Anhydrogossypol

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  • Identifiers

    CAS number
    73728-76-4

    Molecular formula
    C30H26O6

    SMILES
    CC\1=CC2=C(C(=C(C3=COC(=C23)/C1=C/4\C(=CC5=C(C(=O)C(=O)C6=COC4=C56)C(C)C)C)O)O)C(C)C

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  • Odor profile

    Fragrance
    Phenolic 49.11%
    Burnt 35.5%
    Fruity 33.59%
    Spicy 33.03%
    Dry 33.03%
    Woody 30.8%
    Smoky 28.98%
    Musk 25.93%
    Leathery 24.81%
    Medicinal 24.3%

     

    Flavor
    Bitter 93.61%
    Bland 20.48%
    Odorless 19.81%
    Cedarleaf 19.33%
    Parsley 18.71%
    Nitrile 18.28%
    Very strong 18.25%
    Lovage 18.17%
    Indole 17.86%
    Sweet-like 17.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.4

    pKa est.
    9.16 (weak base)

    Molecular weight
    482.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2569°C

    Flash point

    • 239.92 ˚C est.

  • Synonyms

    • Anhydrogossypol
    • 73728-76-4
    • C8WNV9498S
    • (8,8'-Bi-3H-naphtho(1,8-bc)furan)-3,3'-dione, 4,4'-dihydroxy-7,7'-dimethyl-5,5'-bis(1-methylethyl)-
    • NSC89310
    • Dianhydrogossypol
    • 4,4'-Dihydroxy-7,7'-dimethyl-5,5'-bis(1-methylethyl)(8,8'-bi-3H-naphtho(1,8-bc)furan)-3,3'-dione
    • NSC 89310
    • BRN 0375639
    • NSC-89310
    • 4,4'-Dihydroxy-5,5'-diisopropyl-7,7'-dimethylbis(3H-naphtho(1,8-bc)furan-3-one)
    • UNII-C8WNV9498S
    • 4-19-00-03089 (Beilstein Handbook Reference)
    • CHEMBL1978613
    • DTXSID30224050
    • (8,8'-Bi-3H-naphtho(1,8-bc)furan)-3,3'-dione, 4,4'-dihydroxy-5,5'-diisopropyl-'-dimethyl-
    • NCI60_041987
    • 4,4'-DIHYDROXY-5,5'-DIISOPROPYL-7,7'-DIMETHYLBIS(3H-NAPHTHO(1,8-
    • hydroxy-(hydroxy-isopropyl-methyl-oxo-[?]yl)-isopropyl-methyl-[?]one
    • 4,4'-Dihydroxy-5,5'-diisopropyl-7, {7'-dimethylbis(3H-naphtho[1,8-bc]furan-3-one)}
    • {(8,8'-Bi-3H-naphtho[1,8-bc]furan)-3,3'-dione,} 4,4'-dihydroxy-5, 5'-diisopropyl-'-dimethyl-
    • {[8,8'-Bi-3H-naphtho[1,8-bc]furan]-3,} 3'-dione, 4,4'-dihydroxy-7,7'-dimethyl-5,5'-bis(1-methylethyl)-
    • 4,4'-Dihydroxy-7,7'-dimethyl-5,5'-di(propan-2-yl)-3H,3'H-[8,8'-binaphtho[1,8-bc]furan]-3,3'-dione
    • 73728-76-4

