Adlupulone

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  • Identifiers

    CAS number
    28374-71-2

    Molecular formula
    C26H38O4

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

    Safety labels

  • Odor profile

    Fragrance
    Herbal 60.3%
    Fruity 57.41%
    Floral 42.22%
    Woody 38.79%
    Mint 37.88%
    Citrus 36.56%
    Spicy 33.36%
    Sweet 32.95%
    Fresh 32.38%
    Rose 32.07%

     

    Flavor
    Bitter 58.71%
    Herbal 33.1%
    Cedarleaf 20.51%
    Heather 19.97%
    Lovage 19.9%
    Genet 19.84%
    Basil 19.82%
    Broom 19.8%
    Minty 19.54%
    Oriental 19.39%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.9

    pKa est.
    7.58 (neutral)

    Molecular weight
    414.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    513°C

    Flash point

    • 184.03 ˚C est.

  • Synonyms

    • ADLUPULONE
    • 28374-71-2
    • 35049-54-8
    • O2S4D7K08Y
    • 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4,6,6-tris(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxobutyl)-
    • UNII-O2S4D7K08Y
    • 3,5-dihydroxy-2-(2-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
    • CHEBI:136852
    • 4-Cyclohexene-1,3-dione, 5-hydroxy-2,2,6-tris(3-methyl-2-buten-1-yl)-4-(2-methyl-1-oxobutyl)-
    • 3,5-dihydroxy-2-(2-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
    • RefChem:109806
    • 31769-60-5
    • adlupulon
    • 3,5-Dihydroxy-4,6,6-tris(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
    • Phloroglucinol Impurity X
    • SCHEMBL817774
    • DTXSID901318318
    • FA172850
    • XA180098
    • NS00094540
    • Q27894794
    • 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dienone
    • 28374-71-2

