Deoxyhumulone

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  • Identifiers

    CAS number
    4374-93-0

    Molecular formula
    C21H30O4

    SMILES
    CC(C)CC(=O)C1=C(C(=C(C(=C1O)CC=C(C)C)O)CC=C(C)C)O

    Safety labels

  • Odor profile

    Fragrance
    Herbal 47.08%
    Woody 43.29%
    Spicy 42.97%
    Fruity 39.11%
    Phenolic 30.06%
    Sweet 29.36%
    Dry 28.75%
    Mint 27.91%
    Citrus 26.85%
    Floral 25.24%

     

    Flavor
    Bitter 64.22%
    Herbal 28.77%
    Woody 21.29%
    Cedarleaf 20.3%
    Parsley 20.04%
    Heather 20.03%
    Broom 19.98%
    Genet 19.74%
    Lovage 19.74%
    Mild 19.53%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.2

    pKa est.
    9.19 (weak base)

    Molecular weight
    346.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    538°C

    Melting point expt.

    • 83 °C

    Flash point

    • 191.38 ˚C est.

  • Synonyms

    • Deoxyhumulone
    • 4-Deoxyhumulone
    • 4374-93-0
    • 2G8GOM6DZY
    • diprenylphlorisovalerophenone
    • CHEBI:134345
    • DTXSID20195922
    • 3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]butan-1-one
    • 3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]butan-1-one
    • 3-methyl-1-(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)butan-1-one
    • 3-methyl-1-(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl)butan-1-one
    • RefChem:1083150
    • DTXCID60118413
    • Humulone, 4-deoxy-
    • 4-Deoxy-humulone
    • UNII-2G8GOM6DZY
    • 3,5-Bis(3-methyl-2-butenyl)phloroisovalerophenone
    • 3,5-Bis(3-methyl-2-butenyl)phlorisovalerophenone
    • 1-Butanone, 3-methyl-1-(2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)-
    • Desoxyhumulone
    • 1-BUTANONE, 3-METHYL-1-(2,4,6-TRIHYDROXY-3,5-BIS(3-METHYL-2-BUTEN-1-YL)PHENYL)-
    • 1-Butanone, 3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-buten-1-yl)phenyl]-
    • DEOXYHUMULONE, 4-
    • SCHEMBL6125217
    • 3,5-diprenylphlorisovalerophenone
    • {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone
    • 3-METHYL-1-(2,4,6-TRIHYDROXY-3,5-BIS(3-METHYL-2-BUTEN-1-YL)PHENYL)-1-BUTANONE
    • 3-Methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-1-butanone, 9CI
    • 4374-93-0

