Auranetin

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  • Identifiers

    CAS number
    522-16-7

    Molecular formula
    C20H20O7

    SMILES
    COC1=CC=C(C=C1)C2=C(C(=O)C3=CC(=C(C(=C3O2)OC)OC)OC)OC

    Safety labels

  • Odor profile

    Fragrance
    Spicy 53.26%
    Vanilla 51.0%
    Phenolic 49.96%
    Fruity 46.66%
    Floral 44.65%
    Sweet 43.92%
    Woody 38.45%
    Powdery 37.59%
    Smoky 36.47%
    Balsamic 36.21%

     

    Flavor
    Bitter 81.73%
    Parsley 22.85%
    Eugenol 21.92%
    Bland 21.89%
    Cedarleaf 19.87%
    Lovage 19.65%
    Sweet-like 19.59%
    Ripe apricot 19.32%
    Carrot 19.23%
    Ham 19.16%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    7.04 (neutral)

    Molecular weight
    372.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    730°C

    Melting point expt.

    • 141 °C

    Flash point

    • 198.53 ˚C est.

  • Synonyms

    • Auranetin
    • Aurantin
    • 522-16-7
    • 3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
    • 6532ZBU2J5
    • UNII-6532ZBU2J5
    • FLAVONE, 3,4',6,7,8-PENTAMETHOXY-
    • DTXSID40966575
    • 4H-1-Benzopyran-4-one, 3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-
    • 3,4',6,7,8-Pentamethoxyflavone
    • 3,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
    • 12619-61-3
    • RefChem:115578
    • DTXCID601394208
    • 610-798-8
    • SCHEMBL29643349
    • CHEBI:175776
    • 3,6,7,8,4'-pentamethoxyflavone
    • AAA52216
    • LMPK12111612
    • DB-228470
    • 522-16-7

