Humulone

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  • Identifiers

    CAS number
    26472-41-3

    Molecular formula
    C21H30O5

    SMILES
    CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O

    Safety labels

  • Odor profile

    Fragrance
    Herbal 53.31%
    Mint 42.34%
    Fruity 40.83%
    Sweet 40.19%
    Woody 33.03%
    Spicy 31.1%
    Citrus 29.93%
    Floral 26.84%
    Dry 25.89%
    Warm 24.56%

     

    Flavor
    Bitter 67.87%
    Herbal 22.18%
    Odorless 20.69%
    Cedarleaf 20.65%
    Broom 20.09%
    Heather 20.08%
    Genet 19.92%
    Leaves 19.87%
    Lovage 19.79%
    Basil 19.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.2

    pKa est.
    7.26 (neutral)

    Molecular weight
    362.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    496°C

    Flash point

    • 186.34 ˚C est.

  • Synonyms

    • Humulone
    • 26472-41-3
    • alpha-Humulon
    • (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
    • (6R)-3,5,6-Trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone
    • CHEBI:5769
    • (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
    • 2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methyl-2-butenyl)-, (R)-(-)-
    • 2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-, (R)-
    • a-Humulon
    • alpha Bitter acid
    • (6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
    • (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclo
    • RefChem:146908
    • 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dien-1-one
    • 23510-81-8
    • 4-Cyclohexene-1,3-dione, 5,6-dihydroxy-2,6-bis(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
    • 4-Cyclohexene-1,3-dione, 5,6-dihydroxy-4-isovaleryl-2,6-bis(3-methyl-2-butenyl)-
    • VMSLCPKYRPDHLN-OAQYLSRUSA-N
    • Humulon
    • 2,4-Cyclohexadien-1-one, 3,5,6-trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-, (6R)-
    • CHEMBL3814665
    • alpha-Bitter acid
    • 1,4,6-Trihydroxy-1,3-bis(2-isopentenyl)-5-isovaleryl-3,5-cyclohexadien-2-on
    • alpha-Lupulic acid
    • (+)-humulone
    • Humulone (R-Humulone)
    • (-)-(R)-Humulone
    • Phloroglucinol Impurity T
    • SCHEMBL144835
    • orb2279161
    • CHEMBL1592914
    • SCHEMBL13629033
    • SCHEMBL17584889
    • DTXSID501019081
    • HY-N6084
    • BDBM50177000
    • FH65574
    • NCGC00160174-01!HUMULONE
    • NCGC00160174-01
    • DA-69206
    • MS-25761
    • CS-0032512
    • NS00051310
    • G12204
    • AB-342/42478394
    • Q419456
    • ((r)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1oxobutyl)-2,4-cyclohexadien-1-one)
    • (R)-3,5,6-Trihydroxy-4,6-bis(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)cyclohexa-2,4-dienone
    • 3,5,6-Trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one #
    • 23510-81-8

