Lupulone

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  • Identifiers

    CAS number
    468-28-0

    Molecular formula
    C26H38O4

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

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Herbal 63.06%
    Fruity 53.64%
    Mint 40.35%
    Woody 39.62%
    Floral 39.11%
    Citrus 37.28%
    Sweet 35.65%
    Spicy 34.52%
    Rose 31.3%
    Fresh 30.96%

     

    Flavor
    Bitter 59.9%
    Herbal 30.69%
    Cedarleaf 20.35%
    Heather 20.11%
    Genet 19.92%
    Broom 19.88%
    Lovage 19.77%
    Basil 19.55%
    Oriental 19.16%
    Leaves 19.13%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.7

    pKa est.
    7.57 (neutral)

    Molecular weight
    414.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    505°C

    Flash point

    • 188.52 ˚C est.

  • Synonyms

    • Lupulone
    • 468-28-0
    • beta-Lupulic acid
    • 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
    • CHEBI:6574
    • RefChem:1088600
    • Lupulon
    • beta-Bitter acid
    • B'' -Acid
    • Lupolon
    • EINECS 207-405-3
    • .beta.-Bitter acid
    • .beta.-Lupulic acid
    • 2,4-Cyclohexadien-1-one,3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-
    • 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
    • 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-
    • B7425USG94
    • 3,5-Dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
    • 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
    • n-lupulone
    • UNII-B7425USG94
    • hop beta-acid
    • LUPULON [MI]
    • 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
    • SCHEMBL819253
    • CHEMBL480267
    • orb1705291
    • SCHEMBL2431439
    • GTPL12445
    • DTXSID00875553
    • AKOS015896772
    • AKOS040744749
    • FL74820
    • 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
    • DA-55073
    • XL180107
    • HY-124923
    • CS-0089577
    • Q27107249
    • Q55939056
    • 3,5-Dihydroxy-4,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
    • 3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one #
    • 3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
    • 468-28-0