  • Applications

    Adlupulone (CAS 28374-71-2) is a hop-derived beta-acid. In practice it may be used as a component contributing bittering notes and hop aroma in beer-related flavor and fragrance formulations; it is evaluated for antimicrobial activity and processing stability in brewing and food-processing contexts; it can serve as a synthetic intermediate or starting material for the preparation of other hop-derived aroma compounds in industrial manufacturing; in cosmetics and personal care it may be considered as a fragrance ingredient or additive providing hop-like notes; and it is studied as a potential building block in aroma-chemical synthesis, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 344.6
    methanol 223.09
    isopropanol 353.76
    water 0.15
    ethyl acetate 496.53
    n-propanol 376.79
    acetone 673.92
    n-butanol 336.44
    acetonitrile 197.86
    DMF 1600.73
    toluene 351.0
    isobutanol 350.89
    1,4-dioxane 723.19
    methyl acetate 515.66
    THF 1770.31
    2-butanone 703.77
    n-pentanol 298.65
    sec-butanol 395.73
    n-hexane 51.67
    ethylene glycol 57.17
    NMP 2106.98
    cyclohexane 51.51
    DMSO 857.88
    n-butyl acetate 438.52
    n-octanol 154.2
    chloroform 1078.56
    n-propyl acetate 335.64
    acetic acid 477.25
    dichloromethane 828.87
    cyclohexanone 942.73
    propylene glycol 198.53
    isopropyl acetate 437.64
    DMAc 1796.6
    2-ethoxyethanol 427.93
    isopentanol 348.5
    n-heptane 23.45
    ethyl formate 264.2
    1,2-dichloroethane 727.87
    n-hexanol 331.81
    2-methoxyethanol 675.34
    isobutyl acetate 297.46
    tetrachloromethane 162.81
    n-pentyl acetate 385.09
    transcutol 1030.77
    n-heptanol 196.57
    ethylbenzene 195.89
    MIBK 443.49
    2-propoxyethanol 671.7
    tert-butanol 447.28
    MTBE 413.12
    2-butoxyethanol 456.94
    propionic acid 391.13
    o-xylene 224.81
    formic acid 131.38
    diethyl ether 349.55
    m-xylene 252.47
    p-xylene 271.92
    chlorobenzene 466.16
    dimethyl carbonate 387.54
    n-octane 12.97
    formamide 233.31
    cyclopentanone 1393.65
    2-pentanone 590.08
    anisole 356.62
    cyclopentyl methyl ether 726.13
    gamma-butyrolactone 1397.79
    1-methoxy-2-propanol 763.49
    pyridine 770.85
    3-pentanone 477.25
    furfural 811.85
    n-dodecane 8.98
    diethylene glycol 358.74
    diisopropyl ether 147.68
    tert-amyl alcohol 445.14
    acetylacetone 734.54
    n-hexadecane 10.32
    acetophenone 413.19
    methyl propionate 588.49
    isopentyl acetate 464.09
    trichloroethylene 1448.92
    n-nonanol 157.46
    cyclohexanol 392.71
    benzyl alcohol 310.56
    2-ethylhexanol 207.54
    isooctanol 176.64
    dipropyl ether 208.65
    1,2-dichlorobenzene 423.42
    ethyl lactate 244.19
    propylene carbonate 783.44
    n-methylformamide 498.17
    2-pentanol 299.77
    n-pentane 44.28
    1-propoxy-2-propanol 498.62
    1-methoxy-2-propyl acetate 619.81
    2-(2-methoxypropoxy) propanol 425.07
    mesitylene 150.27
    ε-caprolactone 931.57
    p-cymene 115.99
    epichlorohydrin 1551.31
    1,1,1-trichloroethane 818.62
    2-aminoethanol 192.64
    morpholine-4-carbaldehyde 1480.11
    sulfolane 1857.32
    2,2,4-trimethylpentane 35.52
    2-methyltetrahydrofuran 1082.52
    n-hexyl acetate 428.68
    isooctane 25.59
    2-(2-butoxyethoxy)ethanol 545.34
    sec-butyl acetate 313.38
    tert-butyl acetate 503.95
    decalin 48.65
    glycerin 240.53
    diglyme 822.69
    acrylic acid 340.64
    isopropyl myristate 158.91
    n-butyric acid 527.58
    acetyl acetate 344.68
    di(2-ethylhexyl) phthalate 206.24
    ethyl propionate 333.99
    nitromethane 742.83
    1,2-diethoxyethane 397.4
    benzonitrile 305.69
    trioctyl phosphate 143.35
    1-bromopropane 402.53
    gamma-valerolactone 1632.78
    n-decanol 112.78
    triethyl phosphate 177.3
    4-methyl-2-pentanol 211.49
    propionitrile 264.98
    vinylene carbonate 584.98
    1,1,2-trichlorotrifluoroethane 940.8
    DMS 449.61
    cumene 144.1
    2-octanol 139.05
    2-hexanone 383.56
    octyl acetate 223.72
    limonene 169.7
    1,2-dimethoxyethane 623.49
    ethyl orthosilicate 173.8
    tributyl phosphate 170.77
    diacetone alcohol 625.63
    N,N-dimethylaniline 336.08
    acrylonitrile 312.46
    aniline 431.7
    1,3-propanediol 304.51
    bromobenzene 468.89
    dibromomethane 582.27
    1,1,2,2-tetrachloroethane 1312.83
    2-methyl-cyclohexyl acetate 316.74
    tetrabutyl urea 236.06
    diisobutyl methanol 120.38
    2-phenylethanol 355.67
    styrene 224.55
    dioctyl adipate 252.91
    dimethyl sulfate 712.63
    ethyl butyrate 280.64
    methyl lactate 427.94
    butyl lactate 340.16
    diethyl carbonate 193.83
    propanediol butyl ether 379.98
    triethyl orthoformate 228.65
    p-tert-butyltoluene 123.57
    methyl 4-tert-butylbenzoate 456.42
    morpholine 1062.2
    tert-butylamine 260.46
    n-dodecanol 79.76
    dimethoxymethane 794.2
    ethylene carbonate 517.89
    cyrene 503.6
    2-ethoxyethyl acetate 512.26
    2-ethylhexyl acetate 368.91
    1,2,4-trichlorobenzene 577.92
    4-methylpyridine 827.26
    dibutyl ether 157.4
    2,6-dimethyl-4-heptanol 120.38
    DEF 773.91
    dimethyl isosorbide 873.0
    tetrachloroethylene 663.78
    eugenol 412.05
    triacetin 415.67
    span 80 383.86
    1,4-butanediol 134.87
    1,1-dichloroethane 747.55
    2-methyl-1-pentanol 314.81
    methyl formate 372.09
    2-methyl-1-butanol 371.46
    n-decane 15.49
    butyronitrile 274.96
    3,7-dimethyl-1-octanol 175.68
    1-chlorooctane 96.9
    1-chlorotetradecane 39.64
    n-nonane 14.37
    undecane 11.21
    tert-butylcyclohexane 45.84
    cyclooctane 19.86
    cyclopentanol 523.65
    tetrahydropyran 764.04
    tert-amyl methyl ether 365.89
    2,5,8-trioxanonane 542.61
    1-hexene 182.6
    2-isopropoxyethanol 364.81
    2,2,2-trifluoroethanol 196.04
    methyl butyrate 430.68

    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