Xanthohumol B

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  • Identifiers

    CAS number
    189308-10-9

    Molecular formula
    C21H22O6

    SMILES
    CC1(C(CC2=C(C(=C(C=C2O1)OC)C(=O)/C=C/C3=CC=C(C=C3)O)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 56.76%
    Vanilla 43.76%
    Spicy 38.65%
    Balsamic 36.05%
    Odorless 35.33%
    Phenolic 34.73%
    Powdery 29.88%
    Creamy 27.48%
    Floral 26.6%
    Woody 26.23%

     

    Flavor
    Bitter 90.48%
    Odorless 26.72%
    Bland 23.91%
    Parsley 20.0%
    Cedarleaf 19.65%
    Sweet-like 19.57%
    Lovage 19.57%
    Broom 18.86%
    Heather 18.82%
    Ethyl benzoate 18.78%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    8.89 (weak base)

    Molecular weight
    370.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1116°C

    Flash point

    • 232.52 ˚C est.

  • Synonyms

    • xanthohumol B
    • 189308-10-9
    • (E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • CHEBI:66334
    • DTXSID301317586
    • RefChem:195132
    • GlyTouCan:G32409AI
    • DTXCID501747393
    • G32409AI
    • Dehydrocycloxanthohumol hydrate
    • 6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone
    • 2-Propen-1-one, 1-(3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)-, (2E)-
    • CHEMBL520430
    • orb2279387
    • SCHEMBL12961703
    • SCHEMBL29934961
    • LMPK12120299
    • AKOS040735479
    • (2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • Q27134882
    • (2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • rac-(E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • rac-6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone
    • rac-6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-one
    • 189308-10-9

