Sophoraflavanone B

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  • Identifiers

    CAS number
    53846-50-7

    Molecular formula
    C20H20O5

    SMILES
    CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 56.03%
    Spicy 49.43%
    Sweet 37.61%
    Odorless 29.82%
    Woody 29.74%
    Smoky 29.46%
    Medicinal 27.83%
    Balsamic 26.23%
    Herbal 25.55%
    Animal 22.41%

     

    Flavor
    Bitter 90.92%
    Lovage 20.43%
    Cedarleaf 20.26%
    Parsley 19.76%
    Basil 18.57%
    Ripe apricot 18.42%
    Red fruit 18.26%
    Nitrile 18.24%
    Leaves 18.13%
    Heather 18.12%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    10.16 (weak base)

    Molecular weight
    340.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    735°C

    Flash point

    • 231.46 ˚C est.

  • Synonyms

    • Sophoraflavanone B
    • (-)-(2S)-8-dimethylallylnaringenin
    • CHEBI:50207
    • (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
    • RefChem:1098889
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
    • 8-Prenylnaringenin
    • 53846-50-7
    • Flavaprenin
    • (-)-8-Prenylnaringenin
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
    • (S)-8-dimethylallylnaringenin
    • 8-?Prenylnaringenin
    • (S)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)CHROMAN-4-ONE
    • 8-prenyl-naringenin
    • 5L872SZR8X
    • CHEMBL376915
    • YS04
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
    • 8-renylnaringenin
    • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one
    • (s)-8-prenylnaringenin
    • sorphoraflavanone B
    • (-)-8-Prenylnaringenin; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2S)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-, (2S)- (9CI); 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihyd
    • HOPEIN
    • 8-dimethylallylnaringenin
    • Phloroglucinol Impurity Y
    • UNII-5L872SZR8X
    • 8-prenylnaringenin (8-PN)
    • BIDD:ER0149
    • cid_509245
    • orb1297527
    • SCHEMBL1171435
    • SCHEMBL29396586
    • BDBM19460
    • DTXSID60333083
    • AIDS095901
    • GLXC-09019
    • HY-N2787
    • EBC-13162
    • AKOS032948436
    • 8-Prenylnaringenin, analytical standard
    • AT10700
    • FP64928
    • 8-Prenylnaringenin (Sophoraflavanone B)
    • AC-35053
    • AS-82967
    • PD017477
    • DB-253663
    • CS-0023305
    • NS00067003
    • C18023
    • EN300-19006927
    • Q4644281
    • 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-1-benzopyran-4-one
    • (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-1-benzopyran-4-one
    • 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2S)-
    • 53846-50-7

