8-Hydroxygenistein

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  • Identifiers

    CAS number
    13539-27-0

    Molecular formula
    C15H10O6

    SMILES
    C1=CC(=CC=C1C2=COC3=C(C2=O)C(=CC(=C3O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 65.22%
    Odorless 56.21%
    Burnt 40.32%
    Medicinal 30.31%
    Smoky 29.86%
    Spicy 25.35%
    Bitter 21.3%
    Savory 20.48%
    Balsamic 19.87%
    Meaty 19.12%

     

    Flavor
    Bitter 95.2%
    Odorless 22.24%
    Sweet-like 20.52%
    Very strong 20.44%
    Indole 19.99%
    Cedarleaf 19.88%
    Nitrile 19.73%
    Lovage 19.49%
    Rotten 19.42%
    Eugenol 19.35%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    10.12 (weak base)

    Molecular weight
    286.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    864°C

    Flash point

    • 242.39 ˚C est.

  • Synonyms

    • 8-Hydroxygenistein
    • 13539-27-0
    • 5,7,8-trihydroxy-3-(4-hydroxyphenyl)chromen-4-one
    • DTXSID40159329
    • RefChem:1074715
    • DTXCID2081820
    • 4',5,7,8-Tetrahydroxyisoflavone
    • 5,7,8-Trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
    • 5,7,8-Trihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • BRN 1294503
    • Isoflavone, 4',5,7,8-tetrahydroxy-
    • 3-(4-Hydroxyphenyl)-5,7,8-trihydroxy-4H-1-benzopyran-4-one
    • 8'-HYDROXYGENISTEIN
    • 8-OHG
    • SCHEMBL572094
    • orb2814433
    • CHEBI:234032
    • 4H-1-Benzopyran-4-one, 3-(4-hydroxyphenyl)-5,7,8-trihydroxy-
    • FH65340
    • HY-W753779
    • H50811
    • 13539-27-0

