Gossypol

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  • Identifiers

    CAS number
    303-45-7

    Molecular formula
    C30H30O8

    SMILES
    CC1=CC2=C(C(=C(C(=C2C(C)C)O)O)C=O)C(=C1C3=C(C4=C(C=C3C)C(=C(C(=C4C=O)O)O)C(C)C)O)O

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Phenolic 52.24%
    Odorless 36.23%
    Spicy 34.56%
    Burnt 33.56%
    Smoky 31.24%
    Dry 30.71%
    Woody 29.2%
    Medicinal 24.49%
    Balsamic 21.16%
    Leathery 20.31%

     

    Flavor
    Bitter 87.43%
    Odorless 28.01%
    Bland 24.69%
    Cedarleaf 20.69%
    Sweet-like 20.32%
    Parsley 20.09%
    Nitrile 19.75%
    Eugenol 19.66%
    Mild 19.53%
    Lovage 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.9

    pKa est.
    8.6 (weak base)

    Molecular weight
    518.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3028°C

    Melting point expt.

    • 184 °C (from ether); 199 °C (from chloroform); 214 °C (from ligroin)
    • 178 - 183 °C

    Flash point

    • 316.29 ˚C est.

    Solubility expt.

    • Very soluble in methanol, ethanol, cold dioxane, diethylene glucol, ether, ethyl acetate, acetone, carbon tetrachloride, pyridine, chloroform, DMF, lipds. Freely soluble (with slow desomposition) in dilute aqueous solutions of ammonia and sodium carbonate. Slightly soluble in glycerol, cyclohexane. Insoluble in water.
    • Insoluble in water; soluble in alcohol

  • Synonyms

    • gossypol
    • 303-45-7
    • Pogosin
    • Tash 1
    • No Fertil
    • (+-)-Gossypol
    • 7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
    • BL 193
    • CCRIS 2689
    • DTXSID5023110
    • NSC56817
    • NSC 56817
    • NSC-56817
    • NSC 624336
    • NSC-624336
    • BRN 1917878
    • KAV15B369O
    • AI3-22957
    • BL-193
    • NSC624336
    • DTXCID803110
    • CHEBI:28584
    • 8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene
    • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-
    • [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-
    • 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
    • 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)(2,2'-binaphthalene)-8,8'-dicarboxaldehyde
    • Cottonseed Meal Toxin
    • RefChem:782655
    • 2,2'-bis(1,6,7-trihydroxy-4-methyl-5-isopropyl-8-aldehydonaphthalene)
    • 2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
    • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6'7, 7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-
    • 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3-3'-dimethyl(2,2'-binaphthalene)-8,8'-dicarboxaldehyde
    • 90141-22-3
    • (-)-Gossypol
    • (+)-Gossypol
    • (R)-Gossypol
    • (R)-(-)-Gossypol
    • AT 101
    • (+/-)-Gossypol
    • AT101
    • 20300-26-9
    • 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-8,8'-dicarbaldehyde
    • Gossypol, (R)-
    • Gossypol, (S)-
    • MFCD00017352
    • XNA7DR63CQ
    • 8DY2X8LXW4
    • CHEMBL51483
    • 303-45-7 (free)
    • 2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene)
    • Gossypol-d2
    • NSC-726190
    • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-, (+)-
    • [2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)-
    • 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde
    • NCGC00016423-03
    • CAS-303-45-7
    • ST065835
    • racemic-Gossypol
    • 4-08-00-03754 (Beilstein Handbook Reference)
    • 7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde
    • 113580-77-1
    • gosipol
    • ( inverted exclamation markA)-GOSSYPOL FROM COTTON SEEDS
    • ;ssypol
    • 1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)[2,2'-binaphthalene]-8,8'-dicarbaldehyde
    • 7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde
    • Gossypol Sodium Salt
    • Gissypol, (R)-
    • Sodium Salt, Gossypol
    • (S)-(+)-Gossypol
    • Gossypol, (+)-Isomer
    • Gossypol, (-)-Isomer
    • SR-01000597521
    • C30H30O8
    • Gossypol Dipotassium Salt
    • UNII-XNA7DR63CQ
    • Gossypol, (+-)-Isomer
    • Dipotassium Salt, Gossypol
    • UNII-8DY2X8LXW4
    • ssypol
    • UNII-KAV15B369O
    • HSDB 7872
    • Gossypol, 4
    • (S)-Gossypol
    • GO3
    • Gossypol (Standard)
    • Prestwick_1031
    • R-(-)-gossypol
    • Spectrum_000359
    • Spectrum_001521
    • Tocris-1964
    • SpecPlus_000602
    • GOSSYPOL [MI]
    • GOSSYPOL [VANDF]
    • GOSSYPOL, R-
    • 1189561-66-7
    • acetic acid;7-(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)-2,3,8-trihydroxy-4-isopropyl-6-methyl-naphthalene-1-carbaldehyde
    • Prestwick0_000677
    • Prestwick1_000677
    • Prestwick2_000677
    • Prestwick3_000677
    • Spectrum2_001472
    • Spectrum2_001624
    • Spectrum3_001102
    • Spectrum3_001516
    • Spectrum4_000846
    • Spectrum4_001931
    • Spectrum5_000693
    • Spectrum5_001035
    • 2,2'-bi[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]
    • GOSSYPOL [MART.]
    • Gossypol from cotton seeds
    • UPCMLD-DP103
    • NCIMech_000271
    • cid_3503
    • SCHEMBL3939
    • BSPBio_000773
    • BSPBio_002804
    • BSPBio_003191
    • GOSSYPOL, (+)-
    • KBioGR_001451
    • KBioGR_002303
    • KBioSS_000839
    • KBioSS_002001
    • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (-)-
    • 303-45-7

