alpha,beta-Dihydroxanthohumol

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  • Identifiers

    CAS number
    102448-00-0

    Molecular formula
    C21H24O5

    SMILES
    CC(=CCC1=C(C(=C(C=C1O)OC)C(=O)CCC2=CC=C(C=C2)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Spicy 47.31%
    Sweet 46.97%
    Phenolic 39.15%
    Balsamic 37.51%
    Woody 36.09%
    Fruity 34.45%
    Floral 33.46%
    Herbal 27.67%
    Dry 26.18%
    Odorless 25.61%

     

    Flavor
    Bitter 79.86%
    Odorless 24.91%
    Bland 22.4%
    Herbal 21.11%
    Parsley 20.67%
    Lovage 20.6%
    Cedarleaf 20.37%
    Heather 19.53%
    Broom 19.48%
    Ethyl benzoate 19.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.9

    pKa est.
    10.11 (weak base)

    Molecular weight
    356.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    620°C

    Flash point

    • 215.69 ˚C est.

  • Synonyms

    • dihydroxanthohumol
    • alpha,beta-dihydroxanthohumol
    • a,b-Dihydroxanthohumol
    • CHEBI:66332
    • 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
    • 2',4,4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
    • 1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)propan-1-one
    • RefChem:111019
    • 102448-00-0
    • 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
    • 4,2',4'-Trihydroxy-6'-methoxy-3'-prenyldihydrochalcone
    • Dihydroxanthohumol, >90%
    • MLS000863606
    • SMR000440746
    • 1-Propanone, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-
    • CHEMBL510279
    • MEGxp0_001797
    • orb2893559
    • SCHEMBL15704299
    • ACon1_000059
    • BDBM76566
    • cid_10450920
    • DTXSID001355804
    • HMS2267A19
    • CEA44800
    • LMPK12120536
    • NCGC00168833-01
    • BRD-K15951006-001-01-4
    • Q27134880
    • 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-1-propanone
    • 1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-1-propanone
    • 3-(4-hydroxyphenyl)-1-[6-methoxy-3-(3-methylbut-2-enyl)-2,4-bis(oxidanyl)phenyl]propan-1-one
    • 102448-00-0

