2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    129145-53-5

    Molecular formula
    C20H18O6

    SMILES
    CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 59.93%
    Odorless 42.31%
    Spicy 38.58%
    Burnt 35.65%
    Smoky 33.16%
    Medicinal 28.54%
    Woody 25.25%
    Dry 23.26%
    Balsamic 21.31%
    Animal 20.69%

     

    Flavor
    Bitter 92.73%
    Odorless 21.32%
    Cedarleaf 20.74%
    Parsley 20.09%
    Lovage 20.03%
    Nitrile 19.45%
    Eugenol 19.41%
    Sweet-like 19.4%
    Very strong 19.11%
    Bland 19.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.2

    pKa est.
    10.25 (weak base)

    Molecular weight
    354.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    876°C

    Melting point expt.

    • 245 - 248 °C

    Flash point

    • 242.17 ˚C est.

  • Synonyms

    • Gancaonin O
    • DTXSID101128143
    • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
    • RefChem:1061001
    • DTXCID801559646
    • 129145-53-5
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-
    • CHEMBL1915459
    • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
    • orb1681245
    • SCHEMBL4836863
    • SCHEMBL31691719
    • CHEBI:175547
    • EFA14553
    • BDBM50358101
    • LMPK12110726
    • AKOS030553579
    • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
    • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI
    • 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
    • 129145-53-5