  • Applications

    Gossypol (CAS 303-45-7) is a polyphenolic aldehyde derived from cottonseed that finds practical use in several sectors. In agriculture it is applied as a natural pest deterrent/antifeedant to protect cotton and other crops. In coatings and inks it serves as a natural pigment, contributing color and potential functional properties in pigments or decorative coatings. In chemical synthesis, it is used as a starting material or building block for the preparation of derivatives and related organic compounds. In pharmaceutical research, gossypol and its derivatives are investigated as lead scaffolds in drug discovery and development, with ongoing study in laboratory settings. The application profile is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.5
    methanol 1.41
    isopropanol 0.88
    water 0.01
    ethyl acetate 1.09
    n-propanol 1.54
    acetone 2.49
    n-butanol 0.94
    acetonitrile 0.79
    DMF 8.18
    toluene 0.8
    isobutanol 0.85
    1,4-dioxane 5.38
    methyl acetate 1.93
    THF 16.5
    2-butanone 3.18
    n-pentanol 1.2
    sec-butanol 0.88
    n-hexane 0.07
    ethylene glycol 0.83
    NMP 13.4
    cyclohexane 0.06
    DMSO 11.37
    n-butyl acetate 1.44
    n-octanol 0.8
    chloroform 2.46
    n-propyl acetate 1.43
    acetic acid 2.82
    dichloromethane 2.54
    cyclohexanone 4.78
    propylene glycol 0.79
    isopropyl acetate 0.86
    DMAc 10.84
    2-ethoxyethanol 3.65
    isopentanol 0.69
    n-heptane 0.08
    ethyl formate 1.28
    1,2-dichloroethane 2.01
    n-hexanol 1.05
    2-methoxyethanol 4.56
    isobutyl acetate 0.85
    tetrachloromethane 0.45
    n-pentyl acetate 2.23
    transcutol 2.64
    n-heptanol 1.16
    ethylbenzene 0.49
    MIBK 0.95
    2-propoxyethanol 4.64
    tert-butanol 0.88
    MTBE 0.89
    2-butoxyethanol 3.7
    propionic acid 1.83
    o-xylene 0.47
    formic acid 1.89
    diethyl ether 0.99
    m-xylene 0.4
    p-xylene 0.64
    chlorobenzene 0.79
    dimethyl carbonate 1.79
    n-octane 0.07
    formamide 2.7
    cyclopentanone 9.83
    2-pentanone 1.69
    anisole 1.05
    cyclopentyl methyl ether 2.4
    gamma-butyrolactone 8.66
    1-methoxy-2-propanol 2.76
    pyridine 5.65
    3-pentanone 1.62
    furfural 5.85
    n-dodecane 0.04
    diethylene glycol 3.41
    diisopropyl ether 0.21
    tert-amyl alcohol 1.0
    acetylacetone 2.11
    n-hexadecane 0.05
    acetophenone 1.77
    methyl propionate 1.89
    isopentyl acetate 1.23
    trichloroethylene 3.9
    n-nonanol 0.88
    cyclohexanol 0.8
    benzyl alcohol 1.61
    2-ethylhexanol 0.66
    isooctanol 0.88
    dipropyl ether 0.94
    1,2-dichlorobenzene 0.72
    ethyl lactate 1.12
    propylene carbonate 2.45
    n-methylformamide 3.44
    2-pentanol 0.47
    n-pentane 0.05
    1-propoxy-2-propanol 2.56
    1-methoxy-2-propyl acetate 2.01
