Xanthohumol D

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  • Identifiers

    CAS number
    274675-25-1

    Molecular formula
    C21H22O6

    SMILES
    CC(=C)C(CC1=C(C(=C(C=C1O)OC)C(=O)/C=C/C2=CC=C(C=C2)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 44.34%
    Odorless 43.24%
    Spicy 35.79%
    Balsamic 33.81%
    Vanilla 31.36%
    Phenolic 24.9%
    Fruity 24.89%
    Bitter 23.19%
    Woody 23.18%
    Dry 22.81%

     

    Flavor
    Bitter 88.91%
    Odorless 35.7%
    Bland 24.66%
    Sweet-like 20.44%
    Cedarleaf 19.79%
    Nitrile 19.69%
    Parsley 19.34%
    Lovage 19.32%
    Broom 19.17%
    Heather 19.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.0

    pKa est.
    9.63 (weak base)

    Molecular weight
    370.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    920°C

    Flash point

    • 245.58 ˚C est.

  • Synonyms

    • Xanthohumol D
    • 274675-25-1
    • 3'-(2-Hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalcone
    • CHEBI:66335
    • DTXSID801317600
    • (E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methylbut-3-enyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • (E)-1-(2,4-dihydroxy-3-(2-hydroxy-3-methylbut-3-enyl)-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • RefChem:195134
    • DTXCID701747406
    • (2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • XanthohumolD
    • CHEMBL479500
    • orb1684153
    • SCHEMBL12961708
    • SCHEMBL29805526
    • HY-N1066
    • LMPK12120295
    • MFCD17214930
    • AKOS037515351
    • (E)-1-(2,4-Dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • DA-59176
    • MS-25955
    • XX178046
    • CS-0016350
    • F82081
    • Q27134883
    • (E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methyl-but-3-enyl)-6-methoxy-phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
    • rac-(2E)-1-{2,4-Dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one
    • 274675-25-1