  • Applications

    Sophoraflavanone B (CAS 53846-50-7) is viewed as an intermediate and synthetic building block in the preparation of pharmaceutical compounds and agrochemical derivatives, with ongoing work on efficient synthetic routes. It is also evaluated as a potential antioxidant ingredient for cosmetics and personal care formulations, contributing to stability in both oil- and water-based products. In polymers and plastics, sophoraflavanone B may be explored as a stabilizer/antioxidant additive to improve material longevity. For coatings and inks, it can be considered as an active additive or stabilizer to enhance aging performance and appearance. Additionally, it is commonly studied as a starting material for bioactive compound synthesis, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.03
    methanol 77.82
    isopropanol 42.71
    water 0.14
    ethyl acetate 81.82
    n-propanol 31.09
    acetone 298.64
    n-butanol 25.41
    acetonitrile 106.95
    DMF 637.29
    toluene 5.07
    isobutanol 28.59
    1,4-dioxane 230.13
    methyl acetate 136.69
    THF 561.24
    2-butanone 146.35
    n-pentanol 23.72
    sec-butanol 25.78
    n-hexane 0.1
    ethylene glycol 46.15
    NMP 245.85
    cyclohexane 0.29
    DMSO 1493.25
    n-butyl acetate 37.74
    n-octanol 14.23
    chloroform 41.25
    n-propyl acetate 47.18
    acetic acid 168.12
    dichloromethane 25.99
    cyclohexanone 129.3
    propylene glycol 118.96
    isopropyl acetate 53.01
    DMAc 604.05
    2-ethoxyethanol 150.5
    isopentanol 31.48
    n-heptane 0.23
    ethyl formate 55.36
    1,2-dichloroethane 34.4
    n-hexanol 13.28
    2-methoxyethanol 390.76
    isobutyl acetate 33.05
    tetrachloromethane 2.71
    n-pentyl acetate 26.91
    transcutol 716.92
    n-heptanol 12.46
    ethylbenzene 2.84
    MIBK 57.47
    2-propoxyethanol 168.66
    tert-butanol 92.36
    MTBE 31.73
    2-butoxyethanol 66.86
    propionic acid 79.19
    o-xylene 4.3
    formic acid 70.99
    diethyl ether 16.87
    m-xylene 5.21
    p-xylene 5.78
    chlorobenzene 12.12
    dimethyl carbonate 125.78
    n-octane 0.15
    formamide 167.14
    cyclopentanone 322.47
    2-pentanone 84.42
    anisole 32.2
    cyclopentyl methyl ether 58.52
    gamma-butyrolactone 345.87
    1-methoxy-2-propanol 328.89
    pyridine 64.3
    3-pentanone 62.91
    furfural 174.63
    n-dodecane 0.44
    diethylene glycol 215.42
    diisopropyl ether 6.21
    tert-amyl alcohol 40.35
    acetylacetone 234.19
    n-hexadecane 0.52
    acetophenone 44.1
    methyl propionate 120.04
    isopentyl acetate 40.19
    trichloroethylene 94.09
    n-nonanol 14.93
    cyclohexanol 26.67
    benzyl alcohol 35.99
    2-ethylhexanol 10.16
    isooctanol 12.33
    dipropyl ether 16.26
    1,2-dichlorobenzene 14.13
    ethyl lactate 61.36
    propylene carbonate 106.37
    n-methylformamide 234.75
    2-pentanol 17.03
    n-pentane 0.1
    1-propoxy-2-propanol 119.76
    1-methoxy-2-propyl acetate 112.28
    2-(2-methoxypropoxy) propanol 119.45
    mesitylene 3.86
    ε-caprolactone 107.06
    p-cymene 4.51
    epichlorohydrin 358.13
    1,1,1-trichloroethane 30.37
    2-aminoethanol 69.02
    morpholine-4-carbaldehyde 364.58
    sulfolane 479.72
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 96.09
    n-hexyl acetate 41.24
    isooctane 0.35
    2-(2-butoxyethoxy)ethanol 166.84
    sec-butyl acetate 31.46
    tert-butyl acetate 71.95
    decalin 0.39
    glycerin 226.62
    diglyme 320.86
    acrylic acid 90.78
    isopropyl myristate 18.96
    n-butyric acid 84.51
    acetyl acetate 73.33
    di(2-ethylhexyl) phthalate 25.57
    ethyl propionate 47.88
    nitromethane 636.45
    1,2-diethoxyethane 104.51
    benzonitrile 34.5
    trioctyl phosphate 18.32
    1-bromopropane 5.91
    gamma-valerolactone 430.07
    n-decanol 11.62
    triethyl phosphate 25.91
    4-methyl-2-pentanol 16.56
    propionitrile 61.3
    vinylene carbonate 90.84
    1,1,2-trichlorotrifluoroethane 249.29
    DMS 81.98
    cumene 2.87
    2-octanol 8.51
    2-hexanone 49.28
    octyl acetate 24.67
    limonene 5.58
    1,2-dimethoxyethane 258.44
    ethyl orthosilicate 23.08
    tributyl phosphate 24.83
    diacetone alcohol 153.65
    N,N-dimethylaniline 20.73
    acrylonitrile 105.82
    aniline 23.03
    1,3-propanediol 114.43
    bromobenzene 9.4
    dibromomethane 10.02
    1,1,2,2-tetrachloroethane 92.61
    2-methyl-cyclohexyl acetate 32.63
    tetrabutyl urea 36.81
    diisobutyl methanol 11.23
    2-phenylethanol 31.22
    styrene 3.74
    dioctyl adipate 38.44
    dimethyl sulfate 230.95
    ethyl butyrate 32.82
    methyl lactate 164.2
    butyl lactate 45.97
    diethyl carbonate 28.36
    propanediol butyl ether 100.38
    triethyl orthoformate 34.39
    p-tert-butyltoluene 4.98
    methyl 4-tert-butylbenzoate 52.87
    morpholine 263.6
    tert-butylamine 18.09
    n-dodecanol 8.8
    dimethoxymethane 396.87
    ethylene carbonate 81.0
    cyrene 104.37
    2-ethoxyethyl acetate 71.23
    2-ethylhexyl acetate 26.41
    1,2,4-trichlorobenzene 26.51
    4-methylpyridine 51.32
    dibutyl ether 18.28
    2,6-dimethyl-4-heptanol 11.23
    DEF 105.8
    dimethyl isosorbide 205.34
    tetrachloroethylene 32.87
    eugenol 56.41
    triacetin 85.85
    span 80 69.82
    1,4-butanediol 42.08
    1,1-dichloroethane 30.32
    2-methyl-1-pentanol 21.42
    methyl formate 214.42
    2-methyl-1-butanol 23.27
    n-decane 0.58
    butyronitrile 35.91
    3,7-dimethyl-1-octanol 17.86
    1-chlorooctane 4.12
    1-chlorotetradecane 2.26
    n-nonane 0.38
    undecane 0.5
    tert-butylcyclohexane 0.42
    cyclooctane 0.15
    cyclopentanol 54.61
    tetrahydropyran 66.22
    tert-amyl methyl ether 21.93
    2,5,8-trioxanonane 245.47
    1-hexene 0.7
    2-isopropoxyethanol 96.48
    2,2,2-trifluoroethanol 63.3
    methyl butyrate 59.77

    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