2-(3,4-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-3,6,7-trihydroxy-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    139163-16-9

    Molecular formula
    C20H18O7

    SMILES
    CC(=CCC1=C(C=CC(=C1O)O)C2=C(C(=O)C3=CC(=C(C=C3O2)O)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 54.48%
    Odorless 45.69%
    Burnt 40.14%
    Spicy 33.91%
    Smoky 31.62%
    Medicinal 23.74%
    Dry 22.05%
    Balsamic 20.88%
    Woody 20.57%
    Savory 19.29%

     

    Flavor
    Bitter 91.26%
    Odorless 22.61%
    Bland 20.38%
    Sweet-like 20.31%
    Cedarleaf 20.17%
    Eugenol 19.99%
    Parsley 19.98%
    Lovage 19.43%
    Nitrile 19.36%
    Very strong 19.21%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    10.23 (weak base)

    Molecular weight
    370.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1134°C

    Melting point expt.

    • 229 - 231 °C

    Flash point

    • 258.3 ˚C est.

  • Synonyms

    • Neouralenol
    • 139163-16-9
    • 2-[3,4-dihydroxy-2-(3-methylbut-2-enyl)phenyl]-3,6,7-trihydroxychromen-4-one
    • 3,6,7,3',4'-Pentahydroxy-2'-isoprenylflavone
    • 2-(3,4-dihydroxy-2-(3-methylbut-2-enyl)phenyl)-3,6,7-trihydroxychromen-4-one
    • RefChem:909186
    • DTXCID8083438
    • 2-(3,4-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-3,6,7-trihydroxy-4H-1-benzopyran-4-one
    • DTXSID10160947
    • 4H-Benzopyran-4-one, 2-(3,4-dihydroxy-2-(3-methyl-2-butenyl)phenyl)-3,6,7-trihydroxy-
    • SCHEMBL1171358
    • SCHEMBL31467397
    • CHEBI:175757
    • LMPK12111590
    • 3',4',6,7-Tetrahydroxy-2'-prenylflavonol
    • 2-[3,4-Dihydroxy-2-(3-methyl-2-butenyl)phenyl]-3,6,7-trihydroxy-4H-1-benzopyran-4-one
    • 139163-16-9

