6-Prenylnaringenin

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  • Identifiers

    CAS number
    68236-13-5

    Molecular formula
    C20H20O5

    SMILES
    CC(=CCC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 55.73%
    Spicy 49.21%
    Sweet 39.07%
    Woody 29.68%
    Odorless 29.61%
    Smoky 29.45%
    Medicinal 27.91%
    Balsamic 26.48%
    Herbal 25.1%
    Burnt 22.39%

     

    Flavor
    Bitter 90.75%
    Lovage 20.51%
    Cedarleaf 20.33%
    Parsley 19.76%
    Basil 18.61%
    Ripe apricot 18.46%
    Red fruit 18.27%
    Nitrile 18.26%
    Leaves 18.18%
    Heather 18.16%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    10.09 (weak base)

    Molecular weight
    340.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    750°C

    Flash point

    • 230.47 ˚C est.

  • Synonyms

    • 6-Prenylnaringenin
    • 68236-13-5
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
    • 7342WYG80Y
    • CHEBI:27566
    • K-07047
    • RefChem:914069
    • GlyTouCan:G32578PO
    • G32578PO
    • (2S)-6-Prenylnaringenin
    • (S)-4',5,7-Trihydroxy-6-prenylflavanone
    • (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)chroman-4-one
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-, (2S)-
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chroman-4-one
    • SCHEMBL145714
    • UNII-7342WYG80Y
    • orb1297480
    • YS03
    • SCHEMBL29394512
    • GTPL12585
    • DTXSID80218409
    • LMPK12140277
    • AKOS037515358
    • 6-Prenylnaringenin, analytical standard
    • EBC-369051
    • FP69729
    • MS-25193
    • DB-318175
    • HY-107198
    • CS-0027603
    • NS00126925
    • C09832
    • G14141
    • Q27103198
    • 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-6-(3-methyl-but-2-enyl)-1-benzopyran-4-one
    • (2S)-2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-6-(3-METHYL-2-BUTEN-1-YL)-4H-1-BENZOPYRAN-4-ONE
    • (2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
    • (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one
    • 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4h-1-benzopyran-4-one
    • 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-6-(3-METHYL-2-BUTEN-1-YL)-, (2S)-
    • 68236-13-5