  • Applications

    Lupulone (CAS 468-28-0) is a beta-acid component derived from lupulin in hops, and is primarily encountered in brewing where it contributes bitterness and characteristic flavor notes, while exhibiting some antimicrobial properties that can help stabilize and extend shelf life of fermented beverages. In the flavor and fragrance sector, hop-derived extracts containing lupulone are evaluated as sources of bitter notes and aroma components for limited formulation use. In cosmetics and personal care, lupulone-containing hop extracts may be explored as fragrance ingredients or active constituents within hop-derived formulations. In chemical research and industrial synthesis, lupulone can serve as an intermediate or starting material for developing hop-derived aroma compounds and related specialty chemicals. In short, real-world applications are centered on beer production, flavor/fragrance extracts, cosmetics-related formulations, and as a synthetic intermediate in hop chemistry.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 363.43
    methanol 256.95
    isopropanol 361.98
    water 0.25
    ethyl acetate 520.21
    n-propanol 391.08
    acetone 708.06
    n-butanol 341.58
    acetonitrile 224.65
    DMF 1779.02
    toluene 297.11
    isobutanol 352.42
    1,4-dioxane 702.26
    methyl acetate 546.58
    THF 1919.2
    2-butanone 684.73
    n-pentanol 290.93
    sec-butanol 378.63
    n-hexane 43.48
    ethylene glycol 81.98
    NMP 2473.35
    cyclohexane 38.95
    DMSO 1005.75
    n-butyl acetate 479.03
    n-octanol 167.38
    chloroform 1144.47
    n-propyl acetate 367.54
    acetic acid 619.94
    dichloromethane 881.18
    cyclohexanone 945.32
    propylene glycol 273.71
    isopropyl acetate 446.55
    DMAc 1894.97
    2-ethoxyethanol 460.25
    isopentanol 342.74
    n-heptane 22.09
    ethyl formate 302.45
    1,2-dichloroethane 741.9
    n-hexanol 332.01
    2-methoxyethanol 769.09
    isobutyl acetate 327.24
    tetrachloromethane 163.86
    n-pentyl acetate 403.13
    transcutol 1244.81
    n-heptanol 203.75
    ethylbenzene 173.64
    MIBK 458.04
    2-propoxyethanol 737.39
    tert-butanol 445.89
    MTBE 394.2
    2-butoxyethanol 503.22
    propionic acid 467.15
    o-xylene 197.8
    formic acid 188.48
    diethyl ether 323.27
    m-xylene 228.87
    p-xylene 243.53
    chlorobenzene 440.64
    dimethyl carbonate 438.81
    n-octane 11.95
    formamide 290.08
    cyclopentanone 1520.95
    2-pentanone 590.14
    anisole 351.33
    cyclopentyl methyl ether 754.11
    gamma-butyrolactone 1640.3
    1-methoxy-2-propanol 860.52
    pyridine 737.17
    3-pentanone 466.19
    furfural 958.82
    n-dodecane 8.87
    diethylene glycol 428.76
    diisopropyl ether 138.44
    tert-amyl alcohol 424.69
    acetylacetone 784.98
    n-hexadecane 10.12
    acetophenone 420.46
    methyl propionate 620.3
    isopentyl acetate 502.73
    trichloroethylene 1585.8
    n-nonanol 170.24
    cyclohexanol 378.21
    benzyl alcohol 314.03
    2-ethylhexanol 206.63
    isooctanol 184.81
    dipropyl ether 219.19
    1,2-dichlorobenzene 425.77
    ethyl lactate 280.34
    propylene carbonate 936.2
    n-methylformamide 589.12
    2-pentanol 292.08
    n-pentane 35.95
    1-propoxy-2-propanol 556.81
    1-methoxy-2-propyl acetate 692.44
    2-(2-methoxypropoxy) propanol 496.06
    mesitylene 137.32
    ε-caprolactone 1000.99
    p-cymene 117.53
    epichlorohydrin 1688.7
    1,1,1-trichloroethane 859.89
    2-aminoethanol 244.27
    morpholine-4-carbaldehyde 1621.4
    sulfolane 2299.65
    2,2,4-trimethylpentane 32.11
    2-methyltetrahydrofuran 1088.24
    n-hexyl acetate 474.62
    isooctane 23.85
    2-(2-butoxyethoxy)ethanol 628.23
    sec-butyl acetate 330.55
    tert-butyl acetate 540.16
    decalin 41.56
    glycerin 340.91
    diglyme 921.88
    acrylic acid 435.57
    isopropyl myristate 179.58
    n-butyric acid 614.21
    acetyl acetate 368.22
    di(2-ethylhexyl) phthalate 234.48
    ethyl propionate 353.89
    nitromethane 927.73
    1,2-diethoxyethane 404.34
    benzonitrile 319.29
    trioctyl phosphate 168.49
    1-bromopropane 390.88
    gamma-valerolactone 1815.42
    n-decanol 122.17
    triethyl phosphate 198.72
    4-methyl-2-pentanol 210.36
    propionitrile 274.26
    vinylene carbonate 679.72
    1,1,2-trichlorotrifluoroethane 1137.7
    DMS 524.19
    cumene 134.26
    2-octanol 144.16
    2-hexanone 396.11
    octyl acetate 252.03
    limonene 169.72
    1,2-dimethoxyethane 644.45
    ethyl orthosilicate 190.33
    tributyl phosphate 206.75
    diacetone alcohol 687.96
    N,N-dimethylaniline 336.52
    acrylonitrile 338.83
    aniline 406.08
    1,3-propanediol 355.0
    bromobenzene 445.01
    dibromomethane 587.36
    1,1,2,2-tetrachloroethane 1390.32
    2-methyl-cyclohexyl acetate 353.71
    tetrabutyl urea 276.2
    diisobutyl methanol 123.93
    2-phenylethanol 370.25
    styrene 196.2
    dioctyl adipate 300.41
    dimethyl sulfate 867.55
    ethyl butyrate 314.69
    methyl lactate 511.05
    butyl lactate 397.82
    diethyl carbonate 218.08
    propanediol butyl ether 460.84
    triethyl orthoformate 253.58
    p-tert-butyltoluene 127.15
    methyl 4-tert-butylbenzoate 518.68
    morpholine 1039.22
    tert-butylamine 254.51
    n-dodecanol 86.98
    dimethoxymethane 870.09
    ethylene carbonate 594.45
    cyrene 574.23
    2-ethoxyethyl acetate 548.57
    2-ethylhexyl acetate 404.72
    1,2,4-trichlorobenzene 582.41
    4-methylpyridine 814.58
    dibutyl ether 162.98
    2,6-dimethyl-4-heptanol 123.93
    DEF 789.98
    dimethyl isosorbide 1029.17
    tetrachloroethylene 691.14
    eugenol 470.62
    triacetin 513.58
    span 80 462.88
    1,4-butanediol 157.25
    1,1-dichloroethane 780.34
    2-methyl-1-pentanol 302.75
    methyl formate 441.81
    2-methyl-1-butanol 357.62
    n-decane 15.21
    butyronitrile 288.75
    3,7-dimethyl-1-octanol 183.86
    1-chlorooctane 98.5
    1-chlorotetradecane 40.36
    n-nonane 13.95
    undecane 11.17
    tert-butylcyclohexane 41.81
    cyclooctane 15.89
    cyclopentanol 529.62
    tetrahydropyran 688.71
    tert-amyl methyl ether 359.26
    2,5,8-trioxanonane 627.92
    1-hexene 157.34
    2-isopropoxyethanol 383.41
    2,2,2-trifluoroethanol 266.14
    methyl butyrate 464.63

    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