Deguelin

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  • Identifiers

    CAS number
    522-17-8

    Molecular formula
    C23H22O6

    SMILES
    CC1(C=CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 54.21%
    Spicy 41.92%
    Vanilla 40.27%
    Powdery 36.14%
    Floral 34.31%
    Phenolic 33.17%
    Creamy 28.87%
    Woody 27.43%
    Balsamic 23.97%
    Coumarinic 23.16%

     

    Flavor
    Bitter 95.08%
    Bland 19.91%
    Parsley 19.31%
    Cedarleaf 19.31%
    Lovage 18.35%
    Ripe apricot 17.9%
    Sweet-like 17.89%
    Red fruit 17.57%
    Eugenol 16.99%
    Cereal 16.58%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    7.05 (neutral)

    Molecular weight
    394.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    907°C

    Flash point

    • 212.78 ˚C est.

  • Synonyms

    • Deguelin
    • 522-17-8
    • (-)-cis-deguelin
    • CHEBI:4357
    • K5Z93K66IE
    • DTXSID10200231
    • (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
    • (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo(12.8.0.03,12.04,9.015,20)docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one
    • RefChem:919766
    • GlyTouCan:G15155WL
    • DTXCID10122722
    • G15155WL
    • 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one
    • (7aS-cis)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one
    • (-)-Deguelin
    • DEGUELIN(-)
    • MFCD01740600
    • (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one
    • C23H22O6
    • (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one.
    • Tocris-1770
    • SR-01000597503
    • UNII-K5Z93K66IE
    • (-)-Deguelin;(-)-cis-Deguelin
    • Dequelin
    • Legumelin
    • CCRIS 8104
    • Deguelin (6CI)
    • Spectrum_001044
    • 12-alpha-Deoxytephrosin
    • DEGUELIN [MI]
    • Spectrum2_000298
    • Spectrum3_001122
    • Spectrum4_001965
    • Spectrum5_001852
    • SCHEMBL73183
    • BSPBio_002583
    • KBioGR_002434
    • KBioSS_001524
    • SPECTRUM201138
    • MLS006010295
    • SPBio_000236
    • CHEMBL393417
    • orb1300439
    • SCHEMBL29405854
    • SCHEMBL30910172
    • KBio2_001524
    • KBio2_004092
    • KBio2_006660
    • KBio3_002083
    • HMS1923A05
    • HMS3268E12
    • 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-
    • EX-A4158
    • BDBM50505204
    • CCG-39856
    • LMPK12060019
    • s8132
    • AKOS024456769
    • CS-1802
    • EBC-220093
    • FD65404
    • SDCCGMLS-0066380.P001
    • NCGC00025288-01
    • NCGC00025288-02
    • NCGC00025288-03
    • (-)-Deguelin, >98% (HPLC), powder
    • AC-35505
    • AS-56004
    • HY-13425
    • SMR004701363
    • D5646
    • Q5251862
    • SR-01000597503-1
    • SR-01000597503-3
    • SR-01000597503-4
    • BRD-K61401890-001-02-0
    • BRD-K61401890-001-03-8
    • BRD-K61401890-001-04-6
    • (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15,17,19-heptaen-13-one
    • (7AS,13AS)-13,13A-DIHYDRO-9,10-DIMETHOXY-3,3-DIMETHYL-3H-(1)BENZOPYRANO(3,4-B)PYRANO(2,3-H)(1)BENZOPYRAN-7(7AH)-ONE
    • (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H,7aH-pyrano[2,3-c;6,5-f']dichromen-7-one
    • (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one
    • 13,13aS-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-[1]benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aS)-one
    • 3H-[1]Benzopyrano[3,4-b]pyrano[2,3-h][1]benzopyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
    • 3H-Bis(1)benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one, 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-
    • 522-17-8