  • Applications

    Xanthohumol D (CAS 274675-25-1) is a natural polyphenolic flavonoid derived from hops. In industry, it is primarily evaluated as a natural antioxidant and bioactive ingredient for cosmetics and personal care formulations; it is studied as a functional nutraceutical component in dietary supplements; it may serve as a stabilizer and antioxidant additive for polymers, coatings, and inks; it is explored as an intermediate or reference building block in pharmaceutical research and synthesis; and it is being evaluated for agricultural applications as a plant-derived bioactive component. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 123.7
    methanol 161.33
    isopropanol 83.8
    water 0.02
    ethyl acetate 56.37
    n-propanol 105.08
    acetone 503.05
    n-butanol 51.78
    acetonitrile 41.2
    DMF 259.75
    toluene 4.33
    isobutanol 35.78
    1,4-dioxane 133.05
    methyl acetate 83.65
    THF 1594.85
    2-butanone 226.73
    n-pentanol 31.56
    sec-butanol 52.71
    n-hexane 0.12
    ethylene glycol 28.46
    NMP 92.09
    cyclohexane 0.23
    DMSO 1987.54
    n-butyl acetate 9.87
    n-octanol 6.58
    chloroform 11.46
    n-propyl acetate 18.24
    acetic acid 129.35
    dichloromethane 9.53
    cyclohexanone 118.07
    propylene glycol 86.45
    isopropyl acetate 25.26
    DMAc 359.84
    2-ethoxyethanol 150.0
    isopentanol 27.9
    n-heptane 0.11
    ethyl formate 33.55
    1,2-dichloroethane 16.1
    n-hexanol 12.04
    2-methoxyethanol 447.65
    isobutyl acetate 7.65
    tetrachloromethane 1.04
    n-pentyl acetate 7.7
    transcutol 93.84
    n-heptanol 7.04
    ethylbenzene 2.09
    MIBK 30.51
    2-propoxyethanol 87.39
    tert-butanol 83.51
    MTBE 20.44
    2-butoxyethanol 31.79
    propionic acid 48.33
    o-xylene 2.32
    formic acid 48.17
    diethyl ether 18.76
    m-xylene 2.07
    p-xylene 2.75
    chlorobenzene 4.26
    dimethyl carbonate 36.41
    n-octane 0.09
    formamide 113.3
    cyclopentanone 359.07
    2-pentanone 103.66
    anisole 16.98
    cyclopentyl methyl ether 46.11
    gamma-butyrolactone 236.87
    1-methoxy-2-propanol 210.25
    pyridine 57.57
    3-pentanone 43.65
    furfural 71.8
    n-dodecane 0.15
    diethylene glycol 79.54
    diisopropyl ether 1.99
    tert-amyl alcohol 44.78
    acetylacetone 140.41
    n-hexadecane 0.17
    acetophenone 20.64
    methyl propionate 62.92
    isopentyl acetate 10.26
    trichloroethylene 32.67
    n-nonanol 6.77
    cyclohexanol 25.85
    benzyl alcohol 23.94
    2-ethylhexanol 4.62
    isooctanol 5.57
    dipropyl ether 6.43
    1,2-dichlorobenzene 3.3
    ethyl lactate 18.77
    propylene carbonate 35.79
    n-methylformamide 124.9
    2-pentanol 15.56
    n-pentane 0.1
    1-propoxy-2-propanol 42.64
    1-methoxy-2-propyl acetate 31.41
    2-(2-methoxypropoxy) propanol 32.18
    mesitylene 1.14
    ε-caprolactone 59.4
    p-cymene 1.21
    epichlorohydrin 278.8
    1,1,1-trichloroethane 8.95
    2-aminoethanol 79.23
    morpholine-4-carbaldehyde 104.03
    sulfolane 303.74
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 155.17
    n-hexyl acetate 11.23
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 46.4
    sec-butyl acetate 10.27
    tert-butyl acetate 28.4
    decalin 0.17
    glycerin 105.07
    diglyme 76.17
    acrylic acid 38.76
    isopropyl myristate 5.12
    n-butyric acid 51.04
    acetyl acetate 23.39
    di(2-ethylhexyl) phthalate 6.78
    ethyl propionate 16.96
    nitromethane 308.53
    1,2-diethoxyethane 21.41
    benzonitrile 11.67
    trioctyl phosphate 5.45
    1-bromopropane 5.7
    gamma-valerolactone 261.38
    n-decanol 5.15
    triethyl phosphate 6.75
    4-methyl-2-pentanol 7.33
    propionitrile 29.25
    vinylene carbonate 24.05
    1,1,2-trichlorotrifluoroethane 108.25
    DMS 13.71
    cumene 1.36
    2-octanol 4.01
    2-hexanone 36.29
    octyl acetate 7.54
    limonene 1.85
    1,2-dimethoxyethane 145.04
    ethyl orthosilicate 6.03
    tributyl phosphate 6.36
    diacetone alcohol 79.61
    N,N-dimethylaniline 8.68
    acrylonitrile 39.92
    aniline 16.82
    1,3-propanediol 148.7
    bromobenzene 2.74
    dibromomethane 4.87
    1,1,2,2-tetrachloroethane 29.22
    2-methyl-cyclohexyl acetate 9.71
    tetrabutyl urea 11.44
    diisobutyl methanol 3.12
    2-phenylethanol 16.45
    styrene 2.69
    dioctyl adipate 10.38
    dimethyl sulfate 65.01
    ethyl butyrate 9.13
    methyl lactate 52.57
    butyl lactate 12.13
    diethyl carbonate 6.44
    propanediol butyl ether 29.34
    triethyl orthoformate 8.06
    p-tert-butyltoluene 1.29
    methyl 4-tert-butylbenzoate 18.37
    morpholine 231.33
    tert-butylamine 11.44
    n-dodecanol 3.66
    dimethoxymethane 237.18
    ethylene carbonate 22.32
    cyrene 43.04
    2-ethoxyethyl acetate 18.17
    2-ethylhexyl acetate 5.95
    1,2,4-trichlorobenzene 6.32
    4-methylpyridine 32.53
    dibutyl ether 5.43
    2,6-dimethyl-4-heptanol 3.12
    DEF 53.53
    dimethyl isosorbide 54.16
    tetrachloroethylene 11.25
    eugenol 19.11
    triacetin 16.04
    span 80 20.86
    1,4-butanediol 34.09
    1,1-dichloroethane 11.82
    2-methyl-1-pentanol 18.66
    methyl formate 96.4
    2-methyl-1-butanol 26.61
    n-decane 0.22
    butyronitrile 23.73
    3,7-dimethyl-1-octanol 6.02
    1-chlorooctane 1.55
    1-chlorotetradecane 0.76
    n-nonane 0.16
    undecane 0.18
    tert-butylcyclohexane 0.16
    cyclooctane 0.08
    cyclopentanol 69.26
    tetrahydropyran 92.02
    tert-amyl methyl ether 14.56
    2,5,8-trioxanonane 61.1
    1-hexene 1.18
    2-isopropoxyethanol 58.13
    2,2,2-trifluoroethanol 22.97
    methyl butyrate 24.77

    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