  • Applications

    Anhydrogossypol, CAS 73728-76-4, is a natural-origin polyphenolic compound that is primarily evaluated for research and development use. It can serve as an intermediate for the synthesis of gossypol derivatives in chemical manufacturing. It is studied as a stabilizer/antioxidant for polymers and coatings to improve oxidative and thermal stability, and it may function as a pigment or additive in coatings and inks. It has been investigated as a lead candidate for agricultural pest management with antimicrobial properties and as a research reagent to explore pharmacological activity for medicinal chemistry, with use subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.77
    methanol 0.68
    isopropanol 0.52
    water 0.0
    ethyl acetate 1.21
    n-propanol 0.97
    acetone 2.69
    n-butanol 0.9
    acetonitrile 0.66
    DMF 5.17
    toluene 1.7
    isobutanol 0.77
    1,4-dioxane 3.99
    methyl acetate 1.59
    THF 10.6
    2-butanone 3.69
    n-pentanol 1.33
    sec-butanol 0.69
    n-hexane 0.07
    ethylene glycol 0.26
    NMP 10.61
    cyclohexane 0.07
    DMSO 3.78
    n-butyl acetate 2.39
    n-octanol 1.29
    chloroform 5.1
    n-propyl acetate 2.02
    acetic acid 1.45
    dichloromethane 5.59
    cyclohexanone 6.93
    propylene glycol 0.28
    isopropyl acetate 1.18
    DMAc 8.52
    2-ethoxyethanol 2.76
    isopentanol 0.98
    n-heptane 0.07
    ethyl formate 1.29
    1,2-dichloroethane 3.45
    n-hexanol 1.31
    2-methoxyethanol 2.42
    isobutyl acetate 1.95
    tetrachloromethane 0.55
    n-pentyl acetate 4.67
    transcutol 3.9
    n-heptanol 1.6
    ethylbenzene 1.0
    MIBK 1.83
    2-propoxyethanol 4.46
    tert-butanol 0.63
    MTBE 0.9
    2-butoxyethanol 4.59
    propionic acid 1.1
    o-xylene 0.81
    formic acid 0.57
    diethyl ether 0.88
    m-xylene 0.89
    p-xylene 1.48
    chlorobenzene 2.18
    dimethyl carbonate 1.22
    n-octane 0.08
    formamide 1.01
    cyclopentanone 9.86
    2-pentanone 2.6
    anisole 1.75
    cyclopentyl methyl ether 2.43
    gamma-butyrolactone 7.19
    1-methoxy-2-propanol 1.71
    pyridine 7.51
    3-pentanone 2.15
    furfural 6.81
    n-dodecane 0.07
    diethylene glycol 2.36
    diisopropyl ether 0.26
    tert-amyl alcohol 0.87
    acetylacetone 2.98
    n-hexadecane 0.09
    acetophenone 3.35
    methyl propionate 1.62
    isopentyl acetate 2.79
    trichloroethylene 8.01
    n-nonanol 1.51
    cyclohexanol 0.85
    benzyl alcohol 2.59
    2-ethylhexanol 1.15
    isooctanol 1.55
    dipropyl ether 0.93
    1,2-dichlorobenzene 1.97
    ethyl lactate 1.22
    propylene carbonate 2.71
    n-methylformamide 1.86
    2-pentanol 0.47
    n-pentane 0.04
    1-propoxy-2-propanol 2.65
    1-methoxy-2-propyl acetate 2.87
    2-(2-methoxypropoxy) propanol 3.17
    mesitylene 0.4
    ε-caprolactone 5.1
    p-cymene 0.78
    epichlorohydrin 10.09
    1,1,1-trichloroethane 2.01
    2-aminoethanol 0.55
    morpholine-4-carbaldehyde 8.21
    sulfolane 10.62
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 4.18
    n-hexyl acetate 3.73
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 4.16
    sec-butyl acetate 1.47
    tert-butyl acetate 1.48
    decalin 0.1
    glycerin 0.68
    diglyme 6.51
    acrylic acid 1.4
    isopropyl myristate 1.37
    n-butyric acid 1.57
    acetyl acetate 0.98
    di(2-ethylhexyl) phthalate 2.51
    ethyl propionate 1.36
    nitromethane 2.62
    1,2-diethoxyethane 2.56
    benzonitrile 2.58
    trioctyl phosphate 1.62
    1-bromopropane 1.49
    gamma-valerolactone 13.59
    n-decanol 1.02
    triethyl phosphate 1.12
    4-methyl-2-pentanol 0.45
    propionitrile 1.2
    vinylene carbonate 2.76
    1,1,2-trichlorotrifluoroethane 6.63
    DMS 2.43
    cumene 0.72
    2-octanol 1.32
    2-hexanone 3.95
    octyl acetate 1.97
    limonene 0.82
    1,2-dimethoxyethane 4.83
    ethyl orthosilicate 1.11
    tributyl phosphate 1.47
    diacetone alcohol 2.31
    N,N-dimethylaniline 1.63
    acrylonitrile 1.89
    aniline 1.71
    1,3-propanediol 0.94
    bromobenzene 2.24
    dibromomethane 3.13
    1,1,2,2-tetrachloroethane 5.37
    2-methyl-cyclohexyl acetate 2.44
    tetrabutyl urea 3.05
    diisobutyl methanol 0.54
    2-phenylethanol 3.59
    styrene 1.01
    dioctyl adipate 2.2
    dimethyl sulfate 2.39
    ethyl butyrate 1.44
    methyl lactate 1.16
    butyl lactate 3.17
    diethyl carbonate 0.92
    propanediol butyl ether 2.71
    triethyl orthoformate 1.46
    p-tert-butyltoluene 0.66
    methyl 4-tert-butylbenzoate 4.13
    morpholine 4.57
    tert-butylamine 0.3
    n-dodecanol 0.69
    dimethoxymethane 3.0
    ethylene carbonate 2.04
    cyrene 5.63
    2-ethoxyethyl acetate 5.67
    2-ethylhexyl acetate 2.52
    1,2,4-trichlorobenzene 3.27
    4-methylpyridine 4.95
    dibutyl ether 1.17
    2,6-dimethyl-4-heptanol 0.54
    DEF 2.89
    dimethyl isosorbide 6.25
    tetrachloroethylene 4.01
    eugenol 4.86
    triacetin 2.97
    span 80 3.26
    1,4-butanediol 0.69
    1,1-dichloroethane 1.84
    2-methyl-1-pentanol 1.57
    methyl formate 1.53
    2-methyl-1-butanol 1.01
    n-decane 0.14
    butyronitrile 1.24
    3,7-dimethyl-1-octanol 1.05
    1-chlorooctane 0.76
    1-chlorotetradecane 0.32
    n-nonane 0.1
    undecane 0.1
    tert-butylcyclohexane 0.09
    cyclooctane 0.04
    cyclopentanol 1.29
    tetrahydropyran 2.93
    tert-amyl methyl ether 0.89
    2,5,8-trioxanonane 4.71
    1-hexene 0.42
    2-isopropoxyethanol 2.4
    2,2,2-trifluoroethanol 0.67
    methyl butyrate 2.11

    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