  • Applications

    Deguelin (CAS 522-17-8) is a natural rotenoid used in agriculture as an active component in plant-derived insecticidal formulations for pest control. It is also studied as a research tool and lead compound in pharmacology and medicinal chemistry due to its inhibition of mitochondrial complex I, informing investigations into cellular energy and potential anticancer activity. In chemical synthesis, deguelin can serve as an intermediate or reference scaffold for the development of rotenoid derivatives. Its use is typically limited to controlled formulations and research settings, and is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.06
    methanol 2.9
    isopropanol 2.61
    water 0.03
    ethyl acetate 31.06
    n-propanol 3.02
    acetone 31.21
    n-butanol 3.14
    acetonitrile 24.78
    DMF 37.29
    toluene 8.21
    isobutanol 3.15
    1,4-dioxane 31.76
    methyl acetate 32.33
    THF 50.77
    2-butanone 27.35
    n-pentanol 3.38
    sec-butanol 2.39
    n-hexane 0.31
    ethylene glycol 2.56
    NMP 63.04
    cyclohexane 0.92
    DMSO 57.41
    n-butyl acetate 19.78
    n-octanol 3.46
    chloroform 110.71
    n-propyl acetate 21.34
    acetic acid 42.9
    dichloromethane 102.16
    cyclohexanone 46.34
    propylene glycol 1.28
    isopropyl acetate 19.56
    DMAc 86.45
    2-ethoxyethanol 15.24
    isopentanol 4.42
    n-heptane 0.48
    ethyl formate 19.65
    1,2-dichloroethane 52.09
    n-hexanol 4.16
    2-methoxyethanol 17.29
    isobutyl acetate 16.23
    tetrachloromethane 9.38
    n-pentyl acetate 14.71
    transcutol 38.22
    n-heptanol 3.88
    ethylbenzene 4.43
    MIBK 15.23
    2-propoxyethanol 24.36
    tert-butanol 4.16
    MTBE 5.6
    2-butoxyethanol 14.97
    propionic acid 15.12
    o-xylene 6.04
    formic acid 13.71
    diethyl ether 9.85
    m-xylene 5.38
    p-xylene 7.17
    chlorobenzene 18.9
    dimethyl carbonate 32.41
    n-octane 0.32
    formamide 20.11
    cyclopentanone 54.67
    2-pentanone 20.6
    anisole 11.65
    cyclopentyl methyl ether 17.22
    gamma-butyrolactone 74.52
    1-methoxy-2-propanol 12.37
    pyridine 30.43
    3-pentanone 25.03
    furfural 57.32
    n-dodecane 0.48
    diethylene glycol 22.04
    diisopropyl ether 3.72
    tert-amyl alcohol 3.59
    acetylacetone 42.28
    n-hexadecane 0.58
    acetophenone 20.84
    methyl propionate 30.2
    isopentyl acetate 19.86
    trichloroethylene 120.75
    n-nonanol 4.49
    cyclohexanol 6.81
    benzyl alcohol 11.96
    2-ethylhexanol 5.09
    isooctanol 4.2
    dipropyl ether 8.41
    1,2-dichlorobenzene 22.4
    ethyl lactate 14.64
    propylene carbonate 37.52
    n-methylformamide 17.83
    2-pentanol 2.47
    n-pentane 0.32
    1-propoxy-2-propanol 16.17
    1-methoxy-2-propyl acetate 32.78
    2-(2-methoxypropoxy) propanol 22.28
    mesitylene 3.35
    ε-caprolactone 42.15
    p-cymene 4.95
    epichlorohydrin 75.06
    1,1,1-trichloroethane 39.67
    2-aminoethanol 2.85
    morpholine-4-carbaldehyde 62.2
    sulfolane 77.86
    2,2,4-trimethylpentane 0.36
    2-methyltetrahydrofuran 20.7
    n-hexyl acetate 15.11
    isooctane 0.28
    2-(2-butoxyethoxy)ethanol 20.93
    sec-butyl acetate 14.94
    tert-butyl acetate 17.3
    decalin 0.84
    glycerin 5.89
    diglyme 46.41
    acrylic acid 20.26
    isopropyl myristate 8.53
    n-butyric acid 18.32
    acetyl acetate 42.24
    di(2-ethylhexyl) phthalate 12.19
    ethyl propionate 22.4
    nitromethane 94.36
    1,2-diethoxyethane 18.92
    benzonitrile 21.93
    trioctyl phosphate 8.1
    1-bromopropane 13.98
    gamma-valerolactone 77.31
    n-decanol 3.6
    triethyl phosphate 16.82
    4-methyl-2-pentanol 2.93
    propionitrile 17.81
    vinylene carbonate 47.47
    1,1,2-trichlorotrifluoroethane 59.42
    DMS 27.38
    cumene 3.57
    2-octanol 2.57
    2-hexanone 17.24
    octyl acetate 10.27
    limonene 6.23
    1,2-dimethoxyethane 32.78
    ethyl orthosilicate 14.11
    tributyl phosphate 10.64
    diacetone alcohol 18.47
    N,N-dimethylaniline 9.16
    acrylonitrile 28.41
    aniline 12.17
    1,3-propanediol 5.8
    bromobenzene 20.4
    dibromomethane 51.38
    1,1,2,2-tetrachloroethane 72.06
    2-methyl-cyclohexyl acetate 18.32
    tetrabutyl urea 14.7
    diisobutyl methanol 4.07
    2-phenylethanol 14.03
    styrene 5.64
    dioctyl adipate 15.82
    dimethyl sulfate 50.44
    ethyl butyrate 19.34
    methyl lactate 17.2
    butyl lactate 12.53
    diethyl carbonate 18.01
    propanediol butyl ether 8.45
    triethyl orthoformate 17.5
    p-tert-butyltoluene 4.15
    methyl 4-tert-butylbenzoate 21.38
    morpholine 26.64
    tert-butylamine 2.15
    n-dodecanol 3.0
    dimethoxymethane 34.62
    ethylene carbonate 41.41
    cyrene 29.06
    2-ethoxyethyl acetate 26.63
    2-ethylhexyl acetate 17.4
    1,2,4-trichlorobenzene 27.69
    4-methylpyridine 25.55
    dibutyl ether 6.57
    2,6-dimethyl-4-heptanol 4.07
    DEF 29.66
    dimethyl isosorbide 43.84
    tetrachloroethylene 48.19
    eugenol 20.19
    triacetin 29.04
    span 80 13.72
    1,4-butanediol 3.26
    1,1-dichloroethane 32.29
    2-methyl-1-pentanol 4.68
    methyl formate 23.06
    2-methyl-1-butanol 3.71
    n-decane 0.72
    butyronitrile 12.28
    3,7-dimethyl-1-octanol 4.93
    1-chlorooctane 3.35
    1-chlorotetradecane 1.94
    n-nonane 0.53
    undecane 0.57
    tert-butylcyclohexane 0.59
    cyclooctane 0.4
    cyclopentanol 7.09
    tetrahydropyran 17.75
    tert-amyl methyl ether 5.8
    2,5,8-trioxanonane 36.65
    1-hexene 1.44
    2-isopropoxyethanol 13.81
    2,2,2-trifluoroethanol 24.51
    methyl butyrate 24.69

    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