
    cumene 0.21
    2-octanol 1.17
    2-hexanone 2.27
    octyl acetate 1.51
    limonene 0.46
    1,2-dimethoxyethane 12.33
    ethyl orthosilicate 1.33
    tributyl phosphate 1.24
    diacetone alcohol 8.62
    N,N-dimethylaniline 1.35
    acrylonitrile 2.36
    aniline 2.05
    1,3-propanediol 6.58
    bromobenzene 0.22
    dibromomethane 0.37
    1,1,2,2-tetrachloroethane 2.86
    2-methyl-cyclohexyl acetate 1.74
    tetrabutyl urea 2.15
    diisobutyl methanol 0.71
    2-phenylethanol 2.62
    styrene 0.26
    dioctyl adipate 1.98
    dimethyl sulfate 7.32
    ethyl butyrate 1.41
    methyl lactate 6.9
    butyl lactate 3.78
    diethyl carbonate 1.04
    propanediol butyl ether 6.92
    triethyl orthoformate 1.81
    p-tert-butyltoluene 0.37
    methyl 4-tert-butylbenzoate 4.44
    morpholine 14.84
    tert-butylamine 0.99
    n-dodecanol 0.65
    dimethoxymethane 10.17
    ethylene carbonate 1.93
    cyrene 8.03
    2-ethoxyethyl acetate 5.22
    2-ethylhexyl acetate 1.39
    1,2,4-trichlorobenzene 0.95
    4-methylpyridine 3.27
    dibutyl ether 1.08
    2,6-dimethyl-4-heptanol 0.71
    DEF 6.12
    dimethyl isosorbide 11.23
    tetrachloroethylene 1.35
    eugenol 5.26
    triacetin 4.04
    span 80 5.81
    1,4-butanediol 1.79
    1,1-dichloroethane 0.48
    2-methyl-1-pentanol 2.12
    methyl formate 3.24
    2-methyl-1-butanol 3.18
    n-decane 0.04
    butyronitrile 0.97
    3,7-dimethyl-1-octanol 1.28
    1-chlorooctane 0.31
    1-chlorotetradecane 0.13
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.03
    cyclooctane 0.01
    cyclopentanol 4.04
    tetrahydropyran 4.14
    tert-amyl methyl ether 2.57
    2,5,8-trioxanonane 11.97
    1-hexene 0.14
    2-isopropoxyethanol 6.05
    2,2,2-trifluoroethanol 2.09
    methyl butyrate 2.59

    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