  • Applications

    CAS number: 139163-16-9 corresponds to 2-(3,4-Dihydroxy-2-(3-methyl-2-buten-1-yl)phenyl)-3,6,7-trihydroxy-4H-1-benzopyran-4-one, a prenylated flavonoid-type polyphenol; in real-world applications, it is commonly evaluated as an antioxidant and radical scavenger in cosmetics and personal care formulations, contributing to formulation stability and skin-conditioning properties. It can serve as an oxidative stabilizer in polymer and coating formulations to extend shelf life and performance. In pharmaceutical and agrochemical research, it is used as a synthetic intermediate or lead scaffold for natural-product-inspired compounds. It may thus be considered in early-stage drug discovery and agrochemical research programs, and it can provide functional benefits as an additive in cleaning products or other industrial formulations to improve stability and longevity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.49
    methanol 1.52
    isopropanol 1.32
    water 0.01
    ethyl acetate 0.85
    n-propanol 2.61
    acetone 0.21
    n-butanol 1.58
    acetonitrile 0.18
    DMF 10.45
    toluene 0.07
    isobutanol 1.08
    1,4-dioxane 2.69
    methyl acetate 1.34
    THF 11.63
    2-butanone 1.75
    n-pentanol 0.77
    sec-butanol 2.94
    n-hexane 0.0
    ethylene glycol 2.57
    NMP 10.85
    cyclohexane 0.0
    DMSO 10.31
    n-butyl acetate 0.54
    n-octanol 0.88
    chloroform 0.02
    n-propyl acetate 0.48
    acetic acid 3.61
    dichloromethane 0.03
    cyclohexanone 1.33
    propylene glycol 5.18
    isopropyl acetate 0.63
    DMAc 24.91
    2-ethoxyethanol 10.07
    isopentanol 1.13
    n-heptane 0.01
    ethyl formate 0.43
    1,2-dichloroethane 0.05
    n-hexanol 0.59
    2-methoxyethanol 26.81
    isobutyl acetate 0.22
    tetrachloromethane 0.01
    n-pentyl acetate 1.2
    transcutol 21.68
    n-heptanol 1.06
    ethylbenzene 0.06
    MIBK 0.45
    2-propoxyethanol 9.57
    tert-butanol 1.78
    MTBE 0.96
    2-butoxyethanol 6.78
    propionic acid 3.18
    o-xylene 0.09
    formic acid 4.04
    diethyl ether 0.42
    m-xylene 0.06
    p-xylene 0.06
    chlorobenzene 0.03
    dimethyl carbonate 1.54
    n-octane 0.01
    formamide 7.38
    cyclopentanone 3.12
    2-pentanone 0.61
    anisole 0.59
    cyclopentyl methyl ether 1.31
    gamma-butyrolactone 5.57
    1-methoxy-2-propanol 19.82
    pyridine 1.86
    3-pentanone 0.57
    furfural 3.76
    n-dodecane 0.01
    diethylene glycol 9.5
    diisopropyl ether 0.11
    tert-amyl alcohol 3.32
    acetylacetone 1.11
    n-hexadecane 0.01
    acetophenone 0.78
    methyl propionate 1.99
    isopentyl acetate 0.7
    trichloroethylene 0.15
    n-nonanol 1.08
    cyclohexanol 1.0
    benzyl alcohol 0.96
    2-ethylhexanol 0.39
    isooctanol 0.86
    dipropyl ether 0.54
    1,2-dichlorobenzene 0.04
    ethyl lactate 1.52
    propylene carbonate 1.06
    n-methylformamide 3.7
    2-pentanol 1.1
    n-pentane 0.0
    1-propoxy-2-propanol 6.4
    1-methoxy-2-propyl acetate 3.23
    2-(2-methoxypropoxy) propanol 7.27
    mesitylene 0.04
    ε-caprolactone 3.0
    p-cymene 0.11
    epichlorohydrin 4.47
    1,1,1-trichloroethane 0.02
    2-aminoethanol 5.57
    morpholine-4-carbaldehyde 15.94
    sulfolane 10.59
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.99
    n-hexyl acetate 1.54
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 10.11
    sec-butyl acetate 0.47
    tert-butyl acetate 1.28
    decalin 0.01
    glycerin 15.99
    diglyme 15.44
    acrylic acid 3.28
    isopropyl myristate 0.54
    n-butyric acid 2.25
    acetyl acetate 0.34
    di(2-ethylhexyl) phthalate 0.88
    ethyl propionate 0.68
    nitromethane 5.04
    1,2-diethoxyethane 2.46
    benzonitrile 0.25
    trioctyl phosphate 0.66
    1-bromopropane 0.04
    gamma-valerolactone 12.09
    n-decanol 0.67
    triethyl phosphate 0.64
    4-methyl-2-pentanol 0.53
    propionitrile 0.39
    vinylene carbonate 0.83
    1,1,2-trichlorotrifluoroethane 8.13
    DMS 1.75
    cumene 0.05
    2-octanol 0.76
    2-hexanone 0.49
    octyl acetate 0.89
    limonene 0.12
    1,2-dimethoxyethane 7.91
    ethyl orthosilicate 0.7
    tributyl phosphate 0.62
    diacetone alcohol 5.66
    N,N-dimethylaniline 0.53
    acrylonitrile 0.76
    aniline 0.65
    1,3-propanediol 7.51
    bromobenzene 0.02
    dibromomethane 0.01
    1,1,2,2-tetrachloroethane 0.21
    2-methyl-cyclohexyl acetate 0.66
    tetrabutyl urea 1.18
    diisobutyl methanol 0.35
    2-phenylethanol 1.15
    styrene 0.05
    dioctyl adipate 1.11
    dimethyl sulfate 3.6
    ethyl butyrate 0.55
    methyl lactate 5.56
    butyl lactate 2.49
    diethyl carbonate 0.41
    propanediol butyl ether 7.17
    triethyl orthoformate 1.02
    p-tert-butyltoluene 0.13
    methyl 4-tert-butylbenzoate 2.99
    morpholine 9.07
    tert-butylamine 0.42
    n-dodecanol 0.41
    dimethoxymethane 6.32
    ethylene carbonate 0.55
    cyrene 5.44
    2-ethoxyethyl acetate 3.31
    2-ethylhexyl acetate 0.47
    1,2,4-trichlorobenzene 0.14
    4-methylpyridine 0.77
    dibutyl ether 0.58
    2,6-dimethyl-4-heptanol 0.35
    DEF 3.04
    dimethyl isosorbide 8.02
    tetrachloroethylene 0.12
    eugenol 3.67
    triacetin 2.54
    span 80 5.25
    1,4-butanediol 1.51
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.86
    methyl formate 1.58
    2-methyl-1-butanol 1.69
    n-decane 0.02
    butyronitrile 0.23
    3,7-dimethyl-1-octanol 0.74
    1-chlorooctane 0.11
    1-chlorotetradecane 0.04
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 1.67
    tetrahydropyran 1.19
    tert-amyl methyl ether 1.5
    2,5,8-trioxanonane 10.61
    1-hexene 0.02
    2-isopropoxyethanol 4.53
    2,2,2-trifluoroethanol 1.13
    methyl butyrate 0.83

    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