  • Applications

    Auranetin (CAS 522-16-7) is a flavanone of interest as a natural product and synthetic intermediate. In industrial contexts, it is commonly explored as a synthetic intermediate or scaffold in pharmaceutical/biochemical research; investigated as a plant-defense metabolite (phytoalexin) in agricultural studies; evaluated for cosmetic and personal-care formulations as an antioxidant or functional ingredient; considered as an antioxidant/stabilizer additive in polymer, plastic, and coating formulations; used as an analytical reference material or standard for flavanone profiling in chemical analysis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.52
    methanol 0.42
    isopropanol 0.48
    water 0.0
    ethyl acetate 8.22
    n-propanol 0.73
    acetone 4.06
    n-butanol 0.7
    acetonitrile 3.56
    DMF 10.91
    toluene 1.14
    isobutanol 0.72
    1,4-dioxane 5.32
    methyl acetate 8.21
    THF 10.46
    2-butanone 5.55
    n-pentanol 0.83
    sec-butanol 0.85
    n-hexane 0.2
    ethylene glycol 0.57
    NMP 29.57
    cyclohexane 0.43
    DMSO 11.63
    n-butyl acetate 5.1
    n-octanol 0.87
    chloroform 25.36
    n-propyl acetate 4.85
    acetic acid 6.94
    dichloromethane 34.23
    cyclohexanone 10.86
    propylene glycol 0.31
    isopropyl acetate 4.92
    DMAc 22.13
    2-ethoxyethanol 3.56
    isopentanol 0.94
    n-heptane 0.32
    ethyl formate 4.1
    1,2-dichloroethane 18.1
    n-hexanol 1.03
    2-methoxyethanol 3.73
    isobutyl acetate 2.57
    tetrachloromethane 3.6
    n-pentyl acetate 4.17
    transcutol 8.98
    n-heptanol 1.06
    ethylbenzene 1.07
    MIBK 2.9
    2-propoxyethanol 4.72
    tert-butanol 0.97
    MTBE 1.73
    2-butoxyethanol 3.7
    propionic acid 4.25
    o-xylene 1.66
    formic acid 3.0
    diethyl ether 2.4
    m-xylene 1.02
    p-xylene 1.59
    chlorobenzene 3.64
    dimethyl carbonate 9.22
    n-octane 0.18
    formamide 6.56
    cyclopentanone 15.32
    2-pentanone 4.06
    anisole 2.5
    cyclopentyl methyl ether 4.36
    gamma-butyrolactone 26.17
    1-methoxy-2-propanol 2.76
    pyridine 7.87
    3-pentanone 6.17
    furfural 22.67
    n-dodecane 0.14
    diethylene glycol 4.57
    diisopropyl ether 1.01
    tert-amyl alcohol 1.42
    acetylacetone 9.94
    n-hexadecane 0.18
    acetophenone 5.6
    methyl propionate 9.08
    isopentyl acetate 4.87
    trichloroethylene 44.83
    n-nonanol 1.08
    cyclohexanol 1.69
    benzyl alcohol 2.34
    2-ethylhexanol 1.4
    isooctanol 1.15
    dipropyl ether 2.22
    1,2-dichlorobenzene 6.32
    ethyl lactate 3.18
    propylene carbonate 11.92
    n-methylformamide 4.85
    2-pentanol 0.72
    n-pentane 0.18
    1-propoxy-2-propanol 3.35
    1-methoxy-2-propyl acetate 8.47
    2-(2-methoxypropoxy) propanol 5.73
    mesitylene 0.84
    ε-caprolactone 11.67
    p-cymene 1.72
    epichlorohydrin 26.03
    1,1,1-trichloroethane 11.79
    2-aminoethanol 0.69
    morpholine-4-carbaldehyde 19.22
    sulfolane 34.82
    2,2,4-trimethylpentane 0.24
    2-methyltetrahydrofuran 6.68
    n-hexyl acetate 4.04
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 4.9
    sec-butyl acetate 3.27
    tert-butyl acetate 5.28
    decalin 0.39
    glycerin 1.5
    diglyme 15.38
    acrylic acid 6.84
    isopropyl myristate 1.77
    n-butyric acid 4.02
    acetyl acetate 9.29
    di(2-ethylhexyl) phthalate 2.66
    ethyl propionate 5.9
    nitromethane 23.41
    1,2-diethoxyethane 4.47
    benzonitrile 3.69
    trioctyl phosphate 1.69
    1-bromopropane 4.35
    gamma-valerolactone 19.87
    n-decanol 0.83
    triethyl phosphate 5.38
    4-methyl-2-pentanol 0.69
    propionitrile 2.95
    vinylene carbonate 12.33
    1,1,2-trichlorotrifluoroethane 26.57
    DMS 10.32
    cumene 1.04
    2-octanol 0.81
    2-hexanone 3.45
    octyl acetate 2.24
    limonene 2.12
    1,2-dimethoxyethane 8.57
    ethyl orthosilicate 4.61
    tributyl phosphate 2.42
    diacetone alcohol 5.17
    N,N-dimethylaniline 2.92
    acrylonitrile 5.55
    aniline 2.39
    1,3-propanediol 1.13
    bromobenzene 3.95
    dibromomethane 14.23
    1,1,2,2-tetrachloroethane 28.32
    2-methyl-cyclohexyl acetate 5.28
    tetrabutyl urea 3.49
    diisobutyl methanol 1.17
    2-phenylethanol 3.28
    styrene 1.1
    dioctyl adipate 3.82
    dimethyl sulfate 23.73
    ethyl butyrate 5.3
    methyl lactate 4.84
    butyl lactate 3.37
    diethyl carbonate 5.07
    propanediol butyl ether 1.87
    triethyl orthoformate 5.01
    p-tert-butyltoluene 1.52
    methyl 4-tert-butylbenzoate 7.57
    morpholine 6.2
    tert-butylamine 0.64
    n-dodecanol 0.66
    dimethoxymethane 7.33
    ethylene carbonate 8.96
    cyrene 8.59
    2-ethoxyethyl acetate 7.91
    2-ethylhexyl acetate 4.54
    1,2,4-trichlorobenzene 8.7
    4-methylpyridine 5.16
    dibutyl ether 1.69
    2,6-dimethyl-4-heptanol 1.17
    DEF 9.87
    dimethyl isosorbide 14.71
    tetrachloroethylene 21.78
    eugenol 6.37
    triacetin 8.49
    span 80 3.49
    1,4-butanediol 0.65
    1,1-dichloroethane 7.33
    2-methyl-1-pentanol 1.24
    methyl formate 5.7
    2-methyl-1-butanol 1.05
    n-decane 0.24
    butyronitrile 2.03
    3,7-dimethyl-1-octanol 1.08
    1-chlorooctane 1.06
    1-chlorotetradecane 0.5
    n-nonane 0.2
    undecane 0.18
    tert-butylcyclohexane 0.28
    cyclooctane 0.2
    cyclopentanol 2.11
    tetrahydropyran 3.64
    tert-amyl methyl ether 2.33
    2,5,8-trioxanonane 10.78
    1-hexene 0.61
    2-isopropoxyethanol 2.94
    2,2,2-trifluoroethanol 8.01
    methyl butyrate 6.25

    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