Deoxycohumulone

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  • Identifiers

    CAS number
    5880-42-2

    Molecular formula
    C20H28O4

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

    Safety labels

  • Odor profile

    Fragrance
    Herbal 43.76%
    Fruity 43.16%
    Woody 42.22%
    Spicy 41.11%
    Citrus 32.09%
    Sweet 31.33%
    Floral 30.27%
    Dry 29.41%
    Phenolic 28.43%
    Fresh 26.28%

     

    Flavor
    Bitter 64.69%
    Herbal 28.76%
    Woody 22.53%
    Cedarleaf 20.45%
    Broom 20.26%
    Parsley 20.13%
    Heather 20.01%
    Genet 19.97%
    Lovage 19.69%
    Green pepper 19.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.0

    pKa est.
    9.24 (weak base)

    Molecular weight
    332.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    553°C

    Melting point expt.

    • 88 - 89 °C

    Flash point

    • 186.88 ˚C est.

  • Synonyms

    • deoxycohumulone
    • diprenylphlorisobutyrophenone
    • CHEBI:134353
    • 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one
    • 2-methyl-1-(2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)propan-1-one
    • RefChem:919873
    • 4-Deoxycohumulone
    • Desoxycohumulone
    • 5880-42-2
    • 3,5-Bis(3-methyl-2-butenyl)phlorisobutyrophenone
    • 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propan-1-one
    • SCHEMBL24075655
    • 3,5-diprenylphlorisobutyrophenone
    • DTXSID001316660
    • 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-1-propanone
    • DB-303431
    • {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-propyl) ketone
    • 2',4',6'-Trihydroxy-2-methyl-3',5'-bis(3-methyl-2-butenyl)propiophenone, 8CI
    • 2,4-Bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-1,3,5-cyclohexanetrione, 9CI
    • 2-Methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl ]-1-propanone
    • 5880-42-2

