5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    104691-86-3

    Molecular formula
    C20H18O5

    SMILES
    CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=CO2)C3=CC=C(C=C3)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 60.63%
    Spicy 41.41%
    Medicinal 32.43%
    Smoky 32.11%
    Burnt 30.51%
    Odorless 29.64%
    Woody 28.93%
    Animal 26.74%
    Fruity 25.91%
    Leathery 25.87%

     

    Flavor
    Bitter 93.39%
    Cedarleaf 20.12%
    Lovage 19.68%
    Parsley 19.5%
    Nitrile 19.18%
    Very strong 18.93%
    Odorless 18.54%
    Indole 18.49%
    Ripe apricot 18.42%
    Flat 18.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    9.88 (weak base)

    Molecular weight
    338.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    861°C

    Flash point

    • 230.29 ˚C est.

  • Synonyms

    • Lupiwighteone
    • 104691-86-3
    • 5,7,4'-Trihydroxy-8-prenylisoflavone
    • 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
    • S5W46B3BUM
    • DTXSID601132953
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
    • RefChem:912997
    • DTXCID901564595
    • 8-prenylgenistein
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
    • 5,7,4'-Trihydroxy-8-(3,3-dimethylallyl)isoflavone
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; 8-Prenylgenistein
    • 8-Isopentenylgenistein
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one; 8-Prenylgenistein
    • SCHEMBL757741
    • MEGxp0_000421
    • orb1297298
    • CHEMBL3616491
    • SCHEMBL31083055
    • CHEBI:185842
    • YGCCASGFIOIXIN-UHFFFAOYSA-N
    • GLXC-16005
    • HY-N3354
    • EX-A15620
    • LMPK12050196
    • AKOS032950070
    • EBC-615426
    • DA-49786
    • FP137754
    • MS-25142
    • CS-0023972
    • E80612
    • 3-(4-HYDROXYPHENYL)-8-(3-METHYLBUT-2-ENYL)-5,7-BIS(OXIDANYL)CHROMEN-4-ONE
    • 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-
    • 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-chromen-4-one #
    • 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
    • 104691-86-3