  • Applications

    Humulone (CAS 26472-41-3) is primarily used as a natural bittering agent derived from hops, contributing bitterness and hop-derived flavor notes to beer and other fermented beverages. Beyond brewing, it is often evaluated in flavor and fragrance research as part of hop extracts and can appear in cosmetic formulations as a natural-origin ingredient from hops. In pharmaceutical and natural-product research contexts, humulone is studied for potential bioactivities and as a scaffold for lead compounds, with applications largely exploratory and subject to regulatory limits. It may also serve as a starting point for the synthesis of related bitter compounds in industrial research and development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 518.4
    methanol 516.78
    isopropanol 386.44
    water 0.23
    ethyl acetate 320.06
    n-propanol 480.94
    acetone 547.26
    n-butanol 391.88
    acetonitrile 196.01
    DMF 1671.86
    toluene 162.31
    isobutanol 361.66
    1,4-dioxane 483.23
    methyl acetate 378.36
    THF 1369.0
    2-butanone 541.8
    n-pentanol 272.79
    sec-butanol 408.05
    n-hexane 16.79
    ethylene glycol 138.65
    NMP 1778.78
    cyclohexane 17.19
    DMSO 1069.85
    n-butyl acetate 281.51
    n-octanol 95.4
    chloroform 578.63
    n-propyl acetate 205.14
    acetic acid 617.32
    dichloromethane 466.11
    cyclohexanone 682.53
    propylene glycol 332.21
    isopropyl acetate 255.69
    DMAc 1512.04
    2-ethoxyethanol 447.19
    isopentanol 343.34
    n-heptane 7.85
    ethyl formate 215.53
    1,2-dichloroethane 457.82
    n-hexanol 310.68
    2-methoxyethanol 959.35
    isobutyl acetate 157.29
    tetrachloromethane 74.86
    n-pentyl acetate 187.78
    transcutol 829.6
    n-heptanol 134.43
    ethylbenzene 84.34
    MIBK 314.95
    2-propoxyethanol 657.47
    tert-butanol 439.92
    MTBE 257.31
    2-butoxyethanol 349.3
    propionic acid 380.98
    o-xylene 100.83
    formic acid 256.35
    diethyl ether 213.3
    m-xylene 116.75
    p-xylene 101.11
    chlorobenzene 226.05
    dimethyl carbonate 272.67
    n-octane 4.03
    formamide 404.64
    cyclopentanone 1089.4
    2-pentanone 442.49
    anisole 201.44
    cyclopentyl methyl ether 515.45
    gamma-butyrolactone 1115.56
    1-methoxy-2-propanol 872.34
    pyridine 546.76
    3-pentanone 299.55
    furfural 653.22
    n-dodecane 3.21
    diethylene glycol 455.67
    diisopropyl ether 69.01
    tert-amyl alcohol 419.34
    acetylacetone 467.51
    n-hexadecane 3.66
    acetophenone 251.92
    methyl propionate 421.73
    isopentyl acetate 291.96
    trichloroethylene 886.81
    n-nonanol 93.66
    cyclohexanol 345.23
    benzyl alcohol 248.08
    2-ethylhexanol 148.95
    isooctanol 113.28
    dipropyl ether 105.01
    1,2-dichlorobenzene 204.03
    ethyl lactate 192.61
    propylene carbonate 552.19
    n-methylformamide 640.86
    2-pentanol 283.77
    n-pentane 16.85
    1-propoxy-2-propanol 380.45
    1-methoxy-2-propyl acetate 397.13
    2-(2-methoxypropoxy) propanol 321.28
    mesitylene 63.66
    ε-caprolactone 644.08
    p-cymene 54.66
    epichlorohydrin 1261.9
    1,1,1-trichloroethane 402.66
    2-aminoethanol 355.34
    morpholine-4-carbaldehyde 1179.3
    sulfolane 1499.57
    2,2,4-trimethylpentane 14.53
    2-methyltetrahydrofuran 817.51
    n-hexyl acetate 231.5
    isooctane 10.43
    2-(2-butoxyethoxy)ethanol 418.5
    sec-butyl acetate 170.49
    tert-butyl acetate 317.74
    decalin 16.61
    glycerin 406.95
    diglyme 602.37
    acrylic acid 337.06
    isopropyl myristate 77.68
    n-butyric acid 502.82
    acetyl acetate 195.96
    di(2-ethylhexyl) phthalate 123.61
    ethyl propionate 197.11
    nitromethane 753.08
    1,2-diethoxyethane 216.16
    benzonitrile 190.64
    trioctyl phosphate 88.41
    1-bromopropane 216.61
    gamma-valerolactone 1300.1
    n-decanol 66.84
    triethyl phosphate 103.81
    4-methyl-2-pentanol 171.98
    propionitrile 238.47
    vinylene carbonate 394.03
    1,1,2-trichlorotrifluoroethane 813.23
    DMS 242.32
    cumene 63.42
    2-octanol 83.81
    2-hexanone 239.84
    octyl acetate 120.09
    limonene 83.67
    1,2-dimethoxyethane 511.38
    ethyl orthosilicate 97.7
    tributyl phosphate 103.86
    diacetone alcohol 542.78
    N,N-dimethylaniline 184.4
    acrylonitrile 305.38
    aniline 304.09
    1,3-propanediol 467.0
    bromobenzene 193.19
    dibromomethane 320.52
    1,1,2,2-tetrachloroethane 783.9
    2-methyl-cyclohexyl acetate 192.41
    tetrabutyl urea 146.05
    diisobutyl methanol 77.75
    2-phenylethanol 275.38
    styrene 94.3
    dioctyl adipate 132.85
    dimethyl sulfate 502.26
    ethyl butyrate 166.5
    methyl lactate 404.19
    butyl lactate 212.09
    diethyl carbonate 110.57
    propanediol butyl ether 307.94
    triethyl orthoformate 126.05
    p-tert-butyltoluene 60.78
    methyl 4-tert-butylbenzoate 270.68
    morpholine 852.71
    tert-butylamine 208.61
    n-dodecanol 45.58
    dimethoxymethane 707.62
    ethylene carbonate 341.72
    cyrene 397.28
    2-ethoxyethyl acetate 280.73
    2-ethylhexyl acetate 211.56
    1,2,4-trichlorobenzene 282.24
    4-methylpyridine 555.15
    dibutyl ether 65.89
    2,6-dimethyl-4-heptanol 77.75
    DEF 567.33
    dimethyl isosorbide 587.1
    tetrachloroethylene 424.16
    eugenol 278.07
    triacetin 220.66
    span 80 278.53
    1,4-butanediol 175.13
    1,1-dichloroethane 425.09
    2-methyl-1-pentanol 270.18
    methyl formate 413.26
    2-methyl-1-butanol 373.32
    n-decane 5.27
    butyronitrile 230.42
    3,7-dimethyl-1-octanol 116.17
    1-chlorooctane 38.36
    1-chlorotetradecane 15.32
    n-nonane 4.58
    undecane 4.04
    tert-butylcyclohexane 16.23
    cyclooctane 6.58
    cyclopentanol 486.74
    tetrahydropyran 481.8
    tert-amyl methyl ether 244.06
    2,5,8-trioxanonane 411.28
    1-hexene 73.18
    2-isopropoxyethanol 317.31
    2,2,2-trifluoroethanol 214.06
    methyl butyrate 273.14

    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