  • Applications

    Deoxycohumulone (CAS number: 5880-42-2) is a hop-derived bitter acid primarily discussed in hop chemistry and beer flavor research. In industry practice, it can function as an analytical reference standard for hop bitter acids in quality control and method development. It participates in flavor science related to beer and other hop-containing beverages, contributing to bitterness and overall mouthfeel within the humulone family. It is also studied as an intermediate or precursor in the synthesis and investigation of hop-derived aroma and bitterness compounds, and has been examined for antioxidant activity in hop extracts. Its applications are mainly research-oriented and analytical, and use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 275.79
    methanol 192.98
    isopropanol 299.36
    water 0.08
    ethyl acetate 300.04
    n-propanol 290.85
    acetone 534.64
    n-butanol 267.62
    acetonitrile 153.7
    DMF 1278.2
    toluene 126.81
    isobutanol 247.9
    1,4-dioxane 442.76
    methyl acetate 345.11
    THF 1487.68
    2-butanone 493.3
    n-pentanol 188.57
    sec-butanol 302.53
    n-hexane 17.94
    ethylene glycol 56.2
    NMP 1247.59
    cyclohexane 19.09
    DMSO 945.79
    n-butyl acetate 241.36
    n-octanol 84.21
    chloroform 505.25
    n-propyl acetate 179.28
    acetic acid 297.23
    dichloromethane 392.55
    cyclohexanone 628.3
    propylene glycol 218.02
    isopropyl acetate 229.82
    DMAc 1185.85
    2-ethoxyethanol 277.88
    isopentanol 245.57
    n-heptane 9.51
    ethyl formate 170.7
    1,2-dichloroethane 378.68
    n-hexanol 219.87
    2-methoxyethanol 543.73
    isobutyl acetate 145.3
    tetrachloromethane 63.94
    n-pentyl acetate 166.88
    transcutol 534.09
    n-heptanol 114.57
    ethylbenzene 70.0
    MIBK 252.94
    2-propoxyethanol 410.16
    tert-butanol 414.75
    MTBE 283.85
    2-butoxyethanol 240.51
    propionic acid 268.47
    o-xylene 82.67
    formic acid 79.83
    diethyl ether 181.94
    m-xylene 98.91
    p-xylene 99.7
    chlorobenzene 190.13
    dimethyl carbonate 215.37
    n-octane 5.15
    formamide 174.34
    cyclopentanone 1099.53
    2-pentanone 377.94
    anisole 171.78
    cyclopentyl methyl ether 434.05
    gamma-butyrolactone 1024.5
    1-methoxy-2-propanol 601.18
    pyridine 413.86
    3-pentanone 274.43
    furfural 499.28
    n-dodecane 4.4
    diethylene glycol 263.02
    diisopropyl ether 72.49
    tert-amyl alcohol 343.67
    acetylacetone 442.06
    n-hexadecane 5.11
    acetophenone 195.38
    methyl propionate 363.17
    isopentyl acetate 258.47
    trichloroethylene 742.69
    n-nonanol 82.88
    cyclohexanol 279.1
    benzyl alcohol 165.42
    2-ethylhexanol 124.63
    isooctanol 100.9
    dipropyl ether 106.72
    1,2-dichlorobenzene 166.82
    ethyl lactate 138.19
    propylene carbonate 486.44
    n-methylformamide 363.86
    2-pentanol 210.83
    n-pentane 14.37
    1-propoxy-2-propanol 280.99
    1-methoxy-2-propyl acetate 316.2
    2-(2-methoxypropoxy) propanol 208.93
    mesitylene 57.83
    ε-caprolactone 532.32
    p-cymene 53.21
    epichlorohydrin 1037.29
    1,1,1-trichloroethane 356.12
    2-aminoethanol 169.3
    morpholine-4-carbaldehyde 787.87
    sulfolane 1364.17
    2,2,4-trimethylpentane 14.38
    2-methyltetrahydrofuran 739.01
    n-hexyl acetate 208.6
    isooctane 11.21
    2-(2-butoxyethoxy)ethanol 280.71
    sec-butyl acetate 146.88
    tert-butyl acetate 292.09
    decalin 18.36
    glycerin 236.52
    diglyme 420.59
    acrylic acid 217.87
    isopropyl myristate 77.85
    n-butyric acid 342.5
    acetyl acetate 177.36
    di(2-ethylhexyl) phthalate 98.04
    ethyl propionate 177.96
    nitromethane 525.8
    1,2-diethoxyethane 179.4
    benzonitrile 156.65
    trioctyl phosphate 77.29
    1-bromopropane 186.38
    gamma-valerolactone 1034.54
    n-decanol 61.83
    triethyl phosphate 91.04
    4-methyl-2-pentanol 128.41
    propionitrile 183.88
    vinylene carbonate 314.78
    1,1,2-trichlorotrifluoroethane 569.46
    DMS 201.56
    cumene 56.63
    2-octanol 79.99
    2-hexanone 217.3
    octyl acetate 110.71
    limonene 78.71
    1,2-dimethoxyethane 409.89
    ethyl orthosilicate 87.69
    tributyl phosphate 86.0
    diacetone alcohol 417.33
    N,N-dimethylaniline 143.7
    acrylonitrile 213.92
    aniline 218.93
    1,3-propanediol 303.36
    bromobenzene 177.71
    dibromomethane 273.6
    1,1,2,2-tetrachloroethane 637.88
    2-methyl-cyclohexyl acetate 165.71
    tetrabutyl urea 118.48
    diisobutyl methanol 70.69
    2-phenylethanol 191.46
    styrene 78.93
    dioctyl adipate 122.31
    dimethyl sulfate 413.37
    ethyl butyrate 146.99
    methyl lactate 263.94
    butyl lactate 164.17
    diethyl carbonate 100.6
    propanediol butyl ether 219.86
    triethyl orthoformate 116.27
    p-tert-butyltoluene 57.61
    methyl 4-tert-butylbenzoate 200.07
    morpholine 716.35
    tert-butylamine 198.76
    n-dodecanol 45.13
    dimethoxymethane 549.81
    ethylene carbonate 283.36
    cyrene 272.35
    2-ethoxyethyl acetate 221.39
    2-ethylhexyl acetate 190.57
    1,2,4-trichlorobenzene 223.2
    4-methylpyridine 425.49
    dibutyl ether 73.41
    2,6-dimethyl-4-heptanol 70.69
    DEF 427.74
    dimethyl isosorbide 427.74
    tetrachloroethylene 293.06
    eugenol 188.03
    triacetin 186.67
    span 80 208.73
    1,4-butanediol 104.86
    1,1-dichloroethane 380.74
    2-methyl-1-pentanol 195.04
    methyl formate 264.23
    2-methyl-1-butanol 243.42
    n-decane 7.07
    butyronitrile 188.09
    3,7-dimethyl-1-octanol 93.27
    1-chlorooctane 43.5
    1-chlorotetradecane 18.34
    n-nonane 6.39
    undecane 5.49
    tert-butylcyclohexane 19.14
    cyclooctane 7.17
    cyclopentanol 420.0
    tetrahydropyran 466.11
    tert-amyl methyl ether 216.03
    2,5,8-trioxanonane 286.83
    1-hexene 71.46
    2-isopropoxyethanol 218.16
    2,2,2-trifluoroethanol 117.91
    methyl butyrate 242.22

    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