  • Applications

    Deoxyhumulone is primarily encountered as an intermediate in the synthesis of hop-derived compounds and related fragrance/flavor research. In the flavor and fragrance arena, it is evaluated as a precursor and/or reference component for the synthesis of aroma compounds connected to hop systems; in cosmetics and personal care, it may be considered as a precursor for fragrance ingredients; in industrial manufacturing, it serves as a building block in the synthesis of related compounds; and in analytical chemistry, it can be used as a reference standard to support quality control of hop-related constituents in brewing and flavor applications.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 368.53
    methanol 275.92
    isopropanol 362.81
    water 0.2
    ethyl acetate 372.15
    n-propanol 358.64
    acetone 698.15
    n-butanol 306.34
    acetonitrile 207.0
    DMF 1707.1
    toluene 97.03
    isobutanol 294.57
    1,4-dioxane 520.7
    methyl acetate 432.52
    THF 1798.52
    2-butanone 537.66
    n-pentanol 208.74
    sec-butanol 314.46
    n-hexane 12.27
    ethylene glycol 123.38
    NMP 1884.87
    cyclohexane 12.42
    DMSO 1572.46
    n-butyl acetate 300.87
    n-octanol 101.67
    chloroform 513.54
    n-propyl acetate 229.82
    acetic acid 638.65
    dichloromethane 419.08
    cyclohexanone 768.06
    propylene glycol 416.18
    isopropyl acetate 287.14
    DMAc 1469.73
    2-ethoxyethanol 402.01
    isopentanol 283.35
    n-heptane 7.64
    ethyl formate 231.08
    1,2-dichloroethane 399.67
    n-hexanol 220.63
    2-methoxyethanol 979.72
    isobutyl acetate 187.05
    tetrachloromethane 62.96
    n-pentyl acetate 225.21
    transcutol 1111.11
    n-heptanol 130.11
    ethylbenzene 55.24
    MIBK 294.57
    2-propoxyethanol 638.63
    tert-butanol 482.1
    MTBE 264.93
    2-butoxyethanol 340.81
    propionic acid 434.16
    o-xylene 65.92
    formic acid 187.57
    diethyl ether 167.93
    m-xylene 83.3
    p-xylene 86.16
    chlorobenzene 196.03
    dimethyl carbonate 316.78
    n-octane 4.02
    formamide 345.42
    cyclopentanone 1408.16
    2-pentanone 425.67
    anisole 177.21
    cyclopentyl methyl ether 483.48
    gamma-butyrolactone 1559.69
    1-methoxy-2-propanol 970.72
    pyridine 447.19
    3-pentanone 288.03
    furfural 752.79
    n-dodecane 3.9
    diethylene glycol 473.16
    diisopropyl ether 67.94
    tert-amyl alcohol 356.19
    acetylacetone 636.27
    n-hexadecane 4.52
    acetophenone 235.24
    methyl propionate 456.54
    isopentyl acetate 334.69
    trichloroethylene 885.23
    n-nonanol 101.58
    cyclohexanol 294.84
    benzyl alcohol 198.61
    2-ethylhexanol 131.65
    isooctanol 118.03
    dipropyl ether 118.91
    1,2-dichlorobenzene 182.18
    ethyl lactate 211.57
    propylene carbonate 744.75
    n-methylformamide 567.64
    2-pentanol 216.83
    n-pentane 9.67
    1-propoxy-2-propanol 438.79
    1-methoxy-2-propyl acetate 471.83
    2-(2-methoxypropoxy) propanol 356.75
    mesitylene 52.25
    ε-caprolactone 739.07
    p-cymene 54.55
    epichlorohydrin 1406.42
    1,1,1-trichloroethane 406.93
    2-aminoethanol 308.59
    morpholine-4-carbaldehyde 1228.01
    sulfolane 2178.32
    2,2,4-trimethylpentane 11.04
    2-methyltetrahydrofuran 828.22
    n-hexyl acetate 284.64
    isooctane 9.73
    2-(2-butoxyethoxy)ethanol 494.22
    sec-butyl acetate 178.74
    tert-butyl acetate 391.74
    decalin 13.51
    glycerin 503.44
    diglyme 687.64
    acrylic acid 397.85
    isopropyl myristate 105.83
    n-butyric acid 546.54
    acetyl acetate 252.68
    di(2-ethylhexyl) phthalate 143.95
    ethyl propionate 223.36
    nitromethane 1009.73
    1,2-diethoxyethane 244.1
    benzonitrile 183.69
    trioctyl phosphate 110.46
    1-bromopropane 160.12
    gamma-valerolactone 1580.12
    n-decanol 74.65
    triethyl phosphate 123.26
    4-methyl-2-pentanol 149.49
    propionitrile 215.74
    vinylene carbonate 486.08
    1,1,2-trichlorotrifluoroethane 945.64
    DMS 319.83
    cumene 48.1
    2-octanol 88.69
    2-hexanone 246.98
    octyl acetate 154.68
    limonene 79.77
    1,2-dimethoxyethane 527.48
    ethyl orthosilicate 115.41
    tributyl phosphate 136.24
    diacetone alcohol 624.34
    N,N-dimethylaniline 149.26
    acrylonitrile 282.03
    aniline 237.28
    1,3-propanediol 515.78
    bromobenzene 167.02
    dibromomethane 258.95
    1,1,2,2-tetrachloroethane 757.27
    2-methyl-cyclohexyl acetate 226.78
    tetrabutyl urea 176.3
    diisobutyl methanol 84.09
    2-phenylethanol 233.11
    styrene 64.01
    dioctyl adipate 188.34
    dimethyl sulfate 640.77
    ethyl butyrate 198.01
    methyl lactate 437.47
    butyl lactate 254.46
    diethyl carbonate 139.1
    propanediol butyl ether 385.6
    triethyl orthoformate 164.53
    p-tert-butyltoluene 61.69
    methyl 4-tert-butylbenzoate 296.5
    morpholine 898.29
    tert-butylamine 201.19
    n-dodecanol 53.87
    dimethoxymethane 771.61
    ethylene carbonate 426.46
    cyrene 410.19
    2-ethoxyethyl acetate 338.04
    2-ethylhexyl acetate 238.23
    1,2,4-trichlorobenzene 268.41
    4-methylpyridine 454.82
    dibutyl ether 84.62
    2,6-dimethyl-4-heptanol 84.09
    DEF 513.67
    dimethyl isosorbide 703.44
    tetrachloroethylene 332.78
    eugenol 274.88
    triacetin 324.81
    span 80 364.19
    1,4-butanediol 157.74
    1,1-dichloroethane 384.09
    2-methyl-1-pentanol 206.3
    methyl formate 414.34
    2-methyl-1-butanol 270.18
    n-decane 6.28
    butyronitrile 203.67
    3,7-dimethyl-1-octanol 116.18
    1-chlorooctane 44.97
    1-chlorotetradecane 18.64
    n-nonane 5.42
    undecane 4.87
    tert-butylcyclohexane 15.59
    cyclooctane 4.91
    cyclopentanol 496.35
    tetrahydropyran 460.32
    tert-amyl methyl ether 209.76
    2,5,8-trioxanonane 478.49
    1-hexene 51.69
    2-isopropoxyethanol 293.8
    2,2,2-trifluoroethanol 228.06
    methyl butyrate 306.59

    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