  • Applications

    5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one (CAS 104691-86-3) is a prenylated flavonoid with established bioactivity and its practical applications span several industries; typical use cases include (1) serving as an antioxidant and bioactive ingredient in cosmetics and personal care products; (2) evaluation as a phytoestrogen and functional ingredient in nutraceuticals/dietary supplements; (3) use in pharmaceutical research and development as a lead scaffold or for bioactivity studies; (4) use as an analytical reference material and synthetic intermediate in flavonoid chemistry; (5) potential precursor for the synthesis of more complex flavonoids in chemical manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.21
    methanol 2.98
    isopropanol 3.35
    water 0.0
    ethyl acetate 2.71
    n-propanol 5.15
    acetone 9.02
    n-butanol 3.87
    acetonitrile 2.23
    DMF 55.88
    toluene 0.74
    isobutanol 3.67
    1,4-dioxane 11.61
    methyl acetate 6.29
    THF 81.73
    2-butanone 15.24
    n-pentanol 3.48
    sec-butanol 4.36
    n-hexane 0.01
    ethylene glycol 2.52
    NMP 47.97
    cyclohexane 0.02
    DMSO 187.25
    n-butyl acetate 3.48
    n-octanol 1.1
    chloroform 1.0
    n-propyl acetate 3.5
    acetic acid 9.16
    dichloromethane 1.04
    cyclohexanone 18.23
    propylene glycol 9.1
    isopropyl acetate 2.55
    DMAc 87.48
    2-ethoxyethanol 19.17
    isopentanol 3.78
    n-heptane 0.02
    ethyl formate 2.62
    1,2-dichloroethane 1.78
    n-hexanol 1.99
    2-methoxyethanol 48.14
    isobutyl acetate 2.76
    tetrachloromethane 0.08
    n-pentyl acetate 2.9
    transcutol 81.35
    n-heptanol 1.56
    ethylbenzene 0.34
    MIBK 4.21
    2-propoxyethanol 24.71
    tert-butanol 4.91
    MTBE 1.98
    2-butoxyethanol 11.23
    propionic acid 5.74
    o-xylene 0.42
    formic acid 3.29
    diethyl ether 0.93
    m-xylene 0.42
    p-xylene 0.57
    chlorobenzene 0.78
    dimethyl carbonate 4.13
    n-octane 0.01
    formamide 7.0
    cyclopentanone 44.33
    2-pentanone 5.96
    anisole 2.73
    cyclopentyl methyl ether 5.69
    gamma-butyrolactone 35.57
    1-methoxy-2-propanol 36.85
    pyridine 14.18
    3-pentanone 3.83
    furfural 21.72
    n-dodecane 0.02
    diethylene glycol 22.88
    diisopropyl ether 0.26
    tert-amyl alcohol 4.7
    acetylacetone 11.49
    n-hexadecane 0.02
    acetophenone 5.08
    methyl propionate 5.47
    isopentyl acetate 4.58
    trichloroethylene 6.38
    n-nonanol 1.38
    cyclohexanol 3.23
    benzyl alcohol 5.11
    2-ethylhexanol 1.3
    isooctanol 1.65
    dipropyl ether 1.23
    1,2-dichlorobenzene 0.77
    ethyl lactate 5.02
    propylene carbonate 7.87
    n-methylformamide 11.3
    2-pentanol 1.8
    n-pentane 0.01
    1-propoxy-2-propanol 15.86
    1-methoxy-2-propyl acetate 12.66
    2-(2-methoxypropoxy) propanol 17.7
    mesitylene 0.21
    ε-caprolactone 14.87
    p-cymene 0.45
    epichlorohydrin 53.45
    1,1,1-trichloroethane 0.98
    2-aminoethanol 6.86
    morpholine-4-carbaldehyde 48.8
    sulfolane 83.09
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 13.74
    n-hexyl acetate 3.63
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 22.6
    sec-butyl acetate 2.59
    tert-butyl acetate 4.57
    decalin 0.03
    glycerin 22.13
    diglyme 40.25
    acrylic acid 6.91
    isopropyl myristate 1.66
    n-butyric acid 6.32
    acetyl acetate 2.09
    di(2-ethylhexyl) phthalate 3.41
    ethyl propionate 2.98
    nitromethane 25.85
    1,2-diethoxyethane 8.02
    benzonitrile 3.07
    trioctyl phosphate 1.95
    1-bromopropane 0.5
    gamma-valerolactone 78.4
    n-decanol 1.04
    triethyl phosphate 2.49
    4-methyl-2-pentanol 1.39
    propionitrile 2.82
    vinylene carbonate 6.02
    1,1,2-trichlorotrifluoroethane 38.38
    DMS 5.95
    cumene 0.29
    2-octanol 0.89
    2-hexanone 5.88
    octyl acetate 2.25
    limonene 0.6
    1,2-dimethoxyethane 26.82
    ethyl orthosilicate 2.08
    tributyl phosphate 2.48
    diacetone alcohol 17.87
    N,N-dimethylaniline 2.16
    acrylonitrile 5.28
    aniline 3.8
    1,3-propanediol 12.35
    bromobenzene 0.54
    dibromomethane 0.42
    1,1,2,2-tetrachloroethane 5.86
    2-methyl-cyclohexyl acetate 3.9
    tetrabutyl urea 4.61
    diisobutyl methanol 1.08
    2-phenylethanol 4.84
    styrene 0.38
    dioctyl adipate 3.93
    dimethyl sulfate 13.04
    ethyl butyrate 2.83
    methyl lactate 11.4
    butyl lactate 6.34
    diethyl carbonate 1.94
    propanediol butyl ether 12.3
    triethyl orthoformate 3.27
    p-tert-butyltoluene 0.45
    methyl 4-tert-butylbenzoate 7.29
    morpholine 30.6
    tert-butylamine 1.1
    n-dodecanol 0.75
    dimethoxymethane 21.57
    ethylene carbonate 4.32
    cyrene 17.19
    2-ethoxyethyl acetate 8.28
    2-ethylhexyl acetate 2.97
    1,2,4-trichlorobenzene 1.89
    4-methylpyridine 8.65
    dibutyl ether 1.24
    2,6-dimethyl-4-heptanol 1.08
    DEF 9.53
    dimethyl isosorbide 28.69
    tetrachloroethylene 1.76
    eugenol 9.04
    triacetin 7.79
    span 80 10.74
    1,4-butanediol 3.23
    1,1-dichloroethane 0.93
    2-methyl-1-pentanol 3.65
    methyl formate 7.18
    2-methyl-1-butanol 3.94
    n-decane 0.03
    butyronitrile 2.37
    3,7-dimethyl-1-octanol 1.75
    1-chlorooctane 0.23
    1-chlorotetradecane 0.14
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.03
    cyclooctane 0.01
    cyclopentanol 6.54
    tetrahydropyran 6.35
    tert-amyl methyl ether 2.07
    2,5,8-trioxanonane 28.88
    1-hexene 0.12
    2-isopropoxyethanol 11.75
    2,2,2-trifluoroethanol 2.07
    methyl butyrate 4.99

    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