  • Applications

    alpha,beta-Dihydroxanthohumol (CAS 102448-00-0) is a hop-derived polyphenol derivative primarily explored as a chemical intermediate and functional additive. Potential applications include cosmetics/personal care as an antioxidant and stabilizer; polymers/plastics formulations as an antioxidant or stabilizing agent; coatings and inks as a color and surface-stability additive; pharmaceutical/biochemical research as an intermediate in the synthesis of hop-related polyphenols; and as a building block in industrial manufacturing for the preparation of more complex polyphenol derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 167.09
    methanol 229.34
    isopropanol 127.5
    water 0.03
    ethyl acetate 91.15
    n-propanol 143.07
    acetone 473.3
    n-butanol 84.49
    acetonitrile 74.34
    DMF 457.7
    toluene 11.93
    isobutanol 71.52
    1,4-dioxane 246.03
    methyl acetate 127.02
    THF 1300.34
    2-butanone 218.0
    n-pentanol 56.27
    sec-butanol 71.3
    n-hexane 0.25
    ethylene glycol 45.27
    NMP 204.74
    cyclohexane 0.62
    DMSO 1830.21
    n-butyl acetate 30.68
    n-octanol 16.21
    chloroform 77.98
    n-propyl acetate 40.5
    acetic acid 177.23
    dichloromethane 66.27
    cyclohexanone 182.9
    propylene glycol 195.77
    isopropyl acetate 49.34
    DMAc 462.79
    2-ethoxyethanol 179.6
    isopentanol 56.92
    n-heptane 0.26
    ethyl formate 59.55
    1,2-dichloroethane 65.68
    n-hexanol 31.01
    2-methoxyethanol 582.01
    isobutyl acetate 25.69
    tetrachloromethane 4.55
    n-pentyl acetate 22.64
    transcutol 278.59
    n-heptanol 18.36
    ethylbenzene 5.91
    MIBK 57.35
    2-propoxyethanol 165.23
    tert-butanol 147.31
    MTBE 40.2
    2-butoxyethanol 69.51
    propionic acid 87.3
    o-xylene 6.16
    formic acid 59.41
    diethyl ether 28.45
    m-xylene 7.05
    p-xylene 8.51
    chlorobenzene 20.31
    dimethyl carbonate 76.63
    n-octane 0.2
    formamide 146.69
    cyclopentanone 462.02
    2-pentanone 124.06
    anisole 36.4
    cyclopentyl methyl ether 83.18
    gamma-butyrolactone 363.14
    1-methoxy-2-propanol 367.22
    pyridine 99.64
    3-pentanone 66.2
    furfural 149.12
    n-dodecane 0.4
    diethylene glycol 170.58
    diisopropyl ether 5.18
    tert-amyl alcohol 74.68
    acetylacetone 220.98
    n-hexadecane 0.47
    acetophenone 43.43
    methyl propionate 107.35
    isopentyl acetate 32.72
    trichloroethylene 134.75
    n-nonanol 16.35
    cyclohexanol 53.17
    benzyl alcohol 50.86
    2-ethylhexanol 13.76
    isooctanol 14.61
    dipropyl ether 14.58
    1,2-dichlorobenzene 17.13
    ethyl lactate 47.87
    propylene carbonate 98.66
    n-methylformamide 208.35
    2-pentanol 32.03
    n-pentane 0.21
    1-propoxy-2-propanol 93.13
    1-methoxy-2-propyl acetate 78.82
    2-(2-methoxypropoxy) propanol 68.46
    mesitylene 4.05
    ε-caprolactone 116.79
    p-cymene 4.65
    epichlorohydrin 433.13
    1,1,1-trichloroethane 42.56
    2-aminoethanol 132.7
    morpholine-4-carbaldehyde 213.92
    sulfolane 518.25
    2,2,4-trimethylpentane 0.41
    2-methyltetrahydrofuran 205.57
    n-hexyl acetate 32.42
    isooctane 0.36
    2-(2-butoxyethoxy)ethanol 98.85
    sec-butyl acetate 24.36
    tert-butyl acetate 61.58
    decalin 0.65
    glycerin 213.07
    diglyme 173.55
    acrylic acid 75.26
    isopropyl myristate 13.54
    n-butyric acid 113.22
    acetyl acetate 55.78
    di(2-ethylhexyl) phthalate 19.96
    ethyl propionate 36.21
    nitromethane 413.52
    1,2-diethoxyethane 53.28
    benzonitrile 36.02
    trioctyl phosphate 13.81
    1-bromopropane 15.76
    gamma-valerolactone 397.24
    n-decanol 12.08
    triethyl phosphate 19.35
    4-methyl-2-pentanol 18.61
    propionitrile 56.7
    vinylene carbonate 71.19
    1,1,2-trichlorotrifluoroethane 233.6
    DMS 45.28
    cumene 4.42
    2-octanol 10.95
    2-hexanone 55.65
    octyl acetate 19.6
    limonene 6.32
    1,2-dimethoxyethane 204.13
    ethyl orthosilicate 17.1
    tributyl phosphate 16.02
    diacetone alcohol 146.92
    N,N-dimethylaniline 21.49
    acrylonitrile 81.89
    aniline 40.27
    1,3-propanediol 220.06
    bromobenzene 15.48
    dibromomethane 28.85
    1,1,2,2-tetrachloroethane 124.88
    2-methyl-cyclohexyl acetate 27.06
    tetrabutyl urea 26.56
    diisobutyl methanol 9.25
    2-phenylethanol 40.95
    styrene 7.68
    dioctyl adipate 25.75
    dimethyl sulfate 147.36
    ethyl butyrate 24.58
    methyl lactate 120.88
    butyl lactate 33.73
    diethyl carbonate 19.64
    propanediol butyl ether 71.02
    triethyl orthoformate 22.68
    p-tert-butyltoluene 4.68
    methyl 4-tert-butylbenzoate 45.66
    morpholine 378.57
    tert-butylamine 28.12
    n-dodecanol 8.57
    dimethoxymethane 360.16
    ethylene carbonate 64.3
    cyrene 82.18
    2-ethoxyethyl acetate 49.21
    2-ethylhexyl acetate 20.91
    1,2,4-trichlorobenzene 29.08
    4-methylpyridine 73.57
    dibutyl ether 13.37
    2,6-dimethyl-4-heptanol 9.25
    DEF 90.05
    dimethyl isosorbide 126.05
    tetrachloroethylene 44.93
    eugenol 50.3
    triacetin 47.41
    span 80 52.99
    1,4-butanediol 58.04
    1,1-dichloroethane 48.41
    2-methyl-1-pentanol 39.5
    methyl formate 160.6
    2-methyl-1-butanol 52.45
    n-decane 0.58
    butyronitrile 47.66
    3,7-dimethyl-1-octanol 15.74
    1-chlorooctane 4.72
    1-chlorotetradecane 2.28
    n-nonane 0.42
    undecane 0.48
    tert-butylcyclohexane 0.61
    cyclooctane 0.19
    cyclopentanol 114.65
    tetrahydropyran 151.53
    tert-amyl methyl ether 25.69
    2,5,8-trioxanonane 128.08
    1-hexene 2.47
    2-isopropoxyethanol 94.05
    2,2,2-trifluoroethanol 39.16
    methyl butyrate 52.96

    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