  • Applications

    Xanthohumol B (CAS 189308-10-9) is a hop-derived prenylated flavonoid primarily encountered as a research chemical and natural product. In industry, it is evaluated as a bioactive polyphenol with antioxidant potential for cosmetic and personal care formulations; studied for nutraceutical/dietary supplement applications; used as a lead compound in pharmaceutical research to develop flavonoid derivatives from hops; employed as an intermediate in synthetic routes to access hop-derived polyphenols; explored for stabilizing polymers and coatings owing to its radical-scavenging activity; and investigated in agricultural research as a plant-derived functional compound.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 23.35
    methanol 59.79
    isopropanol 42.66
    water 0.03
    ethyl acetate 73.15
    n-propanol 42.59
    acetone 346.33
    n-butanol 28.36
    acetonitrile 67.34
    DMF 284.91
    toluene 8.9
    isobutanol 25.55
    1,4-dioxane 210.99
    methyl acetate 100.13
    THF 1208.27
    2-butanone 168.71
    n-pentanol 19.09
    sec-butanol 25.15
    n-hexane 0.15
    ethylene glycol 13.33
    NMP 115.87
    cyclohexane 0.59
    DMSO 1225.19
    n-butyl acetate 19.09
    n-octanol 9.07
    chloroform 93.08
    n-propyl acetate 29.77
    acetic acid 99.13
    dichloromethane 72.08
    cyclohexanone 138.27
    propylene glycol 23.5
    isopropyl acetate 39.49
    DMAc 386.8
    2-ethoxyethanol 101.74
    isopentanol 23.44
    n-heptane 0.27
    ethyl formate 46.66
    1,2-dichloroethane 68.23
    n-hexanol 10.49
    2-methoxyethanol 234.4
    isobutyl acetate 17.32
    tetrachloromethane 4.73
    n-pentyl acetate 14.08
    transcutol 136.13
    n-heptanol 7.95
    ethylbenzene 3.51
    MIBK 40.93
    2-propoxyethanol 92.11
    tert-butanol 63.24
    MTBE 26.91
    2-butoxyethanol 35.79
    propionic acid 36.64
    o-xylene 4.84
    formic acid 37.99
    diethyl ether 28.88
    m-xylene 4.68
    p-xylene 6.17
    chlorobenzene 15.19
    dimethyl carbonate 60.48
    n-octane 0.19
    formamide 79.16
    cyclopentanone 318.4
    2-pentanone 94.92
    anisole 26.72
    cyclopentyl methyl ether 65.05
    gamma-butyrolactone 254.02
    1-methoxy-2-propanol 137.3
    pyridine 84.25
    3-pentanone 58.03
    furfural 105.92
    n-dodecane 0.37
    diethylene glycol 82.8
    diisopropyl ether 5.25
    tert-amyl alcohol 29.07
    acetylacetone 153.32
    n-hexadecane 0.45
    acetophenone 29.61
    methyl propionate 77.86
    isopentyl acetate 20.77
    trichloroethylene 138.8
    n-nonanol 9.7
    cyclohexanol 25.02
    benzyl alcohol 25.45
    2-ethylhexanol 6.5
    isooctanol 7.67
    dipropyl ether 13.14
    1,2-dichlorobenzene 13.59
    ethyl lactate 24.05
    propylene carbonate 55.91
    n-methylformamide 109.35
    2-pentanol 12.54
    n-pentane 0.17
    1-propoxy-2-propanol 48.75
    1-methoxy-2-propyl acetate 49.98
    2-(2-methoxypropoxy) propanol 42.9
    mesitylene 2.97
    ε-caprolactone 71.65
    p-cymene 3.2
    epichlorohydrin 369.35
    1,1,1-trichloroethane 38.95
    2-aminoethanol 27.2
    morpholine-4-carbaldehyde 153.23
    sulfolane 303.95
    2,2,4-trimethylpentane 0.26
    2-methyltetrahydrofuran 146.98
    n-hexyl acetate 20.66
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 57.79
    sec-butyl acetate 18.59
    tert-butyl acetate 43.31
    decalin 0.44
    glycerin 48.27
    diglyme 118.44
    acrylic acid 35.54
    isopropyl myristate 10.03
    n-butyric acid 51.19
    acetyl acetate 46.86
    di(2-ethylhexyl) phthalate 12.29
    ethyl propionate 30.59
    nitromethane 336.42
    1,2-diethoxyethane 40.81
    benzonitrile 22.04
    trioctyl phosphate 9.2
    1-bromopropane 16.14
    gamma-valerolactone 283.32
    n-decanol 7.51
    triethyl phosphate 14.65
    4-methyl-2-pentanol 9.11
    propionitrile 52.03
    vinylene carbonate 48.86
    1,1,2-trichlorotrifluoroethane 130.33
    DMS 29.78
    cumene 2.53
    2-octanol 5.44
    2-hexanone 43.17
    octyl acetate 13.33
    limonene 4.41
    1,2-dimethoxyethane 193.82
    ethyl orthosilicate 13.1
    tributyl phosphate 11.4
    diacetone alcohol 74.35
    N,N-dimethylaniline 14.91
    acrylonitrile 68.75
    aniline 25.16
    1,3-propanediol 63.22
    bromobenzene 12.3
    dibromomethane 30.61
    1,1,2,2-tetrachloroethane 109.43
    2-methyl-cyclohexyl acetate 18.33
    tetrabutyl urea 18.92
    diisobutyl methanol 5.69
    2-phenylethanol 20.4
    styrene 5.05
    dioctyl adipate 18.35
    dimethyl sulfate 104.46
    ethyl butyrate 18.2
    methyl lactate 48.65
    butyl lactate 16.97
    diethyl carbonate 15.39
    propanediol butyl ether 28.89
    triethyl orthoformate 17.55
    p-tert-butyltoluene 3.14
    methyl 4-tert-butylbenzoate 26.84
    morpholine 236.64
    tert-butylamine 12.68
    n-dodecanol 5.68
    dimethoxymethane 265.59
    ethylene carbonate 47.02
    cyrene 48.37
    2-ethoxyethyl acetate 31.34
    2-ethylhexyl acetate 13.84
    1,2,4-trichlorobenzene 21.78
    4-methylpyridine 55.71
    dibutyl ether 11.29
    2,6-dimethyl-4-heptanol 5.69
    DEF 68.63
    dimethyl isosorbide 82.56
    tetrachloroethylene 47.19
    eugenol 27.58
    triacetin 32.53
    span 80 25.28
    1,4-butanediol 19.35
    1,1-dichloroethane 50.17
    2-methyl-1-pentanol 14.18
    methyl formate 114.29
    2-methyl-1-butanol 18.26
    n-decane 0.58
    butyronitrile 33.48
    3,7-dimethyl-1-octanol 9.59
    1-chlorooctane 3.87
    1-chlorotetradecane 1.75
    n-nonane 0.41
    undecane 0.46
    tert-butylcyclohexane 0.38
    cyclooctane 0.21
    cyclopentanol 53.17
    tetrahydropyran 122.56
    tert-amyl methyl ether 16.8
    2,5,8-trioxanonane 92.43
    1-hexene 1.24
    2-isopropoxyethanol 52.69
    2,2,2-trifluoroethanol 30.69
    methyl butyrate 41.03

    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