Isohumulone

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  • Identifiers

    CAS number
    25522-96-7

    Molecular formula
    C21H30O5

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

    Safety labels

  • Odor profile

    Fragrance
    Herbal 51.19%
    Mint 42.87%
    Fruity 41.58%
    Sweet 41.52%
    Woody 34.71%
    Citrus 31.15%
    Floral 30.09%
    Spicy 28.31%
    Dry 26.67%
    Cooling 24.74%

     

    Flavor
    Bitter 70.52%
    Odorless 21.33%
    Cedarleaf 20.54%
    Broom 20.05%
    Heather 20.01%
    Genet 19.85%
    Lovage 19.29%
    Leaves 19.24%
    Bland 19.09%
    Parsley 18.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.8

    pKa est.
    6.96 (neutral)

    Molecular weight
    362.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    500°C

    Melting point expt.

    • 62 - 63 °C

    Flash point

    • 161.11 ˚C est.

  • Synonyms

    • Isohumulone
    • 25522-96-7
    • 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
    • 3,4-Dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one
    • E2S413495Y
    • RefChem:149427
    • 2-CYCLOPENTEN-1-ONE, 3,4-DIHYDROXY-5-(3-METHYL-2-BUTEN-1-YL)-2-(3-METHYL-1-OXOBUTYL)-4-(4-METHYL-1-OXO-3-PENTEN-1-YL)-
    • 247-072-1
    • 3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-one
    • Isohumulone A
    • UNII-E2S413495Y
    • 3,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-2-cyclopenten-1-one; Iso-n-humulone; IsoHopCO2N
    • EINECS 247-072-1
    • SCHEMBL316229
    • DTXSID90948427
    • CHEBI:197058
    • 3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
    • NS00052115
    • Q3155510
    • 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-
    • 3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-one #
    • 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
    • 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)-1-cyclopent-2-enone
    • 3-Penten-1-one, 1-[1,2-dihydroxy-3-isovaleryl-5-(3-methyl-2-butenyl)-4-oxo-2-cyclopenten-1-yl]-4-methyl-
    • 25522-96-7

