Xanthohumol

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  • Identifiers

    CAS number
    6754-58-1

    Molecular formula
    C21H22O5

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

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Spicy 50.84%
    Sweet 45.65%
    Balsamic 39.17%
    Woody 37.49%
    Phenolic 36.52%
    Fruity 36.07%
    Herbal 31.65%
    Floral 31.12%
    Warm 27.24%
    Dry 26.34%

     

    Flavor
    Bitter 89.21%
    Odorless 24.45%
    Lovage 19.99%
    Cedarleaf 19.89%
    Parsley 19.73%
    Broom 19.45%
    Nitrile 19.42%
    Heather 19.32%
    Genet 19.03%
    Bland 18.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.1

    pKa est.
    9.99 (weak base)

    Molecular weight
    354.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    701°C

    Melting point expt.

    • 172 °C

    Flash point

    • 223.78 ˚C est.

  • Synonyms

    • Xanthohumol
    • 6754-58-1
    • Xantho-flav
    • (E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • T4467YT1NT
    • (2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • CHEBI:66331
    • DTXSID00893171
    • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
    • 2-Propen-1-one, 1-(2,4-hydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl)-3-(4-hydroxyphenyl)-, (E)-
    • (2E)-1-(2,4-DIHYDROXY-6-METHOXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE
    • (E)-1-(2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • XanthoFlav
    • (2E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • RefChem:195131
    • DTXCID601323110
    • 3'-(3,3-Dimethyl allyl)-2',4',4-trihydroxy-6'-methoxychalcone
    • 614-078-4
    • 1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • MFCD00210576
    • (E/Z)-Xanthohumol
    • (E)-1-(2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • Xanthohumol(Random Configuration)
    • 2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalcone
    • 1-[2,4-DIHYDROXY-6-METHOXY-3-(3-METHYLBUT-2-EN-1-YL)PHENYL]-3-(4-HYDROXYPHENYL)PROP-2-EN-1-ONE
    • UNII-T4467YT1NT
    • Xanthohumol?
    • (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • Xanthohumol from hop (Humulus lupulus)
    • Xanthohumol (Standard)
    • SCHEMBL143683
    • CHEMBL253896
    • MEGxp0_000104
    • orb1304306
    • Xanthohumol(RandomConfiguration)
    • SCHEMBL30169731
    • ACon1_001634
    • CHEBI:94745
    • HY-N1067A
    • HY-N1067R
    • BDBM755075
    • HMS3886H19
    • BDBM50384998
    • LMPK12120294
    • MSK166072
    • s7889
    • AKOS016010098
    • AKOS040762512
    • CCG-268086
    • DB15359
    • EBC-437042
    • FX09701
    • (E)-1-[2,4-Dihydroxy-6-methoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)propenone
    • SMP2_000278
    • US20250213569, Compound 58
    • NCGC00180304-01
    • AC-31276
    • BS-17392
    • DA-68730
    • SY288787
    • TS-10147
    • CS-0159153
    • X0068
    • Q408088
    • 2',4',4-trihydroxy-6'-methoxy-3'-prenylchalcone
    • BRD-K77390737-001-01-6
    • Q27166535
    • Xanthohumol, primary pharmaceutical reference standard
    • Xanthohumol from hop (Humulus lupulus), >=96% (HPLC)
    • 1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one
    • 2-Propen-1-one, 1-[2,4-dihydroxy-6-methoxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)-
    • InChI=1/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7
    • Xanthohumol