  • Applications

    6-Prenylnaringenin (CAS 68236-13-5) is a prenylated flavonoid derived from naringenin in hops. In industrial practice, typical applications include: (1) a cosmetic/personal care ingredient acting as a potentially active compound in formulations; (2) a precursor or reference material in pharmaceutical synthesis and analytical method development; (3) a fragrance component in perfumery/fragrance due to its hop-origin notes; (4) plant science and agricultural research as a reference compound for biochemical studies and plant interaction research; (5) used as an analytical standard or reference in laboratory analysis and formulation development, depending on local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.53
    methanol 69.94
    isopropanol 30.33
    water 0.13
    ethyl acetate 72.05
    n-propanol 22.34
    acetone 260.61
    n-butanol 19.36
    acetonitrile 89.42
    DMF 515.75
    toluene 4.95
    isobutanol 21.48
    1,4-dioxane 239.51
    methyl acetate 119.95
    THF 589.89
    2-butanone 127.69
    n-pentanol 19.27
    sec-butanol 18.67
    n-hexane 0.08
    ethylene glycol 35.91
    NMP 192.56
    cyclohexane 0.23
    DMSO 1279.46
    n-butyl acetate 30.6
    n-octanol 12.95
    chloroform 30.96
    n-propyl acetate 42.65
    acetic acid 145.71
    dichloromethane 23.28
    cyclohexanone 121.83
    propylene glycol 105.09
    isopropyl acetate 45.08
    DMAc 501.73
    2-ethoxyethanol 146.47
    isopentanol 24.3
    n-heptane 0.2
    ethyl formate 52.72
    1,2-dichloroethane 29.19
    n-hexanol 10.69
    2-methoxyethanol 379.18
    isobutyl acetate 28.61
    tetrachloromethane 2.05
    n-pentyl acetate 24.86
    transcutol 666.66
    n-heptanol 10.98
    ethylbenzene 2.51
    MIBK 48.87
    2-propoxyethanol 161.7
    tert-butanol 73.42
    MTBE 23.96
    2-butoxyethanol 62.86
    propionic acid 64.45
    o-xylene 3.62
    formic acid 60.88
    diethyl ether 13.02
    m-xylene 4.6
    p-xylene 5.05
    chlorobenzene 11.49
    dimethyl carbonate 103.02
    n-octane 0.13
    formamide 164.85
    cyclopentanone 313.46
    2-pentanone 73.52
    anisole 31.33
    cyclopentyl methyl ether 51.83
    gamma-butyrolactone 352.4
    1-methoxy-2-propanol 310.58
    pyridine 64.17
    3-pentanone 51.57
    furfural 181.3
    n-dodecane 0.36
    diethylene glycol 199.25
    diisopropyl ether 4.67
    tert-amyl alcohol 30.27
    acetylacetone 216.75
    n-hexadecane 0.43
    acetophenone 40.64
    methyl propionate 102.12
    isopentyl acetate 33.64
    trichloroethylene 83.59
    n-nonanol 13.48
    cyclohexanol 21.35
    benzyl alcohol 34.32
    2-ethylhexanol 8.43
    isooctanol 10.52
    dipropyl ether 13.99
    1,2-dichlorobenzene 12.36
    ethyl lactate 52.65
    propylene carbonate 94.97
    n-methylformamide 215.84
    2-pentanol 12.62
    n-pentane 0.07
    1-propoxy-2-propanol 108.93
    1-methoxy-2-propyl acetate 100.24
    2-(2-methoxypropoxy) propanol 107.57
    mesitylene 3.25
    ε-caprolactone 97.56
    p-cymene 3.77
    epichlorohydrin 377.34
    1,1,1-trichloroethane 23.39
    2-aminoethanol 57.97
    morpholine-4-carbaldehyde 333.95
    sulfolane 454.7
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 88.61
    n-hexyl acetate 37.47
    isooctane 0.25
    2-(2-butoxyethoxy)ethanol 159.36
    sec-butyl acetate 25.99
    tert-butyl acetate 61.48
    decalin 0.3
    glycerin 203.17
    diglyme 319.2
    acrylic acid 77.89
    isopropyl myristate 16.38
    n-butyric acid 71.48
    acetyl acetate 64.68
    di(2-ethylhexyl) phthalate 22.97
    ethyl propionate 40.7
    nitromethane 610.03
    1,2-diethoxyethane 98.36
    benzonitrile 32.42
    trioctyl phosphate 15.92
    1-bromopropane 4.34
    gamma-valerolactone 436.83
    n-decanol 10.25
    triethyl phosphate 22.34
    4-methyl-2-pentanol 12.71
    propionitrile 49.68
    vinylene carbonate 83.48
    1,1,2-trichlorotrifluoroethane 231.37
    DMS 71.92
    cumene 2.35
    2-octanol 7.18
    2-hexanone 45.23
    octyl acetate 21.61
    limonene 4.56
    1,2-dimethoxyethane 262.54
    ethyl orthosilicate 20.27
    tributyl phosphate 21.3
    diacetone alcohol 137.5
    N,N-dimethylaniline 18.18
    acrylonitrile 93.79
    aniline 21.2
    1,3-propanediol 99.84
    bromobenzene 8.99
    dibromomethane 8.25
    1,1,2,2-tetrachloroethane 76.65
    2-methyl-cyclohexyl acetate 28.58
    tetrabutyl urea 32.71
    diisobutyl methanol 9.13
    2-phenylethanol 28.32
    styrene 3.47
    dioctyl adipate 34.64
    dimethyl sulfate 193.49
    ethyl butyrate 27.45
    methyl lactate 140.45
    butyl lactate 41.28
    diethyl carbonate 23.65
    propanediol butyl ether 91.54
    triethyl orthoformate 30.39
    p-tert-butyltoluene 4.11
    methyl 4-tert-butylbenzoate 49.27
    morpholine 265.02
    tert-butylamine 12.98
    n-dodecanol 7.52
    dimethoxymethane 370.63
    ethylene carbonate 73.85
    cyrene 98.83
    2-ethoxyethyl acetate 68.49
    2-ethylhexyl acetate 21.65
    1,2,4-trichlorobenzene 23.12
    4-methylpyridine 48.75
    dibutyl ether 17.07
    2,6-dimethyl-4-heptanol 9.13
    DEF 86.6
    dimethyl isosorbide 200.05
    tetrachloroethylene 26.22
    eugenol 54.13
    triacetin 77.4
    span 80 61.77
    1,4-butanediol 37.08
    1,1-dichloroethane 22.19
    2-methyl-1-pentanol 17.78
    methyl formate 207.09
    2-methyl-1-butanol 17.6
    n-decane 0.49
    butyronitrile 30.96
    3,7-dimethyl-1-octanol 15.51
    1-chlorooctane 3.61
    1-chlorotetradecane 1.93
    n-nonane 0.32
    undecane 0.42
    tert-butylcyclohexane 0.32
    cyclooctane 0.12
    cyclopentanol 44.79
    tetrahydropyran 62.35
    tert-amyl methyl ether 16.62
    2,5,8-trioxanonane 231.86
    1-hexene 0.55
    2-isopropoxyethanol 91.09
    2,2,2-trifluoroethanol 53.5
    methyl butyrate 53.25

    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