  • Applications

    Isohumulone (CAS 25522-96-7), a hop-derived alpha-acid, is primarily used in brewing as a bittering agent; during wort boiling, it undergoes isomerization to form iso-alpha acids that contribute bitterness and hop character to beer. It may be used as a flavoring component in beverages and some food formulations to impart bitter notes; it can serve as an analytical reference standard for quantifying hop bitter acids in beer and hop extracts; and it can act as an intermediate in processing hop resins and in the synthesis of related bitter compounds in industrial manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 729.85
    methanol 719.28
    isopropanol 586.39
    water 0.31
    ethyl acetate 676.81
    n-propanol 715.45
    acetone 928.5
    n-butanol 633.51
    acetonitrile 367.08
    DMF 2640.32
    toluene 412.91
    isobutanol 582.38
    1,4-dioxane 896.2
    methyl acetate 680.36
    THF 2366.04
    2-butanone 936.42
    n-pentanol 431.17
    sec-butanol 671.87
    n-hexane 37.11
    ethylene glycol 152.87
    NMP 3271.49
    cyclohexane 44.78
    DMSO 1516.86
    n-butyl acetate 493.01
    n-octanol 153.38
    chloroform 1575.39
    n-propyl acetate 395.43
    acetic acid 1120.07
    dichloromethane 1274.02
    cyclohexanone 1324.23
    propylene glycol 368.36
    isopropyl acetate 520.56
    DMAc 2424.71
    2-ethoxyethanol 694.64
    isopentanol 586.38
    n-heptane 15.62
    ethyl formate 414.67
    1,2-dichloroethane 1084.98
    n-hexanol 459.09
    2-methoxyethanol 1330.14
    isobutyl acetate 290.33
    tetrachloromethane 206.41
    n-pentyl acetate 345.21
    transcutol 1360.94
    n-heptanol 198.96
    ethylbenzene 208.5
    MIBK 556.35
    2-propoxyethanol 983.6
    tert-butanol 639.85
    MTBE 470.76
    2-butoxyethanol 500.68
    propionic acid 660.9
    o-xylene 247.04
    formic acid 442.7
    diethyl ether 459.75
    m-xylene 270.84
    p-xylene 240.29
    chlorobenzene 542.07
    dimethyl carbonate 498.76
    n-octane 7.04
    formamide 735.97
    cyclopentanone 1867.62
    2-pentanone 808.71
    anisole 440.09
    cyclopentyl methyl ether 995.71
    gamma-butyrolactone 1988.82
    1-methoxy-2-propanol 1257.47
    pyridine 1086.24
    3-pentanone 602.08
    furfural 1269.79
    n-dodecane 5.15
    diethylene glycol 604.17
    diisopropyl ether 139.38
    tert-amyl alcohol 687.82
    acetylacetone 899.34
    n-hexadecane 6.11
    acetophenone 528.55
    methyl propionate 797.17
    isopentyl acetate 500.99
    trichloroethylene 2121.49
    n-nonanol 149.85
    cyclohexanol 656.78
    benzyl alcohol 454.85
    2-ethylhexanol 237.56
    isooctanol 174.57
    dipropyl ether 191.78
    1,2-dichlorobenzene 499.85
    ethyl lactate 305.47
    propylene carbonate 1122.96
    n-methylformamide 1058.93
    2-pentanol 507.69
    n-pentane 38.32
    1-propoxy-2-propanol 577.06
    1-methoxy-2-propyl acetate 637.69
    2-(2-methoxypropoxy) propanol 500.26
    mesitylene 143.01
    ε-caprolactone 1290.24
    p-cymene 106.84
    epichlorohydrin 2362.73
    1,1,1-trichloroethane 989.86
    2-aminoethanol 462.65
    morpholine-4-carbaldehyde 2036.85
    sulfolane 2481.81
    2,2,4-trimethylpentane 29.34
    2-methyltetrahydrofuran 1528.12
    n-hexyl acetate 458.09
    isooctane 19.25
    2-(2-butoxyethoxy)ethanol 655.05
    sec-butyl acetate 342.42
    tert-butyl acetate 573.02
    decalin 38.75
    glycerin 507.44
    diglyme 948.68
    acrylic acid 622.41
    isopropyl myristate 138.25
    n-butyric acid 929.72
    acetyl acetate 426.09
    di(2-ethylhexyl) phthalate 205.56
    ethyl propionate 379.21
    nitromethane 1415.64
    1,2-diethoxyethane 380.96
    benzonitrile 396.07
    trioctyl phosphate 135.3
    1-bromopropane 555.7
    gamma-valerolactone 2253.04
    n-decanol 102.09
    triethyl phosphate 185.66
    4-methyl-2-pentanol 297.35
    propionitrile 435.91
    vinylene carbonate 814.94
    1,1,2-trichlorotrifluoroethane 1609.1
    DMS 461.77
    cumene 134.66
    2-octanol 129.96
    2-hexanone 435.72
    octyl acetate 210.33
    limonene 164.72
    1,2-dimethoxyethane 830.85
    ethyl orthosilicate 180.84
    tributyl phosphate 174.54
    diacetone alcohol 822.71
    N,N-dimethylaniline 377.99
    acrylonitrile 538.2
    aniline 644.28
    1,3-propanediol 623.89
    bromobenzene 511.09
    dibromomethane 833.64
    1,1,2,2-tetrachloroethane 1872.19
    2-methyl-cyclohexyl acetate 348.02
    tetrabutyl urea 238.69
    diisobutyl methanol 121.56
    2-phenylethanol 483.44
    styrene 236.62
    dioctyl adipate 235.36
    dimethyl sulfate 909.6
    ethyl butyrate 312.69
    methyl lactate 612.74
    butyl lactate 331.01
    diethyl carbonate 221.14
    propanediol butyl ether 443.77
    triethyl orthoformate 233.52
    p-tert-butyltoluene 111.23
    methyl 4-tert-butylbenzoate 462.6
    morpholine 1514.73
    tert-butylamine 332.37
    n-dodecanol 68.8
    dimethoxymethane 1145.25
    ethylene carbonate 698.83
    cyrene 637.31
    2-ethoxyethyl acetate 514.71
    2-ethylhexyl acetate 381.61
    1,2,4-trichlorobenzene 702.39
    4-methylpyridine 1195.39
    dibutyl ether 128.41
    2,6-dimethyl-4-heptanol 121.56
    DEF 1143.57
    dimethyl isosorbide 902.02
    tetrachloroethylene 1032.22
    eugenol 455.25
    triacetin 415.44
    span 80 412.62
    1,4-butanediol 236.95
    1,1-dichloroethane 1017.75
    2-methyl-1-pentanol 455.14
    methyl formate 712.06
    2-methyl-1-butanol 661.81
    n-decane 9.75
    butyronitrile 440.45
    3,7-dimethyl-1-octanol 192.17
    1-chlorooctane 83.16
    1-chlorotetradecane 27.99
    n-nonane 8.64
    undecane 6.83
    tert-butylcyclohexane 33.9
    cyclooctane 15.38
    cyclopentanol 842.63
    tetrahydropyran 971.64
    tert-amyl methyl ether 467.24
    2,5,8-trioxanonane 633.3
    1-hexene 167.85
    2-isopropoxyethanol 495.78
    2,2,2-trifluoroethanol 451.68
    methyl butyrate 539.44

    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