  • Applications

    Xanthohumol (CAS 6754-58-1) is a naturally occurring prenylated chalcone from hops (Humulus lupulus). In industry, it is used as a natural antioxidant and bioactive constituent in cosmetics and personal care formulations; it is explored as a stabilizer/antioxidant additive for polymers and coatings; hop-derived extracts containing xanthohumol are used in flavor and fragrance profiling for food processing and beverage applications; it is investigated as a lead compound in pharmaceutical research and as a plant-protection/biopesticide candidate in agricultural science; and it serves as an intermediate in organic synthesis to access other prenylated flavonoids. The use cases are conservative and subject to regulatory limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 98.64
    methanol 121.24
    isopropanol 77.79
    water 0.01
    ethyl acetate 75.38
    n-propanol 97.15
    acetone 358.99
    n-butanol 56.74
    acetonitrile 59.67
    DMF 346.67
    toluene 10.17
    isobutanol 48.94
    1,4-dioxane 160.18
    methyl acetate 114.55
    THF 1169.01
    2-butanone 203.56
    n-pentanol 39.03
    sec-butanol 58.35
    n-hexane 0.25
    ethylene glycol 27.45
    NMP 184.46
    cyclohexane 0.49
    DMSO 1450.81
    n-butyl acetate 25.9
    n-octanol 10.88
    chloroform 60.77
    n-propyl acetate 33.78
    acetic acid 119.62
    dichloromethane 50.21
    cyclohexanone 144.09
    propylene glycol 139.77
    isopropyl acetate 42.79
    DMAc 414.42
    2-ethoxyethanol 123.27
    isopentanol 38.87
    n-heptane 0.25
    ethyl formate 42.01
    1,2-dichloroethane 54.21
    n-hexanol 22.6
    2-methoxyethanol 400.65
    isobutyl acetate 21.33
    tetrachloromethane 3.22
    n-pentyl acetate 17.03
    transcutol 219.33
    n-heptanol 12.73
    ethylbenzene 5.08
    MIBK 47.91
    2-propoxyethanol 130.73
    tert-butanol 97.54
    MTBE 35.46
    2-butoxyethanol 50.55
    propionic acid 68.43
    o-xylene 5.18
    formic acid 37.4
    diethyl ether 24.99
    m-xylene 5.66
    p-xylene 7.09
    chlorobenzene 15.41
    dimethyl carbonate 64.79
    n-octane 0.17
    formamide 100.91
    cyclopentanone 419.13
    2-pentanone 105.63
    anisole 31.82
    cyclopentyl methyl ether 73.28
    gamma-butyrolactone 320.55
    1-methoxy-2-propanol 278.21
    pyridine 91.98
    3-pentanone 60.95
    furfural 122.95
    n-dodecane 0.32
    diethylene glycol 114.13
    diisopropyl ether 4.49
    tert-amyl alcohol 59.53
    acetylacetone 175.61
    n-hexadecane 0.37
    acetophenone 35.94
    methyl propionate 96.94
    isopentyl acetate 27.37
    trichloroethylene 115.79
    n-nonanol 11.36
    cyclohexanol 39.53
    benzyl alcohol 39.4
    2-ethylhexanol 11.03
    isooctanol 10.67
    dipropyl ether 13.48
    1,2-dichlorobenzene 13.3
    ethyl lactate 38.21
    propylene carbonate 78.81
    n-methylformamide 151.18
    2-pentanol 24.77
    n-pentane 0.2
    1-propoxy-2-propanol 79.33
    1-methoxy-2-propyl acetate 68.41
    2-(2-methoxypropoxy) propanol 57.66
    mesitylene 3.18
    ε-caprolactone 95.58
    p-cymene 3.88
    epichlorohydrin 390.12
    1,1,1-trichloroethane 35.81
    2-aminoethanol 86.43
    morpholine-4-carbaldehyde 165.16
    sulfolane 462.06
    2,2,4-trimethylpentane 0.37
    2-methyltetrahydrofuran 187.08
    n-hexyl acetate 24.0
    isooctane 0.3
    2-(2-butoxyethoxy)ethanol 80.6
    sec-butyl acetate 21.66
    tert-butyl acetate 53.42
    decalin 0.53
    glycerin 152.33
    diglyme 135.58
    acrylic acid 58.88
    isopropyl myristate 11.04
    n-butyric acid 81.62
    acetyl acetate 44.41
    di(2-ethylhexyl) phthalate 15.48
    ethyl propionate 32.35
    nitromethane 323.37
    1,2-diethoxyethane 42.65
    benzonitrile 27.5
    trioctyl phosphate 10.86
    1-bromopropane 15.59
    gamma-valerolactone 321.45
    n-decanol 8.67
    triethyl phosphate 17.11
    4-methyl-2-pentanol 14.26
    propionitrile 49.62
    vinylene carbonate 52.22
    1,1,2-trichlorotrifluoroethane 196.99
    DMS 37.97
    cumene 3.77
    2-octanol 7.42
    2-hexanone 48.38
    octyl acetate 15.16
    limonene 5.3
    1,2-dimethoxyethane 152.57
    ethyl orthosilicate 14.82
    tributyl phosphate 13.01
    diacetone alcohol 123.91
    N,N-dimethylaniline 18.59
    acrylonitrile 66.21
    aniline 33.67
    1,3-propanediol 135.69
    bromobenzene 12.45
    dibromomethane 23.9
    1,1,2,2-tetrachloroethane 104.66
    2-methyl-cyclohexyl acetate 23.06
    tetrabutyl urea 21.43
    diisobutyl methanol 7.65
    2-phenylethanol 32.19
    styrene 6.6
    dioctyl adipate 20.88
    dimethyl sulfate 125.38
    ethyl butyrate 21.66
    methyl lactate 99.05
    butyl lactate 26.81
    diethyl carbonate 17.14
    propanediol butyl ether 51.49
    triethyl orthoformate 20.03
    p-tert-butyltoluene 3.92
    methyl 4-tert-butylbenzoate 36.85
    morpholine 283.76
    tert-butylamine 21.2
    n-dodecanol 6.37
    dimethoxymethane 284.3
    ethylene carbonate 46.01
    cyrene 68.57
    2-ethoxyethyl acetate 38.87
    2-ethylhexyl acetate 17.42
    1,2,4-trichlorobenzene 23.75
    4-methylpyridine 61.8
    dibutyl ether 10.7
    2,6-dimethyl-4-heptanol 7.65
    DEF 77.35
    dimethyl isosorbide 112.49
    tetrachloroethylene 35.1
    eugenol 38.99
    triacetin 37.11
    span 80 40.98
    1,4-butanediol 33.52
    1,1-dichloroethane 40.37
    2-methyl-1-pentanol 29.03
    methyl formate 112.81
    2-methyl-1-butanol 38.93
    n-decane 0.44
    butyronitrile 38.98
    3,7-dimethyl-1-octanol 11.83
    1-chlorooctane 3.48
    1-chlorotetradecane 1.8
    n-nonane 0.32
    undecane 0.37
    tert-butylcyclohexane 0.5
    cyclooctane 0.16
    cyclopentanol 88.13
    tetrahydropyran 119.85
    tert-amyl methyl ether 24.09
    2,5,8-trioxanonane 102.41
    1-hexene 2.29
    2-isopropoxyethanol 69.73
    2,2,2-trifluoroethanol 25.72
    methyl butyrate 44.09

    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