Colupulone

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  • Identifiers

    CAS number
    468-27-9

    Molecular formula
    C25H36O4

    SMILES
    CC(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 59.9%
    Fruity 57.25%
    Floral 43.34%
    Citrus 40.58%
    Woody 38.58%
    Mint 38.35%
    Sweet 36.97%
    Fresh 33.11%
    Spicy 33.06%
    Rose 32.57%

     

    Flavor
    Bitter 60.09%
    Herbal 32.31%
    Cedarleaf 20.56%
    Broom 20.08%
    Heather 20.06%
    Genet 19.99%
    Basil 19.86%
    Lovage 19.82%
    Minty 19.49%
    Oriental 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.5

    pKa est.
    7.46 (neutral)

    Molecular weight
    400.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    507°C

    Flash point

    • 180.54 ˚C est.

  • Synonyms

    • Colupulone
    • 468-27-9
    • BA8R555DNZ
    • 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
    • 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
    • CHEBI:136851
    • DTXSID80963664
    • RefChem:127556
    • DTXCID601391404
    • 5-hydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohex-4-ene-1,3-dione
    • co-lupulone
    • 3,5-dihydroxy-2-isobutyryl-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
    • NSC650561
    • UNII-BA8R555DNZ
    • Colupulone A; Colupulone I
    • 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(2-methyl-1-oxopropyl)-
    • Phloroglucinol Impurity W
    • I-BUTYROLUPUPHENONE
    • SCHEMBL316240
    • orb1944067
    • orb1991866
    • CHEMBL5596790
    • HY-N10867
    • MFCD00075970
    • NSC-650561
    • DA-52025
    • XC172848
    • HY-167627
    • CS-0637301
    • NS00094539
    • Q27458763
    • 3,5-dihydroxy-2-isobutyryl-4,6,6-tris(3-methyl-but-2-enyl)cyclohexa-2,4- dienone
    • 3,5-dihydroxy-4-isobutyryl-2,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dienone
    • 3,5-Dihydroxy-4-isobutyryl-2,6,6-tris-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienone
    • 2,4-CYCLOHEXADIEN-1-ONE, 3,5-DIHYDROXY-4,6,6-TRIS(3-METHYL-2-BUTEN-1-YL)-2-(2-METHYL-1-OXOPROPYL)-
    • 3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
    • 468-27-9