    2-(2-methoxypropoxy) propanol 1.86
    mesitylene 0.19
    ε-caprolactone 3.89
    p-cymene 0.36
    epichlorohydrin 9.05
    1,1,1-trichloroethane 1.02
    2-aminoethanol 1.46
    morpholine-4-carbaldehyde 9.27
    sulfolane 13.55
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 4.58
    n-hexyl acetate 1.74
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 2.69
    sec-butyl acetate 0.84
    tert-butyl acetate 1.03
    decalin 0.06
    glycerin 1.84
    diglyme 4.63
    acrylic acid 2.46
    isopropyl myristate 0.6
    n-butyric acid 1.63
    acetyl acetate 0.87
    di(2-ethylhexyl) phthalate 1.01
    ethyl propionate 1.13
    nitromethane 4.4
    1,2-diethoxyethane 1.62
    benzonitrile 1.3
    trioctyl phosphate 0.86
    1-bromopropane 0.93
    gamma-valerolactone 12.08
    n-decanol 0.57
    triethyl phosphate 0.77
    4-methyl-2-pentanol 0.31
    propionitrile 1.21
    vinylene carbonate 2.2
    1,1,2-trichlorotrifluoroethane 7.39
    DMS 1.79
    cumene 0.32
    2-octanol 0.77
    2-hexanone 2.17
    octyl acetate 0.94
    limonene 0.38
    1,2-dimethoxyethane 5.3
    ethyl orthosilicate 0.75
    tributyl phosphate 0.74
    diacetone alcohol 1.95
    N,N-dimethylaniline 0.95
    acrylonitrile 1.97
    aniline 1.21
    1,3-propanediol 1.92
    bromobenzene 0.66
    dibromomethane 1.44
    1,1,2,2-tetrachloroethane 2.99
    2-methyl-cyclohexyl acetate 1.2
    tetrabutyl urea 1.4
    diisobutyl methanol 0.29
    2-phenylethanol 1.81
    styrene 0.49
    dioctyl adipate 1.01
    dimethyl sulfate 3.58
    ethyl butyrate 0.95
    methyl lactate 1.77
    butyl lactate 1.86
    diethyl carbonate 0.65
    propanediol butyl ether 2.28
    triethyl orthoformate 1.05
    p-tert-butyltoluene 0.32
    methyl 4-tert-butylbenzoate 2.16
    morpholine 6.43
    tert-butylamine 0.35
    n-dodecanol 0.37
    dimethoxymethane 4.48
    ethylene carbonate 1.81
    cyrene 3.9
    2-ethoxyethyl acetate 3.06
    2-ethylhexyl acetate 1.09
    1,2,4-trichlorobenzene 1.24
    4-methylpyridine 3.0
    dibutyl ether 0.7
    2,6-dimethyl-4-heptanol 0.29
    DEF 2.74
    dimethyl isosorbide 4.03
    tetrachloroethylene 2.4
    eugenol 2.49
    triacetin 1.65
    span 80 1.99
    1,4-butanediol 1.1
    1,1-dichloroethane 1.08
    2-methyl-1-pentanol 0.96
    methyl formate 2.78
    2-methyl-1-butanol 0.82
    n-decane 0.08
    butyronitrile 0.96
    3,7-dimethyl-1-octanol 0.47
    1-chlorooctane 0.39
    1-chlorotetradecane 0.14
    n-nonane 0.07
    undecane 0.05
    tert-butylcyclohexane 0.05
    cyclooctane 0.03
    cyclopentanol 1.87
    tetrahydropyran 2.89
    tert-amyl methyl ether 0.81
    2,5,8-trioxanonane 3.11
    1-hexene 0.32
    2-isopropoxyethanol 2.37
    2,2,2-trifluoroethanol 1.47
    methyl butyrate 1.56

    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