  • Applications

    8-Hydroxygenistein (CAS 13539-27-0) is used as a chemical intermediate and research reagent within the isoflavone class; in pharmaceutical development it serves as a lead scaffold for synthesizing related isoflavone derivatives and for medicinal chemistry studies. It is also employed as a building block in organic synthesis to access more complex natural-product mimetics. In cosmetics and personal care, it is explored as a polyphenolic antioxidant additive in formulations. In analytical and phytochemical work, it can be used as a reference standard or analytical reagent for characterizing isoflavonoids. Additionally, it has been evaluated for potential use in coatings and polymer formulations as an antioxidant or stabilizer, depending on formulation and regulatory considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.98
    methanol 4.48
    isopropanol 6.89
    water 0.0
    ethyl acetate 4.47
    n-propanol 9.0
    acetone 1.74
    n-butanol 10.22
    acetonitrile 0.76
    DMF 25.21
    toluene 0.17
    isobutanol 4.42
    1,4-dioxane 6.09
    methyl acetate 3.56
    THF 78.82
    2-butanone 12.35
    n-pentanol 4.01
    sec-butanol 10.91
    n-hexane 0.01
    ethylene glycol 3.31
    NMP 19.53
    cyclohexane 0.01
    DMSO 142.49
    n-butyl acetate 2.75
    n-octanol 2.03
    chloroform 0.0
    n-propyl acetate 2.92
    acetic acid 2.45
    dichloromethane 0.0
    cyclohexanone 9.98
    propylene glycol 4.19
    isopropyl acetate 3.8
    DMAc 55.99
    2-ethoxyethanol 26.34
    isopentanol 8.52
    n-heptane 0.02
    ethyl formate 1.72
    1,2-dichloroethane 0.03
    n-hexanol 3.03
    2-methoxyethanol 79.58
    isobutyl acetate 0.73
    tetrachloromethane 0.0
    n-pentyl acetate 2.29
    transcutol 28.99
    n-heptanol 2.45
    ethylbenzene 0.14
    MIBK 4.93
    2-propoxyethanol 27.56
    tert-butanol 11.09
    MTBE 3.52
    2-butoxyethanol 11.11
    propionic acid 2.7
    o-xylene 0.22
    formic acid 2.57
    diethyl ether 1.9
    m-xylene 0.17
    p-xylene 0.13
    chlorobenzene 0.02
    dimethyl carbonate 2.04
    n-octane 0.01
    formamide 8.18
    cyclopentanone 20.38
    2-pentanone 8.9
    anisole 1.23
    cyclopentyl methyl ether 7.33
    gamma-butyrolactone 14.91
    1-methoxy-2-propanol 57.32
    pyridine 2.77
    3-pentanone 3.66
    furfural 6.63
    n-dodecane 0.02
    diethylene glycol 21.56
    diisopropyl ether 0.39
    tert-amyl alcohol 12.93
    acetylacetone 7.96
    n-hexadecane 0.03
    acetophenone 1.99
    methyl propionate 6.07
    isopentyl acetate 2.89
    trichloroethylene 0.04
    n-nonanol 2.47
    cyclohexanol 4.91
    benzyl alcohol 1.86
    2-ethylhexanol 1.87
    isooctanol 2.0
    dipropyl ether 2.16
    1,2-dichlorobenzene 0.03
    ethyl lactate 3.37
    propylene carbonate 2.31
    n-methylformamide 9.42
    2-pentanol 6.04
    n-pentane 0.01
    1-propoxy-2-propanol 17.32
    1-methoxy-2-propyl acetate 8.36
    2-(2-methoxypropoxy) propanol 10.71
    mesitylene 0.1
    ε-caprolactone 9.89
    p-cymene 0.26
    epichlorohydrin 12.97
    1,1,1-trichloroethane 0.01
    2-aminoethanol 7.52
    morpholine-4-carbaldehyde 21.7
    sulfolane 36.61
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 17.63
    n-hexyl acetate 3.28
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 16.42
    sec-butyl acetate 2.13
    tert-butyl acetate 5.49
    decalin 0.01
    glycerin 16.69
    diglyme 26.14
    acrylic acid 2.17
    isopropyl myristate 1.51
    n-butyric acid 5.58
    acetyl acetate 0.99
    di(2-ethylhexyl) phthalate 1.22
    ethyl propionate 3.53
    nitromethane 7.65
    1,2-diethoxyethane 5.47
    benzonitrile 0.62
    trioctyl phosphate 1.25
    1-bromopropane 0.05
    gamma-valerolactone 35.66
    n-decanol 1.79
    triethyl phosphate 1.52
    4-methyl-2-pentanol 2.85
    propionitrile 2.0
    vinylene carbonate 1.11
    1,1,2-trichlorotrifluoroethane 8.74
    DMS 1.86
    cumene 0.11
    2-octanol 1.75
    2-hexanone 4.95
    octyl acetate 2.05
    limonene 0.4
    1,2-dimethoxyethane 31.62
    ethyl orthosilicate 1.44
    tributyl phosphate 1.33
    diacetone alcohol 24.79
    N,N-dimethylaniline 0.95
    acrylonitrile 2.7
    aniline 1.17
    1,3-propanediol 23.45
    bromobenzene 0.01
    dibromomethane 0.0
    1,1,2,2-tetrachloroethane 0.07
    2-methyl-cyclohexyl acetate 1.8
    tetrabutyl urea 2.73
    diisobutyl methanol 1.5
    2-phenylethanol 2.34
    styrene 0.09
    dioctyl adipate 2.1
    dimethyl sulfate 5.4
    ethyl butyrate 2.85
    methyl lactate 9.27
    butyl lactate 3.58
    diethyl carbonate 1.12
    propanediol butyl ether 8.03
    triethyl orthoformate 2.6
    p-tert-butyltoluene 0.29
    methyl 4-tert-butylbenzoate 3.51
    morpholine 25.31
    tert-butylamine 1.7
    n-dodecanol 1.17
    dimethoxymethane 22.06
    ethylene carbonate 1.11
    cyrene 8.21
    2-ethoxyethyl acetate 4.08
    2-ethylhexyl acetate 1.66
    1,2,4-trichlorobenzene 0.09
    4-methylpyridine 2.29
    dibutyl ether 1.87
    2,6-dimethyl-4-heptanol 1.5
    DEF 14.14
    dimethyl isosorbide 15.06
    tetrachloroethylene 0.04
    eugenol 4.21
    triacetin 2.85
    span 80 5.91
    1,4-butanediol 3.21
    1,1-dichloroethane 0.01
    2-methyl-1-pentanol 4.06
    methyl formate 3.51
    2-methyl-1-butanol 8.29
    n-decane 0.04
    butyronitrile 2.1
    3,7-dimethyl-1-octanol 2.0
    1-chlorooctane 0.26
    1-chlorotetradecane 0.11
    n-nonane 0.02
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 6.95
    tetrahydropyran 5.43
    tert-amyl methyl ether 5.12
    2,5,8-trioxanonane 18.44
    1-hexene 0.06
    2-isopropoxyethanol 11.79
    2,2,2-trifluoroethanol 0.77
    methyl butyrate 5.22

    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