  • Applications

    2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one (CAS 129145-53-5) has practical applications across several sectors, including as an intermediate in organic synthesis for flavonoid derivatives used in pharmaceutical and agricultural research; in cosmetics and personal care, it may serve as an antioxidant additive or formulation stabilizer; in fragrance and perfumery, its polyphenolic scaffold and prenyl side chain support use as a fragrance ingredient or odorant/fixative; in coatings, paints and inks, it can function as an antioxidant or stabilizer for polymers; additionally, it is evaluated as a precursor for dye/pigment derivatives and as a lead scaffold in pharmaceutical development, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.73
    methanol 1.72
    isopropanol 2.01
    water 0.0
    ethyl acetate 1.27
    n-propanol 3.22
    acetone 2.0
    n-butanol 2.1
    acetonitrile 0.96
    DMF 31.21
    toluene 0.13
    isobutanol 1.68
    1,4-dioxane 7.37
    methyl acetate 3.15
    THF 43.21
    2-butanone 5.64
    n-pentanol 1.73
    sec-butanol 2.8
    n-hexane 0.01
    ethylene glycol 3.68
    NMP 25.21
    cyclohexane 0.01
    DMSO 134.65
    n-butyl acetate 1.46
    n-octanol 0.65
    chloroform 0.06
    n-propyl acetate 1.58
    acetic acid 7.47
    dichloromethane 0.08
    cyclohexanone 5.72
    propylene glycol 11.01
    isopropyl acetate 1.22
    DMAc 59.23
    2-ethoxyethanol 19.66
    isopentanol 1.81
    n-heptane 0.01
    ethyl formate 1.08
    1,2-dichloroethane 0.19
    n-hexanol 0.81
    2-methoxyethanol 51.92
    isobutyl acetate 1.01
    tetrachloromethane 0.01
    n-pentyl acetate 1.58
    transcutol 72.96
    n-heptanol 0.92
    ethylbenzene 0.1
    MIBK 1.53
    2-propoxyethanol 20.93
    tert-butanol 3.1
    MTBE 1.01
    2-butoxyethanol 9.64
    propionic acid 4.54
    o-xylene 0.11
    formic acid 4.41
    diethyl ether 0.45
    m-xylene 0.1
    p-xylene 0.16
    chlorobenzene 0.1
    dimethyl carbonate 2.52
    n-octane 0.01
    formamide 10.07
    cyclopentanone 15.76
    2-pentanone 1.88
    anisole 1.19
    cyclopentyl methyl ether 2.11
    gamma-butyrolactone 20.47
    1-methoxy-2-propanol 37.53
    pyridine 4.59
    3-pentanone 1.2
    furfural 12.7
    n-dodecane 0.01
    diethylene glycol 23.14
    diisopropyl ether 0.12
    tert-amyl alcohol 3.17
    acetylacetone 5.19
    n-hexadecane 0.01
    acetophenone 2.1
    methyl propionate 2.9
    isopentyl acetate 1.94
    trichloroethylene 0.59
    n-nonanol 0.83
    cyclohexanol 1.3
    benzyl alcohol 2.11
    2-ethylhexanol 0.58
    isooctanol 0.94
    dipropyl ether 0.79
    1,2-dichlorobenzene 0.13
    ethyl lactate 3.19
    propylene carbonate 3.69
    n-methylformamide 8.2
    2-pentanol 1.01
    n-pentane 0.0
    1-propoxy-2-propanol 12.92
    1-methoxy-2-propyl acetate 7.5
    2-(2-methoxypropoxy) propanol 14.26
    mesitylene 0.07
    ε-caprolactone 6.83
    p-cymene 0.16
    epichlorohydrin 20.55
    1,1,1-trichloroethane 0.09
    2-aminoethanol 7.54
    morpholine-4-carbaldehyde 37.51
    sulfolane 54.42
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 6.16
    n-hexyl acetate 2.04
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 20.56
    sec-butyl acetate 1.12
    tert-butyl acetate 2.61
    decalin 0.01
    glycerin 31.31
    diglyme 34.39
    acrylic acid 5.42
    isopropyl myristate 0.95
    n-butyric acid 3.37
    acetyl acetate 1.04
    di(2-ethylhexyl) phthalate 1.83
    ethyl propionate 1.35
    nitromethane 18.7
    1,2-diethoxyethane 5.68
    benzonitrile 0.91
    trioctyl phosphate 1.16
    1-bromopropane 0.08
    gamma-valerolactone 49.03
    n-decanol 0.61
    triethyl phosphate 1.28
    4-methyl-2-pentanol 0.7
    propionitrile 1.05
    vinylene carbonate 2.55
    1,1,2-trichlorotrifluoroethane 23.84
    DMS 3.24
    cumene 0.09
    2-octanol 0.54
    2-hexanone 2.16
    octyl acetate 1.34
    limonene 0.18
    1,2-dimethoxyethane 23.78
    ethyl orthosilicate 1.21
    tributyl phosphate 1.4
    diacetone alcohol 13.12
    N,N-dimethylaniline 0.92
    acrylonitrile 2.25
    aniline 1.11
    1,3-propanediol 11.88
    bromobenzene 0.06
    dibromomethane 0.04
    1,1,2,2-tetrachloroethane 0.71
    2-methyl-cyclohexyl acetate 1.86
    tetrabutyl urea 2.55
    diisobutyl methanol 0.58
    2-phenylethanol 1.93
    styrene 0.1
    dioctyl adipate 2.42
    dimethyl sulfate 8.18
    ethyl butyrate 1.29
    methyl lactate 9.03
    butyl lactate 4.06
    diethyl carbonate 0.91
    propanediol butyl ether 11.56
    triethyl orthoformate 1.98
    p-tert-butyltoluene 0.18
    methyl 4-tert-butylbenzoate 4.79
    morpholine 20.82
    tert-butylamine 0.47
    n-dodecanol 0.43
    dimethoxymethane 14.01
    ethylene carbonate 1.73
    cyrene 14.17
    2-ethoxyethyl acetate 5.46
    2-ethylhexyl acetate 1.18
    1,2,4-trichlorobenzene 0.4
    4-methylpyridine 2.32
    dibutyl ether 0.78
    2,6-dimethyl-4-heptanol 0.58
    DEF 4.69
    dimethyl isosorbide 22.98
    tetrachloroethylene 0.26
    eugenol 6.49
    triacetin 5.31
    span 80 8.45
    1,4-butanediol 3.25
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 1.71
    methyl formate 4.87
    2-methyl-1-butanol 2.01
    n-decane 0.01
    butyronitrile 0.75
    3,7-dimethyl-1-octanol 0.94
    1-chlorooctane 0.1
    1-chlorotetradecane 0.06
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 3.13
    tetrahydropyran 2.45
    tert-amyl methyl ether 1.17
    2,5,8-trioxanonane 25.33
    1-hexene 0.04
    2-isopropoxyethanol 10.02
    2,2,2-trifluoroethanol 1.98
    methyl butyrate 2.24

    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