  • Applications

    Colupulone, CAS 468-27-9, is a hop-derived compound present in hop extracts. In the flavor and beverage industry it is recognized as a bittering constituent that can influence beer bitterness and hop-related flavor notes; in perfumery and cosmetics it may be evaluated as a fragrance ingredient or aroma component related to hops. It is also studied for antimicrobial properties, offering potential use in natural preservation strategies or antimicrobial coatings, subject to formulation limits. Additionally, colupulone can serve as a chemical intermediate in the synthesis of hop-related aroma compounds. In agriculture and crop protection research, its antimicrobial activity is being explored for possible use in plant protection formulations. All applications depend on local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 254.39
    methanol 160.69
    isopropanol 267.87
    water 0.11
    ethyl acetate 371.5
    n-propanol 288.75
    acetone 480.28
    n-butanol 267.75
    acetonitrile 152.27
    DMF 1239.08
    toluene 287.41
    isobutanol 275.25
    1,4-dioxane 551.5
    methyl acetate 384.24
    THF 1410.56
    2-butanone 545.22
    n-pentanol 247.06
    sec-butanol 323.8
    n-hexane 49.99
    ethylene glycol 41.82
    NMP 1671.57
    cyclohexane 44.88
    DMSO 635.32
    n-butyl acetate 367.91
    n-octanol 141.1
    chloroform 889.7
    n-propyl acetate 278.07
    acetic acid 337.23
    dichloromethane 650.06
    cyclohexanone 767.58
    propylene glycol 150.01
    isopropyl acetate 338.03
    DMAc 1442.99
    2-ethoxyethanol 332.37
    isopentanol 281.82
    n-heptane 23.2
    ethyl formate 209.27
    1,2-dichloroethane 572.43
    n-hexanol 288.0
    2-methoxyethanol 481.1
    isobutyl acetate 253.44
    tetrachloromethane 129.55
    n-pentyl acetate 309.8
    transcutol 736.57
    n-heptanol 175.41
    ethylbenzene 175.27
    MIBK 354.78
    2-propoxyethanol 535.96
    tert-butanol 351.06
    MTBE 336.73
    2-butoxyethanol 380.75
    propionic acid 290.4
    o-xylene 188.29
    formic acid 90.76
    diethyl ether 268.16
    m-xylene 213.95
    p-xylene 237.47
    chlorobenzene 372.79
    dimethyl carbonate 292.52
    n-octane 12.59
    formamide 164.26
    cyclopentanone 1127.27
    2-pentanone 470.01
    anisole 306.75
    cyclopentyl methyl ether 585.48
    gamma-butyrolactone 1101.57
    1-methoxy-2-propanol 571.05
    pyridine 615.27
    3-pentanone 375.74
    furfural 644.17
    n-dodecane 8.69
    diethylene glycol 270.56
    diisopropyl ether 119.65
    tert-amyl alcohol 364.92
    acetylacetone 538.16
    n-hexadecane 9.96
    acetophenone 350.27
    methyl propionate 445.9
    isopentyl acetate 394.35
    trichloroethylene 1127.92
    n-nonanol 140.65
    cyclohexanol 325.93
    benzyl alcohol 261.97
    2-ethylhexanol 186.07
    isooctanol 154.86
    dipropyl ether 180.88
    1,2-dichlorobenzene 339.97
    ethyl lactate 202.23
    propylene carbonate 633.82
    n-methylformamide 373.77
    2-pentanol 247.61
    n-pentane 39.39
    1-propoxy-2-propanol 402.93
    1-methoxy-2-propyl acetate 494.69
    2-(2-methoxypropoxy) propanol 342.11
    mesitylene 126.16
    ε-caprolactone 739.32
    p-cymene 104.91
    epichlorohydrin 1212.6
    1,1,1-trichloroethane 633.66
    2-aminoethanol 139.41
    morpholine-4-carbaldehyde 1163.8
    sulfolane 1482.89
    2,2,4-trimethylpentane 32.33
    2-methyltetrahydrofuran 874.16
    n-hexyl acetate 354.56
    isooctane 22.85
    2-(2-butoxyethoxy)ethanol 421.09
    sec-butyl acetate 256.68
    tert-butyl acetate 390.53
    decalin 45.42
    glycerin 176.39
    diglyme 630.27
    acrylic acid 247.45
    isopropyl myristate 135.38
    n-butyric acid 405.11
    acetyl acetate 247.11
    di(2-ethylhexyl) phthalate 170.33
    ethyl propionate 277.43
    nitromethane 531.14
    1,2-diethoxyethane 309.98
    benzonitrile 254.85
    trioctyl phosphate 122.67
    1-bromopropane 337.32
    gamma-valerolactone 1301.21
    n-decanol 100.29
    triethyl phosphate 150.35
    4-methyl-2-pentanol 173.64
    propionitrile 215.04
    vinylene carbonate 460.65
    1,1,2-trichlorotrifluoroethane 720.8
    DMS 347.8
    cumene 130.14
    2-octanol 125.47
    2-hexanone 322.73
    octyl acetate 188.28
    limonene 150.4
    1,2-dimethoxyethane 495.05
    ethyl orthosilicate 149.08
    tributyl phosphate 143.22
    diacetone alcohol 494.61
    N,N-dimethylaniline 296.45
    acrylonitrile 245.46
    aniline 351.67
    1,3-propanediol 222.0
    bromobenzene 376.98
    dibromomethane 482.89
    1,1,2,2-tetrachloroethane 1032.06
    2-methyl-cyclohexyl acetate 273.82
    tetrabutyl urea 200.81
    diisobutyl methanol 107.36
    2-phenylethanol 299.27
    styrene 194.1
    dioctyl adipate 206.62
    dimethyl sulfate 536.44
    ethyl butyrate 238.79
    methyl lactate 326.22
    butyl lactate 281.39
    diethyl carbonate 162.01
    propanediol butyl ether 308.49
    triethyl orthoformate 193.91
    p-tert-butyltoluene 112.3
    methyl 4-tert-butylbenzoate 376.34
    morpholine 821.21
    tert-butylamine 214.05
    n-dodecanol 72.12
    dimethoxymethane 585.1
    ethylene carbonate 405.85
    cyrene 422.3
    2-ethoxyethyl acetate 385.31
    2-ethylhexyl acetate 320.4
    1,2,4-trichlorobenzene 456.53
    4-methylpyridine 677.2
    dibutyl ether 136.54
    2,6-dimethyl-4-heptanol 107.36
    DEF 606.18
    dimethyl isosorbide 721.59
    tetrachloroethylene 516.87
    eugenol 339.27
    triacetin 329.19
    span 80 312.57
    1,4-butanediol 106.42
    1,1-dichloroethane 596.14
    2-methyl-1-pentanol 268.43
    methyl formate 280.99
    2-methyl-1-butanol 303.72
    n-decane 14.94
    butyronitrile 230.21
    3,7-dimethyl-1-octanol 154.85
    1-chlorooctane 89.36
    1-chlorotetradecane 36.49
    n-nonane 14.0
    undecane 10.91
    tert-butylcyclohexane 43.31
    cyclooctane 18.52
    cyclopentanol 434.08
    tetrahydropyran 602.74
    tert-amyl methyl ether 306.37
    2,5,8-trioxanonane 423.0
    1-hexene 165.35
    2-isopropoxyethanol 289.93
    2,2,2-trifluoroethanol 140.61
    methyl butyrate 363.03

    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